Are You Losing Deals Over Price or Are You Missing the Real Driver?

Hey, it’s David!

Private equity professionals know that no two deals are alike.

While many assume a deal falls apart because of price -“They must have found someone cheaper”- the reality is often different. More often than not, buyers walk away because they’re uncertain about the value.

The challenge?

Too many dealmakers focus on negotiating the number rather than positioning the value. They fail to probe deep enough into whether the buyer is making a decision based on price, strategic fit, risk mitigation, or long-term synergies. And that’s where deals are won… or lost.

This isn’t just a closing problem, it’s a deal flow problem. If the deals entering your pipeline don’t align with how buyers make decisions, you’ll see lower close rates, longer negotiation cycles, and unnecessary pricing battles.

That’s where the right investment banking team makes a difference. The best deals happen when you’re targeting the right businesses, structuring deals with value alignment, and positioning opportunities to decision-makers who aren’t just shopping on price.

…Are You Negotiating Like a Gate Agent or a Pilot?

On a recent flight, I watched a passenger argue with a gate agent about an upgrade. The agent stuck to the script: “Sorry, the system determines availability.”

But seasoned travelers know that pilots make the final call on last-minute adjustments. The gate agent was locked in a process, the pilot was focused on the bigger picture.

Too many professionals negotiate like gate agents, stuck on rigid price discussions and financial modeling, while the best investors negotiate like pilots, understanding the deal’s true trajectory and adjusting accordingly.

Is Your Buyer Making a Financial or a Strategic Decision?

Every acquisition involves financial analysis, but sellers don’t make decisions based on numbers alone.

Some prioritize maximizing valuation. Others prioritize certainty of close, legacy protection, or deal structure flexibility. If you don’t know which lever matters most, you’re negotiating blind.

How to Probe for the Real Buying Motive

Before structuring the deal, ask:

• “Beyond price, what factors will determine whether this is a successful acquisition for you?”

• “What problem are you ultimately trying to solve with this investment?”

• “Where do you see the most risk in moving forward, and how can we mitigate it?”

• “What has frustrated you in past M&A transactions?”

• “If price were equal, what factors would make you choose one deal over another?”

Their answers will reveal whether you’re negotiating on cost, strategic alignment, or risk reduction.

Structure the Deal to Win, Not Just to Bid

Once you understand how the seller defines success, structure your approach accordingly:

• If they’re price-driven, provide clear valuation logic and strategic upside.

• If they’re certainty-driven, offer simple structures with minimal contingencies.

• If they’re legacy-driven, craft a transition plan that ensures continuity.

• If they’re risk-averse, present earnouts, seller financing, or phased exits to mitigate concerns.

Winning deals isn’t about squeezing price, it’s about structuring offers that sellers want to say yes to.

The Bottom Line: Do Your Deals Align with Seller Motivations?

In private equity, the best deals don’t always go to the highest bidder, they go to the best-prepared buyer. If your firm is missing out on deals, it may not be a pricing issue, it may be a positioning issue.

The best investors don’t just negotiate, they align. Are your acquisitions structured to secure the right opportunities? Let’s talk about how to position your next deal for success.

Are you enjoying the content we’re sharing from BoardSpire?

I’d love to hear from you, so I’d appreciate your feedback in this quick poll:

Thank you!

David