One-on-Ones: The Simplest Thing Most MSP Owners and Managers Skip

If someone on your team is struggling, or worse, quietly on their way out the door, I’ll ask you one question before we dig into anything else: when did you last have a one-on-one with them?

For a lot of MSP owners, the honest answer is something like “whenever I get around to it” or “we talk all the time.” And that’s the problem.

This week I recorded an episode of Tales from the Trenches with Natalie, and we ended up on one-on-ones. It’s a topic that comes up constantly in peer groups because the pattern is so consistent: a manager is frustrated with an employee, or blindsided by a resignation, and when you dig into it, the one-on-ones either weren’t happening or had no real structure behind them.

Why This Keeps Getting Skipped

MSP owners and managers are busy. That’s not a mystery. But skipping one-on-ones to save time is one of those decisions that creates way more time problems down the road. When people leave, you have to hire and train replacements. When performance issues fester, they become real crises. When your team doesn’t know where they stand, you get disengaged employees doing mediocre work.

The time you “save” by not doing one-on-ones gets spent dealing with consequences. It’s not a good trade.

There’s also a trap I see a lot of owners fall into: confusing regular contact with intentional conversation. Talking in the hallway or chatting at lunch is not a one-on-one. A one-on-one is a conversation with purpose. It’s your direct report’s time to tell you what’s working, what isn’t, and what’s in their way.

What a Good One-on-One Actually Looks Like

Short and consistent beats long and sporadic every time. A 15 to 30 minute weekly meeting is far more valuable than an hour-long check-in once a month. Weekly cadence also gives you flexibility. If someone has to miss one, you’re only out a week. Miss a monthly and you might go six or eight weeks without a real conversation.

The agenda doesn’t have to be complicated. Some version of these questions works:

• How are you doing?
• What wins have you had recently?
• What’s getting in your way?
• What do you need from me?

That’s it. The goal is to hear from them, not to fill the time with your own updates. The employee should be doing most of the talking.

One thing I’d add: capture the wins. This sounds small, but it matters. It’s easy to forget what your team accomplished when it comes time for reviews. If you’re logging notes from weekly one-on-ones, reviews become much easier and much more useful conversations.

One-on-Ones Are a Prioritization Tool

One practical benefit that often gets overlooked: regular one-on-ones keep you and your team aligned on what matters most. Your employees need to know their priorities, and that clarity doesn’t happen by accident. A quick check-in every week is a natural place to make sure everyone is pointed in the right direction. I wrote about this more in an earlier post on one-on-ones if you want to dig into that angle.

One-on-Ones Are Not the Place for Discipline

This is important enough to call out directly. If someone makes a mistake or there’s a behavioral issue, handle it as close to the situation as possible. Same day if you can. Don’t hold it for the next one-on-one.

When you start using one-on-ones as the place where bad news gets delivered, people begin to dread those meetings. The whole point of a one-on-one is to create a space where your employee feels safe to be honest with you. Once they start walking in with anxiety about what’s coming, you’ve lost that.

Keep one-on-ones what they’re supposed to be: your employee’s meeting. Keep the hard conversations separate and timely.

The Review Connection

One more thing worth saying: if you’re doing weekly one-on-ones consistently, formal reviews become easy. Nothing should come as a surprise. The review can focus almost entirely on looking forward, talking about career growth, goals for the next six to twelve months, and what you can do to help them get there.

Contrast that with the review where you’re digging through your memory trying to reconstruct the last six months. Or worse, bringing up something that happened months ago as if it’s news. Don’t do that. No new bad news at review time. If something went wrong and you didn’t address it close to the situation, that ship has sailed.

Getting Started

If you’re not doing one-on-ones right now, start simple. Get it on the calendar. Protect it. Use a basic template. Document what comes out of each meeting.

It’s okay if the first few feel a little rough. You’re building a muscle. Talk to your employees about how it’s going and iterate. Perfect is the enemy of good here. A consistent one-on-one practice that’s 80% there is infinitely better than a theoretically perfect one that never happens.

The consistency is the point. Once a week, every week, with intent.