There is a skill underneath M&A advisory that nobody teaches and most people in the industry will not name out loud. It has almost nothing to do with finance. It’s the ability to go deep with a client…to push past the deal and sit with the person behind it. The nuances, the contradictions, the things they cannot say in the boardroom. Mid-market M&A deals are increasingly complex, and the ability to close them has shifted from a technical lens…finance, accounting, legal, operational…to something far more psychological. Managing the people within the transaction has become the single biggest reason deals get completed or fail. Yet it is rarely focused upon, and even less often understood.

In over a decade of advising founders through mid-market M&A transactions, I have come to believe this is one of the most important skills that separates mid-market advisors who simply close deals from those who guide founders through them.

Most founders I work with are men, and most of them do not immediately want to go down the path of vulnerability, of being open, of feeling secure enough to say what they actually think. But it is essential…essential to being in a professional relationship where the psychological understanding is real and substantial. One that can protect clients from the harsh realities of an M&A process, from the many characters in that process, and sometimes even from themselves.

This looks like a client opening up about things far beyond the deal. Sometimes it’s their relationships, or the lack of them. Sometimes their kids. Their fears of their relevance post-close. Their own view of their masculinity, which is unsurprisingly often tied to being successful or to being a founder. A myriad of issues that are not normally discussed in business. But these disclosures and revelations are key for an M&A advisor, because they help guide the client through the transaction in a way that is best suited to their own personal needs. And they can help ensure that clients can stay focused and engaged in the transaction, even when the deal itself feels like more work than it’s worth, and the psychological weight of the process makes the number at the end feel smaller than the founder expected.

These conversations do not happen by accident, and they almost never happen during business as usual. I have had them on boats in the Okanagan, in supercars, on yachts, on ski slopes. Over dinners that ran four hours. On Sunday night phone calls that were not about the deal. And on something as simple as a walk. The settings matter because the conversations they make possible do not survive in conference rooms.

It’s worth noting that these kinds of conversations build real trust and rapport, and the benefit runs in both directions. The advisor gets a clearer picture of what the client actually needs. The client gets an advisor who is no longer just executing a transaction.

This is the part founders should be more aware of than they usually are. An emotionally invested advisor is an advisor who will spend the time, fight harder, and push for what the client actually needs…not simply the outcome that looks good on paper or pays them the most for the least amount of effort. A strong financial result that does not meet the real needs of the client is not a strong result. And an advisor who has not been let into the real picture has no way to know the difference.

There is one more thing worth naming, though it complicates the picture. In my experience, men…particularly type-A founders of the kind who built a company capable of being sold for many millions of dollars…have a harder time opening up to other men than they do to women. I do not think this is because women listen better or are more empathetic. Or that men simply like to look at a woman across the table more….That is the sentimental, stereotypical version, and I do not believe it. Rather, I think it is structural. The type-A male founder is, among other things, a man who has spent his career reading and often competing with other men for threat and status. When he sits across from another type-A man in an advisor’s chair, the reading does not stop. When he sits across from a woman he believes is competent, some part of the vigilance quiets, and in the quiet, things get said and guards come down. And with that sharing often comes an increased willingness, in those same men, to take more heed of what is being said by the woman on the other side of the table.

This is not to say the skillset is reserved for women. It’s not. It can be learned. I actually refuse the belief that only women can have this kind of conversation and this kind of relationship. I don’t buy it. So what can any M&A advisor do to build this particular skill? The first and simplest move is to check the ego. It is not a competition and should you treat it like one…you will lose on all fronts. The second is to be intentional about what is being said…to go deeper, and to treat the conversation with passion, concern, and genuine empathy. The third is to ask questions, and then to ask the harder one underneath the first one.

This skillset does not come without its cost. It is taxing, and it requires far more than one may think. More space. More commitment. More willingness to see the transaction from a lens that may be unfamiliar. And, most importantly, more of the advisor. I was on a call recently with a client who has been having some challenging personal issues while we go through the process of selling his company and as a result, this particular client has been losing his ability to see the forest for the trees when it comes to selling his business. We’ve been dealing with a variety of challenges on items such as net working capital and the introduction of a rather large earn-out to account for a big client that has been brought into the company (a very positive thing overall), which has taken longer than expected to resolve. Yet, while there is a need to talk the technical aspects of the deal with this client I spend an equal amount of time talking about how he is feeling, his mental health and letting him be heard. It requires more than simply doing the technical work required. Multiply that by many deals and many advisors and the compounding effect of this effort is substantial.

This is the part that does not make it into the standard job description of an M&A advisor, and it is the part that quietly saves deals. Founders generally do not lose deals because the deal becomes bad. They lose deals because they lose the ability to see the deal clearly with objectivity. Selling a company is a months-long psychological event layered on top of whatever else is happening in the founder’s life…a marriage under strain, a sick parent, a child in crisis, the founder’s own health, a co-founder disputing the structure, a spouse who has quietly stopped supporting the sale. Any of these will distort the founder’s read of the transaction. They will start resisting terms that are fine. They will start insisting on terms that do not matter. They will get stuck on a single clause because it has become a proxy for something entirely outside the deal.

The advisor who only does the technical work cannot see this happening. They see a client who is suddenly being difficult. A client who is dragging their feet. A client who has become unreasonable about NWC or the earn-out or the holdback. And because the advisor cannot see what is actually driving the behavior, they cannot help the founder get unstuck. Sometimes they make it worse by pushing harder on the technical resolution when the technical resolution is not the problem.

I have come to believe that the advisor’s real job, on a deal of any size, is to hold the parts of the transaction the founder cannot hold alone. The financial and technical structure is the easy part. What is underneath it…the legacy, the next chapter, the marriage, the need to know the legacy will carry on, the question of who the founder will be on the Monday after close…is the work. It is not a skill reserved for women, and I would be suspicious of any advisor, of any gender, who claimed it was. It is a skill any serious advisor can build, if they are willing to sit with the things that most of this industry has trained them not to ask.

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