Lessons on Relationships from The Great CEO Within


June 2020

last updated:

100 N Main St, Memphis, United States. Photo by Khara Woods.

Building companies, like everything in life, is about connecting with people. Across recruiting teams, selling to customers, pitching to investors, and pretty much any other function, relationships make and break companies. The Great CEO Within by Matt Mochary [1] is already a fantastic compilation of tactical advice around these concrete scenarios, so I won’t get into them here. What I’m interested in is what we can learn about human relationships by applying the book’s apparently startup-specific advice into any situation where we interact with people. In particular, there are three concepts Matt touches on that are worth generalizing and expanding here.

1. Ask questions, listen, and summarize back

When people feel distrust or dislike, it’s usually because they don’t feel heard.” The inverse is true as well. Throughout the book, Matt compiles many tips to leverage this insight [2], which I’d summarize in three steps to build trust and empathy:

  1. Be genuinely interested in the other person, and show this by asking questions - about them (family, work, hobbies, story, etc) or the specific issue at hand.
  2. Actually listen to them. Be present and focused.
  3. Repeat back a summary of what they said. This is the most important step, as it makes it crystal clear that you are listening. Do this even if you don’t agree with them, they’ll be more likely to listen to you in return.

2. Don't build relationships only when you need them

By the time you need a relationship, it’s likely too late to build it. This is not just true in goal-oriented situations like raising money from investors or selling your newest product to a customer, but in profound ones like having close friends to lean on during difficult times. Rushing relationships will be an uphill battle, or worse a no go, so proactively put in the time and effort to nurture genuine bonds even when there is nothing in it for you.

3. Embrace deliberate systems

Many of us feel that relationships must be organic and effortless for them to be genuine. We are wrong. Relying on chance encounters, perfect memories, and random calendar openings rarely leads to profound personal and professional connections. It takes humility to recognize that systems, tools, and proactive work make a big difference. These are some that I found especially relevant for me:

  • Write it down. After talking with someone, write down as much info as you can remember, and refer back to it in the next meeting. They’ll appreciate that you cared about the details of their life, and you’ll personally feel more connected going into the conversation, which will inevitably shine through.
  • Introduce cadence. Make a goal to reconnect with someone and meet someone new every week. Have an explicit document of this to look back on and keep yourself accountable as you fill it out every week.
  • Calendarize it. You will never have time to connect with people if you leave it to chance. Block out recurring slots for this in your calendar, and respect them. This will also help build cadence.
  • Request intros. When you talk to someone close, ask them for 2-3 intros to whatever type of person you’re looking to connect with (people to build with, investors, specific engineers, Age of Empires players, etc). Build relationships with these people, and eventually repeat the process with them. This will help you hit the goal of meeting people every week.

Life is always about the people. There aren't many things we can invest time and effort in with such a high return on investment than improving how we relate with those around us. These simple concepts: building empathy by listening and repeating, being proactive, and embracing systems have made a huge difference for me not just professionally, but personally. Give them a shot, you won’t regret it.


[1] The Great CEO Within by Matt Mochary is a must-read in general for entrepreneurs, managers, and yes, CEOs. What's great about it is that it’s heavily opinionated based on Matt’s coaching experience, and while you might not agree with every argument, the result is an incredibly useful and practical handbook that isn't afraid to go beyond broad concepts into concrete and detailed practices

[2] Some of the techniques that Matt lists come from The 7 Habits of Highly Effective People, Nonviolent Communication, and Never Split the Difference.

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