The Wisdom of CEO Coaching

Big Red Car here.  You may have experienced some access issues to The Musings of the Big Red Car in the last day.  This was a hosting issue that is reported to have been corrected.  The Big Red Car is sorry for any inconvenience

So, The Boss is still in Santa Fe and I am still hanging with the house sitter who is turning out to be a very cool chap, indeed.  I am getting a bit of running time that I did not expect but the young man did not know where the freakin’ gas tank fill fitting is located — BEHIND THE BACK LICENSE PLATE, Son.  Behind the freakin’ back license plate.

Anyway, a few calls were made and all is just fine.  I am filled to overflowing with regular — which is pretty damn hard to find these days — and we are on the road again.

The house sitter was wise enough to “consult” with The Boss and get a bit of coaching. Which all brings me to the issue of CEO Coaching and how it can work for, well, a Chief Executive Officer or founder of a startup or small company to enhance performance and hone skills.

CEO Coaching defined

When I use the term “CEO Coaching”, I am including the notions of mentoring, advising and coaching.  Those terms are often used interchangeably and while that is technically not quite correct, it is close enough for our conversation today. You may want to review these posts to get a bit of perspective on the subject.

Mentoring v Coaching — Is There a Difference?

Mentoring — Head Fake Or Worthy Endeavor — A Case Study

Now remember today we are talking about CEO coaching so these references provide a frame of reference but do not really hit perfectly upon what we are discussing today. What most CEOs need and can bend effectively to their purposes is a CEO advisory relationship.

What kind of CEO coach do I need, Big Red Car?

A smart CEO is going to get a CEO coach who has been a CEO himself.

You don’t take advice on flying an airplane from a passenger — though they may have spent a fair amount of time in airplanes — you want to consult with a pilot, someone who has actually flown an airplane

Experience is everything.  There is no substitute for experience and frankly being a CEO is such a unique and difficult position, you need someone who has been in your shoes, Old Sport.

The Boss has been a CEO of public and private companies for over 33 years.  In that period of time, you learn a lot of things.  He has been a Founder of 5 different companies and has dealt with turnaround issues routinely in his business career.

The best teacher is experience but you can RENT experience rather than BUY it — that’s called tuition and it’s a lot cheaper than paying full price all the time.  [Haha, Big Red Car, where do you get this stuff?  You crack yourself up, Big Red Car.]

What are the benefits, Big Red Car?

Well, brilliant CEO, the most important benefit is having someone in your corner whose only duty is to serve you.

When you confide your challenges to The Boss he is not on your Board of Directors or one of your investors and he cannot fire you. This is a very important element of the foundation of trust and candor that will quickly become an essential benefit of the relationship.

The Boss is not going to scold you or assign homework or make your life more difficult.  He is only there to assist you.

You confide the wrong thing in a Boardmember or one of your VCs and you, my dear CEO, will be amongst the unemployed.  Not to suggest that every subject that a CEO and his coach deal with is so desperate but sometimes they are very, very, very important life changing issues and you want to be able to know that they will not become the basis for your being fired.

Bad news alert from the Big Red Car:  Many CEOs of startups and small companies do get fired.  The tenure of a startup or small company CEO is fairly short.  Unfortunate and messy fact of life. Maybe a bit of CEO coaching will forestall that sometimes inevitable event.

It would not be unfair to describe this confidential, experienced sounding board as being the primary benefit of a good CEO advisory relationship.  Someone whose duty is to you exclusively and who has been in that special place.  Bit of wisdom born of experience and familiarity with both triumph and disaster are also nice things to have at your disposal.

How does it work, Big Red Car?

The Boss will typically send you a couple of foundation documents which will allow you and The Boss to discuss intelligently exactly where you are as an enterprise.  Here are a few of those documents.  Click on each document of graphic to see them in their entirety.  Please feel free to keep a copy for your own use.

Wisdom of the Campfire Business Checklist

Wisdom of the Campfire The Business Model

This is not homework but rather a frame of reference for you and The Boss to gauge exactly where you are at this instant in time.  From this review will likely come a number of topics which you are interested in exploring and discussing.

The mechanics, please, Big Red Car?

Well, Old Sport, the process is something like this:

1.  You, the brilliant CEO, will develop an agenda of what you would like to discuss and then set up a Skype call with The Boss.

2.  You visit over Skype usually every other week or weekly depending upon the flow of things.  These calls typically take one to two hours.  The calls can be at a fixed time to work with your schedule.

3.  The Boss follows up with a Memorandum documenting what you discussed and this then leads to some follow up work by both of ya’ll and the agenda for the next visit.

The Skype calls will be coordinated with your schedule, Old Sport.  Time zones are important and you will make sure it works for you.  Some CEOs like a particular day of the week or a time of the day.  All this is accommodated.

Word of note:  when you do this for a protracted period of time, you can really see and chart your progress as you deal with issues and pursue your vision for the company.  You will see and measure your progress and it is a very good feeling.

A word about exemplars

One of the things you get when working with a very experienced CEO is that he will possess a lot of “exemplars” — documents developed and used over a 33 year career of CEO-ing.

Recently a couple of The Boss’s CEO clients were contemplating a sale of their company to a strategic acquirer.  They have never done anything like this in their business careers.

The Boss, on the other hand, had bought or sold over 200 business units and had a nice little Letter of Intent which he had used and perfected.  He was able to provide it to his CEO clients.

Sample Term Sheet company sale

This document provided an informed frame of reference for the brilliant young CEOs to chew on and digest the disposition process.  Tailored to their own specific circumstances, this provides a useful head start.

First move, Big Red Car?

OK, so, Big Red Car, what is the first move in getting a bit of CEO coaching?

Contact The Boss at the following addresses and you can have a chat to discuss the possibility of working together.

[email protected]


Skype: “jeffminch”

You may want to take a look at some of the testimonials on this website.  Navigate the tabs to find them.

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

2 thoughts on “The Wisdom of CEO Coaching

    • .
      The big discriminator is whether they have ever been a CEO and for what period of time.

      You can talk about playing basketball in the school yard but unless you have played before a few thousand folks it is all just make believe — as you well know, baller.


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