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Summary: Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century by Jeff Lawson


To remain competitive in the face of digital transformation, every company must become a software builder. Therefore, the builders of digital solutions – software developers – are crucial to a company’s success. However, most business leaders do not know how to attract, retain and empower them. Getting this right can make the difference between being a disruptor or being disrupted.

Twilio co-founder Jeff Lawson explains the importance of giving software engineers autonomy, and describes how to create and sustain an open, learning environment. He shows how to unleash the power of collaboration between business and tech.


  • Software developers are now essential to the strategy of every business because every company has to become a software builder.
  • Adopt an ‘Ask Your Developer’ Mindset.
  • Make experimentation a part of your culture.
  • To recruit and retain the best developers, know what they regard as important.
  • Successful companies nurture cultures of continuous learning.
  • Maintain start-up energy with a small-team structure.
  • Provide efficient development platforms and infrastructure.

Book Summary: Ask Your Developer - How to Harness the Power of Software Developers and Win in the 21st Century


Software developers are now essential to the strategy of every business because every company has to become a software builder.

Businesses such as Uber, Airbnb and Spotify disrupted their industries, thanks to their talent for building the best software and providing superior customer experiences. For all businesses fighting for customers’ hearts and wallets, building the software that provides these experiences relies on fostering an environment of collaboration between software developers and executives across the organization.

“Business folks and software developers often want the same things – to build awesome products that delight customers…and make money.”

Traditionally, many companies saw IT as a “cost center,” an investment that supports the operations of the firm. In the 1980s and 1990s, companies outsourced this function, and used off-the-shelf software products for internal operations.

“The key to Amazon’s success is that Jeff Bezos understood way sooner than everyone else that he was actually in the software business.”

The web and mobile technologies make a software interface one of the primary ways businesses engage with customers. A better digital experience is the crucial differentiator.

Adopt an ‘Ask Your Developer’ Mindset.

Software developers are inherently creative problem solvers.

“To solve this puzzle, companies must first start by recognizing that code is creative, that many developers are in fact creative problem solvers – and should be treated as such.”

To unlock the potential of your developers, adopt an ‘Ask Your Developer’ mindset:

  1. Assign problems, not tasks. Traditionally, executives on the business strategy side will come to developers with fully drawn out ideas on how to solve these problems and expect software developers to simply turn it into code. Instead, they should come to developers with the problem they are looking to solve.
  2. Celebrate failure. Experimentation is the prerequisite to innovation. In order to build innovative problems, look to failure as a sign of progress. Businesses need to create an environment where developers are encouraged to run lots of small experiments and where failure is celebrated rather than punished.
  3. Keep developers close to your customers. At Twilio, one of the company’s values is ‘Wear the Customer’s Shoes.’ The company asks that everyone solving customer problems, especially software developers, talk directly to the customers and understand the problems. Businesses should remove organizational barriers that separate developers from the people who actually use their software. When developers talk to customers they deliver better, more useful features in less time.

Make experimentation a part of your culture.

The software mind-set favors getting software to customers quickly. Rather than guessing what the customer will like, produce a working version. Let customers try it out and give you feedback. Incorporate the feedback into a new iteration, and then repeat the process. Such experimentation, which accepts potential failures as progress, is the foundation of innovation.

“The more quickly and cheaply you can run experiments, the faster you’ll eventually find something that works.”

Managers make a difference by cultivating a culture that tolerates failure in the name of experimentation. Minimize the fear of failure by establishing that the point of an experiment is to test a hypothesis. Proving your hypothesis correct is valuable, but proving it is wrong can provide useful information.

Assemble a small team and ask its members to address a problem that plagues a particular segment of customers. At the outset, establish the metrics you will use to determine whether the experiment succeeds or fails.

Imagine you developed a problem-solving idea, and hypothesize that it could bring in $500 million. Set your metrics. For example, you might determine you will need to attract 1,000 customers who would each pay $500,000 over five years. To test the hypothesis, first see if you can find one customer willing to pay that amount. Next, determine if the problem is sufficiently common that another 999 customers would pay for it.

Three outcomes of an experiment are possible:

  1. Success – You prove your hypothesis. Now, act promptly on it. Recognize when an experiment is no longer an experiment, but a valuable idea. Keep resources in reserve to launch these winners.
  2. Failure – You have shown your hypothesis to be false. Never punish those running the experiment, because that inhibits others from taking risks. Appreciate the information this “failure” provides. You spent a modest sum to avoid spending millions on an idea that won’t succeed.
  3. Mixed results – When your results are unclear, make sure your experimental design was sound, and that you had clear metrics. Consider whether you had a problem with how you configured the team, and whether you allowed the experiment to run long enough.

“If you swing for the fences, you’re going to strike out a lot, but you’re also going to hit some home runs.” (Jeff Bezos)

Run as many experiments as is feasible. Thomas Edison, for example, experimented with thousands of materials before finding one that validated his hypothesis that he could make light with electricity and a filament. Some of Amazon’s most successful services, including Marketplace, Prime and Amazon Web Services, started as experiments.

To recruit and retain the best developers, know what they regard as important.

Hiring and retaining top-notch developers is not a question of offering high salaries and elaborate perks. As Daniel Pink points out in Drive: The Surprising Truth About What Motivates Us, money is not the primary factor fueling high performance. Software developers perform best and experience the most engagement when their jobs offer:

  • Autonomy – Like workers in any field, software developers are at their best when they work independently within basic guidelines. Managers should provide the resources developers need, and demonstrate that they trust them to make their own decisions. Highlighting autonomy is one of the rationales behind the lack of dress codes at tech companies, because demanding certain attire implies you don’t trust your employees to dress themselves. Find opportunities to underscore your trust in developers’ instincts by including them in discussions of important business decisions.
  • Purpose – Developers want to do more than follow the directions in a “Product Requirements Document.” They want to create something that matters. This could mean anything from devising creative software solutions for customer problems to pioneering new avenues of business.
  • Mastery – A satisfying job offers opportunities to put your abilities to their best use, improve your skills and learn new ones.

Successful companies nurture cultures of continuous learning.

A company should strive to create an open, learning environment. This provides an atmosphere in which people can ask questions and devise ways to find the answers themselves.

Learning involves making mistakes, but many companies have created a culture of punishing people who make errors. The result of such rigidity is a workforce that plays it safe by simply following whatever leadership says. A cautious workforce lacks agility and creativity.

“The cold, dispassionate process of software development common in some companies is a tragedy both for the business and the developers.”

A couple tools that are in practice at Twilio are “Open Project Reviews” and “Blameless Postmortems,” which encourages questioning and learning through. The “Open Project Review” allows everyone to attend a project-status meeting between a chief product officer and individual contributors from different teams.

The software company Twilio, for example, encourages questioning and learning through “Open Project Reviews.” Under this system, everyone can attend a project-status meeting between a chief product officer and a project team. Only those participants essential to the project can speak. Everyone else observes. This practice eases the process of everyone keeping track of what numerous teams are doing, and enables people to learn from the experiments that everyone else is performing.

Another tool is the “blameless postmortem” – a meeting to uncover the cause of a failure. The intent is not to find someone to blame, but to discover any systemic shortcomings that might have allowed the mistake to occur. The process involves asking a series of “why” questions. For example, imagine that a coding mistake has disabled a website. After you rectify the problem, hold an inquest to discover why the mistake occurred. The proximate cause is that the coder made a mistake. But take a step back and ask why the coding caused an outage, and why the faulty code went into production without reviews. By continuing to ask these and other questions, you eventually discover the “root cause.” In this case, it could be that your testing protocols weren’t sufficiently robust. The solution is not to discipline the coder but to reorganize the testing infrastructure.

“An open, learning environment is one where the organization is receptive to not having all of the answers, is comfortable with uncertainty, and strives to get better every day.”

An open, learning environment focuses on preparing the next generation of managers. Companies usually build a management team by promoting top performers into management positions. But competence in one field, such as engineering, doesn’t mean a person is competent in the art of management. The best way to learn is by doing, and it’s important to allow future managers to learn the ropes by having them manage low-stakes projects to prepare them for bigger projects and allow them to lead.

Maintain start-up energy with a small-team structure.

A start-up is usually a high-energy place, in which a small group works with urgency and purpose. As a company grows, it may have difficulty maintaining that sense of mission. One solution is to organize the company around small teams, each focusing on different projects. This is how Amazon scaled to tremendous size without sacrificing innovation and agility.

Such teams require a few organizing principles: They need a clear picture of the customer they serve, whether that customer is external or internal. They should define their mission, a central purpose that team members unanimously accept. The team must set the metrics they’ll use to measure their progress. The metrics will consist of more than quarterly targets, and should measure the long-term progress on the team’s mission.

“By removing layers of overhead, engineers who are close to customers can make low-risk decisions that benefit customers.”

Developers should have firsthand knowledge of customers’ needs and problems. In many companies, certain employees are customer-facing. Those who are, like sales and support staff, should talk with customers and relay their wishes to developers. But as customer concerns filter back, this process can delete nuance. ​​

“People in any field rise to the expectations set for them.”

Bunq, a Dutch online bank, requires developers to participate in the company’s users’ forum, where they encounter customer complaints and feature requests. In a more conventional protocol, customer support teams scan the forums for requests that seem worth pursuing, and pass those on through levels of management until only the most cost-effective reach the developers. When developers scan the forum themselves, however, they may come across a suggestion for an attractive but not crucial feature. Perhaps the developer knows he or she could bring that feature to life quickly and simply. In the end, an idea that probably wouldn’t survive the management filter goes live with little fuss, cultivating customer goodwill and providing the developer with satisfaction.

Provide efficient development platforms and infrastructure.

Many first-rank software companies spend as much as 50% of research and development funds on infrastructure. A sound platform eliminates conflict between speed and quality, and minimizes worries about independent teams duplicating each other’s work.

About the Author

Jeff Lawson is co-founder and CEO of the technology company Twilio.



“Ask Your Developer” by Jeff Lawson is a captivating and insightful book that sheds light on the growing influence of software developers in today’s business landscape. Drawing from his extensive experience as the CEO of Twilio, Lawson explores the critical role developers play in driving innovation, building successful businesses, and shaping the future of technology. This review aims to provide a comprehensive summary and evaluation of the key themes and takeaways from the book.


“Ask Your Developer” emphasizes the importance of embracing software developers as strategic partners rather than mere implementers of technical tasks. Lawson argues that in the digital age, every company is a software company, and organizations that fail to recognize and leverage the power of developers will struggle to remain competitive.

The book is divided into three parts, each addressing a crucial aspect of developer empowerment. In Part I, Lawson delves into the cultural shift necessary for businesses to thrive in the 21st century. He discusses the historical context of software development and highlights the transformational impact of APIs (Application Programming Interfaces) on modern business models. Lawson advocates for a shift in mindset, encouraging business leaders to trust and empower developers as creative problem solvers.

Part II focuses on the symbiotic relationship between developers and business stakeholders. Lawson emphasizes the need for effective communication and collaboration between these two groups. He explores the concept of “code literacy” and explains why it is essential for non-technical professionals to understand the basics of software development to foster better teamwork and decision-making.

In Part III, Lawson explores the role of developers in driving innovation and creating customer-centric products. He discusses the principles of agile development, continuous delivery, and the importance of experimentation in building successful software products. Lawson also emphasizes the significance of feedback loops and user-centric design, urging organizations to prioritize customer feedback and iterate quickly.

Key Takeaways:

  • The Importance of Developers: Lawson highlights the crucial role that software developers play in driving innovation and digital transformation. He discusses how businesses can leverage the skills and expertise of developers to gain a competitive advantage in the 21st century.
  • Developer Empowerment: The author emphasizes the need for organizations to empower their developers and provide them with the tools, resources, and autonomy to excel. Lawson explores ways to create a developer-friendly environment that fosters creativity, collaboration, and productivity.
  • Building a Developer-Centric Culture: Ask Your Developer delves into the importance of cultivating a culture that values and supports developers. Lawson provides insights on how organizations can create an inclusive and supportive environment that attracts and retains top developer talent.
  • Collaboration between Business and Developers: The book explores the critical relationship between business leaders and developers. Lawson discusses strategies for effective communication, understanding the needs of developers, and aligning business goals with technical capabilities.
  • The Future of Software Development: Lawson offers insights into emerging trends and technologies that are shaping the future of software development. He discusses topics such as artificial intelligence, machine learning, cloud computing, and the impact they have on businesses and developers.
  • Developer-Driven Innovation: The author explores how empowering developers can lead to innovative solutions and new business opportunities. Lawson shares examples of companies that have successfully embraced developer-driven innovation and provides guidance on how organizations can foster a culture of experimentation and creativity.
  • Security and Ethics: Ask Your Developer addresses the importance of security and ethical considerations in software development. Lawson highlights the need for organizations to prioritize data privacy, cybersecurity, and ethical practices in order to build trust with customers and protect their reputation.
  • Continuous Learning and Growth: The book emphasizes the importance of continuous learning and personal growth for developers. Lawson discusses the value of investing in professional development, staying updated with industry trends, and fostering a learning mindset within the developer community.


“Ask Your Developer” is a compelling and highly relevant book that highlights the pivotal role of software developers in the success of modern businesses. Jeff Lawson’s extensive experience in the tech industry, coupled with his engaging storytelling style, makes this book an enjoyable and informative read.

The author’s emphasis on cultural transformation and the need for collaboration between business and technical teams resonates strongly. Lawson provides practical insights and actionable advice on fostering an environment where developers can thrive and contribute their full potential. His arguments are supported by real-world examples and case studies, which further reinforce the book’s credibility.

One of the book’s strengths is its ability to cater to both technical and non-technical readers. Lawson strikes a balance between explaining technical concepts in an accessible manner and offering valuable insights for business leaders. The inclusion of anecdotes from his own experiences adds authenticity and makes the content relatable.

However, some readers may find that the book occasionally delves into technical details that could be overwhelming for those with limited technical knowledge. Additionally, while the book extensively covers the importance of developers, it could have further explored the challenges organizations face in attracting and retaining top developer talent.

In conclusion, “Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century” is a compelling and informative book that emphasizes the pivotal role of software developers in driving business success. Jeff Lawson’s firsthand experiences and insights provide valuable lessons for leaders and decision-makers seeking to leverage the power of technology in the digital age. Whether you are a business executive, entrepreneur, or aspiring developer, this book offers practical advice and a fresh perspective on the intersection of technology and business.

Overall rating: 4.5/5

Alex Lim is a certified book reviewer and editor with over 10 years of experience in the publishing industry. He has reviewed hundreds of books for reputable magazines and websites, such as The New York Times, The Guardian, and Goodreads. Alex has a master’s degree in comparative literature from Harvard University and a PhD in literary criticism from Oxford University. He is also the author of several acclaimed books on literary theory and analysis, such as The Art of Reading and How to Write a Book Review. Alex lives in London, England with his wife and two children. You can contact him at [email protected] or follow him on Website | Twitter | Facebook

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