Wolf & Heron

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4 Things that Go Wrong with One-on-One  Check-ins (and How to Avoid Them)

Manager check-ins, one-on-ones, touchpoints… Whatever you may call them, they are the foundation of a strong manager-employee relationship and the lynchpin for supporting your employees in many ways. This 30-minute-or-so recurring meeting between manager and employee seems so simple that it’s often taken for granted and therefore underutilized. They are used as opportunities to get project updates or chat about anything, when they could be so much more supportive of the employee’s professional growth and development. More often than not, we hear about employees or managers who simply put them off, postpone them indefinitely, or end up using the time as status report opportunities rather than truly leveraging their power. 

It’s time to go back to the basics. Here are 4 things that go wrong with your manager check-ins and how to avoid them.

Lack of Trust

Many managers assume that they have their employees' trust, but they don’t realize how easy it is to lose it. A lack of trust often can be the result of several things, many unintentional - from multitasking during these very check-ins, to poor communication.

As a manager, one of the most important things you need to do, particularly in order to create a safe space for an honest conversation, is to actively build trust with your employees.  

To be seen as trustworthy, here’s what you can do: 

  • Be accessible and approachable. Welcome their questions and feedback and avoid being defensive.

  • Ask open-ended questions.

  • Demonstrate active listening by rephrasing what you hear and asking follow-up questions.

  • Practice open and judgment-free body language.

  • Communicate transparently, directly, and frequently.

  • See the whole person; listen with empathy and show respect whether discussing a work or personal issue.

Zero Planning

One-on-one conversations with your employees may feel basic and straightforward. The very simplicity of the meeting creates a situation where many managers (and employees, for that matter) get lazy about them and fail to prepare for them with intentionality. Managers often start their one-on-ones with their employees with a question like, “Tell me about what’s going on this week?” or, “What’s on your to-do list?” These questions may be important to ask somewhere in the conversation, but opening like this sets up the entire touchpoint to be about the employee’s progress on their workstreams. What isn’t as easily or readily surfaced are opportunities to discuss roadblocks, ways to accelerate progress, feedback, or even the big picture.

The solution is self-explanatory. Before each check-in, managers (ideally with employee input) should plan. This can look like a lot of things and is dependent on the employee’s context. But have a sense of what is most important to cover—not in every one-on-one, but in THIS one. Consider things like:

  • The timing of this meeting relative to the annual review cycle

  • The importance and urgency of specific workstreams the employee is focused on

  • Typical cadence of growth opportunities presenting themselves within the organization and how and when to prepare for them

Before you start the meeting, prepare an agenda in partnership with the employee. Know what your goals are for the meeting, and why THOSE goals make sense for THIS meeting. Approach these meetings with a strategic mindset.

Overemphasis on Project Updates

Managers often over-leverage one-on-one meetings as a way to get a read on project progress. This turns the one-on-one into a report out that would have likely been better suited as an email. It also ends up with the unintentional consequence of making the one-on-one more useful to the manager than the employee. 

One-on-ones should serve your employee in a variety of ways. Use the time to answer questions they may have, understand their development goals and help them see themselves at the organization in the future. Check in on the human behind the work as well. Learn about their personal life and mental well-being. Managers that show their employees they see and hear them, strengthen their team and improve retention.

Ad Hoc Scheduling

It’s easy for managers to feel overwhelmed by the number of meetings on their calendars. More meetings and less time for independent work are powerful and energy-sucking workplace trends. That said, one-on-ones should not be the meetings that are sacrificed to the calendar gods. Part of the reason they do fall victim to rescheduling or postponing is because often they don’t feel like intentional or strategic conversations. If that’s the case, refer back to our suggestions on how to approach the meetings strategically.  But if that’s not the case, and the meetings feel important, they may still get pushed because of other reasons. Maybe you want to have the meeting in person, or expect your employee to be the one scheduling the calls. 

Instead, hold onto and honor the meetings. Find a cadence that works for all parties and make the calendar invitation a recurring meeting. Remove the mental burden of remembering to schedule, and instead make it part of your routine. Make sure that you’re in a situation where you’re supporting your employees regularly, and especially when you’re both busy or overloaded. In fact, it’s often in the moments of overwhelm where your support and presence is most important; you can help your employees take a step back and act with intention instead of simply reacting to the fires that need dousing.


Don’t fall into these one-on-one missteps. Instead, build and foster your employees’ trust, approach your employee check-ins strategically, see the whole person and keep the momentum going.

Looking for more and easy way to maximize your one-on-one check-ins? Check out our Inspired Check-Ins card deck, a tool designed to help you have more meaningful and effective conversations with your employees.