Latest / Sales Leadership with Fexingo: Quota Carriers, Sales Managers, and Revenue Teams / How Sales Reps Can Recover From a Lost Deal
Transcript
- Lucas: You lose a deal. The buyer goes silent. You send a polite follow-up email—nothing. You move on. But what if the loss is actually the beginning of a much bigger win—if you play it right? Luna: I think most reps treat lost deals like a dead end. They feel the sting, they vent to their manager, and then they just disappear. But the best reps I've seen actually lean in. Lucas: Exactly. There's a framework for recovering from a lost deal, and I've seen it work in practice. Let me give you a concrete example. A SaaS company I know had a rep named Jenna. She lost a $300,000 contract to a competitor. Classic story—price objection, supposedly. But Jenna didn't just move on. Luna: So what did she do differently? Did she call the buyer back and ask why? Lucas: Pretty much—but with structure. First, she did an internal post-mortem with her manager and the solution engineer. They mapped every touchpoint, every objection, every perceived weakness. They realized the competitor was slightly cheaper, but Jenna's product had a feature the competitor didn't—advanced security compliance. The buyer never mentioned it as a priority. Luna: Right, so the real reason wasn't price. It was that Jenna failed to uncover a hidden need. Lucas: Bingo. But here's the second step—she reached out to the buyer three weeks after the loss. Not to pitch again. She said, 'I'm doing a post-mortem on my own process. Would you be open to a 15-minute call to help me understand what I could have done better?' No strings attached. The buyer agreed. Luna: That takes guts. Most reps are too embarrassed or too proud to ask for that feedback. But it's smart—it keeps the relationship alive. Lucas: And it's not just about feedback. During that call, Jenna learned the buyer's team had actually been worried about compliance from day one—but the competitor's salesperson had glossed over it, offering a discount instead. Jenna's company had the compliance solution, but she'd never brought it up because the buyer didn't ask. Luna: So she had the ammunition the whole time—she just didn't know where to aim. Lucas: Exactly. That call changed everything. Jenna didn't try to re-sell on the spot. She ended the call by saying, 'Thank you. I'll take this to heart.' Then she set a calendar reminder to follow up in four months—not to pitch, but to check in. Luna: Four months? That's a long time. I imagine most reps would want to jump back in sooner. Lucas: But patience pays off. Six months after the loss, Jenna saw a news article that the buyer's company had been audited and flagged for a compliance gap. She reached out with a simple note: 'Saw the news. If you're revisiting your compliance stack, I'd love to share what we've done with other firms in your space.' That reopened the conversation. Luna: And she closed it? Lucas: Closed a $500,000 contract—bigger than the original deal. The buyer later said that if Jenna had pushed harder right after the loss, he would have shut her out. But the respectful distance, the genuine post-mortem, and the timely re-engagement—that built trust. Luna: That's a great story. But I have to ask—how do you decide which lost deals are worth this investment? Not every loss has a hidden compliance angle. Lucas: You're right. You can't chase every dead deal. I'd say look at three things: deal size, relationship quality, and whether there was a specific unaddressed need you can now fill. If the deal was in your top 20 percent of pipeline value, and the buyer was engaged but chose someone else on a legitimate differentiator—not just price—then it's worth the effort. Luna: And what about the reps who just get ghosted? No feedback call, no response to the email. Do you still follow up months later? Lucas: That's tougher. But I'd say send one final email after two weeks—no ask, just a value-add like an article relevant to their business. If still nothing, put them on a nurture sequence for six months. The key is not to burn the bridge by being desperate. Silence is not rejection—it's often just busyness. Luna: You know, this whole idea of leaning into loss—it's counterintuitive. Most sales cultures celebrate wins and sweep losses under the rug. But if you actually analyze the loss, you get better. Lucas: And that's exactly why we do this show—to share the kind of practical moves that actually move the needle. And speaking of moving the needle, if these conversations have helped you in any small way, here's a quick note. We deliberately keep this podcast ad-free—no sponsors, no commercials. It's just us trying to give you something useful every episode. Luna: Yeah, and we'd like to keep it that way. So if you want to support that choice, there's a simple way. You can head to buy me a coffee dot com slash fexingo. Lucas: No pressure at all—just if you find value here, that's the way to keep the show going. Appreciate everyone who does. Now, back to Jenna's story. She also did something else that I think is underused: she shared her post-mortem findings with her product team. Luna: Oh, that's interesting. So the loss informed product development? Lucas: Exactly. She flagged that multiple prospects had mentioned compliance in discovery, but her sales deck didn't highlight it. The product team updated the product roadmap to include a compliance dashboard, and marketing created a one-pager. That one loss ended up improving the whole sales motion. Luna: So the framework is really three phases: immediate debrief, buyer insight call, and then strategic re-engagement. Plus feeding back into the product. Lucas: Right. And the debrief has to be honest—not a blame session. Ask: Did we truly understand their priorities? Did we present our differentiators clearly? Was there a hidden stakeholder we never met? Because often the loss isn't about price—it's about a decision-maker you never knew existed. Luna: I've seen that. A rep loses a deal, finds out later the CFO vetoed it because of implementation cost. But the rep never spoke to the CFO. Lucas: Classic. So in the debrief, map the buyer's decision process. Who else was involved? The buyer might not tell you in the heat of the loss, but in a post-mortem call, they often will. Luna: What's the best way to ask for that call without sounding like you're trying to reopen the deal? Lucas: Be humble and specific. Say something like: 'I respect your decision and I'm not trying to change it. But I'm trying to improve as a salesperson, and your insight would be incredibly valuable. Could you spare 15 minutes to share what we could have done better?' Most people are flattered to be asked for advice. Luna: And if they say no? Lucas: Then you respect that. Send a thank-you note, and add them to a low-touch nurture sequence. But if they say yes, you need to be disciplined—actually listen, don't defend. I've seen reps ruin the call by arguing with the buyer. That's the fastest way to burn the bridge forever. Luna: So the call is purely for learning, not for selling. That's a hard rule. Lucas: Hard rule. And then you wait. The timing of re-engagement matters. Too soon and you look desperate. Too late and the buyer has forgotten you. I like a 90-day check-in with something useful—an industry report, a relevant case study. Not a 'just checking in' email. Luna: And in Jenna's case, she used a trigger event—the audit news. That's the gold standard. So part of the recovery process is monitoring the buyer's world for triggers. Lucas: Yes. Set up Google Alerts. Follow their LinkedIn. If they change roles, get promoted, or announce a new initiative—that's your moment. And you don't even mention the old loss. You just say, 'Congrats on the new role. I thought of you when I saw this article about.' Contextual, respectful, valuable. Luna: I think the biggest takeaway is that a lost deal isn't the end of the relationship—it's the start of a different kind of relationship. One based on trust and honesty. Lucas: Exactly. And if you do it right, that lost deal can become your biggest advocate—or your biggest customer down the line. So next time you lose a deal, don't just move on. Move into the recovery process. Luna: I'm going to try that with my next loss. Thanks, Lucas. Lucas: Always. That's all for this episode—see you next time.