I’ve watched many deals die in the final stretch—not because the customer changed their mind or a competitor stepped in, but because contract negotiations dragged on for weeks. The product was sold. The relationship was strong. Then legal got involved, and everything stalled.

And it’s a bigger problem than most organizations realize. A 2026 survey of 1,200 sales professionals¹ found that 45% of companies lost a deal in the previous six months due to slow quote and contract approvals, while 93% reported significant friction between sales, legal, and finance during the deal process. Meanwhile, the World Commerce & Contracting Association estimates that companies lose an average of 9.2% of annual revenue because of inefficient contract management.

That’s exactly the problem David Tollen has spent his career solving, and it’s why I was so glad to have him present at our Revenue Acceleration Summit as part of the Sales 3.0 Conference series.

David is an attorney, not a salesperson, but he noticed early in his career that top-performing reps were discussing contract terms with customers long before legal got involved. Not at a lawyer’s level of detail, but enough to prevent what David calls “contract sticker-shock.” Customers weren’t blindsided, negotiations moved faster, and deals stayed on track.

His core insight is simple: every contract clause exists to answer one question—how does each side make or lose money? If salespeople understand the business issue behind a clause, they can discuss it confidently and proactively. Legal language isn’t a foreign language; it’s just business risk explained in an awkward way.

David shared a perfect example: the data indemnity clause, one of the most feared lines in any tech contract. He showed how a salesperson can defuse the entire issue in a single sentence, weeks before negotiations even begin—simply by explaining the difference between indemnity and liability before the customer assumes the worst.

What I appreciated most was David’s advice on working with your own legal team. Don’t argue. Don’t lecture. And when you hit a wall—”it’s just our policy”—don’t fight it. Find out who actually knows the reason and go figure it out together.

His philosophy sums it up best: “Always be closing” really means “always be contracting.” The salespeople who embrace that mindset close more deals, with fewer surprises and far less friction.

Given the reality that nearly half of companies have recently lost business because contracts took too long to move through the approval process, and that poor contracting practices can drain almost a tenth of annual revenue, David’s advice feels more relevant than ever. The organizations that win won’t just be the ones with the best products or sales pitches—they’ll be the ones that remove friction from the path to signature.

If you want your team thinking this way, David’s course—Tech Contracts for Salespeople—is available on-demand in short, flexible modules at techcontracts.com. I went in expecting to skim the first few minutes, but I got hooked. There is so much value to be gained from a great course that will put more money in your pocket. Until July 14, Tech Contracts Academy is offering a 15% discount to Selling Power members/subscribers. Check it out here and use discount code POWER.

¹ March 2026 survey by Conga of over 1,200 commerce decision-makers

Gerhard Gschwandtner is the founder and CEO of Selling Power. He has interviewed Marc Benioff and hundreds of the world’s top sales leaders and authors over a career spanning more than four decades. Reach him at gg@sellingpower.com.