One-on-ones

The 1:1 is where you find out what’s actually happening on your team. Everything else — standups, retros, planning — tells you what the team is doing. The 1:1 tells you how they feel about it.

Weekly, 30 minutes, on the report’s calendar not mine. Their agenda first, my agenda second. If they cancel two in a row I ask why; if I cancel two in a row I’ve stopped doing my job.

The opener I use

A framing I picked up from SRE-manager folklore (variations of it are attributed to Roy Rapoport and others). At the start of anything that isn’t a routine check-in: “Do you want advice, action, brainstorming, or to vent?”

Four different responses. When someone wants to vent and I jump to advice, I’ve made them feel unheard. When someone wants advice and I just listen, I’ve wasted their time. Naming the shape of the conversation up front saves both of us fifteen minutes of talking past each other.

Questions I keep in rotation for reports

Not all every week — I pick two or three.

• What’s slowing you down that I could help with?
• What are you working on that you’re proud of? What are you working on that you’re not?
• Where do you feel stuck on the career ladder? What would the next level look like from where you sit?
• Is there feedback you’ve been sitting on for me?
• Who on the team is hardest for you to work with, and what would help?
• What do you want to be doing that you’re not doing yet?

Questions I ask myself before each 1:1

• What’s the last piece of substantive feedback I gave this person? Was it clear enough to act on?
• Do I actually know what they’re working on this week, or am I about to fake it?
• Is there something I’ve been avoiding telling them? Why?

Things I don’t do in a 1:1

• Status updates. If the whole meeting is “what are you working on,” we have a broken standup, not a 1:1. The 1:1 is for the things that don’t come up in standup.
• Ambush. Serious feedback doesn’t arrive by surprise. If someone is going to hear something hard, I’ve told them the topic in advance so they can think.
• Talk more than 50% of the time. Their meeting, their airtime.

Skip-levels

Once a quarter I have a 30-minute chat with each person on my reports’ teams. Same opener, different question list — mostly “what’s your manager doing that you wish they did more of / less of.” I share themes with the manager, never attribution. This is the single best early-warning system I’ve found for problems the manager can’t see because they are the problem.