Building Better CEOs: Lessons From a Veteran Executive Coach

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Sherman Black is an executive coach that specializes in working with CEOs running small and medium-sized businesses. His coaching practice, at least in part, is based on over 35 years of experience leading and transforming companies himself.

Among other things, Sherman spent 15 years as a technology CEO across public and private companies, and in three different industries. He led a public hardware company through a full software transformation into a Gartner Magic Quadrant leader, scaled a VC-backed SaaS company to a successful exit, and spent 13 years on the Boards of public and private enterprises.

His coaching practice specializes in B2B SaaS and technology-driven businesses, and services clients across the U.S., Europe, the Middle East, and Asia.

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Building Better CEOs: Lessons From a Veteran Executive Coach In The Trenches

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Episode Summary with Timestamps

  • 00:00 Introduction to CEO Coaching
  • 02:39 Sherman’s Journey to Coaching
  • 05:11 Understanding CEO Coaches
  • 11:02 When to Hire a Coach
  • 15:02 Choosing the Right Coach
  • 20:52 The Importance of Direct CEO Experience
  • 23:52 Evaluating Cost and ROI of Coaches
  • 28:08 Working with a Coach
  • 33:38 Signs of Outgrowing a Coach
  • 37:30 The Coach’s Relationship with the Board
  • 45:26 Engaging with the Leadership Team
  • 50:49 Operating Systems for CEOs
  • 54:27 Common Blind Spots for CEOs
  • 57:51 Maximizing Board Value
  • 01:00:34 Lessons Learned from Mistakes

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Thanks to our Sponsors

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