Building Better CEOs: Lessons From a Veteran Executive Coach
Update: 2025-09-18
Description
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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Today I'm joined by Sherman Black, a CEO coach who focuses primarily on leaders running small and mid-sized enterprises.
In our discussion today we cover a wide range of topics, including some of the following:
- Misconceptions around what CEO coaches do (and don’t do)
- When & how to hire a coach
- How to think about cost and ROI in making that hiring decision
- Whether a coach needs direct experience as a CEO themselves
- Whether your coach should have a direct line of communication with your Board and/or senior leadership team
- How to quickly evaluate the health of the relationship between the CEO and her direct reports
- How coaches think about popular small business operating systems like EOS
- …and many others
Please enjoy!
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