The Coach In The Room: What Executive Coaches Owe Founders Pre-Transaction

A founder I have been working with for a year called his executive coach two weeks before the LOI was signed. The coach had been with him for six years. The call lasted about forty minutes. The coach asked good questions and the founder hung up calmer than he had been all day. Then the LOI got signed, diligence opened, and the coach was not in the room for any of what followed.

That is the gap I want to write about.

Executive coaching in the lower middle market has, in the last decade, become a serious profession. The coaches I work with are skilled, often credentialed, and almost always in a deeper relationship with the founder than any banker, lawyer, or accountant in the deal. They are the person the founder calls when the wheels come off. They are the person who knows what the founder is actually afraid of. And in most of the transactions I see, they are not in the diligence room, not in the LOI negotiation, not in the post-LOI compression window, and not in the integration period after close.

Some of that is appropriate. The coach is not the deal team. They should not be doing the work of a banker or a lawyer or an advisor. But there is work in the pre-transaction window that no one but the coach is positioned to do, and in my read of the data the absence of that work is part of what produces the Preparation Gap.

I published a working paper on the structural pattern this spring, The Preparation Gap in Early 2026 (SSRN, DOI 10.2139/ssrn.6515478). The named finding is that the gap between LOI value and close value in lower-middle-market transactions is forecastable from observable characteristics of the business and the seller, both of which are measurable in the eight-to-twelve-month window before LOI. The paper looks at the structural drivers. The drivers that get the most ink are the financial ones: customer concentration, working capital, add-back defensibility, management depth. The drivers that get less ink, and that show up almost as frequently in my client work, are the founder-state drivers.

A founder who walks into a buyer conversation underprepared emotionally for the role the conversation actually plays in their life tends to make a different set of decisions than a founder who is ready. The two founders look identical in the data room. The decisions they make at LOI, during diligence, in the gap-and-bridge negotiation, and during the integration period are not identical. The percentage points are not identical either.

This is where the coach has standing.

Three pieces of work the coach can do in the pre-transaction window that almost no one else is positioned to do.

One. Confront the identity question. Most founders have, at some point in the company's life, fused their identity to the business. The transaction is the moment that fusion gets unwound. A coach who has been in the relationship for years can have that conversation in a way that a banker or a lawyer cannot. The work is not therapy. It is helping the founder see the part of their decision-making that is identity-driven and giving them the option to make a different decision.

Two. Build the post-transaction picture before the transaction starts. The founders who do best in the year after a sale are the ones who started building the next chapter of their life before they signed the LOI. New work, philanthropy, board seats, a family rhythm that does not assume sixty-hour weeks, a community that is not exclusively built around the company. None of that gets built in the eight weeks after close. It gets built in the year before LOI, if anyone is paying attention.

Three. Be in the room at the inflection points. The two inflection points that matter most are the LOI decision and the moment in late diligence when the buyer's QoE provider surfaces something the founder did not expect. Both of those moments require the founder to make a high-stakes decision in a compressed window, while the buyer holds the leverage. The founder is making that decision against the backdrop of the work the deal team has done. They are also making it against the backdrop of whatever the coach has helped them prepare for emotionally. Coaches who are in the room for those two moments tend to be present at the moments their work was actually built for.

The objection I usually hear from coaches is that they do not want to be the deal advisor. They are not the deal advisor. The deal advisor is the deal advisor. The work the coach is doing is parallel to the deal work, not in competition with it. The best transactions I have been part of in the last five years have had a coach in the founder's life who was present for the inflection points, not asked to make the deal decisions but present for the human ones that get made underneath the deal decisions.

The coach in the room is not a luxury. In the founders I work with who keep the percentage the data says is forecastable, the coach is part of why.