Individual Transformation & Adaptability with Matthew E. May

Matthew E. May is a distinguished six-time author, esteemed speaker, and currently holds the pivotal role of Senior Strategy Advisor at Insight Partners, a global venture capital and private equity firm renowned for investing in high-growth technology companies spearheading transformation in their respective industries.With a professional journey spanning over three decades, Matt has become a venerated figure in the realm of transformative strategy, innovation, and lean initiatives.His latest contribution co-authored with Pablo Dominguez , “What a Unicorn Knows: How Leading Entrepreneurs Use Lean Principles to Drive Sustainable Growth,” published in early 2023. He was gracious enough to speak to me on my podcast Studio A3R and I invited my Rochester Institute of Technology School of Individualized Studies’ students to both read the book and ask him questions. Here is the second installment of what we learned.

Student Question: There are those who leap into action and those who tend to overthink. How do you get someone who overthinks to take action?

I wrote a previous book called “Winning the Brain Game.” It’s interesting you mention the leap to action versus inaction and overthinking. These are two major thinking flaws I’ve observed. In any ideation session, like a lean process improvement or a strategy design session, these two extremes are evident. The challenge is balancing them. I use exercises to show how we often act too quickly or overthink, making the problem worse. For me, problem-solving has three steps:

• Pain-Storming (identifying the problem)
• Frame-Storming (framing the problem)
• Brain-Storming (exploring ideas for resolution)

This approach offers a balance between identifying the problem and finding solutions. Traditional brainstorming tends to produce conventional ideas, so by introducing “Frame-Storming,” you frame the problem effectively. This ensures the solutions are both useful and novel.

Student Question: Given your extensive experience in writing books and managing numerous projects, how do you maintain focus and motivation while juggling all these responsibilities?

I’d love to say I had a detailed career plan, but in reality, a lot of it has been due to serendipity, being in the right place at the right time, and happy accidents. An important principle I follow is the law of subtraction, summarized as “Creativity thrives under intelligent constraints.” In business writing, there are always deadlines. When you write a business book, typically, you submit a proposal first, which is like a basic marketing or business plan for the book. I usually pitch a one to three-page concept. Once it’s accepted, a manuscript delivery date is set. For example, for “What a Unicorn Knows,” I had six months to deliver a manuscript with six chapters. Based on experience, I know my word production rate and editing process.

What keeps me motivated? The constraint of a deadline. If I don’t meet it, I’m letting down my editor and affecting their work, which I don’t want. It’s about discipline. I can’t write during work hours, so I write in the gaps of my day. I took inspiration from Toyota, where factory workers implement many little ideas annually, often during breaks or outside regular hours. For me, my prime writing time is from 4:30 to 7 in the morning. By 7 am, the household activities start, and distractions emerge. I then review and edit my writing late at night. It’s not uncommon for me to question my earlier writing and rewrite the next morning. That’s how I stay focused and meet my commitments.

Student Question: What insights from your books do you find most valuable, and how can readers apply them to their personal lives?

I’ve always believed in the power of strategy, but it wasn’t until later in my life that I began to apply it personally. Early in my career, many milestones seemed like happy accidents, from landing a job with Toyota to unintentionally publishing my first book. These unexpected twists made me realize that relying solely on chance might not be the best long-term approach. My education at Wharton introduced me to strategy, but I found it too analytical, too left-brained. I’ve always been more intuitive, more right-brained. Then I met Roger Martin from the University of Toronto’s Rotman School of Business. He reshaped my understanding of strategy with his “Playing to Win” framework. Roger taught me that strategy is about making integrated choices that position you for success. This isn’t just applicable to business but to personal life as well. It’s about choosing a path that aligns with your goals, whether in your career or personal aspirations.

You can listen to both Matthew E. May programs anywhere you listen to your podcasts. Our most popular channels are Apple & Spreaker.

In case you missed it, here is What the Unicorn Knows & Organizational & Organizational Change with Matthew E. May.