The 11 Questions Your M&A Advisor Hopes You Never Ask.

Most M&A advisors are excellent at one thing: closing the deal. Their fee is contingent on it. Their reputation depends on it. Their next mandate flows from it. This is not cynicism — it is incentive structure. And incentive structure shapes what they tell you, what they emphasise, and critically, what they let slide.

We've sat across the table from enough advisors — and enough founders who regret listening to them — to know that the questions below are rarely asked. Some because clients don't know to ask. Some because advisors subtly steer the room past them. Some because answering them honestly might slow the deal, and nobody in the room is paid to slow the deal.

Ask every one of these. Before you sign anything.

"What does your fee structure look like if this deal falls apart at due diligence?"

Most success-fee structures incentivise deal completion, not deal quality. If your advisor earns 2% on a $20M transaction, they have a $400,000 reason to overlook problems. Ask specifically: do they earn anything if diligence reveals a deal-breaker and you walk? The answer will tell you whose side they're actually on.

"What are the top three reasons this deal could fail — and what's your plan if they materialise?"

Advisors are trained in deal optimism. This question forces them into adversarial thinking. A good advisor has a crisp answer. A conflicted one will hedge, redirect, or tell you the deal is solid. No deal is solid. Every deal has failure modes. You need to know yours before you sign.

"Who else did you approach before us, and why did they pass?"

This is most relevant on buy-side mandates where your advisor is also representing the seller. Understanding whether this deal was shopped — and who declined — is material information. If three strategic buyers passed, the question is why. Your advisor may not volunteer this. Ask directly.

"What does the target's employee turnover look like in the last 18 months — especially in senior roles?"

Cultural health is rarely in the data room. But a spike in senior departures 12–18 months before a sale is one of the most reliable early-warning signals we know. People leave before trouble becomes visible in the financials. Ask for the HR data. If the target is reluctant, that reluctance is itself data.

"What is the EBITDA adjustment story, and have you stress-tested every add-back?"

Adjusted EBITDA is the most manipulated number in M&A. "One-time" costs that appear every year. Management bonuses that will disappear post-sale. Owner compensation below market. Each add-back inflates the multiple you're paying. Go through every add-back line by line. Ask: if we owned this business for five years, would this cost come back?

"What customer concentration risk exists, and what are the contract terms with the top three accounts?"

A business with 40% of revenue from one customer is a different risk than the headline numbers suggest. More importantly: are those contracts transferable on change of control? Many aren't — and the acquirer only finds out after close. We've seen deals where 30% of contracted revenue technically required customer consent to transfer, and nobody flagged it until month two post-acquisition.

"What IP does the business actually own — and what is licensed, contracted, or borrowed from a third party?"

This is the question three separate clients wished they'd asked before signing. In each case, the answer revealed a structural problem that repriced or killed the deal — after heads of terms were signed, after advisors had been paid retainers, and after the sellers knew they were in a strong position.

Software businesses are especially vulnerable here. Core technology that turns out to be licensed from a founder's previous employer. A proprietary algorithm built on open-source components with viral licensing terms. A brand name with trademark conflicts in key markets. The target will present everything as "owned." Your diligence must verify it. Ask specifically: has IP ownership ever been legally challenged, and is there any outstanding dispute?

"What are the actual integration costs — not just the synergy projections?"

Advisors are excellent at modelling synergies. They are far less enthusiastic about modelling integration costs. Systems consolidation, redundancy packages, rebranding, customer communication programmes, process redesign — these costs are real, they arrive in the first 18 months, and they consistently run 40–60% higher than projected. Get a bottom-up integration cost estimate before you finalise your offer price.

"What regulatory filings or investigations has the target been involved in — at any level — in the last five years?"

Data room disclosure is legally driven. It shows what the target is required to disclose, not everything that exists. GDPR investigations that were resolved informally. Employment tribunal claims settled without admission. HSE notices that were rectified. These don't always appear in standard disclosure but they are material to your understanding of how the business operates. Ask your legal team to make a direct representation request on regulatory history, not just current standing.

"Who are the key people — and what have you done to retain them post-close?"

You are often buying talent, relationships, and institutional knowledge as much as you are buying a balance sheet. If the three people who actually run the business walk out on day 90 because their earn-out is structured wrongly or because they don't respect the acquirer's culture, you've bought a shell. Get retention agreements signed before close, not after. And understand specifically who the target's customers actually call when they have a problem — because that person is irreplaceable.

"What does the seller plan to do after close — and have you verified their answer?"

A founder who says they want to "stay involved and help with the transition" and a founder who is counting down the days to their escrow release are two completely different integration scenarios. One will fight you on every decision. The other will be gone before the ink is dry. Neither is inherently wrong — but you need to know which you're dealing with, and structure the transaction accordingly. Ask directly. Ask their advisors. Ask the CFO who knows them well. The answer you get in the deal room is rarely the whole truth.

These questions are not designed to kill deals. They are designed to give you accurate information before you price, structure, and commit to one. A good target will answer them openly. A good advisor will help you interpret them. A deal that can't survive honest scrutiny is a deal you shouldn't complete.

If you ask Question 7 and the answer is evasive, get a qualified IP attorney into the data room before you proceed. If the EBITDA add-backs in Question 5 don't withstand challenge, reprice the offer or walk. If key person concentration from Question 10 is severe, make retention a condition of close — not an afterthought.