The One Question That Won a Deal with the CEO's Father

Lucas: So there’s a sales story I heard recently that I can’t stop thinking about. It’s about a rep selling enterprise software to a mid-sized manufacturer - family-owned, third generation, about 800 employees. Luna: These are always the toughest deals, right? Multi-generational, tons of emotional history baked into every decision. Lucas: Exactly. The rep had the CEO on board - the grandson of the founder - but there was one stakeholder who kept blocking the deal: the CEO’s father, who was still on the board. A co-founder from the second generation. He’d been through three ERPs, two CRM migrations, and had seen every software vendor promise the moon and deliver a crater. Luna: So the classic skeptical legacy stakeholder. How do you even begin to crack that? Lucas: The rep didn’t crack it with data. He didn’t bring a case study or a cost-benefit analysis. He asked one question, and it changed the entire dynamic. Luna: What was the question? Lucas: He asked: ‘When you and your father started this company, what was the one customer or the one moment that made you believe it was going to work?’ Luna: Wow. That’s not a sales question. That’s almost like a therapy question. Lucas: It is. But the father’s whole face changed. He leaned back, smiled, and told this story about a local bakery that placed a tiny order when no one else would. And the rep listened - really listened - for about ten minutes. When the father finished, the rep said: ‘That’s exactly the kind of trust we want to earn with you. We’re not here to be your next failed vendor. We want to be that bakery.’ Luna: That’s brilliant. He reframed the entire relationship in the father’s own language. He made the software a continuation of the founder’s story, not a disruption. Lucas: Exactly. The father went from blocking to championing within that single conversation. The deal closed three weeks later. Luna: So the question did two things: it showed respect for the legacy, and it created a narrative bridge. But I think there’s a deeper mechanism at play here - something about how memory and emotion override skepticism. Lucas: There is. Psychologists call it the ‘reminiscence bump.’ People over fifty tend to have disproportionately vivid memories from their teens and twenties - the period when they formed their identity. By asking about the founding days, the rep tapped into that bump. He accessed a positive emotional memory that had nothing to do with software. And that positive emotion got associated with the new vendor. Luna: So you’re essentially piggybacking on the neural network of the founder’s pride. That’s a lot more powerful than any ROI slide. Lucas: You know, these conversations we have - breaking down what actually works in a real negotiation - they take time to research, script, and produce. If you’ve found yourself applying even one of these techniques in your own deals, that’s exactly why we keep doing this. And we keep the show entirely listener-supported, no ads, no sponsors. If you’d like to support the work, you can find us at buy me a coffee dot com slash fexingo. It’s a simple way to keep these episodes coming. Luna: Yeah, and honestly, every contribution goes right back into deeper research and better stories. So if this has added value to your toolkit, consider it. Lucas: Alright, back to the psychology. There’s a second layer here that I think is even more practical. The rep didn’t just ask about the past - he asked about a specific moment of triumph. Luna: Right, not ‘tell me about the early days’ which is too vague. He asked for a concrete ‘aha’ moment. Lucas: Yes. And that specificity did something. It gave the father a chance to relive his competence. He got to be the hero of his own story again, not just the grumpy old guy blocking progress. Once he felt that respect, the new proposal didn’t feel like a threat to his legacy. It felt like an extension of it. Luna: That’s the key insight for me: legacy stakeholders aren’t resisting change. They’re resisting irrelevance. You have to show them that their history is the foundation, not an obstacle. Lucas: Exactly. And there’s a tactical takeaway here. When you’re facing a long-tenured skeptic, don’t lead with what’s new. Lead with what’s enduring. Ask a question that honors their journey before you ever ask for their signature. Luna: Have you seen this work in other contexts? I’m thinking about renewals or even upselling existing clients. Lucas: Absolutely. I heard a similar story from a SaaS rep who was trying to expand a contract with a company that had been a customer for twelve years. The procurement director was new and wanted to put the contract out to bid. The rep didn’t fight on price. Instead, she asked the original buyer - who had since been promoted to VP - ‘Do you remember why you chose us back in 2014? What problem were you solving?’ And the VP told the story, got emotional, and personally killed the RFP. Luna: Because the VP’s own legacy was tied to that original decision. If he let the vendor go, he’d be admitting his choice was wrong all along. Lucas: Exactly. It’s a form of commitment consistency bias. People want to remain consistent with their past decisions, especially the ones they’ve publicly owned. Luna: So the question works on two levels: it generates positive emotion, and it reinforces the buyer’s identity as someone who made a smart choice. That’s a powerful combination. Lucas: It is. And I think there’s a caution here too. You can’t fake curiosity. If you ask this question just as a technique and you don’t actually care about the answer, it will backfire. The father in the first story would have sniffed out insincerity in a second. Luna: So the prerequisite is genuine curiosity. Which, if you’re in sales, you should have anyway. But it’s worth saying: this isn’t a script. It’s a mindset. Lucas: Right. The question is just the vehicle. The real work is listening to the story that comes after and finding the thread that connects it to what you’re offering. Luna: So for someone listening who wants to try this tomorrow, what’s the exact phrasing you’d recommend? Lucas: I’d tweak it depending on the person. If it’s a founder or early employee: ‘What was the moment you knew this company was going to make it?’ If it’s a long-tenured buyer who chose a previous vendor: ‘When you first bought from, what was the problem you were trying to solve?’ The key is to ask about a specific positive memory, not a general history. Luna: And then you listen for the emotion. And when they’re done, you say something like: ‘That’s exactly the kind of trust we want to earn.’ Lucas: Exactly. You’re not selling a product. You’re aligning yourself with a story they already love. Luna: Alright, I’m going to try this. I’ve got a call next week with a client who’s been with us for seven years and is dragging their feet on an upgrade. I think I know exactly which moment to ask about. Lucas: Let us know how it goes. I have a feeling the answer will surprise you.