When It’s Time to Sell Your Business, Who Do You Trust to Sit on Your Side of the Table?
Selling a business is unlike most other financial transactions. For many owners, it’s the culmination of years—sometimes decades—of personal sacrifice, financial risk, difficult decisions, and hard-earned accomplishments. The business may represent their largest financial asset, but it also represents something considerably more personal.
I understand that because I’ve sat in that chair.
For 16 years, I owned and operated a business in Southwest Florida. Before that, I spent decades in corporate leadership, responsible for employees, operations, financial performance, and results. I’ve experienced the responsibilities that don’t always appear on a balance sheet, and I understand what it means when the business ultimately depends on you.
When the time comes to sell, choosing who will represent you deserves considerably more thought than simply asking who can find a buyer.
There’s a Difference Between Understanding Business and Having Owned One
Business owners carry responsibilities that can be difficult to appreciate without experiencing them firsthand. You’re responsible for the people who depend on the business for their livelihoods, the customers who trust you, the vendors who extend credit, and the financial obligations that never seem to stop arriving.
I’ve often described business ownership as being responsible for both the front and back of every check that passes through the company. You work to generate the revenue, but you’re equally responsible for ensuring the money is there to cover payroll, expenses, obligations, and everything else required to keep the doors open.
Those experiences shape how I approach business brokerage today. When an owner talks about a difficult employee situation, customer concentration, cash flow, or the emotional challenge of stepping away, I understand the conversation from more than a transactional perspective.
That shared experience doesn’t automatically make someone the right business broker. But I believe it provides a valuable foundation for understanding what a seller is really navigating.
What Should You Look for in the Person Representing Your Sale?
Trust matters, but trust shouldn’t mean simply liking someone or feeling comfortable during an introductory meeting. A seller should expect competence, preparation, discretion, sound judgment, and the ability to communicate clearly—even when the news isn’t necessarily what the owner hoped to hear.
A good business brokerage relationship begins with understanding the company and the owner’s objectives. Why are you selling? What financial outcome are you hoping to achieve? What happens to your employees? Are you prepared to remain involved during a transition? Do you own the commercial real estate, and should that property be part of the transaction?
Just as importantly, your representative should be willing to discuss difficult questions about financial performance, owner dependency, customer relationships, business value, and potential buyer concerns before those issues become obstacles during negotiations.
The right person shouldn’t simply tell you what you want to hear. They should help you understand what you need to know.
Why Not Simply Sell the Business Yourself?
Some business owners are accomplished negotiators. They’ve built successful companies, negotiated substantial contracts, managed employees, and made important financial decisions throughout their careers. It’s reasonable for them to wonder whether they could sell their business without professional representation.
In some circumstances, they can. But selling a business introduces a different set of challenges, including establishing a defensible asking price, maintaining confidentiality, identifying and qualifying buyers, presenting financial information appropriately, managing due diligence, coordinating negotiations, and keeping the transaction moving toward closing.
There is also the matter of time. While an owner is attempting to sell, the company still needs to perform. Employees need leadership, customers need attention, and financial results remain important. A business that begins deteriorating during the sale process can become less attractive to buyers precisely when performance matters most.
Professional representation doesn’t eliminate every challenge or guarantee a particular result. It can, however, provide a structured process, broader buyer exposure, an experienced negotiating perspective, and a degree of separation between the seller’s emotions and the transaction.
For many owners, that combination is worth serious consideration.
The Best Selling Strategy Also Considers the Buyer’s Perspective
One of the most important parts of positioning a business for sale is understanding how a qualified buyer will evaluate it.
The seller naturally remembers the years of effort, the sacrifices, the relationships, and the potential they believe the company possesses. A buyer approaches the opportunity differently. They want to understand the financial performance, risks, management structure, customer relationships, competitive position, and likelihood that the business will continue succeeding after ownership changes.
That difference in perspective matters enormously.
A buyer may question whether earnings are sustainable, whether key employees will remain, whether important customers depend personally on the seller, or whether the business can operate effectively without its current owner. If commercial real estate is involved, the buyer may also evaluate the property’s value, financing, lease alternatives, and suitability for future operations.
I believe effective business brokerage requires understanding both sides of the table. The goal is to help the seller recognize potential concerns early, prepare credible information, and present the opportunity in a way that qualified buyers can understand and evaluate confidently.
A well-prepared business doesn’t simply tell a better story. It gives buyers more reasons to believe that story.
Thinking About Selling, but Not Sure Where to Begin?
You don’t need to have an asking price, a buyer, or even a firm decision to sell before beginning the conversation.
Sometimes the most valuable discussion happens well before the business reaches the market. We can talk about your objectives, the company’s readiness, potential buyer concerns, the commercial real estate if applicable, and what steps might improve your position.
A Business Sale Is a Journey, Not Just a Closing Date
Selling a business rarely follows a perfectly straight line. There may be questions about financial records, valuation expectations, buyer qualifications, financing, due diligence, purchase agreements, employee transitions, and closing requirements.
That’s why I believe the experience of working with a business broker matters almost as much as the initial marketing strategy.
Sellers should understand what happens next, what information will be needed, which decisions require their attention, and how the process is progressing. Consistent communication is essential, particularly when a transaction encounters delays or complications.
I don’t believe owners should feel as though they’ve handed over their business and are now waiting for occasional updates. They should have a clear understanding of the process, reasonable expectations about timing, and someone prepared to explain the opportunities, challenges, and decisions along the way.
Good communication doesn’t mean every update will be positive. It means the seller shouldn’t have to wonder whether anyone is paying attention.
Sometimes the Real Estate Changes the Entire Conversation
Many business owners also own the building or property from which their company operates. In those situations, selling the business may involve two separate assets—and potentially two different buyer markets.
Should the business and real estate be sold together? Would retaining the property and leasing it to the new business owner provide a desirable income stream? Could selling the real estate separately create a better overall outcome? How might financing, property value, lease terms, and the buyer’s capital requirements affect the transaction?
These questions deserve attention early because the structure of the real estate transaction can influence the business sale itself.
Working within CRE Commercial Group and CIBB gives me access to broader commercial real estate and business brokerage resources when these decisions intersect. Combined with my own business ownership and operating experience, that allows me to approach the transaction from a business, real estate, and strategic perspective rather than treating each component in isolation.
The objective is to evaluate the available options and pursue the structure that best supports the seller’s financial and personal goals.
Choosing the Right Representation Is Part of Preparing to Sell
If you’re considering selling your business, I would encourage you to interview the people you’re considering working with. Ask about their experience, their approach to determining an asking price, how they identify qualified buyers, how they protect confidentiality, and how they communicate throughout the process.
Pay attention to whether they ask thoughtful questions about your business—or simply tell you how quickly they believe they can sell it.
After decades of leading and operating businesses, I know that ownership involves far more than the numbers on a financial statement. I also know that buyers need reliable information, realistic expectations, and a compelling reason to commit their capital.
My approach is to bring those perspectives together: understand the seller, prepare the business, anticipate the buyer’s questions, develop a thoughtful marketing and negotiation strategy, and communicate consistently throughout the journey.
Selling your business may be one of the most consequential decisions you’ll ever make. You deserve someone who respects what it took to build it and understands the responsibility of helping you move on to whatever comes next.
When you’re ready to explore that next chapter, I’d welcome the opportunity to sit on your side of the table.
