5 Signs Your One-on-Ones Aren’t Working
Despite all that one-on-one meetings can offer, they can be challenging to navigate, whether you’re new to management or have spent several years in a leadership role. Here some signs that your one-on-ones have gone stale, are unproductive, or are falling short of their potential: you don’t want to go to the meeting, you always go over time, you can’t fill the time, you leave every meeting feeling deflated, or you and your direct report are both on second screens. The author presents several ways to make the most of this valuable time.
One-on-ones are ongoing meetings between managers and their direct reports. For managers, these weekly or biweekly exchanges typically have two objectives: aligning on expectations and building trust with team members. Beyond this, one-on-ones encourage deeper boss-employee relationships and can be used to give and receive feedback, set individual goals, and troubleshoot roadblocks.
Despite all that one-on-one meetings can offer, they can be challenging to navigate, whether you’re new to management or have spent several years in a leadership role. As a leadership coach, I’ve seen people — in every career stage — struggle to balance the conflicting priorities of supporting their direct reports while simultaneously meeting company goals and delivering on the other responsibilities that come with their role. With limited time and resources, many of them wonder: Are one-on-ones really worth all the effort?
My answer is always: Yes, if you use the time productively. But if you have to ask the question, there’s room for improvement.
Here are five common signs that your one-on-ones have gone stale, are unproductive, or are falling short of their potential — and how to make the most of this valuable time.
When your calendar barely leaves time for lunch, canceling your most routine meetings may start to feel tempting. While there will inevitably be times when you need to cancel a one-on-one, they shouldn’t often fall into this category. If they do, take it as a sign that you need to leverage the time differently.
Managers should not attend one-on-ones, but rather lead them. They should serve a real purpose and evolve based on your employee’s needs in the moment. Though they likely adhere to a routine cadence, the agendas for these meetings should be anything but repetitive.
Each employee’s priorities, projects, and tasks can change from week to week. So, ask yourself: What’s motivating both of us to show up today? Are the meetings too unstructured? Or do we rely on the same agenda when we should be adjusting it?
To make sure you’re using the time productively, do a little prep. I advise managers to dedicate the first one-on-one of every month to their direct report’s career-development goals. It’s a good time to check in on people’s short- and long-term ambitions — gauging the progress of their recent work. By designating one meeting per month to career-level topics, it guarantees that every week won’t be the same old, same old, and reminds your employee that you’re a manager who is committed to moving both of your longer-term goals forward.
It can also be useful to create a shared document where you and your direct report collaborate on an agenda for each week. Add topics to discuss in preparation, and encourage your direct report to do the same. This will motivate you both to show up with intention, and also help you keep track of any action items you’re accountable for.
If 30 to 60 minutes every week isn’t enough time to sync up with one person, you have a problem. You’re either going into too much depth and detail, rehashing old agenda items, or getting off track with side discussions.
If your conversation is too detailed, step back and reassess which topics would be better addressed in a more formal meeting focused on a single topic. For instance, if you’re strategically mapping out your direct report’s newest project every week, consider scheduling dedicated time to hash out those details or — even better! — connect them with another team member who can mentor them through it.
Likewise, if you keep getting off track discussing side topics — points unrelated to your employee’s performance and needs — consider whether these issues must be addressed in person or if any can be discussed asynchronously, via email, Slack, or a quick exchange in the hall.
Finally, if you’re rehashing previous meetings and repeatedly going over the same discussion points, without any progress being made, you’re stuck in a loop. While it’s normal for some repetition to take place during one-on-ones — as some issues take longer to resolve and may require weekly updates — these shouldn’t be taking up the majority of your time. Ask yourself: Why do we keep coming back to this topic? What’s stopping us from moving forward? Are we avoiding being direct about a difficult subject?
Let’s say, for example, your employee is experiencing friction with a coworker. Week after week, you discuss the root causes and potential steps forward but, unfortunately, no progress is being made. In this case, you can help move things forward by scheduling a separate meeting to bring the two parties together, or referring your report to HR for further mediation. Conflict and stress are often explored in one-on-ones, but you need to draw a line when the conversation has reached the limits of productivity.
On the opposite end of the spectrum, what if you regularly run out of things to talk about?
There will always be some weeks with more to cover than others. However, if your direct report consistently has little to share or update you on, it could be a sign that they’re not comfortable discussing their needs, obstacles, or anything beyond their to-do list with you.
To create a space in which your team member feels comfortable opening up, you need to develop a strong level of trust. This takes time, and for some employees, more time than others. Your job as a manager is to keep the lines of communication open by showing up consistently and finding new angles to build the relationship — even if the connections take a while to form.
If you’re struggling to engage your report, here are some deep questions to prompt greater discussion:
These questions invite more than yes-or-no answers and encourage even the most-shy team members to open up.
Collapsing after a one-on-one could be attributed to compassion fatigue or even burnout. This is especially true if your direct report is using one-on-ones as venting sessions.
I once had a client who told me that she needed to put her head on the desk after every one-on-one with a specific team member. “He complains for 30 minutes straight and I’m stuck listening to it,” she said. “There’s always someone else to blame for his problems — the company, the team, or me.”
There’s plenty of room to be a kind and understanding manager without becoming a punching bag. Emotional labor can be one of the most exhausting aspects of the job. You need to learn how to identify and protect your own boundaries, especially the emotional ones. Certain personal issues that employees may bring to you might be better discussed outside of work or with a mental health professional who can offer the proper support.
In the case of my client, we developed a plan for her to take back control. To start, she added “venting” as an agenda item at the top of the meeting. “Let it all out!” she said to her direct report. “You have five minutes, then we’ll move on to other topics.” Ironically, inviting her direct report to vent made him aware of how quickly five minutes passed and how much time he had been spending in a negative spiral.
If he fell into complaining after the first five minutes, my client would guide him toward productivity. “I understand that it’s a frustrating project,” she would say, “but what do you have control over? What can you change?”
Coaching her direct report helped maintain momentum in the meeting. She then followed through on feedback, including documenting his struggles and assigning specific tasks to move him along. It took effort to keep him on track, but she no longer felt fatigued to the same degree.
In your own situation, ask: What am I comfortable discussing versus not discussing at work? Are there ways I can be emotionally supportive to my employee without taking on that emotion myself? Like my client, you might try helping your direct report gain more awareness around the draining behavior. Pointing it out by saying something like, “I noticed you brought this up in our last meeting as well. I understand how important this is to you, but I also hate to see it dragging you down at work. How can I best support you?”
If no one’s paying attention, is it even a meeting?
Sadly, it’s common for second devices to compete with live meetings these days — and even more so if they’re virtual. But if you can’t pay attention when it’s just you and one other person, that’s a sign that you (or your direct report) aren’t prioritizing the time together.
Overwhelmed by your endless to-do list, you may be tempted to sneakily scroll through email or check your calendar while your direct report updates you on their work. This is not only rude, but it also undermines your authority and suggests to your employee that you don’t value their time. Chances are, if you’re distracted, your employee will notice — and breaking their trust is not worth answering two extra emails.
You can become more disciplined and focused through practice. Before your meetings, go to a quiet space, silence your notifications, and close any second screens on your laptop. Then, practice active listening. When your employee mentions a challenge they’re facing, for instance, repeat it back to them and say, “Did I get that right?” This will show your employee that you’re present and force you to home in on the conversation at hand.
If your direct report is on a second screen, pause the conversation and ask if they need a moment. Acknowledge that there are many priorities vying for their attention, but that one-on-ones are your one chance to really connect during the week.
It can also be useful to start the meeting by calling it to order. “Let’s get started” nudges people to be present. “Let’s put our phones away for this conversation,” you might say, holding yourself accountable by modeling the appropriate behavior.
Good managers take stock regularly, adjusting one-on-ones to find the best cadence, content, and purpose. Take good care of your own energy and construct your schedule with intention. With some definition and commitment, those one-on-one blocks on your calendar will feel less like obligations and more like opportunities.
Meeting management, Managing employees, Managing people, Management communication, Early career, Digital Article
Jen Dary
Jen Dary is a highly sought-after leadership coach and founder of Plucky where she coaches CEOs, entrepreneurs, and managers at every level. In addition to one-on-one coaching, Jen teaches new managers in her “So Now You’re A Manager” training program and leads small, specialized coaching groups.
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