Why do one-on-ones fail?

Signs your one-on-ones are not working

To fix mistakes, first check whether your one-on-ones are working now. If you see any of these signs, it is time to look at how the conversation goes.

• The team member keeps saying "Nothing in particular."
• Every conversation ends with checking work status.
• Meetings are often pushed back or canceled.
• You talked, but no commitments remain.
• The leader does most of the talking.

If any of these fit, the flow is probably breaking somewhere in preparation, conversation, or follow-up. That is no reason to blame yourself. A researcher writing in Harvard Business Review points out that few organizations give managers strong guidance or training on meeting individually with their employees (HBR, 2022). Below, one-on-ones are split into three stages, preparation, conversation, and follow-up and running them, to show where leaders tend to slip.

What gets missed in preparation

Much of a one-on-one's quality is set before the conversation starts. Walk in unprepared and you tend to talk only about whatever comes to mind.

1. Walking in without an agenda

The meeting is on the calendar, but nobody has decided what to talk about. The team member wonders what this one will be about, and the leader asks whatever occurs to them until time runs out.

• Have the team member write two or three lines on what they want to discuss by the day before. A form with set fields makes it much easier.
• The leader also picks one or two topics to raise, but covers the team member's topics first.
• Ben Horowitz also recommended that employees send the agenda in advance (a16z, 2012).

2. Walking in without rereading the last conversation

Last time you said you would look into something, and you walk into the next one-on-one having forgotten. The team member has to raise it again and starts to feel that speaking up changes nothing.

• Keep the five minutes before a one-on-one free to reread the last notes and action items.
• Start by checking the leader's commitments from last time. Seeing the leader keep their word is what draws out the team member's next topic.

What gets missed in the conversation

Even with good preparation, a one-on-one loses its value when the conversation tilts one way. During the conversation, watch for these three things.

3. Spending the whole time on status

Thirty minutes pass while you scroll through the schedule and completion rates together. Work is an important one-on-one topic, but if you only recheck what was already shared in chat or meetings, the team member feels they have reported twice.

• Get progress in a document or message before the one-on-one, and use the conversation to ask what is stuck and what help is needed.
• Change your first question. Asking about experience instead of progress, such as "What took the most effort this week?", opens the conversation up.

4. Reaching a conclusion before hearing the team member out

The team member starts with "The client keeps changing what they want," and you wrap it up right away with "Check the contract scope first." The advice may be right, but you move on without finding out whether they really wanted to talk about schedule pressure, friction with another team, or simply being worn out.

• Sum up what you heard in one sentence and check it: "So redoing the work every time the requirements change has really worn you down?" The team member usually goes on to say more.
• Then ask, "What would help most right now: my view, a decision, or coordination with another team?" to settle what kind of help they want.
• Which help fits depends on the situation. Someone less experienced may be better served by the leader explaining the way forward; someone experienced may get more from questions that widen their thinking.

5. Questions that sound like evaluation

The leader asks out of curiosity, "Why isn't this done yet?" or "Was that the best approach?", and the team member hears blame. If this repeats, team members start raising problems only after they have solved them.

• Shift the focus of the question from the person to the situation. Instead of "Why is it late?", ask "What affected the schedule?"
• Say up front that ratings and scores are not part of one-on-ones.
• Example questions by situation are in the one-on-one questions list.

What gets missed in follow-up and running them

However good the conversation, if nothing follows, the one-on-one ends as a single good chat. These are the mistakes in closing and scheduling.

6. Ending without commitments

You finish with "Good talk today" and head back to your desks. Without deciding who does what, the next one-on-one starts from scratch again.

• Use the last five minutes to agree on who does what by when.
• Action items are not only for the team member. When the leader owns at least one, the team member sees the one-on-one as something you build together.
• Write what you agreed straight into the one-on-one doc and make it the first thing you look at next time.

7. Postponing it first when things get busy

When an urgent meeting comes up, the one-on-one is the first thing moved. After a few times, the team member learns it can be pushed back anytime and stops putting care into preparing.

• If you must postpone, set the new date on the spot and tell them. A "some other time" with no date is no different from canceling.
• If one-on-ones with the same person have slipped three or more times, the day or time slot may be the problem rather than your intentions. Try a different slot or reset the cadence.

8. Talking with everyone the same way

You run one-on-ones with a two-week hire and a ten-year senior using the same questions in the same order. The new hire lacks information, and the senior spends the time hearing things they already know.

• With new hires, spend more time aligning on how work is done and on expectations. It is fine for the leader to do more of the explaining.
• With seniors, cover broader topics such as decision scope and the direction of the team and organization. See How do you run one-on-ones with senior employees? for details.

Don't try to fix everything at once

Trying to change all eight at once rarely lasts. Look at the signs above again, pick the one that shows up most, and change only that for the next three one-on-ones. Spending one minute right after each meeting asking "What was my first question today?" and "Did we end with commitments?" is enough to start shifting the habit. The fixes in this article are suggestions based on a one-on-one leader training deck from Upstream that Orblit referred to and on field experience.

You can see the change in your notes. If a few months of one-on-one records hold a balanced mix of blockers and how they were solved, agreed goals, and career conversations, your one-on-ones are doing their job. If they only repeat status, the meeting has slid back into a report.

If one-on-ones keep stalling even after you fix these habits, the problem may be structural rather than conversational. The structural reasons, skill, time, information, and continuous management, are covered in Why do teams hold one-on-ones?.