Your Team Doesn’t Need More Check-Ins. They Need Better Conversations.
A few months ago I shared a short post here: Your team doesn’t need more check-ins. They need better ones. It got more of a response than I expected, so I want to go a little deeper this time, and get a little more personal.
Here’s something I don’t say often. In all my years of working, I don’t think anyone ever showed me how to have a really good one on one. That isn’t because my supervisors didn’t care. Most of them were carrying more than I could see. Still, a lot of what I know about these conversations I learned by noticing what was missing.
What It Felt Like From the Other Chair
There were seasons when I walked into my one on one under so much stress that I was close to tears, or close to losing it. I’d sit down, give my updates and walk through what was next. Then I’d leave without saying any of what was really going on. It felt like there was a river between me and the person across the table, and I didn’t know how to get across it.
Sometimes I got feedback in those meetings, but it was general enough that I wasn’t sure what to do with it. My perception was that there wasn’t time to ask what it meant or how I was supposed to put it into practice. So I carried it around and guessed.
Looking back, I didn’t need a longer meeting. I needed an invitation, a real one, to share what I was going through. I think if I’d had that, I would have felt more cared for, and I probably would have done better work too.
I share this because I suspect some people on your team are having a version of that experience right now. We never fully know what someone is carrying into the room, or what they’re keeping to themselves.
The Meeting Most of Us Know
You sit down for your weekly one on one. Your supervisor asks, “So, what’s the status of that project?” You give an update. “Any other updates?” You mention a couple of things. “Okay, what’s next?” You run through your to-do list, and fifteen minutes later you both head back to your desks.
Efficient? Yes. Effective? Not always.
In local government our days are packed. There’s budget season, council agendas, public records requests, resident calls and a dozen things nobody planned for. It makes sense that the one on one turns into a quick status report. But a status report gives you information. It rarely gives you insight, and it almost never gives someone room to say, “I’m struggling.”
Why This Matters for Us as Leaders, Too
Better conversations aren’t only for the employee. All of us have blind spots, and the people who work with us see things we can’t. They know how we’re landing, where our words and actions don’t quite match, what ideas they haven’t had a chance to share, and where they need us to step in or coach them through something.
I was reminded of this recently in a conversation with someone I’ve worked with. She told me she felt she could be honest with me, including telling me when my behavior wasn’t lining up with what I’d said. That meant a lot to me. I have blind spots like everyone else, and I need people who care enough to point them out.
Without relationships like that, we’re all out there fending for ourselves. It’s a hard time to be living and working right now, and none of us should have to do it alone. That kind of trust doesn’t just happen. It’s built a little at a time, in conversations like the one on one.
What a Better Conversation Can Surface
When the one on one goes a little deeper, you start hearing things you can’t learn any other way:
What’s frustrating someone, before a small frustration becomes a big one
What feels harder than it should, which is often where a broken process is hiding
What isn’t being said, whether it’s about workload, the team or you
Where they’re stuck, whether that’s a skill gap, a missing decision or a bottleneck you didn’t know about
What support they need, which isn’t always what we assume
None of this requires a longer meeting. It usually just takes a different question.
Questions That Have Opened Things Up for Me
There’s no need to use all of these. One or two is plenty. Then see where it goes.
“What’s been frustrating lately?” It’s simple, and it’s often the most revealing.
“What feels harder than it should?” This tends to surface the workarounds people have been quietly living with for months.
“Is there anything on the team, or between us, that isn’t getting said?” After you ask, leave a little silence. It can take a moment for someone to decide it’s safe to answer.
“Where do you feel stuck or unsure about the next step?” Asking it this way makes being stuck feel normal instead of like a failure.
“How am I landing with you? Is there something I could do, or stop doing, that would help?” This one takes some courage. It’s also the one that has taught me the most.
“What part of your work have you enjoyed most lately?” It balances out the harder questions and tells you what gives someone energy.
“What would you like to learn or take on in the next six months?” Development conversations get pushed to “later” so easily. This keeps growth on the table.
Listening for What’s Underneath
The questions are half of it. The other half is how we listen.
What happened this week is information. What keeps coming up is a pattern. Maybe the same frustration with another department shows up three meetings in a row, or someone says “I’m fine” while mentioning another late night. Patterns like these usually tell us something long before it shows up as burnout or a resignation letter. I’ve found it helps to jot down a few notes after each conversation so I can see them over time.
Resisting the Urge to Fix Everything
This one is hard for me. When someone shares a challenge, my instinct is to jump in and solve it. Sometimes that’s right, like when it’s a safety issue, a policy question or a decision only I can make. More often, though, the better move is to ask a question back:
“What have you already thought about trying?”
“What do you think the best option is?”
“What would you need to move forward?”
When people get room to work through things themselves, they build confidence. It also keeps us from becoming the bottleneck for every decision.
A Few Things That Help It Stick
Protect the time. When one on ones keep getting canceled, people hear that they aren’t a priority, even if we don’t mean it that way. A short meeting is better than none.
Follow up. If someone names a barrier and nothing happens, they’ll stop naming them. Even a quick “I looked into that, and here’s where it stands” goes a long way.
Make the feedback usable. If you share feedback, leave time to talk through what it means and what different would look like. I know how it feels to walk out holding feedback you don’t know what to do with.
Final Thought
I think about the version of me who sat in those meetings holding it all in. She didn’t need more structure. She needed someone to open the door a little wider.
Next time you sit down with someone on your team, set the status update aside for a few minutes and ask something that makes room for the real answer. You might be surprised by what you learn, about them and about yourself.
If you’re rethinking how you lead your people this year, I’d love to be part of that work. You can reach me at info@srsdconsulting.com.
#LeadershipCommunication #TeamDevelopment #LocalGovLeaders
