Latest / Sales Leadership with Fexingo: Quota Carriers, Sales Managers, and Revenue Teams / How Sales Reps Can Recover From a Deal They Never Should Have Won
Transcript
- Lucas: There is a particular feeling every experienced sales rep knows but rarely talks about. You close a deal, you shake hands, you walk back to your desk, and instead of celebrating, you feel a knot in your stomach. Luna: The dread close. Yeah, I've heard reps describe it as 'I just sold something I'm not sure we can deliver.' Lucas: Exactly. We're trained to see a 'yes' as the finish line, but sometimes that yes is actually the start of a much bigger problem. Today I want to talk about the deal you never should have won — and how to recover from it. Luna: Recover? That implies you're already in the mess. What does that look like on the ground? Lucas: Let me give you a concrete example. There's a SaaS company I know — mid-market CRM player, about 200 employees. One of their senior reps closed a $120,000 annual contract in a single discovery call. The prospect basically said yes to everything. No pushback on price, no extended evaluation, no technical deep dive. Luna: Wait — no technical deep dive for a CRM? That's a red flag the size of a billboard. Lucas: Right. But the rep was on a hot streak, her manager was pushing for quarter-end numbers, and the commission was too tempting. They signed the deal. Fast forward four months: the implementation requires three custom integrations the product barely supports. The customer's champion — the person who said yes — had no real authority. Their VP of Operations hated the tool from day one. The customer churned at month seven, demanded a refund, and left a scathing G2 review. Luna: And the rep? She lost her quota credit, her manager blamed her for the bad booking, and the relationship with the product team soured because they had to scramble on those integrations. Lucas: Exactly. So the question is: when you're already in that situation — six weeks into implementation, the customer is unhappy, you know you should have slowed down — what do you actually do? Luna: I imagine the first instinct is to defend the deal. Blame the customer for changing requirements. But that usually backfires. Lucas: It does. The better move is to get ahead of the problem internally. Go to your manager and say, 'I think we have a misalignment on this deal, and I want to fix it before it blows up.' Most managers would rather hear that at week six than month six. Luna: And what do you say to the customer? 'Hey, we sold you something that might not work' doesn't sound great. Lucas: You don't say that. You schedule a joint session with your implementation team and the customer's key stakeholders — not just the champion. You say something like, 'We want to make sure this deployment sets you up for long-term success. Can we do a quick alignment check on the scope, the timeline, and the success metrics?' Luna: So you're resetting expectations mid-implementation. That's brave. But doesn't it risk the customer saying, 'You should have asked this before I signed'? Lucas: They might. But here's the thing: if you're already six weeks in and the project is shaky, they're already feeling that frustration. Acknowledging it proactively — even apologizing for not catching it earlier — builds trust. I've seen reps salvage relationships by simply saying, 'We dropped the ball on the discovery phase, and I want to make it right.' Luna: How do you fix the scope issue, practically? You can't just ask for more money after the contract is signed. Lucas: You can re-scope. You say, 'Given what we now know, here are three paths. Option A is the full implementation on the original timeline but it requires these resources from your side. Option B is a phased approach — we deliver the core functionality first, then add the custom integrations in quarter two. Option C is we pause and reassess together.' Most customers will pick B because it feels like progress without the risk of failure. Luna: Interesting. So you're trading short-term revenue for long-term retention. But what about the rep who hasn't closed the deal yet? How do you prevent the wrong yes from happening in the first place? Lucas: That's the real skill. I use a framework I call the three fit checks. Before you ever send a proposal, you run through three questions. One: does the product actually solve the problem the champion described — or are you stretching? Two: does the champion have budget authority and organizational cover to push this through? Three: is there a documented implementation plan that both sides agree on before the signature? Luna: That third one is the one most reps skip. They treat implementation as a post-sale handoff, not a closing condition. Lucas: Exactly. I've seen deals where the rep got the signature but the customer's IT team never even saw the product. That's a churn waiting to happen. If you can't get a ten-minute meeting with the technical decision-maker before the contract is signed, you don't have a real deal — you have a hope. Luna: So let's say you run the fit checks and one of them fails. Do you walk away? Or do you try to fix it before the close? Lucas: You fix it before the close. You tell the champion, 'I want to make sure this works for everyone. Can we bring in your IT lead for a thirty-minute call to validate the integration requirements?' If they resist, that's a signal that the champion is either not serious or not influential enough. Either way, you're better off knowing before you spend three months on implementation hell. Luna: That requires confidence. Especially when your manager is breathing down your neck about quarterly targets. Lucas: It does. And honestly, this is where sales leadership matters. If your culture only celebrates bookings, you'll get bookings — and the subsequent churn. The best sales leaders I know actually reward reps for flagging risky deals early. They say, 'I'd rather you lose a deal in discovery than lose a customer in implementation.' Luna: I want to come back to that example of the CRM rep. Did she ever recover from that bad deal? Lucas: She did. She owned the mistake, worked with the implementation team to get the customer onto a scaled-down version, and eventually the customer renewed at a lower tier. It took eighteen months to rebuild trust, but she salvaged the relationship. More importantly, she changed her process. She now does the three fit checks on every single deal, and her win rate actually went up because she stopped chasing bad fits. Luna: So the recovery isn't just about fixing one deal — it's about learning the discipline of saying no to the wrong yes. Lucas: That's the core. The wrong yes is seductive because it feels like a win. But in sales, the real win is a customer who stays, who expands, who refers. And you don't get that by taking shortcuts in discovery. Luna: You know, this episode actually made me think about something. If you've been in sales for a while, you've probably had that knot-in-your-stomach moment. And if today's conversation helped you think about it more clearly — maybe even saved you from a bad deal — that's exactly the kind of value we hope this show delivers. Lucas: Yeah, and we keep the show ad-free because of listeners who find it useful enough to toss a few dollars our way. If today was worth a coffee to you, you know where to find it — buy me a coffee dot com slash fexingo. Luna: And we put that link in the show notes so you don't have to remember it. Now, back to the three fit checks — Lucas, you mentioned that the second check is about budget authority and organizational cover. Can you unpack that a bit more? What does 'organizational cover' actually mean? Lucas: Sure. Organizational cover means the champion has enough political capital inside their company to push the deal through when objections arise. A director of sales operations might love your product, but if the CFO has a grudge against new software spend, that director needs to be able to navigate that internally. If they can't, your deal is fragile. Luna: So you're essentially vetting the champion's ability to sell internally on your behalf. Lucas: Exactly. And you can test this. Ask the champion, 'If your CFO pushes back on the budget, how would you handle that?' Their answer tells you everything. If they say, 'Oh, the CFO trusts my judgment,' that's good. If they say, 'I'll figure it out,' that's a risk. Luna: What about the first fit check — product fit. How do you know if you're stretching? Lucas: One simple test: can you describe the specific problem your product solves for them in one sentence, and does the champion nod without adding caveats? If you find yourself saying, 'Well, our platform can do that, but it might require a workaround,' you're stretching. And the customer will feel that eventually. Luna: Okay, so the three fit checks are: specific problem fit, champion authority and cover, and agreed implementation plan. That's a solid pre-close checklist. Lucas: It is. And I'll add one more thing: the earlier you do these checks, the easier it is to walk away. If you're at the proposal stage and you discover a fit issue, it's harder to back out because you've already invested time. Do it in discovery, in the first or second call. Luna: That requires discipline. But it's the difference between a pipeline full of real opportunities and a pipeline full of time bombs. Lucas: Exactly. And the rep who learns that lesson — even through a painful recovery — becomes a much better seller in the long run.