Kit Lisle is the founder of operators.pe, the world’s leading peer community for private equity backed executives and operating partners, and a fractional operating partner with 30 years in the PE ecosystem. In this episode of Herding Squirrels, Kit breaks down why roughly 80 percent of founder led companies acquired by private equity for the first time go off the rails, and the five specific failure points that cause it. If you’re leading a team through a PE acquisition, a board transition, or any high stakes change, this conversation gives you the exact questions to ask and the timeline to ask them on.

Guest Bio

Kit Lisle runs operators.pe, a collaborative peer community he built from scratch after discovering no formal network existed for PE backed executives and operating partners. With three decades in the private equity ecosystem, he now works as a fractional operating partner, coach, and advisor, helping boards and management teams align after a first time acquisition. He’s spent his career aggregating best practices from experienced operators and sharing them in writing, on stage, and on podcasts like this one.

Find Kit online:LinkedIn | [email protected]

Episode Highlights

[00:00:10] Introducing Kit Lisle and operators.pe

[00:02:38] Why Kit built the community himself after finding nothing like it existed

[00:03:07] The 80 percent failure rate when PE acquires a founder led company for the first time

[00:04:59] The “wait and see” mindset that sets the failure in motion

[00:06:50] The five questions every management team needs answered: who, why, when, where, what

[00:09:00] Fixing the 80 percent with onboarding and organizational due diligence in the first 100 days

[00:10:22] The five risk factors, walked through one by one

[00:15:42] Why the first 100 days should target two quick, visible wins

[00:21:50] Kit’s advice to any leader guiding a team through change

Key Insights

* The wait and see approach backfires: Most PE firms default to watching quietly for a year before acting, hoping to sort out who’s swimming and who’s sinking. Kit argues this is simply inefficient, because it leaves capable people without the tools, like the investment thesis and value creation plan, they need to actually do their jobs. (00:04:59)

* Five questions close the information gap: Management teams stepping into board oversight for the first time should be asking why the deal happened, who holds which decision rights, when the exit is targeted, where the company stands against the plan, and what leadership style the moment calls for. Most of this never gets asked because nobody’s used to a board relationship. (00:06:50)

* Misalignment starts inside the room: A CRO chasing price increases, a CFO cutting costs, and a CEO chasing new logos can each be doing their job well and still be rowing the canoe in three different directions. Alignment has to happen internally, with the board, and with outside stakeholders, not just at the top. (00:10:22)

* “Line of sight” breaks down in the middle: A CEO can hold a clear town hall and still lose the message by the time it reaches a plant manager or regional sales VP. Deployment isn’t complete until the person furthest from the boardroom understands what’s changing, what’s stopping, and what’s in it for them. (00:11:43)

* South to north feedback takes repetition, not a memo: CEOs often assume they have an open channel for hearing what isn’t working. In practice it can take a leader saying “tell me what’s broken” three, four, five times before people actually believe it and start talking. (00:13:12)

* The first 100 days needs visible wins: Kit’s benchmark for early success isn’t a strategy document, it’s small, tangible results the CEO can point to internally and with the board to build credibility fast. (00:15:42)

* A good board meeting isn’t a report, it’s a conversation: Incumbent management teams often walk into board meetings expecting to explain themselves or ask permission. Kit reframes the healthy version: reporting happens beforehand, and the meeting itself is for genuine, candid collaboration on decisions that are still unresolved. (00:15:42)

* Willingness to learn is the real filter: Past the first test of capability, the people who succeed after an acquisition are the ones who ask for feedback with humility instead of waiting for permission. Kit says demonstrating that genuine interest in getting better is half the battle. (00:20:34)

Key Quotes

* “A good board meeting is not a good readout or report. It’s not about getting permission. It’s not about sharing something that you’re doing. It’s really an intellectually stimulating conversation.”

* “If we don’t have alignment, we don’t have good governance and understanding of decision rights or deployment or accountability or the appropriate leadership style, value creation is simply not going to happen.”

* theoperators.pe — Kit Lyle’s peer community for PE backed executives and operating partners

* Kit Lisle on LinkedIn

* Email: [email protected]

About Herding Squirrels

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