In The Trenches
In The Trenches
Steve Divitkos
Who to Hire and Who to Fire
41 minutes Posted Sep 17, 2026 at 10:00 am.
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This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.



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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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This week, I’ve combined two blog posts into a single episode, as the two topics that we’ll explore are so central to the job of any small business CEO: In Part 1, I walk you through the most meaningful lessons that I learned as a CEO related to hiring. In Part 2, we explore the opposite side of the coin, and discuss how, when, and who to fire.


Hiring and retaining the right people (as well as moving out the wrong people) is arguably the most important job of any CEO, and I’d argue that it’s particularly important within the context of a small business, where a single individual can represent as much at 5-10% of the total employee base. If, in a hypothetical world, you could only focus on one thing as a leader, I might argue that this is it.


I hope that you’ll find at least some of my reflections, mistakes and lessons to be applicable to your own situation.