FAQs About Coaching for CEOs and Senior Leaders

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

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

CEOs have myriad problems, opportunities and decisions that they must plan for and respond to. I work as a thought partner to help them think through the toughest issues and make fully formed decisions. Some CEOs are also working on enhancing skills in areas of deficit, which we all have! You should have a coach who is assertive, experienced and who also has your back!

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

At the beginning of any engagement I work with my client to identify what success would look like. CEOs are often just looking for someone to help them think outside of the box or to ensure that they are not just breathing their own exhaust. In that case, they decide what success looks like. Sometimes we’ll use a 360 process to ask their board and teammates how they’re doing. My intent is always to have an impact on the trajectory of my client’s success and also to positively impact the work environment and financial success of the company. 

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

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

As a former CEO and long-time executive, I am able to fully engage with CEOs around the seven imperative questions that 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 is most important right now? (Critical issues)
  • What is the plan? 

The bulk of my interaction with CEOs is around these seven questions, but others that arise are:

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

How much does it cost for 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?

While I have occasionally told a client, “I wouldn’t do that if I were in your shoes!” or “Here is something you might think about.” I don’t tell people what to do. The people 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 will try 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. Will there be things that I can teach you? Probably, but I don’t do lectures. Can I share some 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 get started?

Developing trust and finding a partner takes a bit of time. You and I should talk several times, preferably in person, to make sure that we are a good fit and that I can help you reach your goals. Once we agree to work together, we’ll take some time to clearly identify your objectives and what success will look like and then we will work on a plan. We keep working and revising as necessary until you have what you need!

How often do you we meet?

The short answer is, as much as we need to in order to be successful. I do not limit the time. Most of my 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. In periods where face to face meetings are impossible, video works quit well.

How long do CEOs work with executive coaches?

Until we feel we have successfully dealt with whatever issues you would like to deal with. Ordinarily this is a year or more. If you are looking for more of a sounding board, the relationship can last many years, as long as we are being effective.

What kind of background should someone who coaches CEOs 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 are dealing with. I’ve also been highly trained as a coach and been working with CEOs in this capacity for 15 years. Lastly, you don’t need someone who is a sycophant; you need someone who will speak the truth. I am supportive and assertive at the same time and have the personality to be a partner with tough minded CEOs. You need someone who is capable of helping you make real change and great decisions. I like to have fun with my clients, but we also have tough work to do!

If you are a CEO or senior leader in a mid-market company and would like to have a free 20-minute consultation (e.g. to discuss a current challenge), click here to set up a time.

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