Why Don’t My Check-ins Feel Helpful?

A reader asks:

I have a confession: I’ve stopped doing weekly one-on-one meetings with my staff members. We used to do them, but they weren’t that useful and it felt like we were just going through the motions. Now we just meet ad-hoc when we have something to talk about, and sometimes we all meet as a group to talk about what everyone is working on. Is this really so bad?”


It’s easy to feel like one-on-one check-ins aren’t useful if you’re just going through the motions!  And of course you have better things to do with your time than running down a list of projects and just hearing that “everything’s going well.”

But when check-ins are done right, they can revolutionize the way you manage your staff members. Fundamentally, these meetings give you a “forum” for management — providing a regular time to touch base about each staff member’s work, ask probing questions, serve as a resource, balance priorities across projects, and give feedback. And often your  “one level up” perspective will allow you to spot solutions to problems that the staff member may have missed.

How to do check-ins right

Here’s how to get the most out of your check-ins:

1. Use an agenda. Ask the staff member to email you an agenda beforehand, so that neither of you are walking into the meeting cold. This sample agenda will help keep the focus where it should be: on the week’s main goals, debriefing recent projects, and other key items.

2. But don’t rely solely on the staff member’s agenda. Take two minutes before the meeting to think through what you think is most important to talk about. Thinking through “What am I most worried about? What do I want to make sure we focus on?” can have a big impact on how useful the meeting will be.  For instance, you might realize “the thing I’m most worried about in Julian’s realm is the progress of our organizing work in Detroit — I’m going to really focus on that.”

3. Ask probing questions so that you understand how work is really going. A lot of check-ins go wrong because the manager just asks, “So how’s project X going?” and doesn’t dig deeper. Instead, find ways to really get beneath the surface, asking questions like:

  • What makes you say that?
  • How do you know that you’re on track?
  • What could go wrong?

This page provides plenty more questions you can ask to get beneath the “everything’s fine” and probe how work is really going.

4. Give feedback and debrief recent projects. Reflect on what’s gone well recently and what didn’t meet expectations, and take advantage of the opportunity to discuss what can be learned from recently concluded projects.

5. Make sure next steps are clear. Always end the meeting with a clear agreement about what will happen next, even if it’s just, “Let’s both think this over and then you should bring it up again next week.” It can be especially useful for your staffer to take two minutes to email you a quick summary of what was agreed to (see our sample email repeat-back here), or to at least give you a verbal recap of next steps at the end of the meeting.

6. Don’t substitute group meetings for one-on-one check-ins. Group meetings work well for communication and coordination, but not individual management, where you’ll be giving feedback and really delving into the details of the work. Instead, save staff meetings for conversations that truly involve the entire group and make sure you’re talking individually with each person.