We recently had a Hollywood worthy moment in our boardroom that, on paper, ended a large mid-market M&A deal.

A multi-hour meeting between the buyer (our client) and the seller and their advisors had collapsed into yelling, pointing and people being visibly upset. Advisors on both sides were trying to resolve the situation, to no avail. The seller stood up mid-meeting and walked out of the building, and their advisors followed. By every visible measure, the transaction was over. Our client even said so.

I personally did not think it was. I had been listening, and what I had heard underneath the argument was something different from what most people in the room had heard. The actual words being used. The personalities of the buyer and the seller and how they were struggling with various psychological elements of the proposed structure change and how it impacted them both as people, as leaders and as buyers and sellers of a large M&A transaction. The technical structure of the deal that was, beneath all the noise, the real source of the problem. None of that told me the deal was dead. It told me the deal had a path forward, if someone moved it carefully through the next seventy-two hours.

I told both parties I wanted to keep trying anyways. They both told me, separately, that I was welcome to try but the deal was finished. I went to work anyway. Within a week, the structural issue was reframed with clarity, both sides came back to the table, and the transaction closed a few weeks later. Afterwards, both the buyer and the seller told me explicitly that the only reason that deal got done was the work that went in when it got hard.

I want to be honest about where that read came from. It did not come from technical expertise. It came from years of watching deals fall apart for reasons I had not seen at the time. It came from focusing on the fine minutia of a person and the relationship I had worked hard to build with them during the process. It came from misjudging situations earlier in my career and watching the cost of those misjudgment's compound. From clients I lost because I had not yet learned what I now know. Those were expensive lessons. They happened in the years I was building RWT, when the stakes were high and the margin for error was thin both professionally and personally. And they are precisely the lessons that, years later, let me sit in a collapsed meeting and see something other than collapse.

That is the work that closed the deal. And it is the part of the work that almost no founder thinks they are paying for when they hire an M&A advisor.

Expertise is a known quantity. Judgement is not.

When a founder hires a lawyer to draft a shareholders’ agreement, or an accountant to file a return, they are buying expertise. The work has a defined shape. The output is largely predictable. The professional applies a known skillset to a known problem and produces a result that can be evaluated against a clear standard. It is widely assumed that a shareholders agreement is a shareholders agreement, and that the output quality should not differ dramatically.

Founders hire M&A advisors the same way, with the same belief. That is the misdiagnosis at the centre of this article.

A transaction is not a defined problem. It is a sequence of moments where the right answer is not in any playbook. The variables are immense. When to push a buyer and when to let something go. When to tell your client they are being unreasonable, which can be a very scary thing given that the vast majority of our clients are type A men who know what they want and do not like being told otherwise. When the structural objection on the table is the real issue and when it is cover for something else. When to change your language and support to focus on the person rather than the transaction. When to walk. When to wait. When to push harder. These moments do not reward expertise. They reward judgement. And judgement cannot be evaluated the way expertise can.

This single misdiagnosis explains nearly every mistake founders make in hiring an advisor. They shop on fees, because fees are a comparable input and judgement is not. They shop on brand and deal count, because those are proxies for expertise, which is what they think they are buying. They fire advisors who push back on them, because in an expertise model, an advisor who disagrees with the client is failing to deliver service. They hire late, because they assume the work is mechanical and can be deferred until the deal is in motion. They treat advisors as interchangeable and treat them as though the work is commonplace, where anyone with letters behind their name can do the job, because if the work is execution against a known template, the cheapest credible provider should win. To be clear, I have been fired by clients because I have pushed back hard when they made assertions that did not align to reality. None of this is projection. It is the actuality of my experience leading an M&A advisory firm and being the advisor on many deals.

All of these are rational behaviours if you are buying expertise. They are catastrophic behaviours if what you actually need is judgement.

The advisors who deliver the best outcomes are often the ones who disagree with their clients most often. They tell founders the offer is fair when the founder wants to hear it is low. They tell founders the deal is dead when the founder is still hoping. They push back on price expectations, on timing, on the buyer the founder has emotionally chosen. From the outside, this looks dysfunctional. Why pay someone to argue with you?

It is only dysfunctional inside the predictable expertise model. Inside the judgement model, it is the entire point. The whole reason to hire judgement is that it is separate from yours as a founder. An advisor who agrees with everything a founder says is, by definition, not providing judgement. They are providing only execution. And execution is the cheapest, least valuable part of advisory work. This is exactly where the AI investment banks are hanging their hat, and it is also where deals get done at discounts, because judgement is where deals are bought better and sold for more, with better structures.

The deeper problem is that founders cannot fully evaluate this until after the deal closes. Expertise can be verified upfront through credentials, reference calls, deal counts on a tombstone page. Judgement can only be verified retrospectively, by what happened in the moments that mattered, by the calls that were made when no playbook existed. Which means founders are forced to make the most consequential professional hire of their lives under conditions where they cannot actually assess what they are hiring for. And so they default to the proxies they can assess. That is the trap, and it is the reason the same mistakes repeat across the mid-market deal after deal, and why mid-market deals have such a low probability of even closing.

The boardroom moment I described at the beginning of this essay is not atypical. Some version of it happens in nearly every mid-market transaction worth doing. The deals that close are the ones where someone in the room can read what is actually happening underneath what appears to be happening, and act on that reading before the moment passes. That capacity is not on any resume. It is not in any pitch deck. It cannot be priced into a fee schedule. It is the thing that determines whether a transaction closes or quietly becomes another statistic in why mid-market close rates sit where they do.

The founders who exit well tend to be the ones who figured out, sometimes by accident and sometimes by hard experience, that they were hiring something they could not fully evaluate. They chose accordingly. They valued compassionate disagreement. They paid attention to how an advisor handled hard moments rather than how an advisor priced easy ones. They understood that the difference between a closed deal and a dead one often comes down to a single read in a single moment, made by someone whose judgement they had bet on without being able to test it first.

The founders who do not figure this out are the ones who, years later, tell stories about how their advisor failed them. What failed was not the advisor. What failed was their model of what an advisor was hired for.

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