Selling your business isn’t just another transaction—it’s the payoff for years, maybe decades, of your hard work. According to Michael Shea, Senior Business Broker at Transworld, the single most important choice you’ll make is who you trust to sell it.
Here’s why: more than 80% of businesses listed for sale never sell. Your broker can be the reason you join the successful 20%… or the majority that never close.
Michael Shea has distilled the process into 10 questions every owner should ask before signing with a broker:
1. How many deals have you personally closed in the last year?
Look for a consistent track record—at least 10 recent deals. Firm-wide stats or ancient history don’t count.
2. What have you sold in the past six months?
Recent, relevant closings show your broker is active and effective right now.
3. What’s the size and structure of your firm?
Bigger firms often have the back-office muscle to keep deals moving. Solo brokers may struggle to juggle everything.
4. Do you co-broker?
This should be a hard yes. Co-brokering expands your buyer pool dramatically, but 90% of brokers refuse—limiting your chances.
5. Where will you market my business?
Demand a clear, specific list of paid platforms. Top brokers invest heavily in multi-channel marketing.
6. Do you specialize in my industry?
Industry knowledge helps, but Shea stresses that deal-making skills—negotiation, valuation, closing—are what really sell businesses.
7. Can you show me comps for similar businesses?
You need hard market data, especially on Seller’s Discretionary Earnings (SDE) multiples, to price realistically.
8. Will seller financing be required?
Nearly 90% of Florida small business sales include it. Refusing can cut buyer interest by 40%.
9. Do you work on a success-based fee?
The best brokers get paid when you get paid. Steer clear of large up-front retainers.
10. How will your interests stay aligned with mine?
Compensation should be tied directly to a successful sale—so your win is their win.
The Bottom Line
A great broker isn’t just a middleman—they’re your deal driver, negotiator, and strategist. They bring the buyers, the marketing reach, and the expertise to get you across the finish line.
Ask these questions. Demand clear answers. And choose the broker who’s not just talking about selling your business—but can prove they’ve done it successfully, over and over again.