CEO Coaching — Relationship

Big Red Car here in the ATX.  Things are looking good to a Big Red Car.  Going to be a lovely day with a nice 65F high later today.  Ahhh, On Earth As It Is In Texas?

So The Boss is continuing his thinking as to what makes CEO coaching effective.

This is what I heard him say.  You may want to look at these earlier posts.

CEO Coaching — Experience — discusses the importance of CEO experience as a foundation qualification in an effective CEO coach.  It is impossible to offer effective and useful advice if you have never been a CEO.

CEO Coaching — Chemistry — discusses the development of mutual trust and effortless communication that is the basis for developing useful and essential personal chemistry.

The Relationship

The relationship between an entrepreneur/CEO and their coach is most effective when communication and coaching is consistent over a continuum of time.  It is less effective when it is “hit and miss”.

In a relationship, the entrepreneur/CEO and their coach can work diligently and deliberately on dissecting information, planning the future, developing talents/skills and solving problems.  The problems are not always huge problems but typical startup or growth company problems.

The relationship itself provides the framework to ensure that the challenges are not allowed to morph from “not urgent and not important” to “urgent and important” by virtue of inattention.  Allowing a spark to become a conflagration is one of the biggest challenges of a startup CEO.

It also provides a better communication framework for the CEO coach to gauge the temperament and mood of the entrepreneur/CEO.  Much of how an entrepreneur is influenced is flavored by the current mood of both the CEO but also the enterprise itself.

Change office locations, install new computers, hire a top level pro and you will get a sense of how much stress an enterprise can internalize.  It happens.

A prudent CEO coach is reluctant to suggest alternatives or to offer advice when they are ignorant about the CEO or the company or the environment in which the CEO is operating.  It is tantamount to prescribing medicine without having conducted a thorough physical examination of the patient.

Most progress in building a company is incremental and taken in small measures.  It is difficult to chart progress over the short term but it is amazing to see what one can accomplish over a 2-5 year period.  Constant contact ensures that the road behind informs the decisions of the road ahead.

Initial contact

Most coaching initial contacts come from one of the following reasons:

1.  The entrepreneur/CEO has a particular problem with which she needs assistance and is reaching out to a CEO coach for a “one off” problem solution.  This is the “hair on fire” contact.

2.  The entrepreneur/CEO is seeking a sounding board to bounce ideas off or zone of safety in which to discuss a myriad of challenges.  This is typically the “overwhelmed CEO” contact.

3.  The entrepreneur/CEO is seeking a CEO coach before encountering any problems as a normal part of professional development in much the same way that a prospective golfer would seek out a golf pro to teach him the game.  This is the “contemplative CEO” contact.

All three of these initial contacts are perfectly normal and all can lead to healthy long term relationships.

The “hair on fire” initial contact is a cry for help and a skillful coach will try to deal with the fire before doing much of anything else.  The challenge with this initial contact is that often once the problem is solved, the entrepreneur/CEO is tempted to send the fire brigade home and go back to business as usual until the next fire presents itself.  Progress can therefore become a series of lurches between brush fires and a few that become huge conflagrations.

The Boss will always help an entrepreneur/CEO in any circumstances but prefers, as a general rule, not to be a fire brigade.  He prefers to do the hard work to create a relationship and to really get to understand the CEO’s challenges and not just be an “on call” problem solver.

Preparatory work

To set the foundation for the relationship, it is useful that the entrepreneur/CEO review the Vision, Mission, Strategy, Tactics, Objectives, Values and Culture of their company.  Not to be unrealistic but many enterprises are built around a product and there is no real company building going on just yet — OK, deal with what you have in the absolute confidence that this is perfectly normal for a bit.

Don’t obsess about it but do give it a bit of thought as you will have to build a company sooner or later.  You will eventually have to deal with these basic organizational issues.

Much of what ultimately becomes the Vision, Mission, etc is already formulated in the CEO’s head and nowhere else.  Again, perfectly natural.  The planning process tries to coax it out of that brilliant head, put it on paper, share it with the team and use it as the guiding light of the enterprise.  When done well, it is literally liberating.

When such alignment is achieved amongst the team, the power of the organization is unleashed and multiplied.  Think of planning as a force multiplier when the team “gets” the plan.  Literally, the power of alignment.

The Boss will send you a couple of planning docs which will help you work your way through the process.

Regular contact

Once you have begun to work together, it is very effective to have a Skype call twice a month to discuss whatever the CEO/entrepreneur requires to be discussed while working toward their strategic objectives.  The agenda for this call is set by the CEO.

The calls typically take 60-90 minutes and the communication is broad and far ranging.

At the end of the call, it is useful to sum up by asking:  “What do you see as your most important initiatives in the next couple of weeks?”  This provides some focus.

It is also useful to catalog “parking lot” issues — subjects which merit some future discussion.  This is just for administrative precision and is not homework.

The Boss never allows the CEO to assign himself homework.  No homework.

Why no homework, Big Red Car?  Because CEOs have enough sources of stress in their lives and do not need another.  The result of a good coaching relationship is the relief of tension and stress not the addition of tension and stress.  The world will take care of that.

Follow up

We all process information in a different manner.  The archetype of the A personality captain of the ship is neither true nor necessary.  It is good to sleep on the discussion and take the time to process it.  Let it marinate.

This is one of the reasons why The Boss takes copious notes of the conversation so he can review it again at a later date.

The CEO may often follow up with an email or phone call to put a laser light on a particular subject.

An ongoing relationship is a series of prescribed encounters working on the agenda of the CEO and providing incremental and linked progress over a continuum of time.  Energy must be invested in the relationship to make it work well.

Want to chat, call 512-656-1383 or write to [email protected]

But, hey, what the Hell do I really know anyway?  I’m just a Big Red Car.  Be good to yourself because you earned it.



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  1. Pingback: CEO Coaching --- Zone of Safety - The Musings of the Big Red Car

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