Latest / Closing the Deal with Fexingo: Sales, Negotiation, and Revenue Conversations for Operators / How One Rep Won by Asking for the Buyer's Strategic Plan
Transcript
- Lucas: So I want to tell you about a deal that closed about eighteen months ago. A cybersecurity company — we'll call them ShieldCore — was competing for a seven-figure contract with a regional bank. The rep, we'll call her Maya, was up against a lower-priced incumbent. Luna: Classic scenario. Price pressure, long cycle, buyer has a comfortable vendor already. Lucas: Exactly. Maya had done the usual discovery — pain points, budget, decision criteria. But she was stuck. The bank's IT director was noncommittal, saying they'd 'evaluate options.' So on a call, Maya asked a question that changed everything. Luna: What was it? Lucas: She said, 'Could you share your strategic plan for the next three years? I want to understand where you're heading, not just what's broken today.' Luna: And they actually sent it to her? Lucas: They did. The IT director hesitated, but Maya framed it as helping her align the solution. The director forwarded the bank's publicly available investor presentation and a internal memo about their digital transformation initiative. That's when Maya saw the real opportunity. Luna: What was in the plan? Lucas: The bank had a three-year goal to reduce customer onboarding time from seven days to under 24 hours. That was their CEO's headline metric. Maya realized that the incumbent's product didn't integrate with the new core banking system they were planning to migrate to. ShieldCore did. Luna: So she flipped from 'we're cheaper and better at security' to 'we enable your strategic goal.' Lucas: Exactly. She went back to the IT director and said, 'I see you're moving to a new core system in Q3 next year. Our platform is already certified on that system. The incumbent isn't. If you buy them, you'll have to rip and replace in twelve months.' Suddenly the conversation shifted from price per seat to total cost of ownership over three years. Luna: And the incumbent couldn't pivot because they didn't know the bank's plan. Lucas: Right. Maya closed the deal at $1.8 million — about fifteen percent higher than the incumbent's offer. The bank's CFO approved it because it tied directly to the CEO's onboarding metric. Maya didn't win on price; she won on strategic alignment. Luna: So the key move was asking for a document that most salespeople never request. Lucas: Exactly. And it's surprisingly common that buyers have a strategic plan — either public or internal — that reps never ask to see. Public companies have investor presentations. Private companies often have a 'vision deck' or annual planning document. Even a one-pager will do. Luna: But doesn't that feel intrusive? Like you're asking for confidential strategy? Lucas: It can, if you ask wrong. Maya prefaced it with, 'I want to make sure I'm not proposing something that doesn't fit where you're going. Can you share your high-level direction? Even a public document helps.' She made it about being helpful, not nosy. Luna: And the buyer felt comfortable because the plan was already shared internally? Lucas: Partly. But also because Maya had built enough trust. She'd done three discovery calls before asking that question. It wasn't the first thing out of her mouth. Luna: So timing matters. You can't ask this in a cold email. Lucas: No. You need to have demonstrated some understanding first. But once you have, asking for the strategic plan signals that you're thinking long-term, not just trying to close a deal this quarter. Luna: And if they say no? Lucas: Then you have a signal too. If a buyer won't share their direction, they may not have one — or they may not see you as strategic partner. That's worth knowing early. Luna: What about small companies? Does this work for startups? Lucas: It can, but the plan might be less formal. For a startup, you might ask, 'What's the one metric your board cares about this year?' That's their strategic plan in miniature. Same principle, just smaller scope. Luna: So the question adapts to the buyer's maturity level. Lucas: Exactly. For a Fortune 500, you ask for the three-year plan. For a mid-market company, you ask for the annual priorities. For a startup, you ask for the board metric. Luna: And what about competitive deals where the buyer is already evaluating someone else? Lucas: That's actually the best time to ask. If you're in a competitive deal, the buyer is already comparing. Asking for their strategic plan can help you differentiate on something other than price. Maybe your competitor can't support their future architecture. Maybe your competitor's product is being sunset. The plan reveals that. Luna: So it's a competitive weapon disguised as a discovery question. Lucas: Exactly. And the best part is, the buyer often volunteers information that helps you position against competitors you didn't even know were in the deal. Luna: Any caveats? Times when this could backfire? Lucas: Yeah, two. First, if the buyer's strategic plan is aspirational and not actionable. Some companies have a vision that's just words — 'become the leader in X.' That doesn't give you concrete hooks. Second, if you ask too early or too bluntly, you can seem pushy. You have to earn the right to ask. Luna: So the rep needs judgment. Not just a script. Lucas: Exactly. But for experienced reps, this is a repeatable pattern. Maya now asks for the strategic plan in every enterprise deal. She says it's the single highest-leverage question she asks. Luna: And her close rate went up? Lucas: She says her win rate in competitive deals went from about forty percent to over sixty percent in the year after she started doing this consistently. Luna: That's a huge jump. Lucas: It is. And it's not just about the document — it's about the conversation that follows. When you ask for the plan, you're saying, 'I care about your future, not just your pain.' Buyers notice that. Luna: It also changes the power dynamic. You're no longer a vendor pitching features; you're a consultant helping them reach their goals. Lucas: Exactly. And that's why Maya's deal with the bank closed. She wasn't selling a cybersecurity product; she was selling the ability to hit a CEO metric. Luna: Let me ask you — does this work in shorter sales cycles? Say, a deal that closes in two weeks? Lucas: Probably not. If the buyer needs a decision fast, they already know what they want. Asking for a strategic plan in that context feels like a stall. This technique works best in complex deals with a three-to-nine-month cycle. Luna: So it's for enterprise and mid-market, not SMB transactional. Lucas: Right. But within that sweet spot, it's powerful. And the best part is, it costs nothing to try. You just ask. Luna: I can think of a few buyers I wish I'd asked that question to earlier in my career. Lucas: Yeah, same here. And honestly, that's a good note for us too. If these conversations have moved your work forward in some small way — maybe you've tried a question we talked about — that's why we do this. A handful of listeners chip in monthly through buy me a coffee dot com slash fexingo, and that literally funds making this many episodes. Keeps it ad-free, keeps it focused on techniques you can use Monday morning. Luna: Yeah, it's a small group, but it makes a big difference. So thanks to anyone who's already doing that. Lucas: Alright, back to the topic. So if you're in a long-cycle deal right now and you haven't asked for the buyer's strategic plan, try it. Even if they don't share the document, the conversation alone can reveal more than three standard discovery calls. Luna: And if they do share it, you might find the key to winning a deal you thought was lost. Lucas: Exactly. Next episode, we'll look at a rep who won by asking for the buyer's budget breakdown — not just the total number, but the line items. That's another underused question. Luna: Looking forward to it.