Latest / Sales Leadership with Fexingo: Quota Carriers, Sales Managers, and Revenue Teams / How Top Reps Turn a Lost Deal into a Future Win
Transcript
- Lucas: So Luna, I want to talk about the deal that got away. Not the one you lost last week — the one you lost last quarter, and then never thought about again. Luna: Oh, you mean the one that keeps me up at night? I have a few of those. Lucas: Exactly. And that's the thing — most reps treat a lost deal like a dead end. They move on, they prospect harder, they try to forget it. But the best reps I've watched do the opposite. They treat the loss like a crime scene, and they walk through it with a forensic mindset. Luna: A crime scene. I like that. So what does that actually look like in practice? I mean, you can't just call the buyer and ask, 'Why didn't you pick us?' Lucas: You can, actually. And that's step one. But you have to ask it the right way. Most reps ask, 'What could we have done better?' which is a garbage question. It invites politeness. The buyer says, 'Oh, you were great, it just came down to budget.' And then you learn nothing. Luna: Right. So what's the better question? Lucas: You ask, 'What did the other guys show you that we didn't?' Or, 'If you were me, what would you do differently next time?' You want to get them talking about the real gap, not the safe answer. And you have to promise them you'll use it — otherwise they're just being nice. Luna: That's good. I've also found that timing matters. If you call the day after they signed with a competitor, they're still in the honeymoon phase. They're not going to say anything negative. You have to wait until the deal is actually done and they've had a few weeks to live with it. Lucas: That's a great point. And there's a specific case I want to bring up — a SaaS company I've been following, let's call them Northbeam Analytics. They lost a four hundred thousand dollar deal to a larger competitor at the end of last year. And the rep, a guy named Marcus, did this really disciplined post-mortem. He didn't just call the buyer once — he did a thirty-minute call, then he sent a follow-up with three specific questions, then he called the champion who had been on their side. Luna: So he went deep. What did he find out? Lucas: He found out that the real reason wasn't price, and it wasn't the product. It was that the competitor had a customer success team that was on-site for the first month. That was the tipping point. The buyer had a small team, they were worried about implementation, and they just didn't believe Northbeam could hold their hand. Luna: So it was a trust issue, not a feature issue. That changes everything. Lucas: It does. And here's the kicker — Marcus took that back to his leadership, and they changed their implementation package. They added a dedicated onboarding specialist for the first thirty days. And eighteen months later, that same account came back, because the competitor's implementation had actually been a nightmare. They re-opened the deal, and this time it was worth one point two million. Luna: Wow. That's not just a win — that's a twelve-month compound annual growth rate on a single relationship. It's like the loss was the investment. Lucas: Exactly. And that's the mindset shift. The loss isn't the end of the story — it's data. But the problem is, most teams don't have a system for capturing that data. They rely on the rep to be disciplined enough to do it, and reps are busy, so it doesn't happen. Luna: So what does a good post-mortem process actually look like? I mean, you can't just rely on one great rep. Lucas: Right. And that's what I want to drill into today. There are five questions that I think matter more than any others. And if you get honest answers to these, you'll have a playbook for the next quarter. Luna: Okay, let's hear them. Lucas: First: 'What did we miss?' Not 'What did we do wrong?' — 'What did we miss?' That opens up the door to the things you didn't even know were important. Luna: That's a good one. It's not accusatory. Lucas: Second: 'Who was the real decision-maker?' Because nine times out of ten, the person you were talking to wasn't the only one. There was someone in the background — an economic buyer, a technical gatekeeper — who had a veto you never saw. Luna: And you have to find that person before you pitch, not after you lose. Lucas: Third: 'What did the competitor do better?' This is the one that stings, but it's the most valuable. If you can get an honest answer, you know exactly what to build or fix. Luna: And fourth? I'm guessing it's about timing. Lucas: Fourth is 'Was timing a factor, or was it just an excuse?' Because sometimes the deal is genuinely lost to a budget cycle, and nothing you did mattered. But other times, timing is a smoke screen for 'we didn't have enough value.' You have to ask the follow-up: 'If the budget was there, would you have picked us?' Luna: That's a tough question, but it's the one that separates the real reason from the polite reason. Lucas: And the fifth question — this is the one that most reps skip — is 'What did we learn that can help the next deal?' You have to force yourself to write down one specific action. Not 'we should get in earlier' — that's too vague. Something like 'we need to bring a technical architect to the first demo for accounts over a hundred employees.' That's a concrete change. Luna: So the post-mortem isn't just about the past — it's about the future. It's like the difference between a doctor telling you why you got sick and giving you a prescription. Lucas: Exactly. And that's where a lot of teams fall short. They do the review, they nod, they say 'okay, thanks for the feedback,' and then they move on without changing anything. The best teams — the ones that turn losses into wins — they have a ritual. They put the action item into the CRM, they assign an owner, and they check it at the next team meeting. Luna: I want to come back to something you said earlier — about the champion. You said Marcus called the champion who was on their side. That's a different perspective than the buyer. How much weight should we put on what the champion says after the loss? Lucas: A lot. Because the champion is often the one who fought for you internally. They're the ones who are most disappointed when you lose. And they're also the ones who have the most insight into why the decision went the other way. They heard the internal conversations. They know what the CEO said in the hallway. That's gold. Luna: But do they actually tell you the truth? I mean, they might be embarrassed that they lost the internal battle. Lucas: Sometimes they do, yeah. But you have to make it safe for them. You say, 'Listen, we're not going to pitch you again, we just want to understand.' And you have to give them a little time. Don't call them the day after — give it a week. Let the dust settle. Then they'll open up. Luna: I've also found that the best champions are the ones who want you to win, because your win validates their judgment. So they're motivated to tell you what went wrong so you can fix it for next time. Lucas: Exactly. And that's the thing — the relationship doesn't end when the deal is lost. In fact, the loss can be the start of a stronger relationship, because you're showing that you're a professional who wants to learn. That's rare. Most reps just disappear. Luna: That's a really good point. And I think it connects to what we talk about a lot on this show — the long game. The deal you lose today is the deal you might win in eighteen months, like Marcus did. Lucas: And that's the real skill — not closing, but staying in the game. The reps who win big over time are the ones who treat every loss as a seed they're planting for later. Luna: So what's the one thing a rep can do tomorrow morning to start turning a recent loss into a future win? Lucas: The one thing? Before you even pick up the phone, write down what you think you lost to. Then call the buyer and ask the five questions. But here's the catch — you have to listen without getting defensive. The moment you start explaining, you lose the learning. Luna: So it's a listening exercise, not a talking exercise. That's hard for a lot of salespeople. Lucas: It is. But the ones who can do it — they're the ones who compound their skills. They're the ones who get to the point where they don't lose the same deal twice. Luna: And that's the real competitive advantage, isn't it? It's not having the best product or the best price. It's being the team that learns faster. Lucas: Exactly. And I think that's a good note to end on. Next week, we'll talk about how to turn a win into a referenceable case study — but that's a different kind of post-mortem. Luna: Looking forward to it. For now, if you're listening, maybe take a look at your last big loss and ask yourself: what did you actually learn from it?