You Can't Manage a Team You've Never Asked a Real Question

My one to ones were status meetings in a friendlier font, and it took me an embarrassingly long time to notice that. Thirty minutes, once a fortnight, and I'd have been able to tell you exactly what everyone was working on and absolutely nothing about whether any of them were alright.

Here's the thing about that question. It's not really an enquiry, it's a greeting, and everyone on your team knows it. The correct response is "yeah, good, busy", and you both move on to the ticket list. The meeting ends on time. Nobody has to feel anything.

Then six months later someone resigns, or two of your engineers stop speaking to each other, or a delivery you thought was healthy turns out to have been quietly rotting since February, and you find yourself saying that you had no idea. Which is true. You had no idea because you never asked anything that could have produced one.

A vague question gets a vague answer. Always. People aren't being evasive when they do that. They're being polite. You gave them an easy exit and they took it, the same way you do when your dentist asks if you've been flossing.

Swap the width for a narrow, awkward, specific question, and something different happens.

"What's the most annoying part of your week at the moment?"

"If you could delete one meeting from your calendar with no consequences, which one?"

"What do you think we're getting wrong that nobody's saying out loud?"

"What's the last thing I asked you to do that you thought was a bad idea?"

That last one is the most useful question I know, and it's terrifying the first few times you use it. Ask it in a flat, curious tone, with no defensiveness pre-loaded, and then genuinely do nothing with the answer except thank them. Do that twice and you'll start getting told things you would never otherwise hear.

Notice these are all about a specific thing, a specific week, a specific decision. "Are you happy in your role" gets you nothing. "What's the bit of your job you'd hand to someone else tomorrow if you could" gets you the truth, because it's small enough to answer honestly without making a declaration about your life.

Most of us ruin the good question by rescuing the pause that follows it.

You ask the awkward thing. Three seconds of quiet go by. It feels like a minute. So you fill it: "I mean, obviously everyone's busy, it's been a mad quarter, don't worry if there's nothing." And there it is. You just handed them the escape route and they will take it, gratefully, and you'll never know what they were about to say.

Count to seven. Look at them. Don't nod encouragingly, don't smile apologetically, just wait. Almost every real thing I've ever been told in a one to one arrived after an uncomfortable gap that I had to physically stop myself from filling.

If it helps, remember they're not silent because they've got nothing. They're silent because they're deciding whether it's safe.

Sympathy is the default response and it's nearly worthless. "God, that sounds frustrating" costs nothing and changes nothing, and if it's all you ever do, people stop bringing you problems within about three cycles.

Take an example. An engineer on a 12-person infrastructure team tells you the change approval board is killing him. Three weeks to get a firewall rule signed off, and he's now pre-emptively requesting rules he might need, which is making the rulebase worse, which is making the board more suspicious, which is making it slower.

The sympathetic response: "yeah, that process is a nightmare, we've all been there". He leaves the meeting with exactly what he came in with.

The useful response has three parts and none of them is fixing it yourself. First, write it down in front of him, so he can see it being recorded. Second, say what you're going to do and when: "I'm on the ops governance call on the 14th, I'll take the last six changes and the actual wait times and ask for a fast lane for single-rule changes." Third, tell him what you can't do: "I'm not going to get the board abolished, so don't wait for that."

Then come back on the 15th whatever happened. Especially if the answer was no. A no you delivered is worth ten yeses you promised and forgot.

Ask real questions for long enough and eventually somebody will tell you that the problem is your behaviour. You rewrite their design decisions in review. You escalate to their manager before talking to them. You say yes to the sales team on a Friday and it turns into their weekend.

Everything in you will want to explain. Don't, not in that meeting. Say "thank you, that's fair, let me think about it" and then actually think about it, and come back in a week with one thing you're changing. The explanation can wait. The defensiveness, once deployed, closes the door for about a year.

I got told once that I only ever came to the team when something was on fire, so the sight of me walking over had started to make people tense. My first instinct was to list all the times I'd been around for good reasons. My better instinct, arrived at about two days later, was to start turning up on the boring Wednesdays with nothing in particular to say.

Look at your next one to one. Delete "how's it going" from your opening and replace it with one specific question you're slightly nervous to ask. Write the answer down in the meeting, where they can see you writing it.

Then put the follow-up in your own diary with a date on it, because the question isn't the thing that builds trust. Coming back is.