Latest / Sales Leadership with Fexingo: Quota Carriers, Sales Managers, and Revenue Teams / How to Reopen a Stalled Deal Without Looking Desperate
Transcript
- Lucas: You've got a deal that was moving. Discovery calls went well, demo was strong, the champion was on board. Then silence. No replies to your emails, the next meeting keeps slipping, and your forecast starts looking like a wish. Luna: I've been there. It's the worst feeling — you don't know if they lost budget, went with a competitor, or just got buried. Lucas: Exactly. And the natural instinct is to follow up more often, maybe even offer a discount. But that usually backfires. Today I want to walk through a structured way to reopen a stalled deal — without sounding desperate. Luna: I'm all ears. What's the first step? Lucas: First, resist the urge to send a 'just checking in' email. That's the weakest move. Instead, you need a reason to reach out — something new. The best trigger is new information that changes the value calculus for the prospect. Luna: New information like a product update, a case study from a similar company, or maybe an industry report that validates your approach. Lucas: Right. And it has to be specific to their situation. Let me give you a real example. A friend of mine sells HR software to mid-size companies. He had a deal with a manufacturing firm — $120,000 annual contract — that went dark after the demo. Eight weeks of silence. Luna: Eight weeks. That's painful. Lucas: He didn't send a single 'checking in' email. Instead, he noticed the company had just announced a new plant expansion in the press. So he sent a very short email: 'Congratulations on the expansion. We've seen similar growth at other manufacturers, and one thing that helped them scale was automating their onboarding. Here's a one-page summary of how that worked.' Luna: That's smart. He tied it to their actual news, not his need to close. Lucas: Exactly. The prospect replied within an hour. They set up a call, and within two weeks the deal was signed. The new information — the expansion, plus the relevant case study — gave the prospect a reason to re-engage. Luna: So the key is finding something that matters to them, not just sending a generic update. Lucas: That's the principle. But I also want to give you a specific sequence. This is a three-email sequence for reopening a stalled deal, spaced a week apart. Luna: Let's hear it. Lucas: Email one: the new information trigger. It should be short, reference something relevant to their world, and attach or link to something useful. No ask for a meeting. Just, 'Thought you might find this interesting.' Luna: Low pressure. That's good. Lucas: Email two, a week later: the 'I've been thinking about your situation' email. This one shows you've reflected on their specific challenges. Something like, 'I've been thinking about your team's hiring goals. One thing we didn't discuss in detail was X. Would it be worth 15 minutes to explore that?' Luna: That's a soft ask, but it's grounded in their problem. Lucas: Exactly. And email three, another week later: the break-up email. This is a polite 'I'm going to stop reaching out unless I hear otherwise' email. Something like, 'I don't want to keep cluttering your inbox. If the timing isn't right, I totally understand. If something changes, I'm here.' That often triggers a response — sometimes even 'Oh wait, we're still interested.' Luna: I've heard that the break-up email has a surprisingly high reply rate. Why do you think that works? Lucas: It removes pressure. It signals respect for their time. And it creates a tiny bit of loss aversion — they don't want to lose the option. But here's the thing: you have to mean it. If they don't reply, you actually stop emailing. Luna: Right. The worst thing is to send a break-up email and then follow up again two weeks later. Lucas: That destroys credibility. So the sequence works if you stick to it. But beyond emails, there's another lever: your internal champion. If you had a champion inside the account, they might be able to pull you back in. Luna: How do you approach a champion without seeming like you're using them? Lucas: You ask for their perspective, not their help. Say, 'I noticed the deal has gone quiet. From your side, what's happening? Is there something I'm missing?' That's a safe way to get intel. Often the champion will give you the real reason — budget freeze, a new decision-maker, a competitor showed up. Then you can adjust your approach. Luna: And if the champion is the one going silent? Lucas: That's harder. You might need to find another internal contact. But if the champion has gone dark, it could mean they've lost influence or the project got deprioritized. Either way, a polite check-in with a different stakeholder can sometimes surface the truth. Luna: Let's talk about the psychology a bit. Why do deals stall in the first place? Lucas: Often it's not about your product. It's an internal change — a new boss, a reorg, a budget shift. Or it's analysis paralysis — too many options, fear of making the wrong choice. The prospect goes silent because they don't know what to do next. Luna: So your job is to make the next step easy and safe. Lucas: Exactly. That's why the new information trigger works. It reduces uncertainty. You're giving them a reason to move forward that doesn't feel like a sales push. It feels like a helpful insight. Luna: I want to go back to the three-email sequence. What if the prospect replies to email two but says 'not now'? Lucas: That's actually a good outcome. You can ask, 'What would make it a better time? Is there a quarter you're targeting?' Then you get clarity. You might set a reminder to reconnect in three months. That's better than a dead deal. Luna: Yeah, a 'no' with timing is way better than silence. Lucas: And you can keep the relationship warm by sending one relevant article every couple of months. No asks. Just value. Luna: That's a long game, but it works. I've seen reps win deals a year after the initial stall because they stayed top of mind. Lucas: Exactly. Now, there's one more tactic I want to mention: the 'social proof' trigger. If you get a win in a similar company, that's a perfect reason to re-engage a stalled prospect. Luna: Like, 'Hey, we just helped a competitor of yours achieve X result. Thought you might want to see how.' Lucas: Exactly. But be careful with the wording. Don't say 'competitor' — say 'another manufacturer in your space' or 'a company of similar size.' You don't want to sound like you're violating confidentiality. But that new case study can be a powerful re-engagement tool. Luna: So we've got the new information trigger, the three-email sequence, the champion check-in, and social proof. That's a solid toolkit. Lucas: And one more thing: timing. If you know the prospect's fiscal year or budgeting cycle, time your outreach around that. A deal might stall because the budget was locked, but three months later, new funds open up. Luna: That's a great point. A lot of stalls are just calendar issues. Lucas: Right. So the key is to be systematic, not emotional. Don't take the silence personally. Use a process to reopen the door. And if it doesn't work, move on. Your time is better spent on next opportunities. Luna: Before we wrap, I want to mention something. These conversations take time to research and produce — and we deliberately don't run ads on them. If you find value in shows like this, you can support the work at buy me a coffee dot com slash fexingo. It's a small gesture that keeps us ad-free and focused on content that actually helps you. Lucas: Yeah, that support makes a real difference. It means we don't have to chase sponsors or compromise the format. So if these episodes have helped you in your career, consider throwing a coffee our way. Now, back to the topic — one more tactic I want to share is using a 'critical event' like a conference or trade show to re-engage. Luna: Oh, that's smart. Like, 'I'll be at your industry conference next month. Want to meet up?' Lucas: Exactly. That gives a concrete reason and a deadline. Even if they can't meet, it can reopen the dialogue. 'Can't make it? No problem. Let's set a call for the following week.' Luna: I like that. It's low risk for them. Lucas: Alright, let's recap the playbook. One: find new information that matters to them. Two: use a three-email sequence — value, reflection, break-up. Three: check in with your champion for intel. Four: leverage new case studies or social proof. Five: time your outreach around their calendar. Luna: And the mindset: don't chase, create value. When the prospect feels you're trying to help, not just close, they're more likely to come back. Lucas: Exactly. One more thing I want to leave you with: if you try all this and the deal stays dead, let it go. The worst thing you can do is burn a relationship by being pushy. The same prospect might buy from you in two years at a different company. Luna: That's a good reminder. The sales world is small. Lucas: So be professional, be persistent in a structured way, but know when to walk away. That's the sign of a true sales leader.