A note before you use these questions
This content is educational. These 35 questions are designed to help business owners evaluate M&A advisors — including Scott Sylvan Bell. Watching this video or reading this page does not constitute an engagement, a commitment to work together, or any form of financial, legal, or investment advice.
The outcomes, multiples, and deal results referenced in this content reflect experience and education. They are not a guarantee, promise, or projection of what you will receive when selling your business. Every transaction is different. Results vary based on industry, preparation, market conditions, timing, buyer type, and circumstances specific to your situation.
Before making any decisions about selling your business, work with a licensed M&A advisor, a qualified M&A attorney, and a CPA with transaction experience. These questions exist to make you a better-informed buyer of professional advisory services — not to replace the qualified help your specific situation requires. — Scott Sylvan Bell
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Filmed in Tahiti on March 30, 2026. These are the 35 questions a sophisticated seller should ask before hiring any M&A advisor — including Scott Sylvan Bell. Use them in every advisor conversation you have.
1. What industries do you specialize in and have you sold a company like mine before?
An advisor who has sold businesses in your industry knows what buyers in that space look for. One who has never been inside your industry is learning on your deal. That tuition comes out of your multiple. Industry-specific experience is not a preference — it is a requirement for getting the maximum multiple in your specific market.
2. What is your specific step-by-step process for getting a seller to the top end of the multiple range?
Not a general description of how deals work — a specific sequence. The 5-4-3-2 process gives you the best opportunity to sell in the window you have. This includes tough conversations, eliminating owner dependency, quality of earnings documentation, reduction of client concentration, standard operating procedures, org charts, job descriptions, quarterly planning and execution by department, and accountability meetings. If an advisor cannot describe each stage with specific deliverables — they do not have a process. They have a hope.
3. How do you handle the preparation phase before we go to market?
The difference between an A plus deal and a C deal is almost entirely determined before the first buyer conversation. A great advisor does a dry run first — a mock diligence process before going to market. They build the data room and ask the tough questions so the seller is not surprised when a buyer asks them. If the advisor’s answer to preparation is nothing — that is your answer about the advisor.
4. What does your Titan Thesis process look like and how do you help sellers build one?
A great advisor helps you assemble the proof of your value before a buyer asks for it. The Titan Thesis is every piece of documentation that proves you are the best in the industry — awards, advantages, profit and earnings reports, competitive recon, tracking multiples by quarter, decision bands on your management team, and case studies. If they do not know what a Titan Thesis is or have a version in their process — the seller is going into diligence without a prepared case.
5. How do you determine what my business is worth before we go to market?
Not a rough estimate — a specific methodology. Quality of earnings analysis, EBITDA multiple range, add-back documentation, management team evaluation, standard operating procedures, org chart review, and industry comparable transactions. The advisor who cannot explain how they determine value cannot defend your price to a buyer. Are you an A plus deal — or do you need a couple more quarters to get there?
6. How do you create competitive tension among buyers and what does that process look like?
A single buyer with no competition is a buyer in full control of price. A great advisor takes a generic version of your information to the market first — without naming the company — to gauge interest from private equity, family offices, and private investors. This is the auction phase: inviting multiple buyers to look at the opportunity simultaneously to create genuine competition. This is how you get to the top of the multiple range.
7. How do you handle the LOI Smackdown — when a buyer opens high then reduces during diligence?
The LOI Smackdown destroys seller value more than any other single thing in M&A. A great advisor starts the conversation about expectations early — before the LOI is signed — so the seller understands the pattern and has protections in place. If they have never heard the term or do not have a specific answer — they have watched it happen to their clients without stopping it.
8. What is your specific process for protecting a seller’s position when a buyer comes back after diligence with a revised lower offer?
This is the moment that separates advisors who have done real work from those who have only managed smooth transactions. According to Chris Voss — when somebody comes to you with different terms they want to change, it is your opportunity to change what you want as well. A great advisor has a specific playbook: legal review of the LOI provisions, counter-positioning on deal terms, and the willingness to walk away if the retrade crosses a line. What do they say, what do they do, and what leverage do they deploy the moment a buyer tries to move the number?
9. How do you handle a deal that starts to fall apart during due diligence?
Every advisor looks great when the deal is going well. What do they do when everything is going wrong? A great advisor has a specific playbook for protecting the seller’s position when things get difficult — not a general reassurance that they will figure it out. Ask for a specific example. The answer tells you more than their pitch deck.
10. What is your average time from engagement to close and how does preparation affect that timeline?
A business that goes to market prepared moves faster and at a better price. What does the advisor’s data show about deals where sellers did the preparation work versus those who went to market without it? The answer reveals how seriously they take preparation — and whether they take any engagement regardless of readiness.
11. Walk me through the last deal you closed where the process got difficult — what happened and what did you do?
Every advisor has a highlight reel. Ask for the hard one. The deal that nearly fell apart, the retrade they fought back, the seller who was ready to walk but did not. How they describe adversity tells you more about what they will actually do for you than any pitch about their process. A great answer is specific. A vague answer is a warning.
12. How do you evaluate whether my business is ready to go to market before we start the process?
If the answer is vague — they are willing to take your engagement fee regardless of whether you are ready. A great advisor runs a preparation diagnostic before they engage and tells you honestly what needs to change. A B level deal gets you 80% of market. A C level deal gets you 70%. A D deal — which stands for do not do it — gets you 50%. You deserve to know which one you have before you go to market.
13. What is your approach to managing owner dependency as a risk factor buyers will find?
Owner dependency is the most common multiple killer in mid-market deals. If everything relies upon you as a founder or owner — you are leaving money on the table. How does the advisor help sellers address it during preparation — not after a buyer finds it and uses it against them? The BENCH Framework and DRIVER Test in the Exit Ratio 360™ exist specifically to measure and address this before going to market.
14. How do you handle customer concentration risk when one client represents more than 20 percent of revenue?
This is the second most common multiple killer. What is the advisor’s specific strategy for positioning a business with concentration issues — and what do they advise sellers to do in the years before going to market? Diversification of clients is not a suggestion — it is a preparation requirement for an A level deal.
15. What types of buyers do you typically engage and how do you match the right buyer to my specific business?
Strategic buyers, private equity, family offices, individual buyers — each type values your business differently and comes with different deal structures. How does this advisor decide who to approach and in what sequence? The buyer type determines the multiple, the structure, the earn out likelihood, and what happens to your employees and culture after close.
16. How do you handle confidentiality during the sale process to protect my relationships with employees, customers, and vendors?
A breach of confidentiality during a sale process can destroy the value you are trying to capture. What specific protocols does the advisor use to protect the seller before, during, and after the market process? This includes how buyers are screened before receiving any information about your business.
17. What is your approach when a buyer requests a long transition period or significant earn out?
These structures transfer risk from the buyer to the seller after close. How does the advisor negotiate against them — and when do they advise a seller to accept versus walk away? An earn out only makes sense when you genuinely believe in the growth story and you control the decisions that drive the metrics. When you no longer control the outcome — you walk.
18. How do you prepare sellers for the emotional reality of the sale process?
The sale of a business a founder built over decades is not just a financial transaction — it is an identity event. Your identity is going to shift. You are going to be a different person. This conversation has to happen early. Do you need a therapist, a hobby, a significant other to talk to, something to write? Whatever the therapy is — it needs to start at the beginning of the process, not at the end.
19. What happens if we go to market and the offers do not meet my expectations — what is the plan?
Not every process produces the outcome the seller wanted. What does the advisor do when the market feedback says the business is not worth what the seller expected? Do they help the seller understand why and build toward a better outcome — or do they push for close regardless? The advisor who has no opinion on when to pull back and regroup has never told a client something they did not want to hear.
20. How do you stay current on market multiples and buyer activity in my industry?
The M&A market moves. Multiples shift. Buyer appetites change. A great advisor is constantly reading, constantly talking to people in the market — what is going on in deals, what fell through and why, how come a specific business got the maximum multiple. This is intelligence that comes from active market participation — not a database subscription.
21. What is the biggest mistake you see sellers make and how do you help them avoid it?
The answer to this question tells you more about the advisor’s real-world experience than their pitch deck. A great answer is specific — a named pattern, a documented failure mode, something they have seen cost sellers money. A vague answer is a warning that the advisor has not been close enough to enough deals to have a specific answer.
22. What makes your approach different from every other M&A advisor a seller could hire?
Not a marketing answer — a substantive one. What is actually different about how they prepare sellers, run processes, negotiate deals, and protect multiples? If the answer sounds like everyone else’s answer — it probably is. The advisor who can name something specific they do that others do not is the one who has actually developed a methodology rather than a pitch.
23. If I hired you today and we did everything right — what does the best possible outcome look like for my business and why?
It would be 100% irresponsible to give you a specific answer to this question without knowing your specifics — how your company operates, what opportunities are in the marketplace, what your EBITDA looks like. Anybody who says they can give you an expectation without that information is setting you up for heartache. What a great advisor can tell you is this: when you do the preparation, you have a higher possibility of getting the maximum multiple. The preparation is the answer.
24. What is your specific process for handling a retrade — when a buyer tries to renegotiate after the LOI is signed?
Retrading happens in a significant percentage of mid-market deals. Sometimes it is a legal issue — and the attorney deals with it first. But the negotiating principle is this: if you are going to retrade, we want a different deal too. If they gave you one condition — you come back with two or three. The advisor who has no playbook for this moment has watched it cost their clients money before and will watch it cost you.
25. How do you document and defend add-backs during the quality of earnings process?
Add-backs are legitimate but they are also the battleground where buyers most aggressively reduce seller value. A good CPA can footnote what the add-backs are and why. If you have a real logical reason for an add-back — you can defend it. If you are doing add-back stuffing and trying to get every cent — it signals to the buyer that there are probably other things inside the deal they should look for. Proof and footnotes are the only defense that holds up.
26. What is your process for preparing my management team for buyer interviews during diligence?
Buyers interview your leadership team. What they hear determines their confidence in the business without you. The preparation is mock conversations — getting the team used to answering questions without looking at the owner. They are going to ask about processes, how the company operates, how you do things, problems you have had. The red team exercise that prepares your management team also reveals opportunities inside the business to grow revenue before the sale.
27. How do you handle deals where the seller has a strong emotional attachment to the outcome?
Every founder has one. The price they need, the buyer who feels right, the legacy they want to protect. This conversation has to happen early. Your identity is going to shift — it is going to change. You are no longer going to be going to the office. You are no longer going to be the one taking calls in the middle of the night. The advisor who acknowledges that reality and helps sellers navigate it is protecting more than your multiple — they are protecting the life you are building on the other side of the deal.
28. How do you stay involved and protect the seller from LOI through close — what specifically changes in your role after the LOI is signed?
An LOI is the middle of a deal — not the end. The deal is done when money is wired. The deal is done when the purchase agreement is signed by both parties. Many advisors disengage after the LOI — that is exactly when the seller needs the most protection. A great advisor stays active from LOI through close. The level of engagement they provide from that point forward is a direct conversation — and the compensation reflects the scope of that engagement.
29. How do you evaluate whether a buyer is actually qualified and serious before allowing them into the diligence process?
Unqualified buyers waste time, breach confidentiality, and gather competitive intelligence. The questions that qualify a buyer: what are you looking for, why do you want to buy this company, how do you plan to fund the acquisition? A buyer who gets funding after the LOI — using the LOI as proof to go to a bank or investor — is not necessarily disqualified, but the seller needs to know that going in. How many deals has this buyer closed? If it is their first, they may not be in the number one position in your process.
30. What is your approach to the non-compete and transition agreement and how do you protect the seller’s interests there?
The non-compete and transition agreement are where sellers lose freedom after the deal closes. The goal is the smallest time possible with the least amount of covenants. If a buyer shoots for five years — shoot for three. If they want a large geographic restriction — make it smaller. The key question for the seller is: why do you care about a non-compete unless you are planning to start another company or do consulting? Negotiate scope, geography, duration, and compensation — and fight hardest against the provisions that trap you in someone else’s business after you have already been paid.
31. Have you ever walked away from an engagement because the deal was not in the seller’s best interest?
Yes. Deals have been walked from because the business owner was not easy to work with. Because they wanted to be right and leave money on the table. Because the buyer was not the right buyer. Because the seller changed their mind too many times because they were not really ready to sell. A great advisor has told a seller — you are not ready for this and we are going to have to end this engagement. The advisor who has never done this has closed deals regardless of the outcome for the seller.
32. How do you stay active after the LOI is signed and what is your role during the transition period?
The period between LOI and close is where the seller is most exposed — diligence, working capital negotiations, transition agreement, non-compete scope. What does this advisor actually do during that window and what specific support do they provide the seller in each stage? The advisor who front-loads their effort into getting the LOI signed and then steps back has left you at the most dangerous point in the process without protection.
33. What does success actually look like for me specifically — and how will we both know when we have achieved it?
Success cannot be defined by the advisor — it is a joint conversation between you, your other business owners, and your founders about what the outcome is that you want. A maximum multiple is a range — not an exact number. The advisor who can start that conversation with the right questions and build toward a shared definition of success is the one who will fight for your version of the outcome — not a generic version that works for their track record.
34. What is your specific point of view on when a seller should NOT go to market — and what do you tell them instead?
A seller should not go to market if they are not prepared. If they are not emotionally ready. If they are not financially ready. If they do not have a management team in the right place to make the decisions that need to be handed off. Going to market with a B level deal gets you 80% of what the market is paying. A C level deal gets you 70%. A D deal — do not do it — gets you 50%. The advisor with no opinion on when to wait has never delivered that news to a client. The 5-4-3-2 framework exists specifically because the sellers who prepare early get the deals the unprepared ones never see.
35. How do you stay sharp on the buyer side — what are you doing to understand what acquirers are actually looking for right now?
The M&A market changes faster than most advisors update their knowledge. A great advisor is in active conversations with buyers, attending deal groups, reading industry alerts, talking to people in the market constantly — what is going on in deals, what fell through and why, what got the maximum multiple and how. The advisor who only knows the seller side is missing half the game. The one who understands exactly what a buyer’s analyst is looking for when they open your financials is the one who helps you prepare for that moment specifically.
Those are the 35 questions. Use them in every advisor conversation you have — including any conversation you have with Scott Sylvan Bell. Nothing in this content constitutes legal, financial, or tax advice. If you are serious about selling your business, assemble the right team — M&A advisor, M&A attorney, tax professional. These questions will help you find the right people for that team.
Related: Titan Thesis | LOI Smackdown | What Is Quality of Earnings | Do I Need an M&A Advisor | 5-4-3-2 Exit Planning Framework | Exit Ratio 360™ | Consulting in Paradise | Exit Ratio 360™ on Amazon
About Scott Sylvan Bell
Scott Sylvan Bell is a mid-market exit strategy consultant and the creator of the Exit Ratio 360™ — the only 360-point business evaluation system built specifically for owners of $10M to $250M companies preparing for a sale. He filmed this episode at 1:11AM on his 50th birthday in Tahiti, French Polynesia. His book Exit Ratio 360™ is available on Amazon. Learn more at scottsylvanbell.com/why-scott/.
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