Big Story

The Art of Asking Difficult Questions Without Insulting the Seller

Key Takeaways

• In the lower-middle market, a seller's emotional relationship with the business shapes everything, from how they disclose information to how they respond to due diligence and whether they stay engaged when the process becomes difficult.

• The questions that surface the most valuable insights are rarely the most direct. Buyers who lead with curiosity rather than judgment build trust faster and receive better answers.

• Sellers who feel respected share more. Sellers who feel interrogated often withdraw.

• Buyers still need answers to difficult questions, but how those questions are framed often determines whether they receive honest context or guarded responses.

For most sellers in the lower middle market, a business is not simply a financial asset. It is the result of years, sometimes decades, of hard work, personal sacrifice, and professional identity. It paid for the family home, funded children's education, and created opportunities for employees they often consider extended family. When a buyer sits down for the first conversation, they are stepping into a discussion where nearly everything is personal.

In an experiment involving 152 MBA students, 76% of negotiating pairs reached a successful deal when buyers were instructed to consider the seller’s thoughts, interests, and motives, compared with 39% when buyers focused only on their own role. The sale could not be completed on price alone because the buyer’s maximum price was below the seller’s minimum. Reaching a deal required the parties to uncover compatible interests and add another term, such as future employment for the seller. The study shows that buyers who look beyond the stated position are more likely to find terms that address each side's actual needs.

Buyers who recognize this adjust how they ask questions. Those who do not often approach conversations as if they were reviewing a spreadsheet then wonder why the seller becomes guarded. This approach also aligns with established negotiation research, which shows that open-ended questions encourage trust, richer discussion, and more meaningful information.

The difference between a direct question and a diagnostic question goes beyond tone. It comes down to framing, sequencing, and giving the seller enough space to explain the business in their own words.

Consider a simple example. A buyer who wants to understand why profitability declined can ask, "Why did your profitability drop?" Or they can ask, "How do you think about what happened in the business over the last year?" The first question immediately puts the seller on the defensive. The second invites a conversation. Both aim to uncover the same information, but only one creates an environment where the seller is likely to share the full story.

This distinction matters even more in the lower middle market because transactions are often highly personal. Buyers and sellers typically work directly with one another, and the seller's cooperation remains critical throughout diligence, transition planning, and, in many cases, an earnout period. A seller who feels respected throughout the process arrives at the closing table as a collaborative partner. One who spends four months feeling interrogated often does not.

Putting this into practice is surprisingly straightforward. Start with open-ended questions that let the seller lead the conversation. Listen more than you speak, particularly during the first meetings. Reflect back what you hear before introducing a different perspective. When sensitive topics arise, such as customer concentration, key-person dependency, or margins that differ from industry norms, approach them with genuine curiosity.

For example, instead of saying, "Your top customer represents 40% of revenue. What happens if they leave?" consider asking, "I noticed one customer represents roughly 40% of revenue. Can you help me understand how that relationship has evolved over time?" 

The information buyers need does not change. Customer concentration still matters. Years of lower EBITDA still need to be explained. The owner's post-close role still needs to be clarified. What changes is how that information is uncovered. Sellers who feel respected tend to volunteer context early, making diligence more productive and reducing the likelihood of unpleasant surprises later in the process.

In the lower-middle market, the buyer who listens most during the initial meetings often closes the best deal. That trust pays dividends throughout the diligence process, reduces friction during negotiations, and makes the eventual transition smoother for everyone involved. The strongest deals are built on conversations where both sides are willing to share.

Governance Feed

1. For most founders, the majority of net worth sits locked inside one operating company, often 70% to 95% of everything they own. A sale is the structural reset that turns a single illiquid stake into cash that can be diversified, gifted, or reinvested, making the decision as much about concentration risk as about price. Founder-owned businesses sold to financial buyers had an average personal net worth concentration of 78% at close, the highest among seller groups. Partial recapitalizations now account for 41% of closed lower-middle-market deals, up from 28% five years earlier, as more owners pull liquidity out while staying in the seat. 

2. Advisor fee structures are shifting in ways that change what sellers sign up for. Success fee-only arrangements have climbed to nearly a third of advisors, up from 19% two years earlier, so more advisors now carry the full risk of a deal that never closes. Lehman-style formulas remain the most common success structure, though flat percentage fees have risen from 26% to 36% as advisors move toward cleaner alignment with owners. About 79% still charge some upfront fee, and 77% credit that fee back against the final success fee, which is now the market standard.

3. AI has moved into diligence work, yet trust in its output has not caught up. About 71% of finance teams say AI made research and diligence faster over the past year, while 59% still manually recheck most or all of what it produces, citing hallucinations and missing citations. That verification layer carries a cost. 62% of teams lose 4 or more days per deal to a leadership-required, human-only audit, which accounts for 10% to 15% of a typical 6- to 8-week timeline.

4. The skills that carry dealmakers through the hard moments are mostly psychological and relational. Senior operators describe confidence as a discipline they build through preparation and repeated practice, and they treat influence as something earned through empathy and steady trust at the table. Deals stall on human friction as often as on numbers, and the people who keep teams aligned and handle difficult endings with clarity tend to move outcomes the most. For owners and buyers, leading people is at the center of every transaction.

Thesis Principle

How a deal is structured determines how much the seller keeps after tax. A stock sale taxes the whole gain as capital gains. An asset sale divides the price across asset classes on Form 8594. Equipment gets taxed as depreciation recapture at ordinary rates up to 37%. Goodwill gets taxed as capital gains at 23.8%. On a $5M deal, that split can move the seller's federal tax by about $158K before state tax. Buyers push the price toward the equipment to accelerate the write-off. Sellers push the price toward goodwill for the lower rate. Allocation gets negotiated line by line.

Resources & Events

📅 Smart Business Dealmakers Conference (Denver, Colorado - October 8, 2026)

Business owners, private equity professionals, investment bankers, lenders, and M&A advisors will gather at the Smart Business Dealmakers Conference in Denver to discuss dealmaking trends across the middle market. The agenda includes founder exits, value-creation strategies, capital markets, transaction structuring, and networking with active dealmakers across the region. For owners considering a future sale or investors looking to build relationships, it offers practical insights alongside valuable connections. Details →

📅 2026 M&A Mid-Year Recap & Outlook (Virtual - September 22, 2026)

Hosted by ACG Global in partnership with GF Data, this members-only webinar will examine the key trends shaping the middle-market M&A landscape in 2026. Drawing on GF Data's transaction database, the session will cover valuation trends for private equity-backed companies with enterprise values between $10 million and $500 million, the outlook for deal activity and pricing through the remainder of the year, and evolving seller sentiment. Featuring Bob Dunn (ACG/GF Data) and Scott Linch (Forvis Mazars), the webinar offers timely market insights for private equity firms, investment banks, and corporate development professionals navigating today's deal environment. Details →

📊 Report Spotlight: 2026 M&A Deal Terms Special Report (SRS Acquiom)

Lower middle-market deals (≤ $50M) accounted for 40%+ of all private M&A transactions in recent years, making them one of the market's most important segments. Drawing on data from 4,400+ private-target deals closed through 2025, SRS Acquiom's latest report finds that 29% of LMM deals and 35% of deals up to $25M included earnouts, while private equity buyers participated in 11% of transactions. The report offers a data-driven look at buyer behavior, deal structures, and the terms that shape today's lower-middle market. Read →

For the Commute

Key Talent Retention Before Close (M&A Science)

Financial diligence often gets the most attention during an acquisition, but retaining key employees can be just as important to a successful outcome. In this episode, the M&A Science Podcast explores why talent retention should begin before a deal closes, how uncertainty affects leadership teams, and what buyers can do to maintain trust throughout the transaction. A practical listen for anyone acquiring founder-led businesses where relationships, institutional knowledge, and continuity are critical to preserving value.