Matt Cain is the CEO of Couchbase, a data management platform based in Mountain View, California. He read Michael Smerklo’s E2E post on time management and used it to construct an exercise for his leadership team during his company’s most recent offsite. Michael’s piece focused on using an Eisenhower Matrix to help CEOs learn to manage their time more wisely. Matt walks us through how he turned this thought leadership piece into actual company change.

How do you approach thought leadership exercises with your team?

I am constantly in pursuit of new approaches that can help us get better as a team and as a company. The timing of this particular exercise worked well because we were in the midst of our annual planning process – tackling important issues and building a new multi-year plan. I’m a big fan of multi-day leadership offsites because they give us the time and space to attack important issues in a meaningful way and go deep. We wanted to ensure that we were aligned on what really mattered to us, and how best we could achieve success. We are fortunate to be growing and scaling very rapidly, but ensuring we are tackling priorities in an aligned and efficient way is crucial. Michael’s framework was a simple, but creative way to start that exercise – exploring my personal priorities, initiatives, strengths and weaknesses. It was a really convenient way to allow me to personally demonstrate and model vulnerability while discussing what we want to accomplish as a group.

Matt Cain, CEO of Couchbase. Learn more about Matt below.

How did you use Michael’s thought leadership piece to create an actual team-building exercise?

I spent time ahead of the session preparing what I thought were our most important priorities, and then filled out the 2×2 matrix as Michael suggested in his article. At our offsite, I walked my team through the priority and matrix concept (pictured right). I then asked each of them to fill it out on my behalf and made it clear they would do so without seeing my draft. I explained we would then compare their versions to mine. Some people had worked with me for a long time, while others had not, but regardless the exercise established a trusting environment where we could have this conversation. Getting a level of vulnerability in the corporate arena where you can say: “Here’s something that I ‘suck’ at and here are some things I think I’m good at,” is not commonplace. Asking others you work with to tell you what they think you might be good at or “suck” at is even more rare. You can only enforce that type of dialogue by demonstrating a true willingness to take feedback and get better.

The Eisenhower Matrix from Michael's article.

What was something that surprised you about the exercise?

What really jumped out at me was the nuance behind the areas of perceived disconnect. As an example, during our initial review, several members told me that they thought I was good at networking, where I had it on my dislike list. I strive to build and maintain authentic relationships and connect with and help people, but do not enjoy networking for networking’s sake. My team assumed I enjoyed it because they perceived me to be good at it. In another example, one member of my team said to me that he thought I was really good at micromanaging, which he thought was an important skill, but yet another thing I don’t particularly enjoy. Even the term initially bothered me. We realized that I can be effective at diving into a function or issue in the organization and quickly get at the detail that matters to drive to resolution, which I agree is important. But we also realized I need to be encouraged to do so by my team because it isn’t the my first impulse. My natural instinct might not be aligned to what’s needed in a particular situation, so I have to rely on my team for help. But they need to first understand what those natural instincts are. No one can fix problems they don’t know about. We went on to explore triggers, histories, personality traits, and several other factors that brought us closer together.

What was something both you and members of your team agreed you struggled with?

Process and process creation. We now commonly refer to that as “lower left” activities for me and we have fun with that (them more than me sometimes!). Fortunately, we have process experts and operators within the team that take responsibility in these areas. It’s incredibly empowering to drive people to their “zones of genius” and remove things and are better done by others. Self-awareness emerges, but so too does insight into how leaders throughout the organization need to think about building diverse teams: thinking, experiences, perspectives, strengths, etc.

“You can only enforce that type of dialogue by demonstrating a true willingness to take feedback and get better.”

How do you make these findings actionable in the office?

After we filled out and discussed our findings of the matrix, we labeled each line item as either green or red. Green meant I or the team should allocate more time to these activities. Red meant we want to spend less time. In addition, we intend to use the matrix for all of my leaders, allowing them to go through the exercise and understand how they are over or underexposed in their roles. This will help them be their most effective selves and build the best teams they can.

What advice would you give rising CEOs about interesting thought leadership content they come across or advice they receive?

I’ve been studying leadership and team dynamics – and managing self-awareness for constant improvement – for as long as I can remember. Rooms in my house are covered in leadership and culture books from people I admire. My feedback on leadership is to follow your passion and to constantly be in pursuit of self-improvement. The best performers in the world, regardless of their profession (music, sports, business, etc.) tend to have the most coaches and are the ones that are always looking to get better. The way I pick up resources to help with self-improvement varies a lot over time: sometimes I’m into a book, sometimes I’m into retreats, other times I’m on a long-haul flight and get some direct insights just from being unplugged for hours. There’s no one model; do what works for you, just like working out. Find your recipe, stay committed, and follow your passion.

“My feedback on leadership is to follow your passion and to constantly be in pursuit of self-improvement.”

About Matt Cain

Matt has nearly two decades of experience leading global organizations, he is currently the President and Chief Executive Officer of data management platform Couchbase. Prior to Couchbase, Matt was President of Worldwide Field Operations for Veritas Technologies LLC after serving as Chief Product Officer for Veritas’ $2.5B business. During his tenure, he revitalized the company strategy, increased operational efficiency, delivered growth across the portfolio, and was instrumental in the separation of Veritas from Symantec. Matt previously held a variety of senior leadership positions at Symantec Corporation and Cisco Systems. He holds a bachelor’s degree in Electrical Engineering from Northwestern University and a master’s degree in Business Administration from the Stanford Graduate School of Business.

E2E stands for “entrepreneur to entrepreneur”