What’s top of mind for you right now?#

This is a great open ended question that can surface a variety of things. It could be a technical challenge, a personal challenge, a team challenge, a project challenge, etc. I make sure to nudge people that this doesn’t have to be directly work related as well. There’s one person on my team working on a masters degree. Another has three young children and is working out what the next vacation is or how to balance family and work. It’s a great way to start the conversation and get a sense of what’s going on in their world, and it often opens to some deeper conversations of how I can support.

What’s something that felt harder than it should have this week?#

This question sometimes leaves the impression that something is wrong, but often it surfaces something more ordinary: a dependency that blocked progress, a library that fought back, a hard problem that just took longer than expected. It could have been a nuance in a library being used (good ‘ol Murphys law) that made things take longer to be completed. It could have been a genuine challenge to a hard problem. The nice thing about this question is that it then follows back up with how the solution was found (with a kudos for learning/solving a thing) or it helps communicate something I can go and unblock for them. Sometimes it also surfaces learning opportunities that become a great growth catalyst.

Where do you feel under-supported or under-utilized right now?#

This question was recommended to me and it seemed odd, but has been rather insightful. Something like this is often not raised voluntarily by a person, for potential fear of looking like they are complaining, so it is a sign of care when you bring it up. This question has a great way of surfacing who is quietly drowning, who is bored and ready for more, or where skill gaps or role clarity issues exist. It can open up some great long term discussions. On the flip side, I have one engineer spending half their time on two different squads with varying responsibility so I make sure to ask the opposite: are you being over-utilized right now?

What’s one thing you learned this week, technical or otherwise, that you want to build on?#

I really like the “or otherwise” part of this question. I have one engineer who is quite the handyman and I get to learn about their latest home improvement projects. I have another who is doing a deep dive into Claude for a hobby project and I get a few pointers from them. They also bring those pointers back to the active project work we have. Asking this question helps reinforce a growth mindset, which is something I try to encourage daily in my team. It also builds long‑term capability and “fungibility”, as my CTO calls it.

A few more worth keeping…#

Admittedly these four questions can fill up an entire meeting and often just one of them becomes a huge catalyst for discussion. However, I have a couple of other ones I like to pepper in [:: note to self, maybe make them standard again ::] if it has been a notably quiet meeting.

What’s the one thing you’re most proud of this past week?#

It’s easy to focus on the negatives or blockers, or to even just consider work accomplished as “par for the course.” However, a problem solved, a new resource found, a crazy week that was balanced without going insane, those are things to be proud of and work reminding oneself of as a small means of self care. It can often tease out something they are excited about as well, which unlocks a lot of conversational doors.

What’s one thing you can do 1% better?#

This is one of my absolute favorites. I should just keep this one in there permanently. The way I embrace a growth mindset on a daily basis is to ask myself this very question because we often think about growth in these massive steps but through reading Darren Hardy’s The Compound Effect and other resources, I’ve learned that growth is more successful when it is small and incremental. You won’t see it immediately, but it will compound over time and be much bigger than the “big push” you made for a short amount of time. It also “softens the blow” of how to change. You may think “Wow, I really need to be much better at code reviews.” but not know where to start or try to come with a comprehensive strategy that gets overwhelming. The “1%” approach might just be spending five extra minutes on a code review, being slower and more deliberate. That’s all. Stack enough of those and you become a master reviewer.

Double Bonus: Table Talk Cards#

Sometimes that opening “How is it going” just isn’t cutting the ice or helping foster the deeper conversations. I had been through quite a spell of those meetings. Interestingly enough, one day the office was doing a “clear out” of random things it found in cabinets and there was a cube of “Table Topics” ice breaker questions sitting there. I had seen similar things before and figured it wouldn’t hurt to try them out. We’d either get a chuckle over the cheesy questions they asked or have some really insightful answers that let us get to know each other better and segue into the other topics as well. This has been a WONDERFUL addition to my O3s and I highly recommend giving it a try.

Et vous?#

There’s my current toolkit: four core questions plus a few I keep in rotation for when things go quiet. Will they look exactly like this in another six months? Probably not. That’s kind of the point. Every version taught me something the last one couldn’t.

If your O3s have drifted into standup territory, I hope this gives you something to work with. And if you’ve got a question that reliably opens a door, one you keep coming back to week after week, I’d genuinely love to hear it. I’m always looking for version six.

What’s the one O3 question you’d never give up?