Conversation Leadership Meetings

How to organize the worst one-on-one meeting?

A one-on-one meeting, 1:1, 1 on 1, a one-to-one, a check-in, whatever you call it, it is one of the most important meetings, looking both from a manager’s perspective as well as an employee’s perspective. Unfortunately, those kinds of meetings are the subject of frequent complaints. They became the victim of corporate jokes. People treat them as a necessary evil or a pointless duty. The idea of those meetings is thought to be a waste of time, an unproductive gathering or just a meeting without a purpose. That’s what you typically hear if you ask about feelings towards one-on-ones. 

Below you’ll find a list of the worst practices you could use if you wanted to organize a really bad one-to-one. And if you were in the market for the title of the best poor manager, those guidelines would definitely help you. If this isn’t tempting enough for you, it’s possible that you’re already good at being bad leaving people confused or drained after such a meeting.

Talk throughout the entire meeting

Don’t let your employee share any thoughts. Of course, Ben Horowitz recommends that a manager should only talk for 10% of the time. The rule of thumb is that the rest should be saved for a team member. But who would care about that? Do the opposite.

Waffle on issues that are interesting from your or the company’s perspective. Ask about a status update, future deadlines, corporate strategy and the financial situation of a company. Don’t listen to what an employee has to say. Because what information can you really get from him or her? A one-on-one is actually the best time to share your point of view, not your employee’s. Managers should try to steal the whole conversation from the very beginning. I hope you had a chance to experience that in the past so you know how “pleasant” such meetings can be!

I’ve heard many complaints from people who said that a manager talked too little. They didn’t see any value in one-on-ones because they couldn’t hear their supervisor speak. That’s why the advice here is to listen less and speak more. Focus on yourself, not your employee. Because in the end you’re the boss!

Talk about project and status updates

There is a variety of ways to get a status update. You can do it via email, chat, a daily meeting or any kind of a project management tool. But of course the best opportunity is during a one-on-one. As a busy manager you don’t have enough time to get all important updates during the week. Other managers expect you to give a high-level overview but you don’t know what to say. That’s why during each one-on-one you can simply ask your subordinate to share project related updates. 

Forget about getting feedback, suggestions, ideas, discussing career goals and people’s  issues. There are better conditions to talk about those issues than during one-on-ones. It’s better to resolve them via email or chat. The more time you spend on project related topics, the worse one-on-one you’ll end up with.

Set a strict agenda

If you wanted to kill the spirit of your employee, you’d better not let him or her suggest any topics to discuss. Since you’re the one who organized the session, you are the one responsible for the agenda. Being a facilitator means you should do your best to optimize the agenda in order to utilize each minute of the meeting effectively. There’s no time for irrelevant discussions or silly small talk. Ben Horowitz once said that for him one-on-one is:

“(…) the free-form meeting for all the pressing issues, brilliant ideas, and chronic frustrations that do not fit neatly into status reports, email, and other less personal and intimate mechanisms”

But if you wanted to actually become a facilitator of the worst one-on-one ever, you should prepare a strict agenda and stick to it. Then of course you’d stay 100% focused on achieving the goal that you’d set yourself. 

one-on-one agenda

The best one-on-ones are like a questionnaire. You don’t need to leave any time for creativity and open discussions. Prepare a complete plan with a list of all topics and questions you want to talk about instead. Keeping your one-on-one meeting completely formalized makes you look professional. And that’s what your employees expect from you. One-on-ones are a great tool for leaders and managers but they aren’t meant to improve your relations with colleagues. It’s all about meeting your goal. Focus on the agenda, not your relations with teammates.

Once a month is enough

What’s the point of hearing about problems early on in a private environment? You don’t need to have regular and frequent one-on-ones. It’s enough to gather feedback once a month. Some problems may solve themselves in the meantime. And if those issues don’t get resolved, there will be more topics to discuss later. Save your time for more important meetings and challenges and focus on the real work.

Some managers will tell you that unless you meet with your employees regularly, small problems may grow to be great issues. But it doesn’t necessarily apply to you. After all, your team consists of mature and professional people who will speak up as soon as they start to feel unsatisfied. Instead of demotivating each other and gossiping in the social room they will come to you and ask for a short session. Always.

If it’s possible, cancel, don’t reschedule

If you’re a leader or a manager, you’re probably very busy at work with plenty of meetings and commitments. C-level guys keep asking about important things and sometimes there just isn’t enough time for your subordinates. That’s ok. You’re the one doing the real job there. They should understand that. If you don’t have the time, you can simply skip your one-on-ones. There is no point in rescheduling them because another session will come up soon. 

And what if your employee didn’t have anything interesting to tell you during these meetings? Say you’d try very hard to organize the session but there would be no input from the other side. If that happened regularly, you could simply get rid of one-on-ones. Basically there is no point in wasting both your time. Silence means there’s probably nothing to fix or improve. The fewer one-on-ones are scheduled, the more time you have to do the “real” work.

Action items are optional

Ok, let’s say you’ve spent 30 minutes discussing different topics and you’ve heard couple of complaints from your subordinate. You’ve agreed that all of them are important. Now it’s time to finish the meeting. You can summarize it yourself and invite the respondent for the next session. So let’s get back to reality and your mundane chores. Enough time was spent on complaining and discussing different issues.

And what about commitments and action items? They’re optional. The goal of one-on-ones is to talk about current problems and challenges but not necessarily to find a solution. You don’t need to create any action items because your subordinate is a professional who will take care of everything. And by the way, don’t start one-to-ones with reviewing previous action items because… they don’t exist or they are just in your head. There is nothing to worry about. If the problem still exists, you’ll be notified during the meeting. Talk a lot, complain a lot but don’t take up any actions. That will definitely help you become the worst facilitator of one-on-ones.


I gave you plenty of tips on how to organize the worst one-on-one session ever. I hope that now you have the knowledge required to facilitate such a meeting. If you don’t, feel free to ask me and I’d be glad to supply you with more advice. Each time you’ll need to hold a one-on-one remember about principles mentioned above. Given my suggestions you have two choices: follow them or do the opposite. Take a guess which one you should pick…