Kadenwood
PerspectivesDeal execution

The decision to sell is almost never a financial decision

Owners rarely sell because a model told them to. They sell because something changed: energy, health, a family event, a partner disagreement, or a shift in the sector they no longer want to fund. Recognizing which one is driving the decision determines how much time you actually have.

Author

  • Joshua NaudéManaging Director

Currency

As of August 2026

A worn stone doorstep and closed panelled door of an old commercial building, brass handle catching the light.

What actually triggers the decision to sell?

In our experience, one of five things, and only one of them is about price. Energy runs out. A health or family event forces the question. Partners stop agreeing. The sector demands an investment the owner does not want to make. Or an unsolicited approach arrives and is taken seriously for the first time.

We should be explicit about the evidentiary basis for that list, because there is a great deal of confidently quoted survey data in this area and we could not verify a current, statistically defensible study of US middle-market sale motivations. The taxonomy above is drawn from our own mandate practice, not from a published dataset, and it is labelled that way here for the same reason we would label it that way in a memorandum.

What follows from it is nonetheless practical. Each of the five triggers implies a different amount of available time, a different level of readiness, and a different set of things that will go wrong in diligence. An owner who has decided to sell because they are tired has months or years to prepare. An owner whose business partner has just filed a claim does not.

The single most common error is treating an event-driven decision as though it were a planned one, and then discovering four months into a process that the financial records were built for a business that was never going to be examined. The market punishes that discovery specifically, and the current market punishes it harder than usual.

Why does an event-driven sale cost more?

Because the buyer sets the calendar when the seller cannot. Every structural feature of a process that protects value, competitive tension, the ability to walk away, time to fix a finding, depends on the seller having alternatives, and an owner selling under an event has fewer of them.

The timing pressure is worse than it used to be. Seventy-three percent of senior US investment bank executives expect the diligence process to become more complex over the next twelve to twenty-four months, one in five report that timelines have already extended over the past two years, and of those, 57% report one to three additional months added (SRS Acquiom and Mergermarket, survey of 150 senior US investment bank executives, published 23 February 2026). Fifty-one percent now call technology diligence the single most burdensome element of the review.

Meanwhile the price itself is increasingly settled after signing rather than at it. Ninety-three percent of transactions carry a purchase price adjustment mechanism and 89% of the deals that have one produce an actual adjustment (SRS Acquiom, published 19 May 2026, on a pooled population of transactions closed 2020 to 2025). At the smaller end, 35% of the smallest lower-middle-market deals, meaning those with closing payments at or below twenty-five million dollars, include an earnout, and 29% do across all lower-middle-market deals at or below fifty million (SRS Acquiom, 2026 M&A Deal Terms Special Report on lower middle-market deals, published 5 June 2026). Across all deals carrying an earnout, closer to one in five earnout dollars is actually paid (SRS Acquiom, M&A Earnout and Milestone Trends, published 7 July 2026).

Put those together and the shape of the penalty is clear. A rushed seller signs a headline number, then concedes on the mechanisms that decide how much of it arrives. None of those concessions look like price concessions at the time, which is exactly why they are made.

Five triggers, the time each usually leaves, and the first thing to do about it
TriggerTime usually availableFirst action
Energy has run outMonths to years; the decision is made long before it is acted onUse the runway: thirty-six months of clean monthly financial statements and an early quality of earnings report
Health or family eventWeeks to months, and often not the owner's to controlEstablish who can sign and who can run the business, then prepare the financial package in parallel rather than in sequence
Partners have stopped agreeingUnpredictable; the dispute sets the clockSettle the shareholder position before approaching buyers; an unresolved dispute discovered in diligence prices worse than one disclosed at the outset
The sector needs an investment the owner will not fundOne to three years, until the gap becomes visible in the numbersGo while the deferred investment is a strategic choice rather than a diligence finding
An unsolicited approachWhatever the approaching party allows, which is deliberately shortDo not negotiate before establishing whether there are other buyers; a single-bidder process is priced as one
The five triggers and the timings against them are drawn from our own mandate practice. We could not verify a current, statistically defensible published survey of US middle-market sale motivations, so this table is explicitly not presented as data. The market conditions those triggers collide with are sourced in the surrounding text and in the sources note below.

“The owners who do best are the ones who separate the decision from the transaction by a season. Decide you are going to sell, then spend three months making the business explicable to somebody who has never met you, then go. The ones who do worst call us the week after the thing happened, and every problem in that process traces back to those two events being the same week.”

Joshua Naudé, Managing Director

What is a seller walking into right now?

A crowded market with a thinner buyer set at the top and a record number of businesses competing for attention at the bottom. There were 3,523 businesses brought to market through one lower-middle-market platform in Q2 2026, up 4.79% year over year and the highest quarterly total on record, with six of seven sectors rising (Axial, The SMB M&A Pipeline Q2 2026, published 21 July 2026; the platform serves transaction values of roughly $2.5 million to $250 million).

The sponsor bid narrowed at the same time. US private equity deal value fell 38% to $177 billion in Q2 2026, the lowest reading in two and a half years, and sponsored loan issuance fell 33% alongside it (Sikich, Q2 2026 Credit Market Update, 13 July 2026). Sponsor-to-sponsor sales fell 57% by value to $24.5 billion and 38% by count to 94, the lowest quarterly mark in at least a decade (PitchBook Q2 2026 US PE Breakdown via PitchBook News, 6 July 2026). The second bidder a good middle-market asset used to be able to rely on is not reliably there.

The supply pressure ahead is close to guaranteed. Private equity funds held 32,979 portfolio companies globally as of 31 March 2026, with 34% held for more than five years, and at the current pace clearing the existing US inventory would take a near-record nine years (PwC, mid-year outlooks published around 17 and 23 June 2026, on PitchBook data). Whatever an owner decides, a large cohort of sponsor-owned competitors will be arriving in the same sectors over the next several years.

The variable that genuinely changed this year is the direction of the interest rate conversation. For eighteen months waiting was a free option because cuts were expected; middle-market practitioners now cite talk of a hike and pressure to complete deals before rates rise, and 63% expect activity to increase in the second half of 2026 (ACG and GF Data, Q3 2026 Market Pulse Survey, published 15 July 2026). Waiting has a cost again, and it is no longer obviously smaller than the cost of moving.

What should happen in the ninety days after the decision?

Financial readiness first, because everything else in the process is downstream of it. The prevailing standard for this market is at least thirty-six months of clean, normalized monthly financial statements, with a quality of earnings report commissioned early rather than in response to a buyer's findings; the companies that closed successfully were described as having well-prepared financial packages that minimized re-trading risk (Capstone Partners, Capital Markets Update, 4 June 2026).

Second, decide what the trigger means for the story. A sale prompted by an owner's health is not a sale prompted by a sector shift, and buyers will work out which it is regardless of what the memorandum says. It is far better to name the reason plainly than to have a buyer construct a worse one. In our experience the reason itself rarely costs price; the discovery that the reason was concealed always does.

Third, fix the concentration issues you can fix and disclose the ones you cannot. Customer concentration, supplier dependence and a single key relationship are the three findings that most often turn a signed letter of intent into a re-trade, and all three are more expensive to discover in week ten of diligence than to declare in week one.

Fourth, extend the readiness work beyond financial. The additional diligence time is going into technology, cyber and systems review rather than into financial workstreams; 84% of surveyed executives anticipate increased cybersecurity scrutiny over the next twelve to twenty-four months (SRS Acquiom and Mergermarket, 23 February 2026). A seller who has never been asked about access controls should expect to be, and should not be answering for the first time in front of a buyer.

What if the answer is that you are not ready?

Then say so and use the time, because a delayed process is recoverable and a broken one is expensive. A business that goes to market unprepared, gets re-traded and is withdrawn carries that history into the next attempt, and buyers keep records.

The distinction that matters is between preparation and improvement. Preparation is finite and controllable: financial statements, a quality of earnings report, contracts organized, management depth documented, systems reviewed. Improvement is open-ended and rarely worth waiting for, because the owner who decides to sell has usually stopped being the right person to run a two-year growth plan.

There is one case where waiting is affirmatively correct, and it is narrow. If a single fixable defect is doing most of the damage to the multiple, and the fix is measurable within twelve months, and the owner has the energy to see it through, then fixing it first is worth more than any negotiating tactic. Concentration in one customer is the usual example. Absence of a second layer of management is another.

Everything outside that case argues for going once you are prepared rather than once you are optimized. The market conditions above are not going to be dramatically better in a year, the supply of sponsor-owned competitors coming to market is going to be greater, and the reason you decided to sell will not have gone away.

As of August 2026

Sources: SRS Acquiom and Mergermarket, M&A due diligence study 2026, published 23 February 2026, surveying 150 senior US investment bank executives, for 73% expecting greater diligence complexity over the next twelve to twenty-four months, one in five reporting timelines already extended with 57% of those reporting one to three additional months, 51% calling technology diligence the most burdensome element and 84% anticipating increased cybersecurity scrutiny; SRS Acquiom, M&A escrow and deal terms statistics, published 19 May 2026, for the 93% incidence of purchase price adjustment mechanisms and 89% rate of actual adjustment among deals carrying one, drawn from a pooled population of transactions closed 2020 to 2025 rather than a current-quarter snapshot; SRS Acquiom, 2026 M&A Deal Terms Special Report on lower middle-market deals, published 5 June 2026, for earnouts in 35% of deals with closing payments at or below twenty-five million dollars and 29% across all deals at or below fifty million; SRS Acquiom, M&A Earnout and Milestone Trends, published 7 July 2026, for closer to one in five earnout dollars actually being paid; Axial, The SMB M&A Pipeline Q2 2026, published 21 July 2026, for 3,523 businesses brought to market in Q2 2026 at plus 4.79% year over year and the highest quarterly total on record, across a platform serving roughly $2.5 million to $250 million of transaction value; Sikich, Q2 2026 Credit Market Update, 13 July 2026, for US private equity deal value falling 38% to $177 billion, the lowest in two and a half years, with sponsored loan issuance down 33%; PitchBook Q2 2026 US PE Breakdown via PitchBook News, 6 July 2026, for sponsor-to-sponsor sales down 57% by value to $24.5 billion and down 38% by count to 94, the lowest quarterly mark in at least a decade; PwC, US Deals 2026 midyear outlook, 17 June 2026, and Global M&A trends in private capital 2026 mid-year outlook, published around 23 June 2026, on PitchBook data as of 31 March 2026, for 32,979 portfolio companies held globally with 34% held more than five years and a near-record nine-year clearing horizon for existing US inventory; ACG and GF Data, Q3 2026 Market Pulse Survey, published 15 July 2026, for practitioner commentary on a possible rate increase and pressure to complete deals ahead of it, and for 63% expecting activity to increase in the second half of 2026; Capstone Partners, Capital Markets Update, 4 June 2026, for the thirty-six months of clean normalized monthly financial statements standard, early quality of earnings guidance and the re-trading observation. Two published series of US private equity deal value circulate on different bases; the Sikich figure quoted here is the leveraged-loan-linked series and should not be combined in a sentence with the platform-data series. Companion articles on this site cover whether now is a good time to sell, how long a sale process takes, and what a quality of earnings report costs.

Separate the decision from the transaction by a season, and the process behaves differently.