CEO Coaching FAQ

Frequently Asked Questions About Executive Coaching for CEOs and Other Senior Leaders

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You say that you coach CEOs. What does that mean?

There’s an oft-repeated phrase about CEOs: “It’s lonely at the top,” and it really is. Whom do you talk to?

CEOs have myriad problems, opportunities and decisions to plan for and respond to. I help them think through the toughest issues and make fully formed decisions. Some CEOs also work on enhancing skills in deficient areas, which we all have! You should have a coach who’s assertive, experienced and really has your back!

What results should I get from working with an executive coach?

At the beginning of any engagement, I work with clients to identify what success will look like. CEOs often just seek help thinking outside the box or assurance that they aren’t breathing their own exhaust. Sometimes we use a 360 process to ask their board and teammates how they’re doing. My intent is to have an impact on the trajectory of my client’s success and to positively impact the company’s work environment and financial success.

I’ve had clients with millions of dollars of impact, both top and bottom line, because of our work together. Most of them would also say they can sleep easier. How much monetary and reputational damage occurs with just one bad decision? If you become a better leader, what’s the upside for your company, team and career?

What kinds of issues can an executive coach help a CEO with?

As a former CEO and longtime executive, I fully engage with CEOs around the seven imperative questions they must answer to be fully successful:

  • Why are we here? (purpose)
  • How do we work together? (values)
  • Where are we going? (vision)
  • Where do we play? (strategy question one)
  • How do we win? (strategy question two)
  • What’s most important right now? (critical issues)
  • What’s the plan? (who does what by when)

The bulk of my interaction with CEOs involves those questions, but these topics also arise:

  • Board and investor relationships
  • Team effectiveness
  • Specific skill enhancement
  • “People” problems

How much does it cost a CEO to work with an executive coach?

If you think of this as a cost rather than an investment, I’m the wrong guy. I want to help you have dramatic impact on the future success of your career and business and require an investment commensurate with that level of success. You should plan on a six-figure investment.

Will an executive coach tell me what do to?

Although I’ve occasionally told a client, “I wouldn’t do that if I were in your shoes!” or “Here’s something you might think about,” I don’t tell people what to do. The individuals I work with are very smart — they just need an objective person to help them think through issues. Can I draw upon my 30 years of operating experience to make suggestions? Of course! Will I willingly allow you to make bad choices? No, and I’m pretty assertive, so I’ll do my best to keep you from running over a cliff. However, the process is more about identifying options, foreseeing obstacles and then developing plans to execute the decisions that you make.

Is executive coaching like training?

Not so much. Are there things you will learn from me? Probably, but I don’t do lectures. Can I share tools that other clients have used successfully? Yes. However, if your primary issues are technical knowledge gaps, you need training — perhaps in addition to coaching.

How do I start?

Developing trust and finding a partner takes time. You and I should talk, preferably in person, to ensure we’re a good fit and I can help you reach your goals. Once we agree to work together, we’ll clearly identify your objectives and what your version of success looks like, and then we’ll develop a plan. We work and revise as necessary until you have what you want and need!

How often do we meet?

The short answer is, as much as necessary to be successful. I don’t limit the time. Most clients prefer to meet once or twice a month for an extended period, most often in person, and then contact me if they have a quick-hit issue that we might solve over video or phone. When face-to-face meetings are impossible, video works well.

How long do CEOs work with executive coaches?

Until we successfully handled your issues. Ordinarily, this is a year or more. If you need more of a sounding board, the relationship can last many years, as long as it’s effective.

What kind of background should a CEO coach have?

Would you take ski lessons from someone who couldn’t ski? Of course not! I’ve been in your shoes, made the mistakes you’ll likely make, and understand the issues you’re dealing with. I’m also highly trained as a coach and have worked with CEOs in this capacity for 15 years. Lastly, you don’t need a sycophant; you need a straight shooter. I’m simultaneously supportive and assertive and have the personality to be a partner with tough-minded CEOs. You need someone capable of helping you make real change and great decisions. I like to have fun with clients, but we also have tough work to do!