Your Best SE Has Never Been Coached

Ava: I was talking to an SE leader last week who just took over a team, and he's got this one SE who's been there for SEVEN years. Knows the product inside out. Can demo anything. And has basically had... zero coaching. Ever.

Nate: Right, so he was the entire pre-sales function for most of that time.

Ava: Exactly. He WAS the demo guy. And he's good... genuinely deep product knowledge. But seven years of habits with nobody ever saying "hey, have you thought about doing it differently?" That's a lot of muscle memory to work with.

Nate: And now there's a new leader who can see the gaps... but also knows that if they come in too heavy, they'll break the one person who actually knows how everything works.

Ava: That's the tension. The demos are on autopilot, very feature-centric. Every customer question gets a five-minute show-and-tell whether it needs one or not. But this person has kept the lights on for SEVEN years. You can't just walk in and say "everything you've been doing is wrong."

Ava: Welcome to Leading PreSales. I'm Ava.

Nate: And I'm Nate. Every episode, one idea, five minutes. Today— how to coach a veteran SE who's never been coached before.

Ava: So here's what I think makes this hard. When I was building my team, everyone started fresh. I could shape habits from day one. But inheriting someone with seven years of ingrained patterns? That's a completely different problem.

Nate: It is. And I've seen this quite a few times at scale. You get a new SE Manager who walks in, observes the first demo, sees all these things they want to fix... and their instinct is to download everything at once. "Here's what you need to change."

Ava: Which feels efficient but lands as criticism.

Nate: Exactly. And with a veteran, it's worse. Because they've been SUCCESSFUL. The company survived on their demos. Revenue came in. So from their perspective... what's broken?

Ava: Right. The product knowledge IS a strength. The problem isn't WHAT they know. It's that they've never had to think about HOW they deliver it.

Nate: And that distinction is invisible when you've never had feedback. If nobody ever said "hey, that twenty-minute monologue— half the room checked out"... how would you know?

Ava: You wouldn't. So how do you introduce coaching to someone who's never experienced it without making them feel like they're suddenly failing?

Nate: I had one of my SE Managers deal with exactly this. She inherited someone similar. A decade of experience, fantastic product knowledge, zero structured coaching in his history. And her approach was interesting. She didn't start with what he was doing WRONG.

Ava: What did she start with?

Nate: She asked him what he thought his best demo looked like. What made it great. Got him talking about his own process. And through that conversation, HE started identifying the gaps. He said something like "I guess when I really nail it, it's because I already know their problem going in. When I don't... I just show everything and hope something sticks."

Ava: So he already knew. He just never had someone draw it out of him.

Nate: That's the thing with experienced SEs. The self-awareness is often there, buried under years of habit. You don't have to TEACH them what good looks like. You help them see what they already do differently when they're at their best versus their average.

Ava: I love that. You're not saying "let me show you how to demo." You're saying "you already know what works. Let's make that your default instead of your exception."

Nate: Now you're not a new boss correcting them. You're a partner helping them do more of what already works.

Ava: Okay but here's where I'd push back. That works for the self-aware ones. What about the SE who genuinely believes every demo they run is great? Who doesn't see the autopilot? I've met people like that.

Nate: Fair. Sometimes you need data. Call recordings, talk-time ratios. If someone can't self-reflect, you need something concrete. But even then— lead with curiosity. "I noticed the customer asked the same question in demos two and three. What do you think was going on there?"

Ava: So the data opens the door, but the coaching still comes through questions, not instructions.

Nate: Right. Because the moment you hand them a checklist of things to fix, you've turned a veteran into a trainee. And that's where you lose them.

Ava: So the move here... if you're an SE leader inheriting a veteran who's never been coached— don't start with what's broken. Start by asking them what their best looks like. Let them find the gap between their best and their average. That's where the coaching begins.

Nate: And be patient. Seven years of habits don't change in a quarter. But the first conversation... the one where they realize someone actually cares about making them better, not just correcting them? That's the one that matters most.

Nate: I'm Nate.

Ava: And I'm Ava. See you next episode!