We asked two sales experts

After a deal falls through, what's the most valuable piece of information a rep should try to get from the prospect, and how do you ask for it without sounding desperate?

Scott Clary

Founder - WWA

Most salespeople ask prospects why they lost. But people respond to that politely, not honestly — offering some vague response about budget or timing.

Instead, I ask: "What would've had to be true for this to go differently?"

That changes the whole conversation.

Now, they have to think out loud about a hypothetical rather than evaluate you.

I emailed that question to a prospect after losing an agency pitch a few years ago.

It turns out their CFO had put a budget constraint in place two weeks before our last conversation without telling us. We couldn't win after that.

I never would've known without asking that question — and I would've wasted time ruminating about things that had nothing to do with why we lost.

After that, we restructured how we put proposals together: Send it a few days after, keep it short, and if they don't respond, leave it.

Leslie Venetz

Founder - The Sales-Led GTM Agency

The most valuable thing a rep can learn after a loss is what the buyer needed that they never got. Budget, timing, and authority are placeholders.

The justifications hidden behind those placeholders are always more instructive. Without that understanding, a rep will keep losing deals they should have won.

The way to uncover that information without sounding desperate is to ask for guidance.

Guidance is an ask for help with a specific purpose: to show up better for the next buyer.

Make it clear that the intent is self-improvement rather than salvaging the deal and your buyers will safe being honest.