Latest / Sales Leadership with Fexingo: Quota Carriers, Sales Managers, and Revenue Teams / How Top Reps Turn Gatekeepers into Coaches
Transcript
- Lucas: So there's this moment in almost every complex sale where you've done everything right — you've got a champion, you've got the budget conversation going — and then you hit the gatekeeper. The admin, the EA, the person who controls the calendar. And most reps treat that person like a wall to climb over. But the best reps I've seen recently are doing something completely different: they're turning the gatekeeper into a coach. Luna: A coach? That's a nice reframe. I mean, we've done episodes on gatekeepers before — turning them into champions, getting them to open doors. But 'coach' feels like a different relationship entirely. Lucas: Yeah, and it's a subtle shift but it's powerful. Instead of trying to get the gatekeeper to advocate for you, which is what 'champion' implies, you're asking that person to teach you how to navigate the organization. You're giving them an easy, low-risk way to help you — and because they're the one with the map, they often end up guiding you straight to the decision-maker. Luna: So how does that actually play out in a call? Can you give me a concrete example? Lucas: Sure. I was talking to a rep at a midmarket software company — they sell HR analytics tools, nothing crazy, maybe a two-hundred-thousand-dollar deal. He was trying to get into a CFO at a manufacturing firm, and the EA, a woman named Diane, was clearly the gate. Every call, every email, she'd politely say 'he's not available.' So instead of pushing harder, he flipped the script. He asked Diane for a five-minute call — not with the CFO, but with her. And in that call, he didn't pitch. He asked her for advice. Luna: What kind of advice? Lucas: He asked her what he should know about how the CFO likes to evaluate new software. What's the typical timeline? Who else gets involved? What are some of the landmines he should avoid? And Diane opened up — she told him the CFO was drowning in spreadsheets, that he'd been burned by a vendor last year, and that the real decision was made by a committee of three, not just the CFO. Luna: That's gold. That's the kind of intel you'd normally get after months of meetings, and he got it in one conversation with the 'gatekeeper.' Lucas: Exactly. And the key was that he didn't treat her like a means to an end. He gave her a role — the expert, the guide. He also did something really specific: he asked her if it would be okay if he sent her a short email summarizing what he learned, and if she'd correct anything. That gave her a way to stay involved without any pressure. Luna: So the gatekeeper becomes a collaborator. But doesn't that sometimes backfire? I mean, some EAs are protective precisely because they're told to screen out salespeople. Lucas: Sure, some are. But in my experience, most gatekeepers are just people doing their job, and they're actually a lot more approachable than we think. They get a hundred pitches a day — they're tired of being sold to. When you come in with genuine curiosity instead of a pitch, you stand out. And the ones who are protective? They're often protecting their boss's time, not their boss from ideas. If you treat them with respect and show you're not going to waste their boss's time, they'll often help you. Luna: That makes sense. So what's the actual framework here? You mentioned 'reframe, request, respect' — can we unpack that? Lucas: Yeah, I'm glad you picked up on that. Step one is the reframe: you change your mental model from 'gatekeeper as obstacle' to 'gatekeeper as potential coach.' That changes everything about how you approach them. Instead of trying to bypass, you're trying to enlist. Step two is the request: you ask for help, but specifically — you ask for their perspective, their advice, their read on the situation. Not 'can you get me on the calendar' but 'what would you recommend I know before I talk to your boss?' And step three is the respect: you treat them like a professional, you follow up with them, you keep them in the loop, and you thank them genuinely. That's what turns a one-time interaction into an ongoing alliance. Luna: I love that. And it's not just about getting a meeting — it's about getting the right meeting, with the right agenda, already knowing the pitfalls. That's a huge advantage. Lucas: And the results show it. The rep I mentioned — he had been stuck at the sdr to ae transition for two years. Within two months of using this approach, he'd cut his sales cycle from six months to three. He got into the CFO's office, and because he knew the committee was the real buyer, he asked to present to all three of them at once. That's a meeting that almost never happens if you just ask for the 'decision-maker.' Luna: So it's not just about getting past the gate — it's about getting the lay of the land before you even step inside. That's something any rep can do starting tomorrow. Lucas: Right, and it's especially relevant right now, in August 2026, because buying committees are bigger and more scattered than ever. With economic uncertainty, there's more scrutiny on every purchase. The person who answers the phone often has a clearer picture of the internal dynamics than the exec does — they see who's asking for what, and they hear the rumors. Tapping into that is a competitive edge. Luna: So what's the one thing a rep should do differently tomorrow, based on this? Lucas: Take a look at your current pipeline. Pick one deal where you've been struggling to get to the economic buyer. Next time you call, instead of asking for the decision-maker, ask to speak with the gatekeeper — and ask them one question: 'What do you think I should know about how your company evaluates something like this?' Then shut up and listen. Luna: That's a concrete, low-stakes move. And it's remarkable how often we forget that the simplest questions are the most powerful. Lucas: And it's a skill that compounds. Every time you do this, you get better at reading the signals, at asking the right follow-ups, and at building genuine rapport with people who are used to being ignored or pushed aside. That's the kind of skill that separates the top ten percent from the rest. Luna: You know, it's funny — we talk a lot about the 'human element' in sales, but this is a perfect example. It's not about tricks or scripts; it's about respecting the person in front of you, whoever they are. Lucas: Exactly. And that's something that carries over to how we run this show. We're lucky to have listeners who appreciate that approach, and if these conversations have moved your work forward in some small way, you can keep them coming by supporting the podcast at buy me a coffee dot com slash fexingo. It's a simple way to keep us ad-free and independent, and we're grateful for any listener who finds that valuable. Luna: Absolutely. It's a small gesture that makes a big difference for a show like ours, and we genuinely appreciate every person who's ever contributed. Lucas: So let's bring this back to the field. We've talked about the reframe, the request, the respect. But there's one more layer that I think is worth digging into — what happens after the gatekeeper gives you that coaching? How do you actually use that intel without burning the bridge? Luna: Good point. Because if you go straight to the CFO and say 'your assistant told me you hate spreadsheets,' that's not going to go well. Lucas: Right. The best reps I've seen will take the insight and use it as a way to prepare — they'll structure their pitch to address the committee's concerns, they'll bring a sample output that solves the spreadsheet problem, and they'll do it without ever mentioning where they got the intel. But they also go back to the gatekeeper afterward and say, 'hey, I just wanted to let you know how helpful your advice was — thank you.' That builds the alliance for the next deal. Luna: So it's a long-term relationship play, not just a one-time unlock. Lucas: Exactly. And that's what makes it different from just 'getting past the gate.' You're building a network of internal advocates who aren't necessarily champions — they're just people who are willing to point you in the right direction because you treated them well. That's an asset that pays off down the road. Luna: Have you seen this work in a situation where the gatekeeper is really resistant? Like someone who's been explicitly told to screen out vendors? Lucas: I have, actually. There was a rep at a cybersecurity firm who was trying to get into a bank, and the EA there had a reputation for being a brick wall. She'd been in the role for fifteen years and had seen every trick in the book. So he did something slightly different — he didn't ask for advice right away. He first sent her a handwritten note, just saying he knew she was busy and he'd love her perspective on whether his solution was even relevant for the bank. Then he followed up a few days later. She actually called him back and said, 'You're the first person in a decade who's asked me what I think.' She gave him a twenty-minute walk-through of the bank's procurement process. Luna: Wow. That's a powerful reminder that everyone wants to be heard. Lucas: And it wasn't about being manipulative — it was about genuinely respecting her expertise. She knew that bank inside and out, and he gave her a chance to share that. That's a universal human need, and it works whether it's a CFO or an EA. Luna: So if there's one takeaway from today, it's that the person you're ignoring might be the person who can unlock your next big deal. Lucas: And the best part is, it's a skill that doesn't require a big personality or years of experience. It just requires a shift in mindset and a little bit of humility. Ask for help, listen, and say thank you. That's the whole play. Luna: I love that. Thanks for breaking it down so clearly. And for anyone listening, I'd say try it on your next call — and let us know how it goes. Lucas: Yeah, we'd love to hear your stories. Until next time, happy selling — and keep turning those gatekeepers into coaches.