Negotiation is one of the most fascinating and challenging parts of buying a business. When I first began this journey, I thought it was all about numbers. If I could prove my math, my valuation, and my financing plan, I believed that sellers would naturally agree with me. What I’ve learned over the years is that negotiating with business owners is far more about psychology, relationships, and trust than it is about spreadsheets.
I want to share the lessons that have shaped the way I approach negotiations. Some of these came from wins, many came from mistakes, but all of them represent the practical insights I’ve gained sitting across the table from entrepreneurs who poured years of their lives into building something worth buying.
The Human Side of Negotiation
The first thing I realized is that negotiation isn’t just transactional. Sellers don’t see themselves as simply handing over a set of financial statements. They are handing over years of effort, sacrifices, and personal identity. When I understood that selling a business is emotional, everything changed in how I approached those conversations.
I stopped leading with numbers and started leading with empathy. I ask about their journey. I ask about the moments that were hardest, and the milestones they are proudest of. This isn’t manipulation, it’s genuine interest. When a seller feels heard, the conversation shifts. They are no longer defending their price point; they are engaging with someone who respects their work.
Valuation is Only Part of the Equation
I’ve sat in negotiations where both sides agreed on the general value of the business, but the deal still stalled. Why? Because valuation is only one element. Payment terms, transition involvement, employee treatment, and future reputation often matter more to the seller than an exact number.
One of my early lessons was that a seller might accept a lower headline price if they feel confident their employees will be taken care of, or if they are assured their name will remain respected in the community. I once negotiated a deal where the seller’s single non-negotiable was keeping a longtime office manager employed. Meeting that request made everything else easier.
Listening Creates Leverage
In negotiations, silence can be more powerful than persuasion. I’ve learned that by listening carefully, sellers reveal what matters most to them. It may be retirement security, it may be legacy, or it may be a desire to remain involved in some advisory role.
By listening more than I talk, I gather information that allows me to structure terms in ways that meet their priorities without hurting my own objectives. I don’t try to win every point. I try to win the points that matter most for long-term success, while giving them what they value most in return.
Building Trust is More Important Than Winning Points
Early on, I made the mistake of pushing too hard. I wanted the best possible deal and thought squeezing the seller on every line item was how you won. What I found was that when trust breaks down, even a signed deal becomes fragile.
Now, my goal is not just to win points but to build trust. When I say I will do something, I make sure I follow through. When I uncover issues during diligence, I bring them up respectfully, not aggressively. I’ve discovered that most sellers care less about perfection than they do about dealing with someone who keeps their word.
The Power of Seller Financing
One of the most interesting lessons I’ve learned is how often sellers are open to financing part of the deal themselves. Initially, I thought seller financing was rare. I assumed owners wanted full cash out at close. In reality, many sellers are willing to carry a note if they trust the buyer.
The key is presenting it in a way that feels secure. I show them how the business’s own cash flow will support repayment, and I outline protections for both sides. Seller financing creates alignment—they want me to succeed, because their payment depends on it.
Negotiating the Transition Period
Another overlooked negotiation point is the transition period. Many buyers and sellers agree to vague terms like “a few weeks of training.” I’ve learned how dangerous vagueness can be. Now, I negotiate a specific plan: how many hours per week, for how many months, and what responsibilities the seller will maintain.
This protects me from being left alone too early, and it protects the seller from being pulled in longer than they expected. Clear transition terms create smoother handoffs, better employee confidence, and less stress for both sides.
Learning to Walk Away
Perhaps the hardest negotiation lesson is learning to walk away. There have been times I was emotionally invested, convinced the business was a perfect fit, but the seller refused to move on key issues that made the deal unsustainable. Early in my career, I might have pushed forward anyway. Now, I’ve learned that the willingness to walk away is one of the strongest forms of leverage a buyer can have.
Walking away respectfully keeps the door open if circumstances change later. In fact, I’ve had sellers call me months after a deal fell apart to restart conversations on terms closer to what I had originally proposed.
Managing Ego—Both Theirs and Mine
Every negotiation has ego involved. Sellers want recognition for what they’ve built. Buyers want to feel like they got a smart deal. I’ve had to check my own ego many times. If I approach a negotiation trying to “prove” how clever I am, I usually lose.
Instead, I focus on building alignment. If both of us walk away feeling like we protected what mattered most, that’s success. I don’t need to win every small battle if the war is won, owning the right business under terms that work long term.
The Importance of Patience
Some of my best deals took months, even close to a year, to finalize. At first, I found this frustrating. I wanted quick wins. But I’ve realized that patience is a competitive advantage. Many buyers drop out when negotiations take too long. If I can remain steady, respectful, and consistent, I often end up with opportunities others have lost.
Patience also signals to the seller that I’m not desperate. Desperation kills deals. Calm persistence builds confidence.
Using Advisors Wisely
Another lesson I’ve learned is the importance of involving advisors strategically. Attorneys and accountants are essential, but if they dominate negotiations, the tone can become adversarial. I make sure I, as the buyer, remain the primary communicator. Advisors handle technical details, but I handle the relationship.
This ensures the seller sees me as a partner, not as an adversary hiding behind professionals. It also helps me control the narrative and avoid unnecessary conflict.
Why Negotiation is a Long-Term Game
At this stage in my career, I see negotiation less as a one-time event and more as the start of a relationship. Even after a sale closes, the seller often remains a resource, whether through a formal transition, advisory role, or simply being available for questions. If I burn bridges during negotiation, I lose that support.
So I negotiate with the long game in mind. I don’t just want a good deal, I want a good relationship.
Final Thoughts
The lessons I’ve learned from negotiating with business sellers all come back to one truth: negotiation is not about beating the other side, it’s about building alignment. The best deals I’ve done were not the ones where I felt I outsmarted the seller. They were the ones where both of us walked away believing we had protected what mattered most.
Buying businesses is as much about people as it is about numbers. When I honor that reality, negotiations become smoother, deals close faster, and transitions succeed.
For those starting out, my advice is simple: listen more, push less, and always remember that behind every set of financial statements is a human being who spent years creating what you now hope to buy.
I continue to share insights on acquisitions, private equity, and real estate on DrConnorRobertson.com, where I dive deeper into the strategies and lessons shaping my journey.