CEO Coaches: What do they do, how do they work with CEOs, and why might you consider hiring one?

My Guest

Warren Coughlin is both an entrepreneur and business coach, having worked directly with countless Entrepreneurs and CEOs for upwards of 20 years.

His coaching practice focuses not only on the business itself, but also on the entrepreneur at a personal level, working with them to ensure that they craft meaningful values and live a deliberate lifestyle that is both purposeful and fulfilling to them.

Warren has helped CEOs achieve countless outcomes, some of which include successful exits, 7-figure salaries, and significantly reduced day-to-day operational roles, among others.

Among other tools, Warren is the creator of The Business That Matters Playbook, a tool that streamlines and automates the strategic planning process for CEOs, and Top Right Living, a program that focuses on the personal growth of the entrepreneur in their pursuit of more clarity, balance, joy and meaning in their lives.

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CEO Coaches: What do they do, how do they work with CEOs, and why might you consider hiring one? In The Trenches

Specific Questions and When They’re Asked

CEO Coaching Basics

  • (2:10) What do CEO Coaches actually do?
  • (5:10) How much do you work on the business vs. on the CEOs themselves as people?
  • (7:30) What does a typical coaching engagement with a CEO look like?
  • (10:50) What do you do if a management team member is hesitant to work with a coach?
  • (13:40) What do you say to a CEO who thinks that they don’t need a coach?

How to Hire A Coach

  • (18:50) When is an appropriate time to hire a coach?
  • (23:10) What separates a good coach from a mediocre one?
  • (25:35) Can a CEO to “test drive” a coach before making a commitment to them?
  • (30:55) How much do coaches cost, how do they get paid, and how do CEOs justify the ROI?
  • (34:15) Do coaches ever get paid contingent on certain business outcomes being achieved?
  • (36:45) Does a good CEO coach need to have prior experience as a CEO him/herself?
  • (39:45) How does one even find a coach? Do the coach & CEO need to be in the same city?

Working with a Coach

  • (42:30) For how long do you typically work with a CEO?
  • (44:55) When should a CEO and coach stop working together?
  • (46:10) Is the objective of a good coach to eventually work themselves out of a job?


  • (48:50) What are the most common areas for improvement when first engaging with CEOs?
  • (55:10) What are some mistakes that you’ve made from which you’ve learned the most?
  • (59:40) How do coaches think about “operating systems” like EOS or Rockefeller Habits? 
  • (1:04:00) If you could say one thing to every SMB CEO on earth, what would you say?

Links to All Resources Discussed

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