CEO Coaching — Experience

Big Red Car here.  Well we had a great Christmas in the ATX.  Wow, the Investment Banker and the Perfect Daughter are here and the parental units had been skiing in the ‘Boat and just made it back in time to get the tree decorated.  Much fun and much love.  Ahh, On Earth As It Is In Texas!

So The Boss has been thinking a bit about his CEO advisory and coaching business.  At year end he has cataloged a number of conversations and I will be sharing them with you for a few weeks.  A kind of lessons learned primer on how a CEO can effectively use coaching to her best advantage.

The Big Red Car observes the following important consideration about picking a CEO coach.  Pick someone who has real world experience.

There is a wealth of advice out there.  There is damn little good advice and a tsunami of bad advice.  The discriminator is always the actual experience of the advisor.  Hard truth.

The power of experience

If you were learning how to fly an airplane — the analogy between business and flying an airplane is very compelling (flight plan, takeoff, landing, etc) — you would likely benefit most from an instructor or confidant who had actually flown an airplane.  [BTW, The Boss is an accomplished Bonanza pilot and likes to fly.]

You would benefit from learning from an instructor who had a lot of flying hours in an airplane similar to yours.

The Boss has been a CEO for over 33 years and has met with Rudyard Kipling’s Triumph and Disaster multiple times.

If you can dream – and not make dreams your master;
If you can think – and not make thoughts your aim;
If you can meet with Triumph and Disaster
And treat those two impostors just the same;

[You know you can’t go wrong with a bit of Kipling in the morning, right?  Rudyard had it right.  STFU, Big Red Car, and get on with the story already.]

This experience is what one is ultimately paying for in hiring a CEO coach.

Judgment, good judgment and wisdom

The Boss is very fond of saying the following:

1.  Judgment, good judgment, is the product of experience.

2.  Experience is the product of bad judgment.

3.  Wisdom is the result of experience and the exercise of good judgment over time.

It all ties together.  As a CEO, you are trying to make the best executive decisions you possibly can about, well…………………………….everything.  No?

Rent it

The big takeaway in any coaching relationship is that you are “renting” experience rather than paying full price for tuition.  Tuition is expensive and sometimes requires a bit of failure to really teach the lesson.  Avoid the failure by renting the experience.  Failure is scarring and expensive.  Avoid it when you can.

Since you are effectively renting experience, it is the nature of your coach’s experience that is of paramount experience.

To be an effective CEO coach the Big Red Car thinks you have to be a bit more experienced than Malcolm Gladwell’s 10,000 Hour Rule.  Read about it here in Outliers.

A CEO coach who has three decades of experience is going to be a useful asset.

So, in picking a CEO coach find someone who has deep experience and who has waltzed with both Triumph and Disaster.


Many times what is learned by experience is what not to do and what not to panic about.  Young CEOs are often worried sick about what they do not know they do not know.  Bit of the Rumsfeld in that one.

Again — young CEOs are often worried about they do not know they do not know.

Seasoned business executives are able to understand — through experience — which concerns will kill you and which just come with the rarefied C suite.

Employee retention rates are very important particularly amongst senior executives but losing and calmly replacing that senior executive with an even better hire is what a seasoned coach can talk you through.

Dealing with a Board?  Normal.

Dealing with funding?  Normal.

Dealing with partners?  Normal.

The list goes on and an experienced CEO coach can talk you through the shoals and get you back on dry land.  Why?  Because HE has done it a lot of times himself.  No amount of mousse in your hair will substitute for real experience.

[Do not apply this to cars.  If you have a great, faithful, loyal and wonderful 1966 Chevy Impala convertible do NOT be falling prey to the siren song of a BMW convertible.  Trashy little sluts all.  STFU, Big Red Car, everything is not about you.  Sheesh!]

But, hey, what the Hell do I really know anyway?  I’m just a Big Red Car.  Call The Boss 512-656-1383 or email him [email protected] if he can help you.