The 5 mistakes you’re likely making in your one-on-one meetings with direct reports

Don’t waste your time. Make sure you’re getting the most out of your one-on-one meetings with your direct reports. 

You’re feeling good: You’ve started to hold regular one-on-one meetings with direct reports. But have you paused to ask yourself, lately, “Am I making the most of them?”

The question is worth asking. One-on-one meetings with direct reports can have a surprisingly large impact on your team’s performance. In Google’s widely known 2009 manager research code-named “Project Oxygen,” they found that higher-scoring managers were more likely than lower-scoring managers to have frequent one-on-one meetings with their team members.

Our own survey results revealed a similar narrative: After surveying 1,182 managers and 838 employees from all over the world this past year, 89% of managers said that one-on-meetings positively affect their team’s performance – and 73% of employees said that one-on-one positively affect their team’s performance, as well. For both managers and employees, the majority of them think of quite highly of one-on-one meetings.

However, let’s zoom in on these numbers. When you look at our own survey we conducted, there’s a differential between the perceived effectiveness of one-on-one meetings. More managers (89%) seemed to believe that one-on-one meetings positively affected their team’s performance than employees (73%) did. In fact, the difference between the two are significant – 16 percentage points!

This suggests that while both managers and employees seem to find one-on-one meetings as positively affecting a team’s performance, there’s a gap in perceived effectiveness between the two. Managers seem to think one-on-ones are going a whole lot better than employees do. Despite all the time and energy we’re investing in holding these one-on-one meetings, it’s likely that employees themselves aren’t benefitting from one-on-one meetings much as they could.

And so, as we ask ourselves the question, “Are we making the most out of our one-on-one meetings with direct reports?” the answer is, “Probably not.”

Based on the research we’ve done around one-on-one meetings over the past few years, the data from Know Your Team we’ve collected in working with over 15,000+ people, and countless interviews and anecdotes shared in our online leadership community, The Watercooler, here are the 5 biggest mistakes we often make as leaders when it comes to one-on-one meetings – and what we should do instead to get more out of them.

Mistake #1: You reschedule your one-on-ones often.

The other day, I was looking at my calendar for the week and saw I had a one-on-one meeting with a direct report scheduled on Wednesday. “Oh man, not this Wednesday,” I thought to myself. That was a particularly stacked day, and, boy, was I tempted to reschedule the one-on-one meeting. I almost did…

Then I remembered: If I cancelled or rescheduled this one-on-one meeting, what does that say to my direct report about how I value hearing her perspective? When you do something consistently, it shows that you value it. If you’re not serious about something, you don’t do it regularly.

I also thought, “If I postpone the one-on-one by a week, what meaningful information from that particular moment in time might I miss?” Most managers hold one-on-one meetings every single week because it helps establish a pulse of how the other person is feeling. When you’re meeting one-on-one very week, you have a baseline for where someone is at, and what the red flags are when they waver. Postpone or cancel the meeting and you forgo part of that pulse. In fact, Gallup found that employees whose managers hold regular meetings with them are almost three times as likely to be engaged as employees whose managers do not hold regular meetings with them.

Now this doesn’t mean you’re never allowed as manager to reschedule a one-on-one meeting (e.g., an important meeting comes up, you’re out of town). Understandably, we’re all busy. Merely realize that our busy-ness is a threat to a big part of what makes one-on-one meetings so effective: Their consistency.

Mistake #2: You’re 100% sure what the purpose of a one-on-one meeting is.

“Tell me the latest on X” or “What’s going with Y project?” If you’ve ever uttered those phrases during your one-on-one meeting with a direct report, you’ve unfortunately made a grave error 🙂 This is because we often misconstrue what the purpose of a one-on-one meeting is.

The purpose of a one-on-one meeting is not to get a status update. Rather, the true purpose of an effective one-on-one meeting is to unearth feedback, issues, and concerns within the team. In our survey of 1,182 managers and 838 employees, we found that 46% of managers and 28% of employees both saw the #1 purpose of a one-on-one meeting as “uncovering potential issues.” Wobbly team dynamics, unforeseen customer glitches, frustrating negotiations with partners, unnerving observations in the market – these are the issues a single one-on-one meeting can uncover. Rarely do you get the opportunity to talk about this stuff, otherwise. Focus your one-on-one on uncovering these potential problems and issues.

Mistake #3: You never seem to carve out enough time to prepare ahead of time.

In our recent survey we conducted of 1,182 managers and 838 employees, we found 36% of employees believe their manager is only “somewhat prepared” – and 40% of employees think their manager is “not prepared” or “not prepared at all.” Woof. We have some work to do! As managers, we’re woefully underprepared for our one-on-one meetings – and as a result, we’re severely hurting our chances for our one-on-one meetings to be as effective as they could be.

Preparing for a one-on-one meeting with direct reports can take as a little as 15 minutes, and involves three main steps:

  1. Review the latest meeting and relevant status updates about what your direct report is working on. This way, you don’t waste valuable time during the meeting getting up to speed.
  2. Pick 1 – 3 focus areas and brainstorm 5 – 10 questions you’d like to ask. The most useful one-on-one meetings tend to focus on one or several of these areas: Feedback, Issues/Concerns, Career Direction, and Personal Connection. (You may want to check out our One-on-Ones Tool in Know Your Team, which offers agenda templates and hundreds of questions around these focus areas.)
  3. Calibrate your mindset. A one-on-one meeting is vital time to listen. You’re not kicking off or delegating new projects, you’re not defending decisions or espousing the team’s vision – you’re there to figure out where your direct report is at, mentally and emotionally, and where they want to go.

You can read more about how to prepare for a one-on-one meeting as a manager, here.

Mistake #4: You never ask for your direct report’s input on the agenda.

One of the biggest, most common mistakes we make as leaders is forgetting to get input on what the one-on-one meeting agenda should be, ahead of time. After all, the one-on-one meeting isn’t just your meeting – it’s your direct report’s meeting, too. You want them to feel bought into the process, that they have a real stake, and that you’re not just trying to interrogate them.

As a result, a best practice that’s utilized by many members in our online leadership community, The Watercooler, is to collaborate on a shared agenda for the one-on-one meeting ahead of time. In Know Your Team, we have a One-on-One tool that makes it very easy to this – but you can also use a shared Google Doc to kick off a shared agenda. Here’s an example of an email you could send to your direct report to ask them for their input on the one-on-one meeting agenda:

Hey [EMPLOYEE’S NAME],

I’m really looking forward to our one-on-one meeting later this week. I took the liberty of kick starting an agenda for the meeting – but would love your input on what topics we should discuss.

Feel free to add the topics you’d like to discuss here: [LINK to Google Doc]

Thanks! [YOUR NAME]

We also have countless of shared agenda templates and questions in Know Your Team, that helps automate this whole process for you  🙂

Mistake #5: You ask, “How can I help you?” during your one-on-one meetings.

You might be thinking, “Wait a minute, Claire. I ask this question, ‘How can I help you?’ all the time. How is this possibly a bad question to ask?” Well, it is for several reasons. And trust me, I’m guilty of asking this question as much as you are. Learning how counterproductive this question is surprised me as well.

First off, the question “How can I help you?” is enormously intimidating to an employee. There’s a reason that 9 out of 10 times that you ask it, that the other person says, “Hmm nothing I can think of right now.” It’s because you, as the boss, are putting pressure on the other person to critique your job. You’re giving them no parameters, no direction, as to what kind of feedback or critique you’re looking for… And so your direct report will often think the safest response is no response.

Secondly, asking “How can I help you?” puts a burden on the employee. You’re asking your direct report to do the heavy lifting of figure out how you should be doing your job better as a leader. There are plenty better questions you can ask – questions that, no doubt, require a little more thought ahead of time to come up with. For example instead of asking, “How can I help you?” try asking:

  • What do you find challenging about my management style
  • What aspect of my work do you think I can do a better job?
  • Do you think I’ve been a little micromanaging with how I’ve been following up on projects?
  • Have I not been as cognizant of reasonable timelines, like I should have?
  • Would you like more or less direction from me? Why/why not?
  • What’s a recent situation you wish you handled differently? What would you change?
  • When have you been annoyed, peeved, or bothered by me and something I’ve done?
  • Could I be doing a better job outlining the vision and direction for where we’re headed?
  • Am I giving you enough information to do your job well?

In Know Your Team, we share 100+ one-on-one meeting questions just like this, that you can use, so you don’t have to come up with fresh questions every time, from scratch.


Keep in mind this number: There’s a 16 percentage point difference between managers’ and employees’ perceived effectiveness of one-on-one meetings. Your one-on-one meetings with direct reports are high leverage… but only if you’re taking the right steps to make the most of them.

Don’t waste your time – or theirs. Avoid these key mistakes.


Claire is the CEO of Know Your Team – software that helps you avoid becoming a bad boss. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

6 thoughts on “The 5 mistakes you’re likely making in your one-on-one meetings with direct reports

  1. good article
    typo: very->every
    “When you’re meeting one-on-one very week, you have a baseline for”

  2. Fantastic Article!

    The points that stood out for me were:

    Mistake #1: You reschedule your one-on-ones often.

    Mistake #2: You’re 100% sure what the purpose of a one-on-one meeting is.

    Mistake #5: You ask, “How can I help you?” during your one-on-one meetings.

  3. Really Great Article!

    I have been asking “How can I help you?” I now I see the clear drawbacks to this. I try to make a point to spend time with each of my people every week, but everyday demands make this unrealistic. I think that the importance of this gets lost and is not something that is clearly visible in a spreadsheet.

  4. Thanks for the thoughtful and useful advice. One question here, do people use the term ‘direct reports’ at Basecamp? I know it’s a very concise and descriptive term, but it seems so corporate I would avoid using it personally, it feels very impersonal.

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