Graduation — CEO Coach

Big Red Car here in the ATX in a grayish, cool day. A great day for a ride in a convertible!

So, I’ve been in CEO coaching mode for about five years now and there have been some great successes. Some failures, but way more successes.

CEO coaching assignments don’t last forever — neither does high school or college.

There comes a time when a CEO is best served by getting a different view of things or to just take a breather. Some CEOs finish their work and are ready to move. Other CEOs sell the company and no longer are CEOs.

The Big Red Car (actually The Boss, but I’m taking over the space in his head) has had all of the above.


One of my first clients was a SaaS company which was grappling with all the things which would nudge one to seek assistance. The CEO was a solid guy — salty and experienced — and was ready to improve his business.

“When the student is ready, the teacher will appear.”

For some extended period of time the CEO had regular coaching sessions and, slowly but surely, began to make the tough decisions and changes which drove him to a better place. He had the usual issues: money, investor relationship, hiring world class people, relocating the business, and streamlining some processes. Meanwhile, he was running his business on a growth trajectory.

He received some focused coaching, but the solution to every one of his issues was inside his head. His CEO coach showed him where they were.

In a three year period, he remade that company and worked his CEO coach out of a job. Contrary to one’s initial reaction, a good CEO coach wants to be worked out of a job by a great CEO.

That’s what I mean when I say “graduation.”


Part of any discussion with a CEO coach is the end game. Where do you see your baby going over the next five years?

Sometimes, the answer to that question is to monetize the blood, sweat, and tears.

An exit strategy discussion is part of normal planning. Obviously, an exit means the CEO coach goes away, so it is like a graduation.

Sometimes an exit is an individual — the CEO leaving for a number of good and practical reasons. The Big Red Car has guided two CEOs to do just that on financially favorable terms.

Another CEO client built his enterprise to such a powerhouse that he was able to sell it for nine figures $X00,000,000! Hello, America!

This CEO was a hard worker, but like a lot of CEOs needed some assurance that his instincts were sound. When he could rent some experience or obtain an exemplar, he did that.

Exits are both ends and beginnings.

Shutting the company down

The Boss (haha, I get the credit for the successes and The Boss can wallow in the failures) had to assist four companies to wind up their affairs in an orderly manner.

In every instance, the CEOs reached out to validate what was already spinning in their heads. The Boss, who has a checklist for everything, went down the list and they concluded it was time to pull the plug.

There is a right way to do that for a number of reasons. The entrepreneur is going to want to rest up and go back to the same well in the future. The entrepreneur has to ensure the liquidation conforms to IRS rules so that any investment can be converted to a tax loss for tax accounting purposes. There is a right way to do this.

Starting up a new enterprise by a serial CEO

Serial CEOs make interesting clients. They know a lot more than first time entrepreneurs. They know what they don’t know. Think about that for a second. They know what they don’t know.

Because of this, they often seek out a coach before they finalize the hypothesis which will drive their deal. They know the advantage of doing their work up front and are much more orderly in their approach to founding a company — hey, they’re SERIAL entrepreneurs, right?

This seems to more common amongst entrepreneurs who live outside the US and who are doing something inside the US. Not sure why.

Firing the client

Sometimes — on two occasions — the CEO coach has had to fire the client. This is necessary because the client doesn’t pay attention or take the work seriously. On one occasion, the fired client wised up and came back to the fold. On another occasion, the client just disappeared. It happens.

So, dear reader, there you have it. CEO coaching is not a lifetime gig. It will be as long or as short as the client requires. Sometimes, there is triage work to be done and sometimes there is a long term campaign which results in a great exit. Each circumstance is different.

The flavor of the day, today, is entrepreneurs seeking additional funding. More second and third rounds than seed rounds.

A good CEO coach can assist an entrepreneur with the big issues that ultimately confront every CEO.

CEOs — Doing Tough Things Shoptalk

But, hey, what the Hell do I really know anyway? I’m just a Big Red Car. 



2 thoughts on “Graduation — CEO Coach

  1. I’m curious as to, in your experience, which do you see more of: CEO’s looking for 2nd and 3rd round angels doing so because they’ve sort of botched the early stages and are looking for get healthy/second chance investment, or is it more of they’ve done it right and are looking for that next step/expansion investment?

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