Skip to Content

Book Summary: Can We Talk? Seven Principles for Managing Difficult Conversations at Work

Can We Talk? (2021) outlines the seven communication principles essential for successfully navigating difficult conversations in the workplace, be it asking for a promotion, delivering negative feedback, or resolving a professional conflict.


Communication Skills, Personal Development, Career Success, Business Culture, Business Conflict Resolution and Mediation, Business Communication, Running Meetings and Presentations

Introduction: Learn the seven key principles for navigating difficult discussions well.

Silence isn’t always golden.

Just look at the numbers: according to the startup Bravely, 70 percent of employees admit to avoiding challenging conversations with their colleagues. Now, this might not be so striking if not for a 2016 study that found that every failed conversation costs companies $7,500 and 7 days of work. Not only that, but a 2008 report revealed that the average employee spends 2.8 hours every week managing difficult situations – situations that might have been avoided if we weren’t so reluctant to have hard conversations in the first place.

[Book Summary] Can We Talk? Seven Principles for Managing Difficult Conversations at Work

Silence isn’t always golden.

Workplace issues don’t just go away when we ignore them. Instead, they turn toxic. Poor, or absent, workplace communication inevitably ends up eroding organizational trust, worker satisfaction, and productivity. So don’t ignore difficult issues – get talking!

Whether you’re asking your boss for a raise, delivering feedback to your direct reports, or navigating a tricky office etiquette dilemma, learning to take charge of the conversation will get you one step closer to achieving the results you want.

In these summaries, you’ll learn

  • what a one-sided conversation is and how to avoid it;
  • the one mistake that invariably derails negotiations; and
  • what your inner child can teach you about workplace communication.

Confidence is the key to productive communication.

Do you want the bad news or the good news first?

Let’s start with the bad news. There’s no handbook for navigating difficult workplace conversations, no manual on how to ask your boss to stop micromanaging, and no step-by-step guide on how to tell Gary from accounts that he has onion breath.

The good news, however, is that if you understand the seven principles of effective workplace communication, these difficult conversations will start to become a whole lot easier.

So, let’s start with the first of our seven principles: confidence.

Confidence is key to navigating difficult workplace situations productively.

To begin with, you need confidence to initiate conversations. Marketing manager Rishi lacked the confidence to pull his boss aside and ask for a raise, even though he’d taken on more responsibility since his team downsized. Instead, he fell into a common trap. He had the conversation in his head. Over and over and over. Each time, Rishi imagined his boss giving more and more reasons to refuse his raise. Until eventually, he talked himself out of approaching his boss at all. The problem? You can’t anticipate someone else’s reaction. If Rishi’d had the confidence to request a raise, his boss may well have approved it.

Without confidence, you can ignore your gut instincts and derail working relationships in the process. That’s exactly what happened to Danielle, whose boss pulled her up on a shoddy report. Danielle knew the report wasn’t her best work and her gut instinct was to offer her boss an unreserved apology. But self-doubt kicked in and Danielle reached for excuses. She blamed another department for giving her the wrong numbers. She implied her boss hadn’t allocated her enough time to finish the report. Danielle knew her boss wanted her to own her actions but she didn’t have enough confidence to do that. As a result, her relationship with her boss deteriorated.

But, when you are able to inspire confidence in others, you instantly reframe your tricky requests into reasonable asks. Louise had just started a new role when she was obliged to ask for time off to deal with a personal matter. She assured her boss she’d make up the work later. Her boss approved the leave instantly. Why? Well, Louise had already made several deposits into the bank of trust, by working late to meet a deadline and covering for a sick coworker. If Louise hadn’t proven herself a hard worker, her commitment to making up missed work might have just sounded like an empty promise.

In short, confidence is the key to initiating conversations, allowing your best instincts to dictate your dialogue, and priming others to respond favorably to your requests. So . . . should people lacking in self-confidence just give up on difficult conversations now?

Not at all. Confidence isn’t an innate quality but a muscle that can be trained. The Buddha says, “What we think, we become.” So think yourself confident! Start your day with an affirmation, a phrase that clarifies your ambitions and intentions into a positive statement. You can come up with your own, or try these on for size: I can do what I set my mind to. I’m strong and capable. I can rise to any challenge. Once you’re thinking confidently, challenge yourself to initiate difficult dialogues – but, where possible, try and start small. Tackle the least intimidating issues on your to-do list, then work up to bigger problems.

Make clarity a priority.

Your boss tells you to lift your performance, but she doesn’t tell you where you need to improve. A colleague wants your help on a project, but you have no idea what sort of time commitment is involved. You try to tell your manager you’re unhappy with your current role, and he nods along, but weeks later your situation is unchanged.

What’s the problem with all of these conversations? Well, one or both of you hasn’t been clear about what they want or need out of the discussion.

And that’s what brings us to the second of our seven principles: clarity. In difficult workplace discussions, clarity is your number one priority.

Before you begin a conversation, work out what you want from it. Set a concrete goal, like “I’d like to work more closely with the design department,” rather than, “I want a more creative role.” Ask yourself what you want the other person to do directly after your conversation – perhaps you’d like them to give you a raise, assign you to a new team, or give you more thorough feedback at your next performance review. And decide ahead of time what you’re prepared to risk to achieve your desired result. There’s nothing worse than threatening to quit your job, only to have your boss take you up on the offer! Then again, if you’re prepared to take on extra responsibilities or make a transfer to achieve your objective, then your partner needs to know that.

No matter how the conversation unfolds, keep your objective in mind. You’re all about clarity, but the other person may not be. If they try to deflect focus, steer back to your objective and stick to facts. For example, in response to a poor performance review, a deflector might say, “Sharon’s numbers are worse than mine!” Respond with something like, “We’re here to talk about you and how you can manage a 5 percent increase in your sales by next quarter.” Or they might deflect with a sob story. Here you can be kind but firm. Try something like, “Hey, I’m so sorry things are tough at home. But unfortunately, we still need to talk about your poor performance. Is now a good time or should we reschedule for tomorrow morning?”

While you should be prepared for the conversation to go poorly, don’t be surprised if it goes well. If the other person offers to meet your objective, that’s your cue to close the conversation, establishing next steps if necessary. If your boss says, “I’d hate to lose you but I guess I could talk to HR about a transfer,” don’t ask “Are you sure?” Get your boss’s commitment to set up an HR meeting then thank them for their time.

Compassion has a place in professional communication

It’s important to be clear what you want from a conversation and to stick to your guns about getting it. But there’s one communication principle that trumps clarity – and that’s compassion, our third principle. Let’s look at this exchange between Matt, a manager, and Damian, his report. Damian, a star player on Matt’s team, was recently promoted at Matt’s insistence. But in this new role, Damian has disappointed. Matt wants to know why. The conversation starts well. Demonstrating confidence and clarity, Matt lays out his concerns and asks Damian to account for his poor performance.

Damian tries to explain, but his answers aren’t satisfactory. Matt pushes. Damian breaks down. He’s going through a divorce and his father is terminally ill. Note that Damian hasn’t defaulted to a sob story to explain away his performance – he’s genuinely struggling. But – at exactly the point where he should have stopped to empathize with Damian – Matt brings the conversation back to Damian’s job and how he can improve. In doing so, he misses an opportunity to do something more powerful than simply achieving his conversational objective – to demonstrate compassion.

So, why is compassion so important?

As a rule, people want to work with, and for, compassionate people. No one wants a boss who doesn’t care that their Grandma just died or a colleague who only grumbles about the extra workload when someone on their team breaks a leg. Demonstrating empathy and compassion for others helps establish goodwill and rapport – two things that go a long way toward smoothing out potentially difficult workplace interactions.

What’s more, demonstrating compassion can often turn an adversarial conversation into an opportunity. Let’s say a colleague mistakenly accuses you of leaving some key info out of a report, and you don’t like his agitated manner. You’re tempted to say something snarky like, “If you read the report properly you might see that the numbers are right there.” But, you choose not to escalate and practice compassion instead. You say, “I’m certain I did include those numbers – the index shows they’re on page 35. I know how easy it is to miss these things when you’re under pressure.” Now you’ve corrected your colleague’s mistake and signaled you know he’s working hard in a stressful situation. You had to put your ego aside – after all, you weren’t at fault here – but you’ve effectively defused a difficult discussion.

Some people are naturally skilled at practicing compassion. Don’t worry if that’s not you! The deeper your connection is with someone, the easier it is to show compassion toward them. So work on your connections with your colleagues. Try and find shared interests – they’re a great foundation for building professional relationships. Put in time getting to know them as individuals. But remember, you can’t build rapport instantly. All that chit-chat in the shared kitchen and small talk before Zoom meetings is an investment in your workplace connections. And watch your nonverbal communication as well. Expressing empathy while also leaning away or failing to make eye contact will only make you come off as insincere – in which case, you’d be better off keeping your mouth shut!

Curiosity is a virtue.

Getting in touch with your inner child can pay dividends when it comes to workplace communication. Before you get too excited, We’re not suggesting finger-painting sessions instead of weekly stand-ups or mandatory afternoon naps. But we are suggesting you tap into a childlike sense of inquisitiveness next time you face a difficult conversation.

Kids are full of questions – Why is the sky blue? Why can’t I eat chocolate for dinner? As adults, we’re less likely to ask questions than to form judgments. And more times than not, our judgments are likely to be wrong, or at least only partially right. To get the full picture, you need to get curious, which is our fourth principle.

Asking lots of questions not only helps you get a better handle on the issue you’re discussing, it signals to others that you welcome their input and value their opinions. Questions like, Why do you think this happened? And, What do you think our next steps should be? invite your partner to collaborate on achieving a constructive outcome from your discussion.

Conversations that shut down before you achieve your objective can be frustrating. So, curiosity is your friend, here! When you sense someone is trying to close down a conversational topic, try asking an open-ended question, the kind of question that can’t be answered with a simple yes or no. These questions can reignite dialogue and allow you to steer the conversation back to where you want it.

But, beware of too many conversational tangents. When a dialogue wanders off-topic, that can be because you’re thinking creatively and considering new angles. But, there are times you need to stay on topic and focus on delivering a performance review rather than musing over your favorite ice-cream flavors. There’s nothing wrong with a firm but polite statement along the lines of, “Well, back to the topic at hand – let’s take a look at those conversion metrics.”

You can win through compromise.

Conversation isn’t a competitive sport – in order to “win” what you want out of a dialogue, your partner doesn’t necessarily have to lose. When you meet each other halfway, everyone can walk away from a conversation feeling like they’ve won. Which brings us to our fifth principle, compromise.

Here’s how to have win-win discussions:

Keep things respectful. You might be making a straightforward request for time off, or you might be grappling with a big-picture issue on which you and your teammate can’t see eye to eye. No matter how simple or complex the conversation, you’ll derail it the moment you disrespect the other person. The perceived disrespect will take precedence over the topic at hand, whether they show it or not.

If you know you’re about to initiate a tough conversation and you’re anticipating some pushback, put in some work prediscussion. Clarify why you’re talking and keep that at the top of your mind during the discussion. If your dialogue drifts away from the why, pull it back. And if you’re making a request, work ahead of time to make sure you articulate it as clearly as possible. Don’t just ask your boss for “more responsibility” – say exactly which tasks you’re interested in taking on and suggest a timeframe for doing so.

In the middle of negotiations, it can be easy to forget your objective and focus instead on trying to force the other person to agree with you on every point. Remember, you don’t need to agree with each other on everything in order to reach a satisfactory result. You might think a client is underpaying you, while your colleague might think they’re a bad fit for your brand – competing rationales shouldn’t stop you both from deciding to drop them as a customer.

Difficult discussions and complex negotiations take a lot out of everyone involved. Even if the other person is saying things you don’t want to hear, make it clear you value their involvement. Thank them for their feedback and opinions. Don’t interrupt while they’re talking. Avoid accusatory language and prioritize I-centric statements – so, “I feel overwhelmed by my workload” rather than “You’ve offloaded way too much work onto me.” If you really feel like you’re hitting a wall, don’t be afraid to take a break. Set a time to pick up the conversation at a later date.

Build credibility to win better communication outcomes

As you work your way up the corporate ladder, there are a few things you can expect to automatically accrue along the way: more money, more status, and a more impressive job title. But there’s one quality that won’t automatically accrue no matter how close you get to the C-suite – and it also happens to be a prerequisite for professional success. I’m talking about our sixth principle: credibility. You can be an intern, yet still inspire trust and confidence in others. And you can be a CEO, yet still struggle to bring others on board with your vision.

Luckily, credibility is a quality that you can cultivate. Here’s how:

This may sound obvious but make sure you know what you’re talking about. Learn about the field you’re working in – and remember, developments in your area will continue to take place long after you’ve received your qualifications. Stay on top of current research and trends. The same principle applies to meetings and presentations. If you’re pitching a client, make sure you’ve researched their business model thoroughly. If you’re attending a budget meeting, have the latest figures on hand.

Next, aim for consistency. Acing a presentation or dazzling a client once won’t win you credibility points. But making a habit of performing your work to a high standard will. So will consistently prioritizing your team’s success above your own, responding promptly to requests and queries, and completing projects on deadline. When people know they can count on you, that’s when they see you as credible.

Finally, own your mistakes. You can be knowledgeable, skilled, and a consistent high performer and still make mistakes. That’s okay! But the moment you deflect blame for your failures onto someone or something else, all that credibility you’ve worked so long to build up evaporates. If you make a mistake – and you will – take full responsibility for it. What’s more, share your learnings. Say something like, “I rushed those proofs through without seeking input from the graphics department – I know now how important their input is at this stage and I won’t do it again.”

So, how does credibility come into communication specifically, you might ask? It’s simple. If you demonstrate credibility in what you do, during conversations your colleagues will trust in what you say. Do you want to push an employee to take on a new role? Recommend a left-field new hire to the hiring manager? Implement a new high-risk, high-reward marketing strategy? If your partner thinks you can walk the walk as well as talk the talk – that is, if they trust you – then you’re much more likely to get a positive response.

Develop the courage to initiate tough conversations – it’s worth your while.

Here’s the honest truth: sometimes workplace conversations are downright unpleasant. You can clarify your objectives beforehand, ask the other person all the right questions, compromise adeptly, and reach a mutually satisfactory outcome – and still find every second of the discussion deeply uncomfortable. What’s more, some of the high-stakes situations where you most need to advocate for yourself – like if you’re experiencing workplace harassment, for example – are the most nerve-wracking to broach with your colleagues. So, how can you muscle through tricky conversations and stand up for yourself effectively? That’s where our seventh and final principle comes in: courage.

Fear of discomfort is often what holds us back from initiating difficult but necessary discussions. Someone takes credit for our work, but we decide not to call them out on it. Someone on our team isn’t pulling their weight, but we decide not to make waves by calling it to our boss’s attention. Here’s the thing: not talking about the problem won’t make it go away. As long as the problem persists, so do our feelings of discomfort and dissatisfaction. Moreover, if you consistently fail to assert yourself, your colleagues may take advantage of that fact. If you don’t push back when others pawn their work off on you, odds are they’ll continue to overload you with work.

Still on the fence about whether to start a particularly difficult conversation? Ask yourself these questions: If I don’t do something about this now, will I regret it later? What’s stopping me from initiating this discussion? Is it a valid reason for not speaking out? What’s the worst thing that could happen if I do say something? What’s the worst thing that could happen if I don’t say something?

Let’s say you’re ready to start a difficult dialogue, but you’re still feeling nervous. That’s okay. Some people are born with courage. The rest of us can practice it. Unless the issue at hand is time-sensitive, it can be helpful to build your courage by doing a dry run. Choose a low-risk conversation. Perhaps a colleague takes too long to answer your emails and you want to confront them about it. Write a short script, refine it, then run through it a few times before you embark on the conversation itself.

Not all these low-risk conversations will go smoothly. Some may be total failures. And that’s fine! Remember the words of entrepreneur Alan Weiss, “If you’re not failing, you’re not trying!” The idea here is to build the courage and confidence you need to stand up for yourself where it really counts.

Final Summary

The most important thing to take away from this is this:

The only thing worse than having difficult workplace discussions is not having difficult workplace discussions! Draw on the key principles of confidence, clarity, compassion, compromise, curiosity, credibility, and courage to communicate problems and resolve them successfully.

And here’s some actionable advice to get started: Don’t be blindsided by difficult conversations.

There are a few surefire signs that your boss is about to sit you down for a difficult discussion. They no longer seek out your opinion. Previously long conversations are now terminated after a minute or two. They avoid returning your calls or responding to your emails. If you’ve spotted one, or more, of these signs – act! Brush up on the seven principles of effective workplace communication and get ready to make your case.

About the author

Roberta Chinsky Matuson is a globally known thought leader who helps leaders achieve dramatic improvements in employee engagement, retention, productivity and profitability. Based in Brookline, Massachusetts, she is the CEO and founder of Matuson Consulting, where she works with Fortune 500 companies and mid-size, emerging companies to create teams that achieve extraordinary results. She is known globally as “The Talent Maximizer®.” She is a seasoned speaker and the author of five books and blogs for Fast Company, Glassdoor, Forbes, and Thrive Global. She is frequently cited in national media including The New York Times, The Wall Street Journal, Chicago Tribune,, and NPR.

Table of Contents

About the Author xi
Acknowledgments xiii

Introduction: The Seven Principles for Managing Difficult Conversations 1


Confidence: Trusting Yourself and the Other Party 21
The Land of Should Have, Could Have, Would Have 22
New Math: Why Things Aren’t Adding Up 24
The Problem with Having Conversations in Your Head 24
Trust Me: Why You Need to Trust Yourself 26
Signs You Don’t Trust Yourself (and What to Do about It) 33
Using Confidence to Navigate Difficult Conversations 36
Trust: The Cornerstone of All Relationships 39


Clarity: Making Your Point Clearly and Listening with an Open Mind 45
Let’s Be Clear Here 45
Establishing the Right Objective 48
The Four Factors to Consider When Preparing for a Difficult Conversation 53
Planning for the Worst and Expecting the Best 58
Assessing Your Readiness to Proceed 62
Handling Difficult Conversations Remotely 63
Keeping Your Cool When Things Heat Up 65
Can You Hear Me Now? 68
Listen, Don’t Assume 71
Why the Need to Be Right Can Bring about the Wrong Results 73


Compassion: Be Empathetic and Understanding 79
The Need for Compassion and Empathy 80
Putting Yourself in Someone Else’s Shoes 82
The Art of Building Rapport 85
Nonverbal Communication and Body Language 88
Slow Down to Speed Up the Conversation 91
Being Present 93
Hyper-empathy: Is There Such a Thing as Caring Too Much? 96


Curiosity: Asking Questions Rather Than Shutting Down 101
The Power of Inquisitiveness 102
Tapping into Your Inner Child 103
Why Curiosity Didn’t Kill the Cat 106
Stop Stifling Curiosity in Others 107
The Impact Curiosity Has on Conversations 112
Regaining Control When a Conversation Derails 116


Compromise: Earn Respect by Respecting Others 121
Achieving Mutual Respect 121
Finding Common Ground 126
You Cut, I’ll Choose 128
You Want Me to Do What? Using Influence To Get What You Need 131
Stepping Back to Move Forward 134
Dialing Down Highly Charged Conversations 136
Caution: Dead End Ahead 138
Knowing When to Stop Talking 140


Credibility: Recognizing Your Word Is Only as Good as Your Actions 145
What Credibility Is 145
What Credibility Is Not 151
The Power of Perception 153
Reading the Room: Is Your Credibility on the Decline? 155
Changing Perception: Can It Be Done? 160
Establishing Credibility with Remote Employees 162


Courage: Navigating the Obstacles 167
The Courage of Your Talent 167
Getting Comfortable with Discomfort 171
Office Politics: Navigating Highly Charged Conversations 174
Choosing Your Battles Wisely 180
Taking Your Power Back: Having the Courage to Stand Up and Advocate for Yourself 182


Bringing It All Together 187
Putting the Pieces Together 187
Out of This World Difficult Work Conversations 191
What to Do Next after an Awkward Conversation 194
Creating a Drama-Free Work Environment 197
Staying on Track 202
Keep Talking 204
Index 209

List of Tables
Table 2.1  Social Styles
Table 2.2  Conversation Readiness Assessment
Table 6.1  Credibility Assessment


Are you avoiding an uncomfortable conversation at work? If you’re an executive or a team leader, strengthening your organization’s ability to have difficult conversations is necessary and worth the discomfort.

The key to successful dialogue starts and ends with changing the conversation. Recognizing that it takes two people to engage in meaningful outcomes, Can We Talk? outlines what each contributor needs to do to achieve the best possible result. Using examples from everyday work situations, this book offers guidance on how to create the right conditions for a meaningful discussion. The author identifies the seven key principles that enable both parties to gain a deeper understanding of what the other person may be thinking and will help establish their point of view more clearly: confidence, clarity, compassion, curiosity, compromise, credibility, courage.

Can We Talk? includes examples and advice from those who have been there and thrived, as well as lessons learned from conversation failures and example scripts of productive conversations. Readers will learn how to prepare, start and manage the potentially challenging exchange of words that typically occur at work, and come away with an understanding that for any conversation to take place, both parties must be engaged.

Video and Podcast


“Who doesn’t cringe when they hear the words, Can We Talk? And yet the truth is, those conversations we’d prefer to avoid are essential. I love how Roberta clearly guides us through the process of finding our voice so we can say what most needs to be said. This book is invaluable for leaders or for anyone who works.” – Sally Helgesen, author, How Women Rise, The Female Vision, and The Web of Inclusion

“One of our six Core Values at Saxbys is “Care Personally and Communicate Openly” – simply because we know how critical, yet difficult human communication can be. Roberta’s book does a fantastic job identifying both the importance of actually having difficult conversations while also providing the guidance to have them effectively.” – Nick Bayer, Founder and CEO of Saxbys

“If you want to keep your employees, then you’ve got to get them talking. Roberta Matuson’s book will do just that. With memorable stories and examples (including the author’s own first-hand experiences of difficult conversations quickly going south) Can We Talk?provides readers with tools to actively build better relationships up, down and across the organization.” – Dr. Bev Kaye, co-author Love ‘Em or Lose ‘Em and Up is Not the Only Way

“Where was Can We Talk? when I needed it most? All those well-meaning but frequently awkward conversations that could have been better for all if I had read this. Roberta proves once again that she is the subject matter expert.” – Julie Kahn, President of Regan Communications

“Roberta’s Can We Talk? gives managers and individual contributors a comprehensive toolbox on how to handle difficult conversations in a productive and constructive manner, and elevate performance and employee engagement. It’s a must-read for anyone who wants to be successful in their career.” – Polina Ware, PhD, Global R&D and TS&D Director, Rogers Corporation

“If you’ve been holding back from saying what needs to be said at work, Can We Talk? is the book for you. No topic is off the table here. This is a must-read for business owners, leaders and employees looking to find their voice and power up their communication skills.” – Dorie Clark, author of Reinventing You and executive education faculty, Duke University Fuqua School of Business

“Roberta has done it again! I find myself wishing I’d had this book when I was a new professional. Roberta’s practical approach and no-nonsense language make this the playbook for improving employee performance. Her planned approach is sure to make giving tough messages a lot easier, and that is the first step to ensuring your employees are exceeding your expectations.” – Jay Hargis, First Vice President, Learning and Development Officer, Apple Bank

“Everything you need to know about communication and relationship building at work is right here! Solid insights and practical advice from one of the world’s leading authorities on executive coaching and employee engagement.” – Marshall Goldsmith is the New York Times #1 bestselling author of Triggers, Mojo, and What Got You Here Won’t Get You There.

“Can We Talk? is a fast-pass framework to help you move past one-sided conversations, better your career and achieve a more humanistic workplace.” – Marlene Chism, Author of From Conflict to Courage: How to stop avoiding and start leading

“Can We Talk? is essential reading for anyone looking to improve their work relationships and build trust through more effective communication. Can We Talk? is one of those books that you’ll refer to time and time again.” – Jenn Mann, Chief Human Resources Officer, SAS

“There’s nothing more important in business than the ability to communicate effectively with those above, below and across from you. In Can We Talk?, Roberta provides readers with a game-changing framework to help them safely navigate through any tough work conversation, while successfully building strong relationships along the way.” – Laura Huang, international bestselling author of EDGE: Turning Adversity into Advantage, and professor at Harvard Business School

Read an Excerpt/PDF Preview

Download the free bonus chapter which is not available in the book

About the author

For more than twenty-five years, Roberta Matuson, president of Matuson Consulting, has helped leaders in highly regarded companies, including General Motors, Takeda, and Microsoft, and small- to medium-size businesses, achieve dramatic growth and market leadership through the maximization of talent.

She’s the author of five books, including Evergreen Talent: How to Seed, Cultivate, and Grow a Sustainable Workforce and the international bestseller Suddenly in Charge: Managing Up, Managing Down, Succeeding All Around, a Washington Post Top 5 Business Book for Leaders.

Roberta is also a LinkedIn Top Voice in Workplace and Leadership and the author of seven LinkedIn Learning courses. Her courses can also be found on Skillsoft, MentorBox, and Knowable.

Roberta is one of a handful of people who have appeared as a guest of Bill O’Reilly on Fox’s O’Reilly Factor and who left the show unscathed.

You can reach out directly to Roberta Matuson at [email protected]. Connect with her on LinkedIn and follow her on Twitter @matuson.


This book would not have been possible without the support of my agent, Linda Konner, who worked her magic to secure a book deal on my behalf during a pandemic. I’m incredibly grateful for your tenacity.

Thank you to my editors, Kathe Sweeny and Heather Wood, who helped shape this book, and the staff at Kogan Page. Your suggestions and encouragement along the way were greatly appreciated.

I’d also like to acknowledge my mentor, Alan Weiss, whose guidance has served me well over the years. Your constant push for me to think bigger has resulted in the completion of book number six.

Lastly, a big thank you also goes out to my colleagues, Hugh Blane, Gail Bower, Graham Binks, Noah Fleming, and Lisa Larter. I listen way more than you may think and am grateful for your advice and friendship.


The Seven Principles for Managing Difficult Conversations

How Did We Get Here?

The year was 1993, and the day started like any other. I commuted into downtown Boston and rode the elevator up to my office, ready to face a new workweek. Little did I know, that on this day my life was about to change. Before going into more detail here, let me set the stage for what I thought for sure was a dream—well, more like a nightmare.

Back in the early ’90s, I was stuck in a job that I didn’t love and worked for a boss who made the fictional character of mean boss Miranda Priestly, played by Meryl Steep in the movie The Devil Wears Prada, look like an angel. In fact, I’m reasonably sure that Streep spent a few days with my boss getting her moves down.

Admittedly, my relationship with my manager got off to a rocky start. You see, I was hired by her predecessor who left shortly after I started. At that time, I didn’t give much thought to the changing of the guard, as bosses are a lot like trains. One pulls into the station, sits for a while, departs, and another one arrives soon thereafter.

From day one, my new boss and I didn’t see eye-to-eye on much, making it extremely hard to be successful in my role. She wasn’t the type to mince words. She rarely said anything. She didn’t need to, as you could usually tell what she was thinking by looking at her frowning face.

I spent a year of my life doing somersaults trying to please her. I honestly thought I was making progress until that fateful day when my boss stopped by my office and said those three words no one wants to hear. “Can we talk?” followed by “Come see me in my office.”

My boss then exited as quickly as she had arrived, which was a good thing, as I didn’t want her to hear my heart sinking to the bottom of my stomach. I did my best to pull myself together before taking a seat in her office.

Here’s how that “conversation” went.

Boss: You’re not meeting my expectations (followed by a brief pause). Although, I’m not sure I ever told you what they are.

Me: (looking dumbfounded): Okay.

While all the while, I was thinking, “What the heck?”

She then went on to share what her expectations were, as well as everything I was doing wrong. I sat in shock and kept thinking, “How could I possibly know what her expectations were if she never told me? She went to Harvard. Maybe they taught mind reading there. I attended Northeastern University, where Mind Reading 101 was not a college class offered.”

I may have been confused by what my boss had just said. However, I was very clear about one thing. This was the beginning of the end of my time with the organization.

Our time together could have ended very differently, had my boss read an advance copy of Can We Talk? Seven Principles for Managing Difficult Conversations at Work. But then again, I might never have written this book had she done so.

I wish I could tell you that this awkward conversation was the only one I experienced throughout my career. Unfortunately, there were plenty more, which I’ll be sharing throughout this book.

Crazy encounters, like the one I described, are still taking place in workplaces across the globe and even in outer space (more about that later.) I’m on a mission to make sure what happened to me doesn’t happen to you or anyone else you know.

Too many work conversations are one-sided. They’re more like a monologue than a dialogue. This has to change if we are ever going to get to a place where we can achieve better outcomes and a more humane workplace.

I’m writing this book because I don’t want others to go through what I experienced. I was young (well, maybe not that young) and didn’t realize that I was giving my power away by sitting there and failing to respond. Power is a funny thing. Once you give it away, it’s hard to get back.

Throughout this book, I’ll encourage those of you on the receiving end of a difficult work conversation to embrace what may come your way. If you do so and participate from a place of good intent, you’ll experience rapid personal growth. Some of the most challenging experiences often result in the most amazing transformations, which is partially what this book is about.

We have a lot of work ahead of us to get to the place where we can regularly have meaningful and effective conversations in the workplace. Consider the framework that I’ll be outlining in this book to be your fast-pass. When you use what you learn here, you’ll be able to move to the front of the line, which is reserved for effective leaders and happy employees.

I’ve put together this framework to help you improve your relationships with your boss, peers, and teammates. Through coaching and consulting with hundreds of clients over the years, I have developed and fine-tuned a model that consists of seven principles to help you hold difficult conversations.

My clients are probably much like you. They want to feel good about their work, and they want others to feel the same way. It’s not an easy undertaking to achieve, but certainly doable. Here are the seven principles that will enable you to achieve similar results to some of my best clients.

The Seven Principles


The first principle is confidence. It takes confidence to present your side of the conversation in a way that will have the other person engaged enough in the conversation to be open to hearing your thoughts on the matter at hand. I’ll walk you through some exercises you can use to build confidence and share stories on how confidence helped others successfully conduct some pretty hair-raising conversations.

You’ll learn ways to trust yourself, so you can confidently handle any challenging situation that may come your way. We’ll explore the impact one-sided conversations have on business relationships and your career and what you can do as an employee to ensure your voice is heard. We’ll also examine why you need to take the time to build a trusting relationship with someone, before jumping right in and saying what’s on your mind, and what happens to those who don’t.


The second principle is clarity. If you’ve ever had a conversation with someone and left thinking, “What was their point?” then you know firsthand the importance of getting clear on what you hope to achieve before saying something. We’ll also explore why it’s important to listen with an open mind, so you can come to terms with an outcome that works for both parties.


Next up is compassion. All too often, we approach conversations with little empathy. We don’t take the time to understand what’s really going on with the other person, whether an employee, a boss, or a coworker. We simply charge ahead and are then completely taken off guard when the conversation doesn’t go as planned. We’ll look at ways to gain a better understanding of where someone is coming from so that you can adjust your stand accordingly.


Principle four is curiosity. It’s easy to jump to negative conclusions when someone says, “Can we talk?” Most people immediately get defensive when hearing these words. This chapter will explain how to use curiosity to move conversations from fear and apprehension to exploration, so both parties end up in a better place than where they started. I’ll be providing you with prompts to help you launch the conversation on a positive note, as well as a list of open-ended questions to help you gain a better understanding of the situation at hand.


Principle five is compromise. Let’s face it. Most challenging conversations end in compromise, so why not start there? Think about all the time and energy you’ll be saving when you enter the discussion with a plan in place that both parties can be moderately happy with. The focus here will be on asking for what you want and settling for getting most of what you asked for.


Principle six is credibility. If you want people to listen to you, then you need to give them a good reason to do so. After all, your word is only as good as your actions. Saying things like, “You need to listen to me because I’m the boss” or “I know what I’m doing,” when clearly you don’t, can do more harm than good. Readers will learn how to take a step back and work on building credibility before powering forward.


We’ll tie up the framework with principle seven, courage, and successfully navigating power dynamics in the workplace. Office politics is perhaps the most challenging situation employees face. This topic is not for the faint of heart, which is why I’ve saved this topic for the end. My hope is that having read this book, you’ll have the skills and tools required to safely navigate through the political minefields that are part of every organization.

It takes courage to go into the “lion’s den,” and have a discussion with someone who perhaps sees things very differently than you or holds more power than you do in the organization. In this chapter, we’ll look at some of the biggest obstacles that get in the way of having a productive conversation and what you can do to overcome these. I’ll be sharing how others overcame some pretty challenging scenarios and how you can do the same.

As you move through this book, I encourage you to take the time to work through the exercises and incorporate what you’re learning into your everyday conversations. Naturally, you may want to modify some of the scripts offered here to best match your personal communication style.

Give yourself permission to take some risks and try a few of the different approaches that you might have easily dismissed in the past. Who knows, you may decide that you (and your team members or your boss) like the newer version of yourself more than the person you were before reading this book.

Let’s get the conversation rolling.

We’re Heading for a Crash

Have you ever witnessed an accident about to happen while sitting there, unable to do anything about it? I have. In fact, it was my car that was hit.

Years ago, when I lived in Houston, Texas, I was waiting at a traffic light behind another car when I saw a vehicle coming toward me. I looked around to see if I could get out of the way, but there was nowhere for me to go. I braced myself as the driver of the car sideswiped my vehicle. I was lucky. I wasn’t hurt, and some witnesses corroborated my story. It turns out the driver of the other vehicle was driving under the influence. I later learned this wasn’t her first time doing so. One would hope that after her first DUI, her behavior would have changed. Unfortunately, this was not the case.

Sometimes it takes a while for people to get to a place where they understand their approach is harmful to others and may eventually end in their own demise. Let’s hope this driver got the help she needed before doing any more harm.

It’s been my experience that most people don’t wake up in the morning thinking, “How can I make someone’s day crappy?” Nor do they approach conversations with the goal of making someone weep. Yet, this sort of thing happens on a daily basis. And then, of course, there are the unsaid conversations. You know the ones that I’m talking about, as some of you probably have some of these conversations swirling around in your head. They go like this: “I’m so frustrated with Bill’s work performance. I’m not going to assign him any more plum projects.” Or, “If Donna makes one more wrong move, she’s out of here!”

The thing about unsaid conversations is that they can create havoc without the other person even knowing there’s a storm brewing. To me, unsaid conversations are the most dangerous. They remind me of the very small no-see-um insects. Pain can be inflicted by these insects before you are even aware of their existence, which means as the receiver (or the intended receiver), there’s nothing you can do to protect yourself.

The Avoidance Epidemic: Why This Needs to Change—Stat!

The avoidance of difficult conversations has grown into a full-blown epidemic. In terms of personal communication, people are getting super good at avoiding sticky conversations, especially those related to politics. This is probably a good thing, given that no one ever comes out a winner in these sorts of conversations.

Most of us know at least one person (or we may be that person) who was fired and said, “I had no idea this was coming.” Their response to being fired isn’t about going on the defense, as a result of being let go. It’s simply their truth.

There are enough stories of folks being fired with little to no warning, no feedback, and no help or support from their bosses to improve what was lacking to fill at least one mystery book—perhaps even a trilogy. That’s the real crime here.

According to workplace resource startup Bravely, a whopping 70 percent of employees are avoiding awkward conversations with their boss, colleagues, and direct reports.1 The fact that so many people are avoiding conversations is having a dramatic impact on the health and well-being of organizations and their employees. Here’s how:

New research from Joseph Grenny and David Maxfield, authors of Crucial Conversations, conducted in December of 2016 found that every single conversation failure costs an organization $7,500 and more than seven workdays.2

An August 15, 2017, study, released by leadership development and conversation experts at Fierce, Inc. found that 53 percent of employees are handling “toxic” situations by ignoring them. By doing so, they are allowing toxic employees to continue to wreak havoc on the workplace.3

A July 2008 report published by CCP Human Capital, found that employees spend 2.8 hours per week dealing with difficult situations—amounting to approximately $359 billion in paid hours.4

As a result, employee engagement and organizational trust are declining, while workplace stress is rising. We have to take action and slow this epidemic down, or we may never recover from the damage that is being done.

We have to start somewhere. Let’s start with one conversation at a time.

The Conversation Equation

I’ve been a party to a number of workplace conversations, and here’s what I’ve observed: It takes two people to have a conversation, although you wouldn’t know it when hearing how most challenging workplace conversations go.

Here’s what a typical workplace conversation sounds like:

Boss: Can we talk?

Employee: Okay.

Boss: You’re not meeting my expectations.

Employee (looking bewildered): Uh, Okay.

Boss: I’m putting you on a performance improvement plan. You’ve got ninety days to turn things around.

Employee: Okay.

The boss leaves the conversation, thinking, “Hey, that went pretty well!” The employee leaves thinking, “What the heck was that all about?” (Okay, more than likely, the employee is thinking something else, which I can’t very well include here.)

This could have been a very productive conversation and an opportunity for both parties to hit the reset button. In this case, the boss should use a technique I call the “success shuffle.” The success shuffle is similar to the game of shuffleboard; only instead of taking turns moving a disk, each participant receives a turn moving the conversation forward.

The leader needs to take the initiative. “Can we talk?” followed by “You’re not meeting my expectations” is like sending the first two disks flying off the board.

You need to start with a precision shot. For example, starting by highlighting something positive the employee has done recently is a better way to start the conversation off right. The rules of shuffleboard and the success shuffle are similar. Players alternately take turns, which is a good reminder for those who tend to dominate conversations. In the success shuffle, you don’t get to speak until the other person responds, even if that means you sit in silence.

At first, this may feel awkward. You may be tempted to jump in and rescue the other person from the silence. Don’t do it! Remember, this conversation may have been going on in your head for weeks, while in all likelihood, this is the first time the other person has heard what you’re saying. Give the person you’re speaking with time to process what’s been said and to respond. Resist the temptation to formulate your next move until you see where the shot has landed.

Here’s where the similarities to the game of shuffleboard and this process end. In the game of shuffleboard, players sling shots in an effort to knock opponents off their game. In life, this kind of behavior is known as one-upmanship. For one person to win, the other person has to lose. This is not at all what we’re going for here. What we need here is a win-win.

Both the game of shuffleboard, as well as the success shuffle game of language can be improved significantly with patience and practice, which is why I suggest you immediately put to use the skills you’re learning here. I’ve had many complicated work conversations over the years. I can say with 100 percent certainty that once you master the skills needed to conduct effective conversations, your life will change in ways you cannot even imagine.

Five Signs a Tough Conversation May Be Coming Your Way

People say all the time, “I would never have imagined…” or “I never saw this coming.” Yet, in hindsight, the signs were all there. They just didn’t want to see them.

I can relate. I mentioned earlier that I thought my relationship with my boss had gotten better. I wanted to believe this was the case so much that I ignored some of the telltale signs that would have indicated we were about to have one of those kinds of conversations. Had I been more aware, I could have been prepared, and the outcome may have been different. Or, at a minimum, the scarring I experienced from that day may never have occurred.

Sign Number One: You’ve Gone from Right-Hand Man to No Man’s Land

You used to be your boss’s right-hand person—the first one she turned to for help. She’d say things like, “I don’t know what I’d do without you” or “Why can’t everyone on the team have your work ethic?” Now, you’re invisible. Your offers to help go in one ear and out the other. Nowadays, you wonder if she’d even notice if you stopped coming in for work.

A similar occurrence happened to a client of mine. “In the past, one of the biggest signs I missed that a tough conversation was coming was not noticing how irritated my boss was after I contradicted her in a customer service meeting. After that meeting, everything seemed to be normal except she hardly asked for my opinion anymore regarding strategic decisions, amongst other things. A few months later, she asked me if we could talk, left me waiting in her office for over ten minutes, and told me I was fired because I was too argumentative. I was absolutely blown away!”

Sign Number Two: Twitter-sized Conversations with Your Manager Are the New Norm

In the past, conversations with your boss often carried on for hours. The two of you would go back and forth with one another, brainstorming the next great idea. Now, you’re lucky to get an email response back that is more than 280 characters when asking a question.

Sign Number Three: Your Boss Avoids You at All Costs

This one may seem like a no brainer, yet most people haven’t a clue that they’re actually the reason the boss is avoiding them. Instead, they convince themselves that their manager is overwhelmed and doesn’t have time to exchange pleasantries. Or that their boss is not one of those touchy feely kinds of leaders you read about in articles on great leadership.

Before you dismiss your boss’s behavior as being their problem and not yours, consider the following:

Can you pinpoint a specific moment in time when your boss went from being friendly to being standoffish? Perhaps you failed to deliver your best work on a high-profile project. Or a family matter prevented you from keeping a commitment you made to your boss.

Did you receive a rating on your latest performance review that was lower than expected with little explanation as to why this was so? You chose not to probe further, for fear your boss might say something you were not ready to hear.

Have you been complaining a lot more lately rather than being more helpful to your manager? You didn’t mean for this to happen. However, it appears you’ve made a common error of mistaking your boss for a friend.

Sign Number Four: You Can Do No Right

Your work is being sent back to you with loads of corrections and with little explanation. You do what most employees do. You accept the revisions and avoid asking how you might have gone off track. This pattern continues until the boss reaches a point where they no longer trust you to do the work you’ve been assigned.

You quickly conclude that your boss is nit-picky. You’re frustrated, but most likely not as frustrated as your boss. Your boss asks to schedule a meeting with you. You put the date on your calendar, with little thought as to why you’ve been summoned to the boss’s office.

Sign Number Five: Your Boss No Longer Returns Your Calls, Texts, or Emails

You’ve tried reaching out several times to speak to your boss about an important matter. Your calls go to voicemail. You try following up with an email. Again, no response. As a last resort, you text. Still no reply. You ask your teammates if they’ve had a hard time reaching your boss. They find your question puzzling, as they’ve noticed no difference in response time from your leader.

Your boss may be formulating a plan to address a situation with you. He or she is not looking forward to the conversation, so they do what many people in this situation do. They avoid any communication until they’ve mustered up the courage to say what’s on their mind.

Don’t make the fatal mistake most people make. No news (or, in this case, no response) is not good news. As soon as you realize you’re being ghosted, make a plan to be seen by your manager. Do this even if you suspect this may be your last meeting with this person. It’s better to know exactly where you stand than it is to remain in a state of flux.

Keep in mind that it’s not uncommon for managers who are dis­satisfied with staff members to avoid directly addressing issues that are bothering them. They will often dodge, deflect, procrastinate, and pray the whole problem will go away. Remember this the next time you sense a change in the way your boss is communicating with you.

Rather than sticking your head in the sand (right beside your boss), it’s best to take steps to fix things before the situation gets to the point where your relationship is beyond repair. We’ll go into detail on exactly how to do this throughout this book.

Creating the Right Conditions: Set the Stage for Successful Conversations

Preparation: Ready, Set, Go

The focus when planning for a difficult conversation should be on how to create something from this talk. Think about how to build an outcome that not only gets you through this situation, but also has you looking forward to the follow-up conversation that will bring you one step closer to what you’re trying to achieve. With this in mind, think about where it’s best to hold this exchange and when to address certain situations.

Location, Location, Location

Where you discuss a highly charged matter could very well determine how the other person reacts, and could directly impact the outcome you hope to achieve.

I was a newly hired department head who was involved in what began as a casual discussion with a subordinate hired by my predecessor. This employee told me they thought they had been hired to replace the former leader and wanted to know about some of the promises verbally made regarding the future. Specifically, pay, incentives, and future job movement were on hand.

At first, I was taken aback by the boldness and directness of the conversation. I asked questions to understand better how this employee perceived the future unfolding. The employee stated that the department’s former head informed them that they would take over the department when he retired and would be entitled to executive benefits for longevity and compensation as an executive, which went with the new title. I asked for more detail into the executive benefit and salary piece they were alluding to, and the employee said that they would think that it would be similar to what I had received.

Because of this being an HR department and the nature of the jobs, we both had access to personal and confidential information, so I assumed that they knew the terms of my compensation package. I made the mistake of offering up not the specific amounts of my package but the general details of what was offered to me to stay as an executive of the company until retirement. Upon revealing this general information, the employee asked for a written document stating they would receive those same terms in the future. I declined and went so far as to say that they would not be getting the job because I now had the job, and I wasn’t planning on leaving the position, nor would I be anointing a predecessor this early in my tenure. I asked that the employee drop the conversation as I realized I had said too much, and they had gotten so little in the way of answers. This left both the employee and myself in a tumultuous situation for future work engagement.

Looking back on the conversation and then moving forward, I knew I should not have entered into the conversation as casually as it started. I should have shut down the conversation and allowed for a more structured dialogue in a more professional environment than walking outside to the vehicles after the end of a long workday.

By doing so, I would have had time to investigate what may or may not have been said to this employee, prepared a more thoughtful response, and kept the focus on the employee—which is where it belonged.

A. J. Jenness SHRM-CP

VP/Director of HR, Admiral/Fremont Beverage

Like A. J., I learned firsthand how location can directly impact the outcome of a conversation. Early in my career, one of my managers decided to address a situation that was weighing heavily on his mind. He did so in the office elevator, which was fine when we were the only people riding up to our floor. However, what began as a productive conversation quickly fell apart as the elevator kept stopping and others got on.

There is a reason that hospital elevators have signs reminding staff not to discuss patient information in the elevator. Some conversations are not meant to be heard by others. You can’t help but listen in on a juicy conversation when it’s happening less than a few feet behind you. This is why where you hold a difficult conversation is as important as what you plan on saying. Yet, few people give enough thought to this.

Today’s unique office environments can add a level of complexity in terms of where to best hold a challenging work conversation. Some people work in workplaces without walls, and a large number of employees are working virtually.

If your workspace doesn’t afford you much in terms of privacy, try reserving a conference room with blinds for your meeting. When broaching topics, such as an employee termination or the need to place a team member on a performance improvement plan, consider whether it’s best to have this conversation face-to-face with team members who work remotely.

Preparing for the Worst and Expecting the Best

I generally consider myself to be a somewhat optimistic person. However, when it comes to challenging work conversations, I’ve found that it’s best to prepare for the worst. This way, no harm is done when things go better than planned.

Consider the following:

All possible outcomes when you ask, “Can we talk?” There are only a limited number of responses that can occur when you pose this question. They are:

“Sure!” followed by “I’m so glad you brought this up.” In this scenario, you’ve just been given the green light. Keep your foot on the accelerator and steer the conversation as planned.

Tears, followed by “Why do I have a feeling something bad is going to happen?” Here’s where you’re going to need to pump the brakes, to slow things down. Diving into a conversation with someone who is completely caught off guard (whether they should be or not is irrelevant here) will not get you any closer to where you want to be. In this situation, it’s best to pause and allow the other person to regain their composure. Then assess whether it makes sense to continue the conversation or establish a time to reconvene.

“No, this isn’t a good time.” You’ve just been asked to come to a complete stop. You’re best response is something like, “Okay. Let’s take out our calendars and establish a date and time for us to speak.”

“No.” You’ve just hit a brick wall. It’s hard to argue with a boss who says this or a coworker who doesn’t want to engage. You’ll have to decide how far you’re willing to go to address this issue or if you’re best off letting things be. If one of your direct reports says this to you, then of course you can’t simply accept no for an answer. In this situation, you’ll need to turn your question into a statement and say, “Perhaps you’ve misunderstood. We need to talk.”

Staying cool as the conversation heats up. If you’re going to get to the heart of the matter, then tempers may flare. It’s during times like these where you’ll be tested to stay calm. Some people find it helpful to count to ten before responding. This allows them to catch their breath and gives them a few seconds to phrase their response in a way that won’t add more fuel to the fire. Others find active listening works well to diffuse the situation. Reframing what someone else has said, and repeating this back to them, signals to the other person they’ve been heard. They are then usually more open to what’s said next.

Focus on what you hear, rather than on how you want to respond. Often, we’re so busy thinking about how we will respond that we fail to deeply listen to what the person in front of us is saying. To help you avoid this misstep, consider asking clarifying questions, such as, “Can you say more about that?” or “Why do you feel this way?” This will help you stay engaged in the conversation. Challenge yourself to talk less during a difficult conversation and listen more. You’ll be amazed at how much better conversations go when people feel they’ve been heard.

Avoiding the stuck ketchup syndrome. Some of you may be old enough to remember the ketchup commercial where singer-songwriter Carly Simon sang the song “Anticipation” as we waited for the ketchup to pour out of the container slowly. I don’t know about you, but I was pretty convinced that the ketchup was stuck and would never flow smoothly. Much to my surprise, once the ketchup started flowing, it didn’t stop. Sometimes we have a hard time getting the juices flowing when discussing an uncomfortable situation. Yet, if we make an attempt to start, the conversation will begin to flow. Here’s the thing about conversations: Both parties usually go back and forth more than once, which allows us plenty of opportunities to recraft our message, depending on how the other person responds. The key here is to be patient and give yourself permission to have a slow start. Your success in handling these situations won’t be measured on how quickly you plow through them, but instead, on the taste you leave in people’s mouths.

Anticipating Success

Have you ever argued with someone where you continued to push your agenda, even after you won? I have and know of many others who have done this as well. We’re so focused on stating our position and proving that we’re right that we completely miss the part where the other person says, “Okay, I can see where you’re coming from. Where do we go from here?” Instead, we refer to our speaking points to ensure everything we’ve written down gets said.

Earlier I stated that it’s best to go into these types of conversations expecting the worst. However, that doesn’t mean you shouldn’t be prepared for success. With enough practice and coaching, you’ll learn how to effortlessly address these situations as part of everyday conversations with the people you work with. You’ll also learn to pick up on the cues that indicate someone has gotten what you said and is ready to move forward with you.

In the next chapter, we’ll explore the first principle for navigating difficult conversations at work, which is confidence. In my consulting and coaching practice, I have found that confidence is one area where small improvements can make a big difference in the way we present ourselves and how others see us, which is why I’m starting the conversation here.

Key Learning Points

Sometimes it takes a while for people to get to a place where they understand their approach is harmful to others and may eventually end in their own demise.

Most people don’t wake up in the morning thinking, “How can I make someone’s day crappy?” Think about this before passing judgment and taking action that you may very well regret.

The problem with unsaid conversations is that they can create havoc without the other person even knowing there’s a storm brewing. What’s left unsaid can do more damage than words that may be spoken.

Avoidance of difficult conversations has grown into a full-blown epidemic. When deciding whether to begin a challenging discussion, consider whether you want to join the outbreak or be part of the cure.

It takes two people to have a conversation, although you wouldn’t know it when hearing how most challenging workplace conversations go. When having a conversation with someone, make sure you’re not the only one doing all the talking.

As tempting as it might be to stick your head in the sand to avoid a conversation that may be coming your way, it’s best to take steps to fix things before the situation gets to the point where your relationship is beyond repair.

Preparation matters—a lot! When preparing for a deep conversation with someone, remember to give considerable thought as to where you’ll be holding this meeting, as well as the timing, as both factors can significantly influence what transpires after you are both done having your say.

Prepare for the worst and expect the best. Think about all possible outcomes (both good and bad) that may occur when you say the words, “Can we talk?” Have a response ready to go to ensure the conversation remains on track.

Don’t forget to prepare for success. Be prepared for this moment so that you don’t wind up saying more than needs to be said.


1 Understanding the conversation gap: Why employees aren’t talking, and what we can do about it, Bravely, July 2019, (archived at

2 Costly conversations: Why the way employees communicate will make or break your bottom line, VitalSmarts, 6 December 2016, (archived at

3 Toxic Employee Survey: 2017, Fierce, Inc., 15 August 2017, (archived at

4 Human capital report: Workplace conflict and how business can harness it to thrive, CCP, July 2008, (archived at



Trusting Yourself and the Other Party

A difficult conversation tends to go best when you approach the conversation feeling self-assured, which is why I’ve chosen confidence as the first principle of Can We Talk?. Throughout this chapter, we’ll be examining the connection between self-confidence and the need to trust yourself and others. I’ll be sharing signs that indicate you don’t trust yourself and will be offering up suggestions on what you can do about this. Included will be a discussion on mindset and the impact your beliefs have on your actions. I hope that your confidence in your ability to handle tough work conversations will rise as you challenge yourself to step forward and take on those conversations that you know need to happen.

Fear and self-confidence are inextricably linked, especially when it comes to having challenging conversations. Many of us are fearful that we’re going to screw up a conversation and perhaps make things worse than they already are. Our fears are often unfounded and are reinforced by that little voice we hear in our head or that little guy or gal on our shoulder telling us untruths like, “This isn’t going to go well” or “What makes you think you’re the expert?” or “This person is never going to change.” Simply put, you don’t trust yourself, or you don’t trust the person you’re speaking with, which is why so many important conversations never take place. You figure, “Why bother?” So, you don’t, which can lead to a host of other issues.

The “little voice” you’re hearing is there to protect you, even when you don’t need protection, and is caused by self-doubt. For example, you want to ask your boss for a well-deserved promotion. Yet, there’s this voice in your head saying things like, “Are you kidding me? You’re good, but you’re not that great.” Or, “Don’t you think if you were ready for a promotion your boss would have given you one already?” This voice wants to protect you from the damage that might occur to your self-esteem should you not be awarded the job. Therefore, you don’t ask for a promotion. You quickly regret your decision when your peer advances, especially if this person is now your new boss.

These voices are like little signs that point to one road and one road only—the road of self-doubt. Simply put, you don’t trust yourself, or you don’t have a trusting relationship with the person you’re about to speak with. The goal here is to eliminate (or at least significantly reduce) self-doubt. You can increase self-confidence and trust. But to do so, you have to change your mindset and be open to taking a different path. You also have to be willing to take risks. We’ll be setting a new course with our final destination being a street called trust throughout this chapter.

The Land of Should Have, Could Have, Would Have

In my work as an executive coach, clients often walk me through several different versions of the same conversation they’ve had with an employee, their boss, or a board member. First, they tell me what transpired, followed by the discussion that went on in their head. Often there is another version that many feel compelled to explain, which is what they wished they had said, and I hear many variations of: should have, could have, or would have. All of this second-guessing leads to exhaustion, followed by frustration, and often regret. Sound familiar?

Here’s a conversation that recently took place between my coaching client, whom we’ll call Don, and his boss Catherine. “My boss Catherine called me into her office the other day and raked me over the coals,” Don said. This is a case where Don’s second-guessing himself resulted in a difficult conversation going from bad to worse. I’ll also show you how this situation could have been avoided.

Catherine: I expected this report to be on my desk when I arrived on Friday morning. I had no choice but to go into the executive leadership meeting without our findings. I was embarrassed when the CEO called upon me with a question about data included in our report, and I had nothing to share with him.

Don: We never received the revenue numbers from you. Therefore, we couldn’t finish the report. You also handed us another assignment earlier in the week and instructed us to get that done. You know we’re understaffed and can’t hire anyone until you approve the requisition that’s sitting on your desk.

After some reflection, Don concluded that he had handled the situation with his boss poorly. Don went on to tell me exactly what he should have said in his boss’s office:

Don: I can certainly see why being called upon by the CEO and not having the information you needed in front of you to respond would have been embarrassing. I sincerely apologize for that. I take full responsibility for not coming to you on Wednesday when I first realized that we were still waiting on the revenue information needed to complete our report. I’ve learned a valuable lesson and can assure you it won’t happen again.

The language that Don used with his boss made a bad situation worse. His manager wasn’t looking for excuses. She was looking for an apology and assurances that she wouldn’t find herself in this predicament again.

In Don’s do-over conversation, he took complete responsibility for failing to deliver as promised. He apologized to Catherine for making her look bad in front of the executive team and vowed to do better. From my perspective, Don hit the bulls-eye when he shared with me what he should have said. He was right on target, knew what to say, yet, he didn’t say it. Why? Because he didn’t trust himself enough to do what he needed to do. Instead, he let the little guy on his shoulder cloud his judgment. That guy was saying, “Protect yourself at all costs. Don’t be the fall guy.” As a result, Don focused on placing the blame elsewhere, which didn’t serve him well. Instead, he should have been looking for a way to reestablish trust with his boss. It bears mentioning that it took a long time for Don to recover from this mistake.

New Math: Why Things Aren’t Adding Up

Admittingly, it’s been a while since I attended school. However, I remember the concept of “new math,” which is basically a more innovative way to approach a problem that results in the same answer you would have gotten had you used “old math.” No matter which style of math you prefer, the equation 1 + 1 always adds up to two—or does it?

As I mentioned before, sometimes workplace discussions between two people include three or four voices: the little guy or gal sitting on people’s shoulders, whispering sweet little nothings into their ears like, “Oh, you don’t really want to say that, do you?” Or “You’re just a guy pretending to be a boss. Everyone knows you don’t know how to manage.” That’s when 1 + 1 can equal 3 or sometimes 4.

Some people can quickly quiet the voices in their heads or the little people on their shoulders. Then there are the rest of us who have difficulty speaking our minds for fear of what others will think. Instead, we let these conversations play out in our minds in a continuous loop, which can severely impact our mental health. We have to stop these kinds of internal discussions before they destroy us.

The Problem with Having Conversations in Your Head

I don’t know about you, but I can spend hours talking to myself. I can easily come up with a dozen reasons why I’m not going to confront someone, along with another dozen reasons why I should. If we’re keeping score here, the side that calls for nonconfrontation usually wins.

Here’s what I’ve found to be true of conversations in your head.

These kinds of conversations are for the sender, not the receiver. Here’s what I mean by this. I never think about how the other person might react to something that I say in my head. The focus is on me and what I want to sling at someone else. Of course, by the time I’m done conjuring up all sorts of ways to express my thoughts and feelings, I’m fired up on all cylinders. So much so, that sometimes I even forget what the specific topic was that I wanted to address! Which leads to my next observation.

One-sided conversations with yourself go nowhere. How can you possibly resolve a misunderstanding or an issue you may be having with someone if they have no idea there’s a problem? You can’t!

We’ve all participated in the silence is golden game. Someone says, “Is there something on your mind that you’d like to talk about?” You say, “No.” You’re not ready to discuss the situation or you think they’ll respond negatively to what you have to say. They probe a little bit more, and you react with abbreviated answers like, “Everything’s fine” or “I don’t want to talk about it.” From that point forward, you do your best to avoid one another.

In reality, there is no way for you to know for sure how the other person will respond. It’s like trying to play chess with one player. Your time would be better spent telling the person what’s on your mind and hearing their reaction before preparing a response.

The simplest way to get things out of your head is to write them down. Take a moment and jot down what’s on your mind. Is the matter worth further discussion? If the answer is yes, then schedule a time to speak with the other person. Some of you may be thinking, “I’m not having this conversation because I don’t know what to say.” That’s not uncommon. Here’s how to overcome this hurdle. To prepare for the meeting, write down some bullet points of what you’d like to get off your chest. You can take this one step further by scripting out the conversation ahead of time. Don’t worry about committing your script to memory. It’s better if you don’t sound overly rehearsed. If you need to, you can always refer to your notes. However, as you work through this, if you begin to realize that something is merely an annoyance or a one-off situation, then consider letting it go.

Trust Me: Why You Need to Trust Yourself

Every now and again, I’ll watch some home movies that show me brazenly prancing through my old neighborhood in Queens, New York, at the ripe old age of three. I was bold as well as confident. I trusted that I’d somehow make it back home safely. Of course, there was always a parent a few feet behind me. At the time, I probably didn’t realize this, as I appeared to be a woman on a mission, without any regard as to who or what was around me.

I don’t quite remember what age I was when I began to trust others more than I trusted myself. All I know is that at some point I began to seek approval from people whose opinions I thought mattered more than mine. It might have been in elementary school, where I was first taught that the teacher is always right. I know now that this is not true.

What about you? Do you trust others more than you trust yourself? If so, why is this so? I’m guessing that from time to time, people seek your advice. Why do they trust your opinion more than their own? Why would they ask for your point of view if they didn’t value your take on a situation? Something to think about the next time you start to second-guess yourself.

For most of us, including myself, self-trust can be tricky. We tend to doubt ourselves, or perhaps we hang onto memories of a situation that didn’t exactly go as planned. Or maybe our gut tells us to do one thing and our mind tells us to do another. These experiences make it difficult to trust yourself and create challenges with personal and work relationships. No one knows this more than one of my coaching clients. When you read her story, you’ll understand a bit more why she spent a great deal of time second-guessing herself about a management decision she knew had to be made.

This is my client’s story.

We were entering our busiest season, and my boss asked if I knew anyone looking for work. I immediately thought of my sister, who was available and had the skills needed to help us get through the rush.

Early on in her employment, my sister began making careless mistakes. As soon as this happened, I considered calling her into my office and asking her about this. However, I didn’t. I kept second-guessing myself. Every time I told myself that this week would be the week I’d have this discussion, the little voice inside my head would tell me to wait. I would make up excuses like maybe I was expecting too much of a new employee, or perhaps I didn’t train her properly. The mistakes continued until it got to the point where I could no longer look the other way.

I called my sister into my office and casually asked, “Hey, have you gotten back to these customers?” She hesitated and said, “I don’t remember. I’ll check.” Then she wouldn’t get back to me. She missed numerous deadlines and never gave me a heads-up. When I finally did confront her about this, she’d say things like, “I thought someone else was taking care of this,” or “Don’t worry, I’ll get to it.” This went on for several months.

I finally hit my breaking point when one of our dedicated long-term employees, who was picking up the slack for my sister, threatened to quit. It was at that point that I realized how much damage I had done by second-guessing myself and being afraid to confront this situation.

I scheduled a call over Zoom since, at the time, we were all working remotely due to the Covid-19 crisis and didn’t tell her what the meeting was about, but I think she knew. I began our call by saying, “Your performance has been substandard and is impacting the rest of the team.” I then went on to list specific performance issues and the impact this was having on the organization. She didn’t contest anything that I stated. I then said, “I have no choice but to fire you.” She said she understood.

It’s been several months since that conversation, and I still think about it. I know in retrospect it was the right thing to do. In fact, if I had to do it over again, I think I still would have hired my sister, as she had the right skills and could start immediately. Most importantly, I should have trusted myself and my ability to manage this situation. I knew early on that things weren’t going to work out. Yet, I allowed my sister to remain in her job way longer than I should have, which in the end wasn’t fair to the people I managed or my sister.


When my client first shared some of her employees’ challenges, I couldn’t understand why she hesitated to terminate this employee. The pieces began to fall into place when she later revealed that the employee she was about to fire was her sister. While my client says if she had to do it over again, she’d still hire her sister, that’s a move I’d try to avoid. It’s challenging enough to manage people. Now imagine going home to your parents and having to explain to them that you just fired their daughter!

My client started to second-guess herself when she first realized her sister was making costly mistakes. She later confessed to me that she knew all along what needed to be done and that she didn’t trust her ability to handle the situation the correct way. Had she trusted herself and addressed the situation as it unfolded, she would have avoided what she described to me as “one of the most stressful periods of my life.”

When meeting with her sister, my client made some common mistakes. She took her sister’s word at face value, even though the evidence she had didn’t align with what her sister was saying. She also didn’t come out and tell her sister what would happen next if her performance levels remained the same. Here’s a better way to handle a sticky situation like this one.

The moment she realized that something was amiss, my client could have called her sister into her office and said the following: “I need your help. It appears that some customer concerns are still pending. Let’s go line by line and see which customers are waiting for a return call.” Starting the conversation by asking for help demonstrates to the other person that you’re there to find a solution and not looking to merely place blame for the problem. At this point, her sister may have opened up and asked for additional support to complete her work. My client could have then discussed whether or not her sister enjoyed this job and if this work was a good match for her skill set.

Let’s say her sister responded by saying that she loved her job and felt this was the perfect position for her. This is when I’d advise my client to go deep and not just skim the surface. Perhaps she could have said something like, “I can appreciate that. However, we have to discuss your overall job performance. Within the past few weeks, you’ve made three significant mistakes, which have resulted in severe customer service issues.” I’d then advise my client to present her sister with concrete evidence that these customer service problems were directly related to her poor job performance. I’d take this conversation one step further and let her sister know that if certain performance expectations were not met, this could lead to further disciplinary action up to and including termination. By doing so, my client would have then laid out her expectations and had a roadmap to follow should her sister continue to underperform.

Having second thoughts about what to say, or whether or not you should even say something at all, is common when faced with a difficult conversation, especially when you lack confidence in your ability to strategize your next move. As you can see from the example above, taking time to develop a roadmap can be extremely helpful and will help keep you on course.

It’s understandable to second-guess yourself on occasion, especially if you’re faced with a situation you’ve never encountered. However, if second-guessing is your go-to move, then it’s time for a course correction. To do this, you have to first acknowledge you have a problem before you can remedy the situation. Once you recognize that you have a habit of second-guessing yourself, your next move is to work on trusting yourself more.

Practices to Overcome Self-Doubt

Here are some things you can do to enhance your ability to trust yourself. Let’s begin with starting your day off right.

Start Your Day with a Positive Mindset

No doubt you’re familiar with the term “mindset over matter.” I can attest from personal experience that this saying is more than just three words you put on one of those motivational posters that hang in the company lunchroom, which is why I find it extremely helpful to begin each day with an affirmation. Affirmations are positive, specific statements that help to overcome self-sabotaging negative thoughts. When you look in the mirror each morning, tell yourself something positive. To quote the wise words of Buddha: “What we think, we become.”

Here are some of my favorite affirmations to help you positively start your day. Feel free to use these or come up with your own:

I can do whatever I set my mind to.

What other people think of me doesn’t make me who I am.

I’m good enough.

I’m in charge of how I feel.

Today is going to be a great day!

My life matters.

Life is great!

I’m smart and capable.

I have so much value to offer others.

Here are some of the many benefits you’ll receive when you build your confidence.

Build Bench Strength

Rather than attempting the most difficult tasks or conversations at hand, start with the ones you believe you’ve got a pretty good chance of handling reasonably well. Let’s say you have to provide feedback to two people on your team who are not performing up to standard. The first team member is trying very hard but is a bit disorganized. You’re now at a point where you can no longer look the other way.

The other employee refuses to accept feedback and blames everyone else for his shortcomings. You know you have to address this situation. However, you hesitate because you’re relatively sure how they will react when you take this on.

I’ve heard advice from others who say you should tackle the most challenging situations first. You know, get the bad stuff out of the way. That advice may work for people who are good at diffusing situations and are great at quickly getting to the heart of the matter. You may not be there yet, which is why I’m suggesting you get a few wins under your belt before going into the lion’s den.

Speak with the disorganized employee first. Offer suggestions to help this employee better organize their work. After you’ve completed this task, schedule a date and time to speak with your other employee. You can push this date out a week or two to give you ample time to finish reading this book.

Be Decisive

I once worked with a leader who would make a decision and then change his mind. He drove me and everyone else around him crazy. Imagine how much time this leader wasted as a result of overthinking everything. Or maybe you don’t have to imagine if this story sounds a lot like you.

Being decisive requires you to make choices and adjust along the way. Forget trying to be flawless. Effective decision-making is about considering your past experiences, analyzing the current situation, making a risk-reward comparison, and, most importantly, believing in yourself.

Here’s an exercise you can use to help you become a more decisive person:

Write down a decision that you need to make.

Quickly jot down options worth consideration. (Note: do not go back to this list and add more options.)

Next to each option, record all the pluses and minuses associated with that choice.

Select the best alternative.

Now, move onto the next decision.

Developing confidence has greater benefits than enabling you to have more productive conversations. People who trust themselves implicitly make better decisions in choosing who to be around and how to show up every day. Generally speaking, they’re happier and less stressed out than those who are always second-guessing themselves.

What have you got to lose? Pick a couple of ideas that feel right to you or push you a bit out of your comfort zone and give them a try.

Increase Positive Self-Talk

Look, we seem to have no problem with negative self-talk. How often do you tell yourself you’re not good enough to do something? Does your mind immediately go to thoughts like, “I’m terrible at that,” or “Why would anyone choose me for this job, promotion, or project?” or “How on earth could I ever have a conversation like that?”?

Now imagine what would happen if you took your negative self-talk and turned it into positive self-talk. What if instead of convincing yourself you were terrible at doing something, you told yourself that perhaps you’re not the best. However, with practice, you could be decent and maybe even great at something. What if instead of asking yourself why anyone would choose you over someone else for a job, promotion, or project, you said to yourself, “These people would be lucky to have me on their team!”?

Now let’s apply this idea to a conversation that you’ve been avoiding. Rather than thinking, “Oh, boy. There’s no way this is going to go well,” you say to yourself, “With preparation and practice on my part, we should be able to have a productive conversation that will enable us to move forward.”

Here are a few more tips to help you build self-confidence.

Make Note of Your Successes

At the end of each day, write down one or two successes you experienced that day. Keep this in a journal or pin this list up on your bulletin board. Don’t waste time worrying about whether or not something is worthy of being considered a success. You’re the judge and jury here.

Each morning, before you begin your workday, review your success list. This list is an excellent reminder of how capable you are and will help you start your day off positively.

Be Kind to Yourself

Rarely will everything go according to plan, which is why you need to forget being perfect. Instead, when conversations don’t go as well as you hoped they would, take time to analyze what, if anything, did go well. Ask yourself what you could have done differently to achieve a better result.

Consider seeking feedback from a trusted colleague or a coach or mentor. Sharing how a conversation went with someone you trust to tell you the truth will prevent you from overthinking things. Chances are, you did way better than you think!

Signs You Don’t Trust Yourself (and What to Do about It)

Here are some signs that you don’t trust yourself and what to do about it.

You Have a Hard Time Recognizing, Understanding, or Believing in Your Innate Value and Worth

Perhaps you were told, by someone you trusted, that you weren’t smart or that you’d never amount to anything. Maybe this was said to you more than once by a parent or even your boss. You bought into whatever was stated about you and now you can’t rid yourself of these feelings.

First off, consider the source. Was the person who told you these things knocking you down to make themselves feel or look better? Did others mentally abuse this individual? Did you seek their opinion or were they delivering unsolicited feedback? The last question is essential, as unsolicited advice is for the sender—not the receiver.

Now that some time has gone by, are you in agreement with their conclusion? If the answer is no, then throw the baggage that’s weighing you down off the train. I’ll explain exactly how to do this further on in this chapter. If you’re unsure whether these people are right, or you still have a negative self-image, consider getting some professional help.

You Often Defer to Others

You know the answer to a question being asked in a meeting, yet you wait for others to speak before offering your response. You’re worried about how you’ll look if no one else agrees with what you have to say. That’s the least of your problems. A number of my coaching clients defer to others in meetings and find this kind of behavior is limiting their career options. Remaining silent while other people steal your thunder does more harm than good.

The next time you’re in a meeting and a topic comes up that’s in your wheelhouse, ask yourself, “What’s the worst that can happen if I speak up?” Then jump right in and contribute. After all, no one is shooting at you. What you have to say could very well be right on target or a springboard to another idea worth consideration.

You Believe What Others Say More Than You Believe in Yourself

You know something to be true. Yet, the moment someone challenges your assumption, you immediately cave.

You’re in a particular role for a reason. Somewhere along the way, someone saw something in you that made them want to hire you. If you don’t believe you’re deserving of the job you’re in, then why would anyone else believe this? The next time someone challenges you, whether this person is your coworker, superior, or employee, take a pause. Count to ten. Then ask yourself this one simple question: “What evidence do I have that this person is right and I am wrong?” If after asking this question, you believe there’s a fairly good chance you’re correct, then be prepared to state your case. Here are some conversation starters you can use to begin the discussion and build confidence:

“I can appreciate why you might feel this way. Perhaps I haven’t explained myself as clearly as I thought I had.”

“I understand what you’re saying. However, have you considered…”

“Help me to understand why you believe this is the best course of action.”

“I appreciate your point. With your permission, I’d like to continue to explore our options here.”

“Thank you. That’s an interesting idea. However, the data supports my findings. Let’s discuss this further.”

“You know I’ve always valued your opinion. However, I’d be remiss if I didn’t push back here.”

You Rarely Try New Things

When is the last time you said yes to something that was totally out of your comfort zone? If it’s taking you longer than a minute or two to come up with something, then you’ve just run into another sign that you don’t trust yourself as much as you should.

Some people think that sticking with the same routines is about knowing oneself well enough not to take excess risks; it’s actually the opposite. Trusting yourself means that you’re in a place where you’re willing to step out of your comfort zone and do new things.

I remember the first (and last) time I parasailed. I was hanging out with some new friends I had made in Australia, who invited me to observe them parasailing. I enthusiastically said yes. I watched from the sidelines as they worked with the parasailing instructor, and then they took off, flying above the hill! I thought that looked like a really cool thing to do. After my friends were up in the air, the instructor turned to me and asked me if I wanted to give it a go. I thought about all the reasons why doing this was a terrible idea, and then said yes. I trusted myself enough to know that no matter how things went, I’d be okay.

I suppose you think this is going to be one of those stories where the hero (me) goes sailing off fearlessly into the sunset. Actually, the opposite happened. As soon as I went to take off, the winds began to pick up. I got caught in a crosswind and wound up tumbling down the hill. My body hurt a bit from the fall, but not as much as my ego. Other than that, I was okay and survived to face another day.

Experiences, like the one I just described, make us who we are. Your version of a bold move may be standing up to your boss and telling that person the way they’re speaking to you is unacceptable. Or perhaps you had to fire an employee who was a friend. Things didn’t go exactly as planned. However, this ex-employee still waves hello when you see one another at church.

We’re better than we think we are, even if (or perhaps because) we’ve had a few mishaps along the way. Go ahead. Extend yourself beyond your comfort zone. Fear will fade as you begin to get some successes under your belt. Take the baggage you’re carrying and set it down. Now, don’t you feel lighter and a bit more nimble?

Using Confidence to Navigate Difficult Conversations

Remember the first time you went to the gym and lifted weights? I do. I thought I could handle a lot more weight than I could. Boy, did my body suffer the next day. However, I didn’t let my discomfort or my ego deter me. I went back the next day, and the day after, and built up my strength.

There’s no magic diet or pill for strengthening your inner trust muscle. That’s probably a good thing, as false promises are just that. The way to build inner trust is to establish and commit to a routine. The keyword here is commit, as we all know people with gym memberships who rarely use them. Of course, these same people wonder why they’re not making any progress in their health goals! Here’s a real-life example of how one executive used confidence to successfully charge through an extremely tough conversation.

Confidence and Trust

As mentioned earlier, sometimes conversations stall or derail because we don’t have a trusting relationship with the other party. Here’s a case in point.

Working in law enforcement for over twenty-nine years, you learn many lessons. Midway in my career, recently promoted to a captain position as the first female in a predominantly male office, establishing trust was more than a priority. My approach coming into a new environment was to observe and handle immediate issues based on a risk assessment analysis along with urgency dictated by the profession in policing. With regard to personnel issues, I felt it would be a good strategy to take the time to become familiar with employees, look over past performance in their personnel files, and allow myself time to develop a rapport and then a relationship. That approach played out much better in my notes and thoughts than it did upon arriving at the office on my first day.

My second-in-command, a lieutenant, had been given the charge of overseeing operations before my assignment. As I quickly discovered, he carried the interim title loosely. Briefed and prepared, I knew ahead of time the office was behind in meeting significant timelines for reporting, absenteeism was high, there was lack of supervision on shift schedules, morale was acidic, and overtime was well outside of the budget. Still thinking I could employ some of those initial approaches, I had to make a hard pivot to moving from relationship building to being more authoritative after receiving pressure from those above me. It took me off guard, the swift expectancy of their demands; it was only the first day. However, I was also newly promoted and on probation. After a few pleasantries around the office to introduce myself and complete the “Golden Hour,” I met with the lieutenant in my office.

He had no idea the train was traveling down the tracks and he was sitting on the rails. Not new to counseling, but new to commanding, I said to him, “Supervisors need to be working, not all on vacation at the same time. I need you to make sure they are monitoring overtime, hard to do if they’re not here. At the same time, absenteeism is high because there’s no one being held accountable. Much of this stems from lack of leadership and holding people to the fire, until now.”

He sat back in his chair, looked at me wide-eyed, and said, “Excuse me, you have no idea what I’ve had to deal with while there has been no captain for months in this office. You come in here and tell me what’s not right and then want me to snap to and get all these things done. I know there’s a lot messed up right now, but you don’t even know what’s going on.” After giving myself a moment of not flinching at his tone, but internally churning over my next move, it came to me. “I know it’s not something I want to have to talk with you about on the first day either. And, you’re right. It will take me a while to know the command and all that’s going on. That’s why I need you to work with me as we resolve these issues. This is what I need to get done, and it’s our responsibility to work on them with urgency. Is this something you can do?” He was silent and then surrendered to the moment, agreeing to the work at hand.

I didn’t have time to build a deeply connected trust relationship with my lieutenant, but I was able to plant seeds for a future harvest. My approach was shortsighted until I took the time to use active listening when he had the courage to share what he was feeling. It was a moment where I could have chosen to slay him or hear him—choosing enmity or empathy. And considering, is this the hill to falter on? Or do we move forward unified to stand in the larger battles, of which we had many? I’ve found the success of leadership is not built in a silo of ourselves; it’s made through the collective rumbling and reckoning of many.

Jonni Redick

President, JL Consulting Solutions

Unfortunately, you don’t always get to control the timing of when you have to have a tough work conversation. Had Jonni waited, she would have run the risk of losing the respect of other team members. The chaos the department was experiencing may have worsened and put the public at risk. She had to weigh out the risks of letting things ride, until such time as she had established trust, or immediately taking action.

Here’s what Jonni did well. She was direct and open with her employee regarding the current status of the department. She told her employee what she needed and then asked him if he was up to the task. By doing so, she was able to quickly bring this employee over to her side, where together, they were able to resolve the issues that were weighing the department down.

If you find yourself in a similar situation, I’d suggest that you have the conversation as soon as you notice there’s a problem. Most leaders will wait. They’ll hope and pray that things get better. Rarely is this ever the case.

You owe it to your employees to provide them with honest feedback, which is what Jonni did. Perhaps without even knowing it, she started the process of building trust with her employee by being willing to take on this challenging situation early in their relationship.

Trust: The Cornerstone of All Relationships

Have you ever done something willingly for someone whom you didn’t trust? The key word here is willingly. Sure, we’ve all done things because we had to. And when we do, we usually don’t put our heart and soul into getting something done. We do the minimum. Now compare this to when someone whom you trust and respect asks you to do something. Chances are you do what they’ve asked you to do, and then some. Low levels of trust may help to explain why, when you’re having a challenging conversation at work with an employee, peer, or boss, things don’t go according to plan.

Bank of Trust

Many years ago, when our daughter Lexi was seven years old, my husband Ron took her to the bank to open up a savings account. Ron intended to use this visit to the bank as a learning opportunity to teach our daughter how to be fiscally responsible. He also wanted Lexi to understand the theory behind compound interest, so that she would get into the habit of saving at a young age. What happened instead is that we all learned a valuable lesson.

The bank manager was explaining what would transpire with my daughter’s savings, including a discussion on interest and bank fees. At the time, interest rates on savings accounts were hovering around 6 percent, which sounds like a lot by today’s standards. The manager went on to say they’d be taking out eight dollars a month as a service fee on her modest $300 savings account.

My husband told me that as the manager kept on talking, our daughter appeared perplexed. She later confided in him that she couldn’t wrap her head around the idea that in the end, she would be paying the bank to hold her money, since the monthly fee far exceeded what she would be making in interest. She turned to her dad and said, “Why would I want to do this? I’m losing money here.”

My husband was speechless. Lexi was right to ask this question. The bank manager failed to establish trust with our daughter. She didn’t explain that once Lexi had a certain amount in her account, the fees would go away. Lexi did what any other smart investor would do. She picked up her piggy bank and left and deposited her money in a bank that offered no-fee accounts for young savers.

I use this bank of trust example all the time in my coaching. I explain to my clients the importance of making deposits into their bank of trust savings account, as well as how to do so, and what happens when you need to make a withdrawal and your account is empty. Here’s what I tell them.

You never know when you’re going to need to ask someone for something. If you’ve made some trust deposits into the account that you have with this person, then you stand a good chance of being able to make a withdrawal (asking for something and having them say yes) when you need it. If the account is empty… well, you can guess how the conversation will probably go.

Here are ten ways to establish a healthy trust account:

Be completely honest in your dealings with others.

Do something for someone else, before asking them to do something for you.

Do what you say you will do.

Step up and have someone else’s back during a meeting.

Give praise in front of others.

If you fail to do something that was asked of you, let the person know before they find out from someone else.

Give credit where credit is due.

Admit when you are in the wrong.

Apologize for your mistakes.

Volunteer to help someone in need.

Now let’s apply this concept to a common situation that happens at work. In the first scenario, the person making the request doesn’t have enough in their account to make a withdrawal. The second example demonstrates what happens when you have saved and planned for a rainy day.

Setting the Scene

You’ve been on the job for less than a year, and you’d like to request time off during your company’s busy season. You know you can get all of your work done before you go. However, your boss has no idea if this is so.

Scenario Number One

Several months ago, one of your coworkers unexpectantly went out on medical leave, thereby leaving your boss scrambling to cover this position. You stepped up and volunteered to work late and on weekends to help your boss through this challenging period. You did so while keeping up with your work.

You’ve done a great job of establishing a trusting relationship with your manager. You say to your boss, “I know I haven’t been here long enough to qualify for vacation time officially. I also know December happens to be the busiest time of the year for our department. However, would you consider granting me a few days off so I can visit my family over the holidays? I’m willing to come in the weekend prior, to make up the time, and promise my work will be complete before I depart.”

You’ve got a trusting relationship with your boss and you’ve done a nice job of presenting your case for time off, which includes your plan for completing your work before leaving. Your request is approved.

Scenario Number Two

Your boss calls the team together and shares the news that your coworker is taking a medical leave. She then asks for volunteers to take on some of your colleague’s tasks. You keep your head down and pretend to be taking copious notes.

In a meeting with your boss, she reveals that she’s feeling extremely stressed about completing certain goals on time, now that your team is down a person. You respond by saying, “Yeah, I’ve got a ton on my plate and have no idea if I’ll even be able to complete everything that’s been assigned.” Several weeks later, you approach your boss and say, “I know it’s our busy season, but I sure could use some time off. I’d like to take vacation time next Tuesday and Wednesday. Can you approve this for me? I’ll do what I can to get through my to-do-list.”

Your request is denied. It should come as no surprise that your request has been declined. You haven’t made any deposits into your trust account with your boss. She has no reason to believe you will be able to get everything done prior to leaving. In fact, she’s fairly sure you won’t, given that you told her you don’t think you have the bandwidth to complete what’s already been assigned. You also failed to give before asking for something. The lesson here is that you can’t make a withdrawal when there is nothing in your account. This rule applies in banking, as well as in business.

In the next chapter, we’ll be discussing the second principle, which is clarity, and the need to get clear on exactly what you wish to get out of a conversation, before charging forward.

Key Learning Points

Lots of people are having “should have,” “could have,” “would have” conversations inside their heads. All of this second-guessing leads to exhaustion, followed by frustration, and often regret.

One-sided conversations with yourself are time wasters. These conversations go nowhere. You can’t possibly know what the other person might say until you speak with them.

Consider writing down what you want to say to someone. Then, ask yourself if the matter is worth further discussion. If the answer is yes, then schedule a time to speak with the other person.

If something is merely an annoyance or a one-off situation, then consider letting it go.

You can’t expect others to trust you if you don’t trust yourself.

To enhance your ability to trust yourself, use positive self-talk, note your successes, and be kind to yourself.

Signs that you don’t trust yourself include not believing in your innate value and worth, often deferring to others, and rarely trying new things. The way to overcome this is to develop your inner trust muscle.

Take note of your successes. You’re much better than you think.

To strengthen your inner trust muscle, start each day with a positive affirmation. Build bench strength by starting with tasks and conversations you’re reasonably sure you’ll succeed with and work your way up to the more challenging situations.

Making a withdrawal from your trust account when you don’t have enough “funds” in it will result in relationship bankruptcy, which you may never fully recover from.



Making Your Point Clearly and Listening with an Open Mind

You’ll never get where you’re going if you don’t know where you want to go, which is why, when dealing with difficult situations, you must have clarity on where you want to go before heading out to have a conversation. This is why I’ve chosen clarity as one of the seven principles for navigating difficult conversations at work. With this in mind, you have to establish the right objective and give consideration to a number of factors that will help you prepare for a high-stakes conversation. It’s also important to plan for the worst and expect the best, which I’ll explain in more detail in this chapter. We’ll also be discussing the need to assess your readiness to proceed as well as how to handle difficult conversations remotely. Advice on how to keep your cool when things heat up and speaking in a way that will allow others to hear you loud and clear will be explored more fully. Finally, we’ll end this chapter with a discussion on why the need to be right can bring about the wrong results and what you can do to avoid this.

Let’s Be Clear Here

How often have you walked away, after chatting with someone, with a confused look on your face? The meetings may have lasted thirty minutes, or even longer, yet you still had no idea what transpired.

Perhaps it was one of those meetings where your boss placed you on a performance improvement plan. Your manager was speaking so fast that your mind couldn’t catch up. Or maybe your coworker was asking you to provide them with some assistance. They were a bit unsure what they specifically needed from you. All they knew is that they could have used your help. You may have said no to their request because you were uncertain about how much time would be needed from you to assist them. Or worse, you may have said yes just to stop this perplexing exchange, even though you weren’t fully committed. You then let your coworker down because you didn’t have the skills or bandwidth to help.

Most meetings ramble because people wait until the last minute to figure out precisely what they want to happen before beginning the meeting. Some people never figure this out before starting, which explains why we often leave these kinds of discussions shaking our heads in confusion. That was me over twenty-five years ago. I was the person who, after speaking with my boss, walked out of the meeting shaking my head in confusion. Here’s what transpired.

One of the co-owners of the company came to me and out of the blue ranted off a list of things he was not happy with. He dashed out of my office as quickly as he had arrived, without so much as giving me a chance to ask any questions. My first thought was, “Where the heck is this coming from?” followed by “What an ___” (you fill in the blank). I went home that night and replayed the conversation over and over again. Needless to say, I didn’t get much sleep.

The next morning, the co-owner walked into my office and asked me if I had a second. I said, “Sure.” And then he did something that surprised me even more than the “little chat” we had had the day prior. He apologized. He said he had gone home and told his wife what he had said to me. She told him he was an ___ (yep, the exact word that I was thinking). I told him his wife was right. Hey, she was!

He then went on to say that he hadn’t thought through exactly what he wanted to say and how I might react. Nor was he clear in his own head where he wanted us to go from here. His apology arrived a day late. The night prior, I made the decision to check out of the organization. When I left, I didn’t leave the company. I left him.

It’s been over twenty-five years since that memorable encounter, and I still can’t get this conversation out of my head. People share similar stories with me all the time, which indicates to me that we still have a lot of work to do in terms of clarity and workplace conversations. Here’s a true story, shared by one of my clients, about what can happen when you don’t have clarity.

A senior leader for our organization was hired two years ago. In the first few months, he exhibited enthusiasm, was knowledgeable about topics, and presented multiple ideas. In meetings, he was given assignments, his input was solicited, and the expectation was he would follow up, but he did not. The behavior of not seeing things through continued. This shortfall also affected his peers, who expected his follow-through and needed his participation.

The behavior of not seeing things through continued even after this initial period.

A one-on-one conversation ensued that addressed his presence and commitment to the organization. I met with the employee in my office; I stated, “There seems to be a clear disconnect between how you view yourself and your accomplishments and what your colleagues are saying.” He stated, “I don’t understand and would like specifics.” I stated examples, “Emails stating solutions with no follow-up or collaboration, lack of follow-up on key projects, leaving early, and absence of visibility.” I asked him if he was committed to the role. He stated he was but was not aware of the image he was portraying. We decided to work on the weaknesses, and if not resolved over the course of four months, we would have further discussion about his future in the organization.

In my opinion, in the initial one-on-one discussion, the expectation was to deliver on the assignments. However, the employee did not see this, nor was it made clear. In hindsight, the conversation was about his commitment to the organization and presence. It should have connected his lack of follow-up and attention directly to being a team player and his direct responsibilities to the team. A more direct conversation may have avoided this now more difficult situation. Things have since deteriorated further, to the point colleagues and superiors have noticed.

Ronald Bryant

President, Western and Northern Regions

Baystate Health

As you can see from Ron’s story, clarity is critical for resolving a difficult situation. Otherwise, you may wind up like Ron and find yourself going down a path to nowhere. Ron’s first clue that the message he intended to deliver was getting lost in translation was when his employee said he was not aware of the image he was portraying. Ron wasn’t talking about image—he was talking about poor work performance. Had he picked up on this, he could have redirected the conversation back to the performance issues impacting the team, which is the behavior that Ron wanted to see change. Ron also spent considerable time discussing this employee’s commitment to the organization, rather than the underlying issue—lack of follow-through. In being more direct, he could have said something like, “I’m talking with you because your lack of follow-up and attention is posing problems and affecting other members of the team.”

It’s interesting to note that Ron thought he was making his point clear. However, in retrospect, he realized this was not the case. To ensure his message was hitting the mark, Ron could have asked some clarifying questions after presenting his case, questions like, “What’s your understanding of what I just said?” or “What exactly are you committing to do differently as a result of our conversation?” If the employee response was in any way off base, Ron would have then had the opportunity to say, “Hold on. I think you’re missing my point. Let me be specific here.” He could have then spelled out exactly how he saw the situation and his expectations going forward.

Getting clear and expressing precisely what you mean has to be a priority if we are to stand a chance of stopping the mass exodus of employees fleeing organizations in search of better bosses. We’d also be able to dramatically reduce the cost of employee turnover if we were more clear in our conversations.

Establishing the Right Objective

Too often, the main objective for people who are about to enter a tricky conversation is to get it over as quickly as possible. If that’s your objective, don’t be surprised if things don’t go according to plan. Keep in mind that you may have had plenty of time to think about what you want to say. However, the person you’re speaking to is often hearing this for the first time.

The success of any challenging conversation will be decided long before the conversation starts, which is why you need to first come to terms with what you want for the relationship. Do you see a particular conversation as an opportunity to clear the air and move forward? Or is this meeting merely a formality—meaning HR says you have to have a certain number of discussions on a particular topic before terminating an employee?

You may be wondering why knowing this is so important. How much time you devote to a challenging work conversation, as well as how you’ll position yourself, will vary, depending on how you foresee your relationship unfolding. If you’re looking to build a stronger relationship with the person you are speaking with, you’ll most likely be willing to put in the time and effort required to achieve consensus. If you’re merely going through the steps that will allow you to end the relationship, you’ll be brief and will choose your words carefully to avoid problems down the line should the employee decide to take this to HR, or worse, to a lawyer.

Once you know what you want out of the relationship, the next step is to get laser-focused on the outcome(s) you wish to achieve before scheduling a meeting. If you know going in what you want coming out, you’re more likely to get it.

I’m sure many of you have been in a similar situation as Ron. You begin a conversation intending to go down one path and wind up on another. In Ron’s case, commitment and presence weren’t really what he was going after. These were underlying symptoms that were pointing to a bigger problem—lack of follow-up, which was negatively impacting the team and the hospital.

I’ve known Ron for years, and he’s not a guy who minces words. Had Ron been more exact on the behavior change this employee needed to make before conversing with the employee, he would have been more explicit when addressing the situation. He’s a great leader, and I have no doubt that he will use this opportunity as a learning experience. He’s not going to make this same mistake twice.

Here are some questions to help you become crystal clear on your objectives before addressing a sticky work situation.

What’s the Purpose of This Conversation?

Are you looking to blow off steam, or do you genuinely want this relationship to improve? Do you want your boss to take notice of your contributions, or are you simply providing information? Is there a particular behavior you’d like your coworker to stop or start doing, or are you merely venting? Essential questions like these are often not given proper consideration, which is why many of these conversations go nowhere or somewhere unexpected.

Let’s say someone’s actions are impacting you in a negative way. You may have every right to be angry or disappointed. However, telling your boss, peer, or team member off could result in unintended consequences. Before taking this approach, think about the damage you may do to your relationship or even your career. Then, if at all possible, choose a different path.

What Specifically Do I Want the Other Person to Do after Our Discussion Ends?

Have you ever been to one of those meetings where the person leading the meeting spent most of the time going down their list of items they were unhappy about yet never explicitly stated what they expected to happen next? I have. These types of meetings can be maddening. If you’re like me, you probably left scratching your head, wondering what precisely the purpose of that meeting was and what, if anything, you were supposed to do next.

Before asking someone to speak with you in what could be an uncomfortable conversation, establish what you want the person or people in the room to do when they leave that meeting. When you’re clear on the next step, you may choose a different course of action than what you initially thought you’d do.

Here’s what I mean by this. Let’s say you’ve decided that you’re not interested in hearing what people have to say about a particular situation. You merely want to give folks a status update and inform them that you’re incredibly disappointed in the team’s revenue numbers. There’s no point in pulling people into a room just to hear you speak. You may be better off delivering your message in an email, where you can spell out exactly where things stand and what you expect going forward. If need be, you can then schedule one-on-one