Coaching for Early Stage Founders

Being a founder or executive can be lonely.  Because you are responsible for many people, there is a natural filter you inevitably turn on when you communicate with your team.

In order to avoid panicking the rest of your team, you believe there are problems you have to wrestle with by yourself.  And maybe you have cofounders— but they also have problems to deal with in their own departments, and therefore they are stretched thin already.

My coaching approach says you shouldn’t have to wrestle with these problems alone. I now serve as your equal thought partner to help you unpack your most seemingly-impossible dilemmas.

By working in partnership, I agree to challenge you to take the problems you have been handed and determine the best course of steps to proactively solve them.  And you agree to do the work, complete the actions you say you’ll do, and be open to thinking in patterns that differ from your normal way of problem-solving.

Most of the time, the problems we face today are not new. I bring a unique coaching perspective not only as a former COO and experienced operator, but as the former Chief of Staff to Matt Mochary.

During my time as a CoS, I was privileged to sit in on the majority of Matt’s coaching sessions with companies like Canva, Loom, Vendr, Brex, Coinbase, and many more. As a result, I have had the chance to pattern-match, study the anatomy of what makes a company function smoothly, and which solutions work (and which that don’t.)

During our sessions, when appropriate, I share the lessons and frameworks I learned in an anonymized way while observing these golden nuggets of coaching sessions. This is because I think it’s easier for you to learn from others’ mistakes, rather than re-making the same mistakes they made already.

By working together, you remain committed to listening to the stories I share with you with an open mind. You, of course, still get to consider whether these stories are applicable to you or not.

I believe the best way for folks to improve is by exercising their action muscle. The more intentional you are as a CEO, the better you will perform - even if the action you decide to take is to “take no action.” You methodically decided to do this, rather than simply letting it happen.

In our coaching sessions, the question I will ask you most frequently is, “Is there an action item here?” I feel borderline religious about this question to the point where I have a post-it note on my laptop with this question (and have a feeling you’ll begin to ask yourself - and others around you - this question constantly.)

You can read more about why next actions are so important here in my write up on bias towards action.

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I will ask you during our coaching session to share specific examples of issues you are working through. But during that process, I will also help you identify themes that occur in your life. I believe that many of the problems we unpack as CEOs and leaders are symptoms rather than the root problem. It’s not enough to just cover issues: we should be holistic in addressing problems from a first-principles perspective.

For example, if you are unpacking a problem around conflict between team members, I would be remiss if I didn’t ask you about the company culture, about you as a CEO and the example you set for your team, and how you might behave outside of your company. Like the various muscles in your body, your behavior is also all interconnected.

Therefore, we will diagnose the actual issue together, staying open-minded and curious on what it might be, and peel back the figurative layers of the onion together until we arrive to the fundamental root of the problem.

I take pride in always showing up to all of our coaching sessions prepared, and expect you to do the same. Our time is best used when we are both ready to jump in.

Additionally, as an operator, I believe in flexible structure. There are some coaches who work better in an ad hoc format without a real agenda; there are others who love having the same structure over and over again to create stability and predictability. I know coaches who use both formats, and respect them and their methods.

When we coach together, we have a structure by which we’ll unpack the agenda. You’ll also have your dedicated coaching hub, so you can add in any issues and topics you want to cover before our session begins. I think there is power in documentation, so you’ll never have to think, “That session was great — … but what did we cover? I already forget.” Everything we discuss, go over, and unpack will be available to you, along with all the write-ups and action items I suggest.