CEO Coaching: What is it, How does it work and Why do the best CEO’s have one?

I’m commonly put in the “CEO Coach” bucket. I get it. I’ve had the chance to work alongside great CEOs who’ve had their name up in lights. Naturally, I’m labeled the CEO Coach by association.

Let me throw a wild statement out there, which might seem in opposition to everything I do: CEO Coaching is broken. At the bare minimum, it’s broken in the way most people think about it.

What do most people think CEO coaching is?

Most people think CEO Coaching as a private, safe place for CEOs to come, share their struggles, get all the answers and come back “from the mountain top” (so to speak) and share the infinite wisdom they gained. It sounds nice, but that doesn’t work.

CEO Coaching should be more like seeing the CEO in the game.

Sports clichés are overdone but imagine for a second that Tom Brady, arguably the greatest quarterback of all time, has a QB Coach (he actually has many different coaches and trainers).

Imagine if Tom Brady was to go to his QB Coach, share his struggles (“I want more touchdowns!”), get all the answers, and come back to the team to share all of the infinite wisdom he gained. Even at first brush, it’s ridiculous. But let’s double-click on the analogy:

Think about all the other variables the QB Coach missed out on in this scenario: did the QB Coach even watch the game? How did Tom react to the defense? Did he miss wide-open receivers? Was the game plan playing to the strengths of the team? The list goes on and on.

However, many CEO coaches only get the story the CEO brings. They didn’t even watch the CEO in the game. How could the CEO Coach possibly know what to say – beyond some platitudes – without seeing the CEO in the game?

Most CEO Coaches never see the CEO in the game.

The truth is, the game is where the coaching opportunities happen. That’s why I focus on watching the leaders in the game.

Who uses a CEO coach and why don’t more?

Jeff Bezos uses a CEO coach. Google’s Larry Page uses a CEO coach. Even Steve Jobs used a coach. Studies prove there’s a relationship between high performance and coaching.

However, two-thirds of CEOs don’t use a coach but close to 100% would be receptive to using a CEO Coach. Why don’t more CEOs use a CEO coach? I’ll explain more in this post.

Why do CEOs use a coach?

Leaders use CEO coaches for a variety of reasons. I’ve been used as a CEO coach for many purposes: a sounding board, a trusted confidant, a sanity check or even a marriage counselor.

One CEO told me:
“You’re equal parts mentor, peer and armchair psychiatrist.”

Many CEOs use a CEO coach over the course of their career. It shouldn’t surprise you – do athletes accomplish success without great coaches? No athlete would be embarrassed they use a coach, yet many CEOs believe they don’t need a coach of their own.

What does a CEO Coach Do?

All CEOs make promises and set goals. They make promises to their investors, team, customers, and family. They set goals to help deliver on those promises.

The best CEO coaches help CEOs keep their promises and meet their goals. Furthermore, it helps if the CEO coach has walked a mile in the CEO’s shoes before.

Promises and goals are different for everyone. The steps required to take a company public are very different from the steps needed to transition the business to a family member or rapidly scale the business.

Any good CEO coach will help the CEO (and others in the business – more on that in a moment) around the results of the business.

First, CEO Coaches need to build a solid foundation.

How does effective CEO Coaching Work?

The only way to be an effective CEO or executive coach is by developing trust with the CEO. Without it, results suffer. I start every CEO Coaching relationship with the highly evolved Leadership + Growth Assessment. It’s the process I’ve developed working with over 11,000 leaders across a variety of sectors and sizes.

Many CEO coaches will simply start a relationship with the CEO (some without even meeting the CEO – they do everything via video calls or phone calls). However, I’ve found that to build the trust, context is important.

That’s why I spend several days interviewing key stakeholders of a business before I spend any meaningful time with the CEO. I’ve found the ideas and solutions to keep the promises and meet the goals of the business are almost always within the business already. It’s the leadership’s job to unlock that potential. It’s my job as the CEO Coach to help the leadership unlock that potential within themselves and within the business.

After I interview key stakeholders, I prepare myself to spend up to two full days with the CEO – typically offsite and away from the distraction of the office. I let him or her see their people, their leadership style, and their company through my eyes. It’s an intense time with a ton of questions, pressure-testing, and deep thinking.

During the time together, the CEO and I agree on a handful of issues (3-5, not 200) that are standing in the way of them keeping their promises and meeting their goals. These issues are typically strategic and are either being under-invested in or are getting in the way of success. We spend time creating the commitment and actionable plan needed to drive results and get the desired outcomes.

Successful CEO coaching

At the end of our time together, it’s incredibly clear. You either change your goals, or you implement the plan we developed together. It’s that simple. And that complex.

This intense, but liberating, session becomes the Six Month plan for CEO coaching. This brings me to the next key point.

Key Areas When Coaching CEOs

There are four main areas I focus on when coaching a CEO: Developing a World-Class CEO, People + Culture, Execution Insurance and being a Canary in the Coal Mine. Let me explain more about the key areas where I coach CEOs.

Developing a World-Class CEO

This is the most obvious area of coaching. The main goal is to ensure the CEO is ready to Scale. Tactically, this all depends on the CEO and their strengths and weaknesses. The quickest way to ensure the CEO is ready to scale is to complete a CEO Competency Mapping Assesment. This simply evaluates the CEO against their job description (which usually isn’t clear). We then develop a plan to help fill in the gaps – either through self-development or by enabling others to help with weaknesses.

People + Culture

While People + Culture can sound soft, this area of coaching is all about ensuring the business has a high-performance culture. Coaching CEOs in this area typically involves some level of assessment and creating a baseline of current talent and thinking through current and future needs.

We’ll also conduct periodic 360s and position competency mapping on key leaders, providing personalized coaching, where needed.

One of the biggest areas we focus on is designing the right org chart. While it sounds unsexy, Org structure drives behavior. It’s crucial to the success of any business.

Execution Insurance

Once you’ve found product-market fit, your biggest risk is execution at scale. We help design systems in processes to ensure the strategy is translated into execution (or a bad strategy is corrected quick enough). We’ve developed the Growth Playbook to help companies scale after they’ve found product-market fit.

Canary In the Coal Mine

This is the area where CEOs don’t think they will use a coach, but it’s one of the most valuable aspects of working with a CEO Coach. When I coach a CEO, I’m one of the few people talking to other people across the org and with the board. That allows me to be a Canary in the Coal Mine – predicting issues before they show up in the results.

Every Executive Coaching Relationship Needs Accountability

A CEO Coach can easily (and often unintentionally) be shoved into the “therapist” role for the CEO. However, this leads to insufficient accountability. If the CEO Coach is simply a sounding board, how will you know if you’ve moved the needle? The CEO Coach will (or at least should) be judged on results. Simply listening doesn’t drive results.

That’s why I’m extremely intentional about setting not only the six-month goals for the relationship, but I also have my CEOs fill out a Growth Update before every coaching call.

Before every call, I ask the CEO to provide me a quick update on what has happened since our last call, the 1-2 things they want to discuss and the desired outcomes from the coaching call. Paired with our six-month goals, this provides us with an intense level of focus for our time together. We’re able to accomplish a lot in a minimal amount of time. I typically talk to the CEOs I’m working with 1-2 times a month on a formal, planned basis and many informal interactions (phone calls, texts, emails, etc.).

Without the Growth Update, the potential for distraction is high. Accountability is low. Progress is typically stalled.

Every six months, I have every CEO review me and our working relationship. I ask them if they accomplished what they thought we should accomplish and if they would hire me all over again, knowing what they know now. If the CEO wants to, we then dive into what the next six months look like.

Why don’t more CEOs use coaching?

I think more CEOs don’t use coaches because they don’t fully understand how to utilize a coach. CEOs read headlines about other CEOs getting coaches, so they think, “If so-and-so has a coach, so should I….”

There’s even a scene in Silicon Valley where the main character is criticized for his leadership ability. He says, “Well, the Twitter CEO got a CEO Coach, I’ll just get a CEO Coach to fix it.”

That attitude is like going to the gym and telling a trainer you want to train. That’s not helpful. What do you want to train for? Running a marathon? Or being a bodybuilder? Those are both very different training programs.

Not just the CEO

CEOs are notoriously guilty of having the CEO Coach only talk to the CEO. To use the trainer analogy again, that’s like hiring a personal trainer that doesn’t know how well (or bad) you are eating or sleeping. It’s an important part of the puzzle.

Typically, insight from other employees will be key to coaching a CEO and the business. Other employees see the CEO’s blind spots daily. It’s also key to the growth of the business.

CEO Coaching + the Tools

A chainsaw can be a great tool.

A great tool for cutting down a tree, a terrible tool for brushing your teeth.

A chainsaw great tool for cutting down a tree. But a terrible tool for brushing your teeth. Not every job requires a chainsaw (or a toothbrush). The best CEO Coaches know what tools to apply and when. They are tool agnostic. They are not trying to sell you on their tools. They simply want to provide you the best tools.

There are countless tools – but if you don’t know how to use them, they are useless – or even worse: dangerous. The same is true in building a company.

360s, 1:1s, latest management fads, Performance Reviews, OKRs, the list goes on and on. I help CEOs pick the right tools, in the right sequence and help them use the best tools to help them keep constantly increasing the value of their business.

Who I Really Coach

While I’m labeled a CEO coach all the time, I’m really the coach of the business. The business is a legal person (it has its own tax number and all). The business is where the game is being played, where the CEO and their team are constantly trying to figure out how to win.

The business is like a growing kid (or an aging parent, depending upon the business).

That means I’ve had to disagree with the CEO for the sake of the business. I’ve had to coach CEOs out of their role because it wasn’t right for the business.

The business is my ultimate client. The CEO is the ultimate caretaker.

Furthermore, if the business isn’t successful, the people in the business won’t be successful. This includes the CEO.

Could this help your business?

Read how I start working with every CEO in CEO Coaching: through the highly evolved Leadership + Growth Assessment or download this guide that outlines what you should be looking for in a coach.

Read enough? Shoot me a quick note and we can see if it’s a good fit:


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