Latest / Closing the Deal with Fexingo: Sales, Negotiation, and Revenue Conversations for Operators / The Sales Rep Who Won by Asking the Buyer to Fire Someone
Transcript
- Lucas: So there's a B2B software rep I know — sells warehouse management systems, the kind of thing that costs a couple hundred grand and takes six months to implement. Luna: Big deal, long cycle. High risk for everyone involved. Lucas: Exactly. She's been working this prospect for four months. A mid-size distributor, about four hundred employees, running on an ancient system held together with spreadsheets and prayer. The logistics director — let's call him Mark — knows they need to upgrade. He's got budget approval, he's done the ROI analysis, he's narrowed it down to two vendors. Luna: So she's in pole position. What's the holdup? Lucas: Mark keeps stalling. Every time they get close to a decision, he introduces a new concern. Integration risk. Training time. What if the implementation disrupts peak season. All reasonable on the surface, but our rep senses something else is going on. So she asks a question that could have ended the deal right there. Luna: I'm guessing it's not 'what's your budget?' Lucas: She says: 'Mark, if we could wave a magic wand and implement the perfect system tomorrow, would that actually solve your problem? Or is there someone on your team who's going to resist this change so hard that it doesn't matter what software you buy?' Luna: Whoa. That's a loaded question. She's essentially asking him to name a person he'd need to move on. Lucas: And he pauses. Then he says: 'My warehouse manager, Dave. He's been here twenty-two years. He designed the current process. He thinks any new system is a threat to his job. And honestly? He might be right.' Luna: So the rep just named the elephant in the room that everyone was pretending wasn't there. Lucas: Right. And this is where the strategy gets interesting. The rep didn't say 'you should fire Dave.' She said: 'It sounds like you have two decisions to make. One is about software. The other is about people. And if you only make the first decision, the second one will sabotage it.' Luna: She reframed it as a leadership challenge, not a sales objection. Lucas: Exactly. And by the way — if these kinds of conversations have moved your work forward in some small way, we keep this show ad-free thanks to a handful of listeners who chip in at buy me a coffee dot com slash fexingo. It's not a big ask. Just mentioning that that's how the lights stay on here. Luna: Yeah, it makes a real difference. And it lets us keep digging into stories like this one without any sponsor chatter. Lucas: So back to Mark. He calls his boss. They decide to offer Dave a generous severance and a consulting arrangement to document his tribal knowledge before he leaves. It's handled respectfully. And then, within two weeks, Mark signs the deal — five-year contract, six figures. Luna: But that could have backfired spectacularly. What if Mark had gotten defensive? What if he'd decided the rep was overstepping and walked? Lucas: That's the risk. And it's why this move only works when certain conditions are met. First, the rep has to have already built significant trust. She'd spent four months learning Mark's business, his frustrations, his team dynamics. She wasn't a stranger making accusations. Luna: So the timing matters. You can't ask this question on the first call. Lucas: Absolutely not. Second, the buyer has to already suspect the personnel issue themselves. Mark knew Dave was a problem — he just hadn't said it out loud. The rep's question gave him permission to face it. If the buyer is genuinely unaware, this question feels like an attack. Luna: How do you know if they're aware? You'd need to hear clues in earlier conversations. Lucas: Right. You listen for phrases like 'some people just don't get it' or 'I've got a few team members who are set in their ways.' That's the buyer signaling. Third — and this is crucial — the rep has to frame the observation as a shared hypothesis, not a judgment. She said 'if we could wave a magic wand.' That's a hypothetical. It gives the buyer room to agree or deflect without losing face. Luna: What if the buyer deflects? Say Mark had said 'no, Dave is great, he'll come around.' Lucas: Then you drop it. You don't push. The rep would have said something like 'fair enough, I'm glad to hear that. Let's talk about how we can make Dave a champion of the new system.' And you move on. The door is still open for the buyer to come back later if they change their mind. Luna: So the move isn't about forcing a firing. It's about surfacing a hidden obstacle. Lucas: Exactly. And the reason it works so well is that most sales reps are terrified of anything that touches personnel. They think it's not their place. But the buyer's internal team is often the biggest barrier to a successful implementation. If you ignore it, you're selling a solution that can't succeed. Luna: I want to push back a little though. There's a real danger that the rep becomes the scapegoat. If the firing goes badly, Mark might blame her for planting the idea. Lucas: That's a valid risk. And it's why you never explicitly recommend firing anyone. You present the two decisions — the software decision and the people decision — and let the buyer connect the dots. If Mark fires Dave and regrets it, that's on his leadership, not on the rep. But if the rep had said 'you should fire Dave,' then yes, she'd own the fallout. Luna: So the framing is everything. 'I'm seeing a pattern. Are you seeing it too?' Not 'here's what you should do.' Lucas: Right. And the best reps I know do this in a way that shows genuine concern for the buyer's outcome. The rep in this story genuinely believed that if Dave stayed, the implementation would fail and Mark would be unhappy with the software. She was willing to risk the deal to prevent that outcome. That's actually a form of integrity. Luna: It's also a power move. By raising the real issue, she demonstrated that she cares more about Mark's success than about closing the deal. That deepens trust even if the conversation is uncomfortable. Lucas: Exactly. And in this case, it worked. Mark later told her that her question was the most honest conversation he'd had with any vendor. He said 'everyone else wanted to sell me software. You wanted to help me run my business better.' Luna: That's the ideal outcome. But let's talk about the conditions where this doesn't work. When should a rep absolutely not go there? Lucas: First, if you haven't earned the right. If you're early in the relationship, stay in your lane. Second, if the buyer is underperformance pressure and might be looking for a scapegoat themselves. You don't want to become the excuse for a firing that was already going to happen. Third, if the personnel issue is obviously a legal landmine — like a protected class situation or a pending discrimination claim. You are not an HR consultant. Stay out of that. Luna: So you're not advising reps to become amateur HR detectives. You're saying there's a narrow window where this is the smartest move in the playbook. Lucas: Exactly. And I'd argue that window appears more often than reps think. Because the human dynamics of a buying decision are always present, but most sales training ignores them. We teach product knowledge, objection handling, closing techniques. We don't teach how to ask 'is there someone on your team who will kill this project?' Luna: What about the buyer who says 'yes, but I can't fire them. They're a relative of the owner' or 'they've been here forever.' Then what? Lucas: Then you have a different conversation. The buyer is now telling you that they don't have the authority or willingness to remove the obstacle. That's actually valuable information. It tells you the deal might not close, or if it does, the implementation will be painful. You can decide whether to proceed with that risk. Luna: So it's a diagnostic tool as much as a closing tactic. Lucas: Exactly. And sometimes the best outcome is walking away. One rep I know asked this question, the buyer acknowledged the problem person was his own brother-in-law, and the rep politely bowed out. Six months later, the brother-in-law left, and the buyer called the rep back. Because the rep had earned credibility by being honest about the risk. Luna: That's a longer play. But it works because the rep didn't push a deal that was doomed. Lucas: Right. So the takeaway for today: if you're deep in a complex deal and you sense a person-shaped obstacle, consider naming it. But only if you have trust, only if the buyer is already hinting at it, and only if you can frame it as a shared observation. The question 'what would happen if that person left?' is powerful — but you have to be prepared for the answer. Luna: And be ready for the answer to be 'nothing,' which means you just lost the deal. But sometimes that's the right outcome. Lucas: Exactly. Not every deal is worth closing. But every rep should know how to have the conversation.