Latest / Closing the Deal with Fexingo: Sales, Negotiation, and Revenue Conversations for Operators / The Rep Who Lost by Asking for Too Much
Transcript
- Lucas: So there's this deal I keep thinking about, from a few months back. A rep at a mid-sized software company had been working a prospect for about six months. They'd built real momentum — the buyer was genuinely engaged, had looped in procurement, was already talking about implementation dates. Luna: That sounds like a deal that's basically in the bag. Lucas: Right, until the rep decided to push for a three-year commitment with an annual price increase baked in, plus a penalty clause if the buyer wanted to exit early. All of that came out in the final proposal, without any prior discussion. Luna: Ouch. So what happened? Lucas: The buyer went silent for a week. Then came back with a one-line email: 'We've decided to pause this initiative.' And that was it. The rep lost a deal that was weeks from closing, all because of a last-minute ask that felt like a landmine. Luna: That's brutal. But I have to ask — was the three-year ask really that unreasonable? Lucas: On paper, no. In context, yes. And that's the thing we want to dig into today. Because there's a fine line between asking for more and asking for too much, and crossing it can sink a deal that was otherwise yours. Luna: So what's the difference? Is it about timing, or the size of the ask, or something else? Lucas: It's partly all of those, but the core issue is what I'd call 'readiness mismatch.' The buyer had signalled they were ready to commit to a pilot, maybe a one-year deal. They hadn't signalled any appetite for a three-year lock-in. The rep overreached because he was thinking about his quota, not about the buyer's decision-making process. Luna: But isn't it a rep's job to ask for the bigger commitment sometimes? To, you know, 'expand the deal'? Lucas: Sure, and there are times when that's exactly right. But the key is to test that water early and often, not to spring it on them at the finish line. You have to create a sense of safety in the negotiation. If the buyer feels like you're hiding something or trying to trap them, they'll run. Luna: So what should he have done differently? He'd already sent the proposal — was it too late? Lucas: Not necessarily. He could have picked up the phone the moment he sensed hesitation, and said something like, 'I want to make sure the terms work for you. What's giving you pause?' Instead, he waited a week, then followed up with a pushy email asking if they'd had a chance to review. That just added pressure. Luna: I've seen that happen a lot — the follow-up email that's more about the rep's anxiety than the buyer's needs. Lucas: Exactly. And the thing is, the buyer didn't say 'no' to the product. They said 'no' to the deal structure. Those are very different things, and a skilled rep can often salvage the product while adjusting the structure. Luna: So what's the lesson for our listeners? Is it simply 'don't ask for too much'? Lucas: Partially, but it's more nuanced. It's about understanding the buyer's risk tolerance and their internal decision-making timeline. You have to ask yourself: 'What have they told me they're comfortable with? What signals have they given me about budget cycles, about procurement rules, about their own boss's appetite for risk?' Luna: Right, and if you've done that discovery properly, you should have a pretty good sense of where the boundaries are. Lucas: And if you haven't, then the last-minute ask is a gamble. And in this case, the rep lost. But there's a more productive way to think about this: instead of asking for a bigger commitment at the end, you can build it into the conversation earlier, as a natural part of the negotiation. Luna: Can you give us an example of that? Lucas: Sure. Let's say you're selling a CRM platform, and you know the buyer typically signs one-year deals. Early on, you might ask, 'How does your team think about multi-year commitments? Some of our best customers find value in a two-year agreement because it locks in pricing and reduces implementation overhead.' That's a low-pressure way to gauge their appetite. Luna: And if they say 'we never do multi-year,' you know not to go there. Lucas: Exactly. And if they say 'we've considered it,' then you have a green light to bring it up later, framed as a solution to their needs. The mistake is bringing it up as a surprise add-on when they're ready to sign. Luna: What about the penalty clause? Is that ever a good idea? Lucas: A penalty clause is a red flag for many buyers. It signals that you expect them to want to leave, which undermines trust. If you need to protect against early termination, a better approach is to offer a discount for a longer term, rather than a penalty for leaving early. Luna: That's a good point — make it a benefit, not a threat. Lucas: And then there's the annual price increase. That's often seen as greedy unless it's clearly tied to inflation or increased value. You have to justify it, or it feels like a trap. Luna: So what's the takeaway? How do you know when you're asking for too much? Lucas: I think it comes down to a simple test: if your request would surprise the buyer, you've probably gone too far. The best negotiators are predictable — not in a boring way, but in a way that builds confidence. They never throw curveballs at the last minute. Luna: That makes sense. And it's a good reminder that the deal isn't just about the product, it's about the relationship. Lucas: And relationships are built on trust. If you ask for something that feels out of left field, you're telling the buyer you don't understand them. And that's a deal-killer, no matter how good your product is. Luna: So for our listeners who might be in the middle of a negotiation right now, what's one thing they can do today to make sure they're not overreaching? Lucas: Before you send any proposal, take a step back and ask: 'If I were the buyer, would I sign this without hesitation?' If the answer is no, then you have work to do. You need to either adjust the terms or have a conversation about them before you send it. Luna: That's a good self-check. And I'd add: don't be afraid to negotiate against yourself a little. If you've built in too much, it's better to walk it back than to lose the whole deal. Lucas: Right. And that's actually a good segue to something we talk about a lot on this show: the importance of being flexible. The best closers are the ones who know when to hold firm and when to give a little. This is a great example of where giving a little could have saved the deal. Luna: And we should mention, if you've been getting value from these conversations, and you want to help keep them going, you can support the show at buy me a coffee dot com slash fexingo. It's a small way to say thanks and keep us ad-free. Lucas: Yeah, we don't run ads, and listener support is what makes that possible. So if you've ever gotten a tip from a past episode, that's a way to give back. No pressure at all. Luna: Okay, back to the deal. So we've talked about what the rep did wrong. But what if the buyer comes back after a few weeks and says, 'Actually, we might be interested again' — how should the rep handle that? Lucas: That's a great question. If the buyer re-engages, the rep should acknowledge the misstep, apologize for pushing too hard, and ask what terms would make them comfortable. It's a second chance to prove that he can listen. Luna: And if the buyer doesn't re-engage, what do you do? Lucas: You take the lesson. You don't burn the bridge — maybe in a few months, the buyer will be ready. But you also don't keep chasing. That just looks desperate. You move on and apply what you learned to the next deal. Luna: That's solid advice. And it's a good reminder that every lost deal is a chance to get better. Lucas: Exactly. And on that note, let's leave our listeners with this: the best ask is the one that feels like a natural next step for the buyer, not a leap of faith. If you're not sure, ask questions first. The deal will be there.