Picture a boardroom table. On one side is a seller in their mid-fifties, with their M&A advisor, their lawyer, and their accountant. On the other side is the buyer, perhaps the same age, with their M&A team…maybe internal, maybe external…and the various advisors who are engaged with them on every transaction. From a ten-thousand-foot view, there is no real distinction between the two groups. Same attire. Same documents. The same ceremonial weight to the moment.

And yet the truth of the room is altogether different.

What divides the two sides is what the deal at the table actually represents to each of them. For the buyer, this is one of perhaps hundreds of transactions they will move through over a career as a mid-market private equity firm or strategic acquirer. For the seller, it may be the only chance to monetise a life’s work or otherwise accomplish the goal they set out to achieve when they started their company. The two parties are not doing the same activity at different volumes. They are doing categorically different things that happen to share a closing table.

For one, it is a business deal. A way to make more money or accomplish some strategic objective.

For the other, it is what I have come to call a life deal. A defining moment, often the end destination toward which an entire career has been pointing, sometimes without the seller fully realising it until it is in front of them.

Why this distinction matters

Understanding this is critical to how mid-market companies actually get bought and sold.

Most buyers move past the emotional significance of a seller letting go of their life’s work, often without realising that it was ever in the room. Most sellers, in turn, do not see the asymmetric, largely unemotional approach that comes from one party having completed dozens or hundreds of these transactions and the other completing one. Each side is operating on a different map of what is happening between them, and most of the time neither side fully knows it. I have written elsewhere about the psychological challenges the M&A process carries for the seller, and I will keep writing about it, because it is the part of the work the industry continues to overlook.

The cost of the mismatch is not abstract or hard to measure (you’ll see later in this article that it can cost many millions of dollars). Deals close badly, and often not at all, because the buyer failed to recognise what kind of deal they were actually in. And conversely, deals fall apart entirely because the seller never recognised what kind of room they were actually sitting in. Yet, in the deals that look successful on paper, founders quietly walk away three years later wondering why a transaction that hit all of its stated objectives still feels like something was taken from them they did not know to protect.

The distinction between a business deal and a life deal is not a minimal point. It is the most consequential variable in the room, and it is the one nobody puts on the agenda.

What this looks like in practice

Recently we worked on a deal that started to stall out after months of due diligence. Our client had a very personal reason for wanting to sell their company…the kind of reason that does not fit on a CIM and does not get raised on a management call, but that fundamentally drives every decision the seller makes through the process. The buyer, on the other side, was very interested in the business itself and focused on making sure both the business and the deal were as de-risked as possible. Due diligence dragged on way beyond a typical period but the real mistake made by the buyer was that they failed to consider the actual needs of the seller.

At face value, this is what mid-market M&A is supposed to look like. A motivated seller. An interested buyer. A clean fit on paper.

The reality is that this level of nuance is, in my experience, missed by the vast majority of buyers. They focus on the workload to close…risk management, the diligence list, the financial model, the legal review, the closing checklist…while overlooking the life context the seller is moving through as a direct consequence of selling. In this particular situation, our client needed speed. They had a life event happening that required their full personal and family attention, and the buyer entirely overlooked the meaning of that. They proceeded with a slow and steady approach, methodical and self-paced, without acknowledging the human reality shaping the seller’s decision to proceed at all.

To be fair to the buyer, the pace they kept was not unreasonable on its own terms. It was simply blind to the seller’s. They missed the window…and in missing it, they caused our client to begin to question whether selling still made sense at all.

What the buyer missed out on was a phenomenal company at an attractive market valuation. They failed to read the impact the deal was having on the seller and their family during the brief window when reading it would have mattered. And as much as we pushed, and as much as we explained the position our client was in, the buyer remained methodical…moving ahead at a consistent, entirely self-serving speed.

In the end, the buyer’s pace cost them millions of dollars of upside and maybe even a lost deal (we shall see). While the deal stalled, our client signed several large new clients and the market for their product strengthened. It is a case study in why delays are not benign in M&A…they are often the most expensive variable in the room, and the one buyers most consistently underestimate.

Fast forward to now. We are working on a meaningfully higher total transaction value, with 25% more cash at close in order to bring the seller back to a yes. The life moment that once made the deal urgent has shifted. The decision to sell is no longer as connected to the seller’s life as it was a few months ago, and a different number is what it now takes to honour both the original premise and the time that has passed since.

This is more common than the industry acknowledges. Sellers come to a transaction for any number of reasons…a health concern, time with a parent or partner, a long-postponed sabbatical, a new chapter waiting on the other side, a desire to spend more time with their kids before they go off to college. Whatever the reason, it is often time-sensitive, often emotionally charged, and almost always invisible on the buyer’s side of the table unless someone in the room takes the trouble to get to know the seller well enough that it begins to surface and more importantly, that they actually listen. Buyers who cannot read this rarely realise what it costs them…in deal terms, in price, in the goodwill that compounds across the next decade of their reputation.

For this stalled out deal, the delays cost no less than $10m in valuation growth that would have immediately been that of the buyer should they have understand and met the underlying requirement of our client. And more importantly, what our client really needed at the time was compassion and empathy yet they were faced with more due diligence questions, more typical buy-side go forward protocols and a continued reminder that this deal had a different meaning for the buyer versus our client the seller.

What the best buyers and sellers do with this

The deal I have described is not unusual. The pattern repeats often enough that, over time, it has taught me what the difference looks like between buyers and sellers who navigate this well, and the ones who do not.

The point of naming the distinction between a business deal and a life deal is not to make the two sides adversarial. It is the opposite. It begins with empathy for the seller and a real curiosity about what is driving them to the table in the first place. The deals that close well… the ones founders are still glad about three years later, and the ones buyers point to in their case studies…are almost always the deals where someone in the room recognised the asymmetry and worked with it rather than around it.

There are postures on both sides of the table that change the room.

The best buyers intentionally understand the human variable. They recognise that the seller across from them is moving through something the buyer has not personally experienced in the same way, and they use empathy and compassion to build that awareness into the rhythm of the deal. They ask different questions. The buyers who do this consistently close more deals at better terms than the buyers who do not, because sellers who feel seen negotiate differently than sellers who feel managed. Being seen is not a soft variable. It is one of the most material variables in mid-market M&A.

The best sellers learn the shape of a business deal without losing the shape of their own life deal. They hire advisors whose deal count meaningfully approaches the buyer’s. They learn the few mechanics that actually matter…working capital, SPA, earn-out structure…and they refuse to enter rooms without a working understanding of them. They also refuse to be paced by the buyer. A seller who can calmly say I need three days to think about this has changed the dynamic of the room more than almost any other move available to them. The pause is not retreat. It is the quiet reassertion of the seller’s own life inside a process that is otherwise designed to move past it.

And the best advisors name the asymmetry openly and push for understanding. This is the advisory move that most often does not get made, and the one that most often unlocks the deal when it does. Being vocal, in a room of professionals about the actual reasons a seller is selling their business and the deep underlying requirements of doing so is consequential. They outline the life deal requirements in as clear as terms of possible…It is the clearest move available, and experienced buyers tend to listen because they have seen what happens in the rooms where nobody made it. Naming the truth of the room is, in the end, the work the seller is paying their advisor to do.

The deals that close well

A business deal and a life deal can close at the same table. They can close at the same price, on the same terms, with the same documents signed by the same hands. From the outside, they look identical to a deal where only one of them was happening.

They are not identical. The deals that close well are the ones where both sides recognised what they were actually doing, and where someone in the room had the ability to name the difference out loud, and the care to do so without apology.

A business deal is what closes the transaction. A life deal is what the seller takes home. The deals worth doing are the ones that honour both... and the rooms worth being in are the ones where someone is paying attention to the second.

This is an essay from Uncommon Capital, a newsletter on mid-market M&A by Reece Tomlinson, Founder & CEO of RWT Capital Corp.

‍