Transformative Books We Read Together as a Leadership Team

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Incorporating Reading Into Our Planning Meetings

At the start of each quarter, the four Barrel partners meet for an all-day planning meeting. The format of this meeting used to focus heavily on identifying various issues in the business and putting our heads together to see if we could resolve them. The goal of each planning meeting was to come away with a solid slate of key initiatives to accomplish over the next 90 days.

Five years ago, as a supplement to the meeting, we began incorporating a reading assignment. I personally began to curate a book for each quarter and asked the partners to read and come prepared to discuss in detail. We allotted an hour and took turns sharing our takeaways. The activity initially felt like a nice addition and a way to introduce fresh new ideas and vocabulary to our discourse.

Over time, as we kept at it, the books became more and more central to the experience of the planning meeting. The lessons and ideas we took away seemed to open up and sync our perspectives, allowing us to examine challenges and opportunities in the same ways.

Over the past few quarters, we decided to experiment further with our all-day meeting format and made the reading more central to the experience. Rather than spending hours rehashing issues that were already being worked on anyway, we committed to making our planning meetings more about ideas, discovery, and long-term thinking.

The Books

I went back and compiled the list of all the books we’ve read together in the past five years. Seeing them in chronological order, it’s interesting to see how we’ve expanded our thinking as a leadership team influenced by not only the ideas in these books but also the accumulation and interaction of the ideas over time.

Below are the list of books and some notes on how they impacted us.

1. Traction: Get a Grip on Your Business by Gino Wickman

This was our introduction to the Entrepreneurial Operating System (EOS), which was a helpful framework for getting us to work “on” the business instead of in it. The main takeaway for us was to embrace the power of systems and processes along with a cadence of weekly, quarterly, and annual accountability measures to make progress on initiatives while have a clear eye on progress and goals.

As with many SMB operators who’ve embraced EOS, we found a great deal of value and continue to incorporate various aspects of the framework. We’ve opted not to be gung-ho EOS purists and have not engaged with an integrator to “properly” implement the full system, so we don’t pretend to be fully committed EOS-powered business, but nonetheless, reading this book together was a good first step in helping us see the benefits of trying on different operator frameworks.

2. The Business of Expertise by David C. Baker

We’ve followed the writings of creative entrepreneurship consultant David C. Baker for nearly a decade and have found his advice and ideas generally helpful for our agency business. The Business of Expertise didn’t surface any ground-breaking new ideas from Baker but was a nicely packaged volume of reinforcing lessons on the value of positioning and how firms must commit to becoming experts if they are to remain competitive and relevant.

At the time we read this book, we were still struggling to properly position ourselves. Our attempts to take our existing client roster and create positioning around them (e.g. “the collection of these clients feels like healthy lifestyle“) was ultimately unsuccessful. In hindsight, it was the fear of turning work away that kept us from embracing a more effective position. However, the concepts in the book remained very much top of mind and would come in handy when we finally faced overcame our fears.

3. Radical Candor by Kim Scott

This book was a popular management book at the time we read it, and the theme of giving and receiving feedback resonated with us. We realized that we were often fearful of receiving critical feedback from team members. Without being fully conscious of it, we often shut down avenues for people to surface or highlight improvement areas and blind spots.

In the ensuing years, we’ve continued to reflect on the importance of feedback and explored ways to encourage feedback communication throughout the organization. It’s still a daily challenge and we are far from figuring it out as a company, but I know the partners and I are aligned in our view that all feedback, negative or positive, is helpful information that can aid us in being better leaders.

4. The Fifth Discipline by Peter Senge

What initially felt like a dense and difficult read eventually turned into a text that I’ve come back to over and over again, mining it for new lessons and reminders about the challenges of building a true learning organization. I’ve written extensively about The Fifth Discipline on this blog and have recommended and given out countless copies of the book.

Of the many lessons from the book, the concept of personal mastery–living a life of vision and purpose while embracing a relentless desire to continue learning and growing–has been a life-changing insight for me.

Organizations learn only through individuals who learn. Individual learning does not guarantee organizational learning. But without it no organizational learning occurs.”

As Barrel’s leaders, our best bet is to focus on ourselves as individuals and model the learning we’d love to see in the organization.

5. Managing The Professional Service Firm by David H. Maister

This book opened our eyes to the fact that there’s much to learn from studying businesses beyond our spheres of digital, creative, and marketing agencies. Law firms, investment banks, consulting firms, accounting firms, and countless other professional service firms operate with very similar business models and have faced the same challenges of business development and talent management that we have. The tips and advice in the book were incredibly practical and useful, some that we quickly implemented and others that we hope to get around to putting in place. Check out my blog post on “The Importance of Marketing to Existing Clients” to get a sense of the lessons offered up in this book.

6. Trusted Advisor by David H. Maister

Another book from Maister, Trusted Advisor is about establishing, nurturing, and deepening relationships with clients and understanding the dynamics at play in an authentic, mutually beneficial client-advisor relationship.

Over the years, we’ve come to value the relationships we develop with our clients and have tried our best to cultivate a culture where we strive for win-win situations and honest conversations with clients. This book has been helpful in providing us with vocabulary to talk more fluently about developing stronger client relationships. For example: the need to be great active listeners who ask insightful questions and also remember the clients’ answers; the courage to have honest conversations even if they’re about unpleasant realities; and avoiding self-orientation, which includes the need to sound smart, to have the last word, and to always be right.

7. Changing on the Job: Developing Leaders for a Complex World by Jennifer Garvey Berger

We were introduced to Adult Development Theory, which outlines different “forms of mind” that adults inhabit in the way we make sense of the world and how we interact with others. The theory furnished us with new ways to think about our interactions with team members and to become more aware of the different ways people interpret and process communications and situations.


A table from Changing on the Job about how the different “forms of mind” have very different perspectives and how they make sense of authority.

8. The E-Myth Chief Financial Officer: Why Most Small Businesses Run Out of Money and What to Do About It by Michael Gerber and Fred Parrish

Books like E-Myth CFO, which goes into the nuts and bolts of running a small business with easy-to-understand descriptions of things like process designs, setting metrics, and managing cash flow are great periodic refreshers to help us re-align on the fundamentals of business and to appreciate the simplicity of the game we play. I summarized the key lessons I took away in this blog post.

9. Work Rules!: Insights from Inside Google That Will Transform How You Live and Lead by Laszlo Block

It was inspiring to read detailed accounts of Google’s scaled up people operations, especially the way they put an emphasis in recruitment and hiring of great talent. As a small business, it’s sometimes hard to fathom the resources that a Google puts into their hiring process, but nonetheless, we took away a number of good lessons from the book including team-wide surveys to get a pulse on the culture, splitting performance evaluation and people development, and building more structure to support collaborative input from team members during the recruitment process.

10. Getting Things Done: The Art of Stress-Free Productivity by David Allen

We fancy ourselves to be highly capable and productive workers, but a book like Getting Things Done is a humbling reminder that there’s always room for improvement. Although we may not have become hardcore GTD converts, there were many enlightening lessons around weekly habits, organizing tasks, leveraging checklists, and applying the framework to different aspects of life. As with other books, we were introduced to different perspective and new language in thinking about how the mind works, how we perceive our work, and how different systems and structures can make things feel more seamless. Here’s my blog post where I shared some of the most impactful takeaways.

11. Les Schwab Pride in Performance: Keep It Going by Les Schwab

We thoroughly enjoyed the highly personal and inspiring autobiography of legendary tire chain shop founder Les Schwab. I had to source the books from various used book sellers since they stopped printing years ago. Les Schwab’s straightforward prose and endless wisdom around customer service and people management made for a quick read and fun discussion. We still sometimes recite Schwab’s common phrase “life is hard” whenever we find ourselves in a well of self-pity and need to shake ourselves out of it.

12. The Road Less Stupid: Advice from the Chairman of the Board by Keith J. Cunningham

Cunningham’s book is chock-full of practical advice and tips for small business operators, much like the E-Myth CFO mentioned above. The most significant takeaway for us was the concept of “Thinking Time” and the need to give ourselves space to ponder tough questions about the business ranging from how we treat our customers to how we instill a culture of accountability. Building the muscle to explore such questions in a proactive manner versus having to deal with issues reactively was an important lesson that we don’t need to be beholden to circumstances and can largely chart our own path of creating something great.

13. Playing With Movement: How to Explore the Many Dimensions of Physical Health and Performance by Todd Hargrove

Sometimes the best way to understand concepts is to develop analogies. This is one of the reasons I love team sports so much because of the parallels with business and running organizations. Reading Playing with Movement, we were able to dive deeper into the concept of self-organizing complex systems while talking about body parts and things that were familiar to us from personal experiences–back pains, injuries, and exercise. We spent our book discussion time drawing out different analogies to the business, talking about “stressors” that our team felt, the futility of top-down corrective treatments, and the importance of embracing “play” as a way to allow capacity-building.

14. What is Strategy? by Michael Porter

This was an essay that was part of Harvard Business Review’s 10 Must Reads collection under Strategy. We were inspired by the “Activity Map” that Porter discusses in his essay to show how businesses can benefit from clearly defining their positioning while accepting trade-offs. We each presented our respective Activity Maps on what Barrel’s future could be in terms of our services offering. It was a highly engaging exercise that prompted deeper discussions and some important decisions in the following weeks and months around our positioning.

15. An Everyone Culture by Robert Kegan and Lisa Laskow Lahey

We were introduced to the concept of a Deliberately Developmental Organization and the possibilities of building a culture that challenges people to identify and work on their weaknesses, openly provide each other with feedback, and be unafraid to bring their full selves to work every day. I wrote about this in my post “Desired Future State for Our Culture”.

The book also prompted us to engage in the Immunity to Change exercise, where we each came prepared to openly and deeply share an improvement area while uncovering and admitting our fears. This was a powerful experience that expanded our ability to be vulnerable with each other and to deepen our understanding of our respective wants and fears.

16. The Path of Least Resistance by Robert Fritz

The right book at the right time is such a powerful combination. If we had read this book even a year ago, I don’t think we would have fully appreciated its message. Luckily for us, the growth of the business and the expansion of our leadership team has enabled the partners to focus more on long-term vision, for which this book had some really compelling ideas.

The book inspired a visioning exercise for the planning meeting. I asked the partners to come prepared with answers to 3 scenarios that had them thinking about the future 12 months from today. Sharing these visions was a great deal of fun and incredibly energizing.

Barrel partner Lucas published a blog post summarizing some of his key takeaways from the book.

17. Leadership and Self-Deception: Getting Out of the Box by The Arbinger Institute

This book introduces the concept of being inside or outside “the box” which is really about our ability to see other people as human beings with feelings, aspirations, challenges, etc. When we are “inside the box”, we default to prioritizing our own agenda and perceptions, treating others as objects while justifying our behavior by placing blame on others. Being “outside the box” is about having greater self-awareness in our interactions with others, to check ourselves on feelings of resentment, disappointment, or frustration, and to develop a keener sense of empathy.

As part of our discussions, we each shared a couple of personal “in the box” moments from our past, ranging from our interactions with Barrel team members as well as family and close friends. It was a powerful session with a great deal of self-reflection and vulnerability.

18. The Motive by Patrick M. Lencioni

In this book, we read about reward-centered leadership vs. responsibility-centered leadership and how to avoid falling into the trap of being reward-centered.

I wrote a blog post that summarizes the takeaways from this book. For our discussions, we ranked what we felt were the most challenging behaviors of a responsibility-centered leader going off of the five traits outlined by the author. The two behaviors that landed at the top were: 1) Having difficult and uncomfortable conversation and 2) communicating constantly and repetitively to employees.

We’ve come to really push each other to improve in both of these areas, celebrating our willingness to take on difficult conversations on a weekly basis and also encouraging each other to repeat and reiterate certain messages and themes to the team regularly.

19. The Joy of Selling by Steve Chandler

This small book was a treasure trove of memorable lessons. I published a blog post sharing some key takeaways from the book. What we’ve all come to learn over time is that no matter our day-to-day role, as partners in the business, selling is something we have to be comfortable doing on a regular basis. Either we’re selling our services to clients, selling our culture to recruits, or selling our vision to employees–the ability to connect, inspire, excite, and close is invaluable.

20. The Cold Start Problem: How to Start and Scale Network Effects by Andrew Chen

We had fun talking about the stories of well-known startups such as Uber, Tinder, and Airbnb and how they were able to solve their initial “cold start” with focused growth experiments that, over time, led to greater adoption and global scale. I chose this book because even though we are not a VC-backed startup looking to develop a popular product, understanding the concepts and being familiar with these stories can be very valuable for us in our own discussions with clients and prospects about their businesses.

21. The 7 Habits of Highly Effective People by Stephen R. Covey

I had read this book nearly a decade earlier but did not absorb as much at the time due to immaturity and perhaps weaker reading comprehension. Reading and discussing this book as a group, it was clear to us why 7 Habits is one of the most popular and celebrated personal development books every written. In some respects, you could argue that 7 Habits and Dale Carnegie’s How to Win Friends and Influence People (see my blog post on this book) are the two classics from which all self-help and personal development books over the past 50 years have been derived from.

We spent 3+ hours talking about this book and shared dozens of quotes and concepts that inspired us. Not long after our discussion, I wrote a blog post on the concept of the “emotional bank account” and applied it to running an agency business.

22. Becoming Trader Joe: How I Did Business My Way and Still Beat the Big Guys by Joe Coulombe and Patty Civalleri

The origin story of Trader Joe by its founder was entertaining and contained a lot of sage business advice as well as tidbits about the popular grocery chain. We had fun stretching some of the examples (e.g. virtual distribution system, pricing products, developing private label lines, unorthodox radio advertising, etc.) and trying to come up with equivalent approaches with our agency business. What was sad is the regret Coulombe expresses in having sold Trader Joe’s and ultimately not having bet on himself to ride out the economic and business challenges of the early 1980s. It made me think about Barrel, Barrel Holdings, and my continuing desire to want to keep going and not sell.

The Joys of Learning Together

The beautiful thing about having read the same texts together is that it creates a foundation for shared language and perspectives. While we may have our own slightly varied interpretations, the shared act of reading in the same order and having time to discuss what we’ve read has helped us to develop an intellectual bond that keeps on paying dividends in our daily interactions or during moments when we have to make big decisions together.

Every book is an infusion of ideas, concepts, and learnings that enrich the conversations among the partners. It’s neat to hear each other trying to describe situations or explain approaches using terminology and phrases that we picked up from our reading. Over time, these learnings continue to layer on and in some ways compound into greater insights and pattern recognition, helping us to see and anticipate things that we never would have imagined just a few years ago.

We remind ourselves every now and then that regardless of the financial outcome of Barrel or the prestige that growing the business may bring, the most important thing is to appreciate and embrace the journey itself. The learning, the creative process, the relationships, and the challenges. Reading books together, as simple as the activity may be, has been an enhancing agent, making the journey all the more rewarding and fulfilling.

Note: Originally published July 12, 2021. Updated with new books and edits on July 10, 2022.

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