One Skill Per Quarter — That's It

Nate: I need to tell you about a mistake I made. Years ago, when I was still running my first team at a large ERP vendor. After every deal review, I'd give feedback on three or four things. "Your discovery was shallow, demo ran long, you missed the pricing objection, and the follow-up email was generic." All in ONE conversation.

Ava: Oof. How did that land?

Nate: They'd nod. Write nothing down. Do exactly the same thing the following week. I thought they weren't listening. Turns out... I was the problem. You can't improve four things at once. You can barely improve one.

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

Nate: And I'm Nate. Every episode, one idea, five minutes. Today: why skill development in your 1:1 works only when you do LESS, not more.

Ava: So I do skill development in my check-ins — it's the ten-minute middle section we talked about. But I'll be honest, I sometimes feel like I'm spreading too thin. I have SEs who need work on discovery AND demo skills AND executive presence. You're telling me I've been overloading them?

Nate: Here's what I learned the hard way and what I now drill into every one of my managers: one skill per quarter. Per SE. That's it.

Ava: One skill for a whole quarter? That feels... really slow, Nate. What about the SE who's struggling with multiple things?

Nate: Especially that SE. Because here's what happens when you pick three development areas — they make marginal progress on all three and master none. Three months later your manager is having the EXACT same conversation. When you pick one... they go deep. They practice it consciously every week. And by the end of the quarter, it's not something they're working on. It's something they own.

Ava: Okay... I can see that in my own team actually. I had an SE where I was pushing on discovery and demo structure simultaneously. He improved a little on both but never really nailed either. It took forever.

Nate: Classic pattern. The focus is what makes it stick. But here's the key — how you PICK the skill matters as much as the constraint.

Ava: How do you pick?

Nate: Observation first, not assumption. I tell my managers — sit in on their SEs' calls. Watch the demos. Read the follow-up emails. Don't go by reputation or gut feeling. Find the ONE thing that, if they fixed it, would have the biggest impact on their win rate. That's your pick.

Ava: But what about what the SE thinks they need? I'd want my team to have a voice in this.

Nate: Absolutely. And that conversation is actually powerful. You say: "I've been watching your calls. I think the biggest unlock for you this quarter is discovery depth. What do you think?" Sometimes they agree. Sometimes they push back with something you didn't see. Either way — you align on one thing together. And that alignment is what creates buy-in.

Ava: Okay, and then in the weekly 1:1... what does the ten minutes actually look like? Because I tend to just ask "how's the skill development going" and get vague answers.

Nate: Three questions. Every session. First: "How did you apply the skill this week?" Get a SPECIFIC moment. Not "it went well" — walk me through what happened. Second: "What felt hardest? Where did you get stuck?" That's where the real coaching happens. And third: "What would you do differently if you could replay that moment?"

Ava: That last one is sneaky good. It forces reflection without YOU having to give the answer.

Nate: That's the whole point. Coaching is asking the question that makes them think... not giving the answer that makes you feel smart.

Ava: I've DEFINITELY been guilty of the "let me tell you what I would have done" monologue. My team is probably sick of it.

Nate: We've all been there. The shift is from "let me tell you" to "walk me through your thinking." One corrects behavior. The other builds judgment. And judgment is what you actually want your SEs to develop — because you can't be in every room with them.

Ava: That's true. Especially in a scale-up where things move so fast. I can't review every deal. I need them to THINK like I would, not just do what I'd do. Okay, one more thing though — how do you track progress over a quarter? Because in week one the energy is high, but by week eight...

Nate: You notice and NAME the progress. Even small wins. One of my SE directors does this brilliantly. She'll say, "Last month you were jumping to the demo in the first ten minutes. Today you held discovery for twenty-five minutes and uncovered the real budget holder. That's REAL progress." Specific recognition beats generic praise every time.

Ava: "Good job" means nothing. "I noticed you did X differently and here's the impact" — that reinforces exactly what you want them to keep doing. I need to get better at that.

Nate: And log the commitments. What did they say they'd practice this week? Write it down. Both of you. Because next session you're going to ask about it. Accountability without documentation is just hope.

Ava: "Accountability without documentation is just hope." I'm stealing that.

Nate: It's yours. What's the move?

Ava: This is your baby — you take it.

Nate: Pick one person on your team — or if you lead leaders, have your managers do this. Look at their last five calls or demos. Find the ONE skill that would move the needle most. Then in the next 1:1, propose it: "I think your biggest unlock this quarter is X. What do you think?" Align on one skill. One. And ask them to come to the next session with a specific example of how they practiced it.

Ava: And when they do — even if the attempt was clumsy — acknowledge the effort. Progress over perfection.

Nate: I'm Nate.

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