CEO Coaches
5 min read

CEO Coaches

Every world-class athlete has a coach: every tennis player at Wimbledon, every golfer in the PGA, and every hitter in the MLB. An athlete without a coach is incomplete.

So, why don't we think the same way about coaches for CEOs? Perhaps it's because of the idealized notion that strong leaders should be stoic and invulnerable. Perhaps it's because it’s harder to quantify the impact of coaching on the health of a company and the bottom line. Perhaps it's because we don't value mental health the same way we do physical? I'm not sure, but it is my experience that coaches are absolutely crucial for growth in all areas of life.

At the start of this year, I was squarely in the 'no-coach' camp. So, when our COO Luke broached the subject of me getting a coach, my initial reaction was negative. Things were going well, the business was growing, and people were happy. What could I learn that I couldn't teach myself?

However, Luke is perceptive and has an annoying habit of being right, so I asked around for someone who might be a good fit. I eventually got introduced to Matt Mochary, who has transformed both my business and life during our work together over the last three months.

Matt is a really interesting guy; he founded a company in the early 2000s and rode it through the boom. After he sold it, he produced and directed a couple of documentaries and then set up a charity to retrain ex-cons as truck drivers. Now he spends his days coaching CEOs simply for the joy of it.

Prior to meeting Matt, I had read a draft version of his book The Great CEO Within, which convinced me that he absolutely knew his stuff.

Matt's coaching methodology is to act as a shadow CEO one day a week, including sitting in on all the one-on-one meets with the senior team and on the leadership meeting. Matt's initial focus was on improving my personal productivity with a set of tools like GTD and a series of audits of my time and processes.. Once I was convinced of the benefit, he moved his focus to my senior team and the rest of the organization.

There's no way to do Matt's work justice in this short post, but I'll try to outline some of the main areas that his work has impacted Clearbit and me most.

One-on-One Feedback Cycle & Radical Candor

Prior to Matt, we had neither a structure nor a two-way feedback cycle in our one-on-ones. Matt showed us that creating a safe space for critical feedback and enforcing feedback cycles are fundamental aspects of a self-healing organization.

We now have structured one-on-ones with a section for two-way feedback. Managers make a commitment to their reports to give clear, candid feedback, and they expect critical feedback in return.

From now on, Clearbit will always be a safe place for critical feedback. The company has made a commitment to not only listen to but also to encourage critical feedback.

Accountability and Impeccable Agreements

Prior to Matt, agreements made between two people were not recorded and therefore were often forgotten. Agreements were also often handed down without getting buy-in from the other people involved.

Now, in our structured one-on-ones, managers and direct reports come up with their own agreements together. These agreements are specific, measurable, actionable, time-bound, and stored for everyone to see in Asana.

Conscious Leadership

Prior to Matt, we weren’t practicing Conscious Leadership. Sometimes we were more concerned with being right than with finding the truth.

We have now committed to the principles of Conscious Leadership. This means taking responsibility (but not blame), learning through curiosity, feeling all feelings, speaking candidly, eliminating gossip, practicing integrity, showing appreciation, engaging in play, and being open to “exploring the opposite.” To understand these principles further, I highly recommend reading 15 Commitments of Conscious Leadership.

We now give this book to all new employees during their on-boarding process, and we have begun related annual workshops.


Matt showed me how leading from a place of vulnerability rather than authority builds trust and loyalty. Prior to Matt, I tried to keep up a façade with the wider team and act as the stoic leader that is such a caricature in American business.

I now try to lead from a place of vulnerability and openness. I routinely share my deepest fears about the organization. It turns out that people cannot only handle the truth, but also respect it.  If you demonstrate trust in people, they will return it in abundance.

My hopes are that my new approach to leadership has begun to trickle down to create an atmosphere of greater trust, community, and shared purpose, and that this shift has helped my team understand and trust me more individually, too.


While we have practiced some degree of transparency (investor updates, internal finances, etc), Matt showed us we can always go further to engender additional trust. Although we do not make performance and compensation transparent, we want to push the envelope to make as much of the company as transparent as possible.

Matt guided us to make public more of the leadership meeting, including the updates from the various departments in the org.

Conflict Resolution

At any organization, areas of conflict, if not addressed, lead to brewing resentment and a lack of trust. Resolving conflicts is both an art and a science.

Matt showed me that the key aspect to conflict resolution is to make sure people know they've been heard and understood. As long as people deeply believe you are really listening to them and have their best interests at heart, they will commit to a decision (even if they don't necessarily agree with it).

The book Non-violent Communication has been exceptionally useful in this regard. Still, I've found that this skill is best learnt by watching an expert (i.e. Matt) in practice.

Objectives and Key Results (OKRs) and Alignment

Prior to Matt, we had no system for tracking company progress toward goals and aligning team and individual goals with company goals. We kept track of product progress and revenue goals, but not at a granular level.

With Matt’s help, we implemented OKRs org-wide to ensure the company is aligned and progress can be tracked. We come up with company-wide OKRs every quarter, after which each department determines their own related OKRs, and then each individual does the same.

This valuable process enables us to spot and address misalignment and other issues immediately. We track progress week-by-week in our one-on-ones using a traffic light doc - here's a good example of our process. This process makes it simple to see improvements (or degradations) over time.

Get a Coach!

So, why have a coach?  A coach can help:

  • Identify the areas where an investment of time and effort will bring the executive the most performance improvement.
  • Set a plan for making that improvement, which is hopefully informed by the coach’s experience of what has worked for other people in a similar situation.
  • Hold you accountable to that plan.

Getting a coach was one of the best things that has happened both to my business and personal life. Matt has given us the tools needed to scale Clearbit into an incredible organization. If you're lucky enough to get some of Matt's time, I urge you to take it. Otherwise, I suggest reading the resources above and searching for someone who's right for you.

Thanks to Abby Reider for editing.

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