How Are You — Really?

Nate: So something happened last week that's been stuck in my head. One of my SE directors — solid leader, great track record — came to me and said he's losing one of his best people. No warning signs. Performance was strong, engagement seemed fine. Just... gone. Handed in notice on a Monday morning.

Ava: No warning at all? Nothing in the one-on-ones?

Nate: That's what I asked him. He said, "I always ask how she's doing. She always says she's fine." And I thought... that's the whole problem right there. She WAS telling him. "Fine" was the signal. He just wasn't hearing it.

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

Nate: And I'm Nate. Every episode, one idea, five minutes. Today: why "how are you, really?" is the most underrated question in SE leadership — and how most of us are asking it wrong.

Ava: Okay so... I do the personal check-in with my team every session. Five minutes, first thing. But I'll be honest — I sometimes wonder if I'm getting the REAL answer or just a polished version. What did you figure out?

Nate: After that conversation with my director, I dug into this. Talked to my best managers — the ones with high retention, high engagement scores. And they all do something different from the "how are you, good, great, let's move on" pattern.

Ava: Which is?

Nate: They don't ask "how are you." Ever. They ask something specific enough that "fine" isn't a valid answer. "What's been the most draining thing since we last talked?" or "What's giving you energy right now?" You can't deflect those with a one-word answer.

Ava: Huh. I ask "how are you feeling about this week" which is... still pretty deflectable, now that I think about it. My newer SEs definitely give me the polished version. The ones who've been with me for two years open up, but that's because we've built that trust over time.

Nate: Right. And here's what I think the shortcut is — you go first. One of the best managers I've ever worked with, early in my career, would start every check-in with something real about his own week. Nothing dramatic. Just... "Honestly, I'm a bit fried from QBR prep" or "I had a rough conversation with my boss yesterday." It gave me permission to be honest too.

Ava: So vulnerability from the leader changes the WHOLE dynamic. That makes sense — if you're sitting there perfectly composed asking "how are you," the implicit message is "give me the professional answer."

Nate: Exactly. And there's a second piece. Listen for the pattern, not just the answer. If someone says "busy" three weeks in a row... that's not a status update. That's a signal. Are they overloaded? On too many deals? Is their AE dumping work on them?

Ava: But how do you track that? I've got twelve people. I can barely remember what I had for lunch yesterday, let alone what each SE said in their check-in two weeks ago.

Nate: Write it down. Quick note after each session. Not in a creepy surveillance way — just "Sarah mentioned she's frustrated with the Acme AE" or "Marcus is excited about the new demo environment." Then two weeks later, you follow up. "Hey Marcus, how's that demo environment working out?"

Ava: And THAT tells them you actually listened. Not just heard — listened. Okay, I don't do that consistently enough. I do it with my direct reports informally but I've never made it a system.

Nate: The managers who do this well have noticeably better engagement. I've seen it across my whole org. It's the difference between a check-in and a checkbox. Following up on what someone told you last time — that's how trust compounds over months.

Ava: You know what bugs me though? The people who NEVER open up. I have one SE who's been with me for a year and still gives me... nothing personal. Great performer, no complaints, but I have no idea what's going on in his head.

Nate: Some people are private. That's real. But in my experience... if you get "I'm fine" from every person, every week, for months? That's not eight private people. That's a leader who hasn't cracked the code yet. For the individual holdout — keep showing up. Keep asking specific questions. Keep going first with your own stuff. Some people take six months to trust the meeting. That doesn't mean you stop trying.

Ava: Patience as a leadership strategy. Not my strongest suit, but... point taken. What's the move?

Nate: Your next one-on-one, replace "how are you" with one specific question. "What's been the most frustrating thing since we last talked?" Ask it... then don't say anything for ten seconds. Let the silence work. And after the meeting, write down one thing they said that wasn't about a deal. Follow up on it next time.

Ava: Ten seconds of silence. That's going to be the hardest part.

Nate: That's exactly why it works.

Nate: I'm Nate.

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