Most one on one meetings are either too long and unfocused or too short and pointless. I have been on both sides. As a manager running them and as an employee sitting through them wondering why I was there.
The sweet spot is 20 minutes with a structure. Here is the one I use.
The format
Minutes 1-5: The employee talks. What are they working on this week? What is going well? This is their time. You listen. You do not interrupt with your agenda.
Minutes 6-10: Blockers and problems. What is in their way? What do they need from you or someone else to move forward? Your job here is to take notes and commit to action, not to solve everything in real time.
Minutes 11-15: Your input. This is where you share context they might not have. Company updates, changes in priority, feedback on their work. Be specific. “That report you sent Tuesday gave me exactly what I needed for a client meeting” is useful. “Good job this week” is not.
Minutes 16-20: What is next. What are the top priorities for the coming week? Is there anything that needs to shift? Do you both agree on what matters most? End with clarity, not with “sounds good, see you next week.”
Rules that make it work
Never cancel. The fastest way to signal that you do not care about your team is to consistently cancel one on ones. If you have to reschedule, reschedule the same day. Do not let it slide to next week.
The employee sets the agenda. Not you. If they do not have anything to discuss, that is a signal worth paying attention to. Either they are disengaged, or your relationship is not one where they feel comfortable bringing things up. Both are problems.
No laptops, no phones. Twenty minutes of undivided attention. If you cannot give someone 20 minutes without checking your email, you are telling them where they rank.
What most managers get wrong
They use one on ones as status updates. If all you are doing is asking “what is the status on Project X,” send an email. The one on one is for the stuff that does not fit in an email. How someone is actually doing. What is frustrating them. Where they want to go next.
They talk too much. The employee should be talking 60-70% of the time. If you are talking more than that, you have turned a one on one into a monologue. Your team already hears you in group meetings. This is their time.
They skip the hard conversations. If someone is underperforming and you do not bring it up in the one on one, where exactly are you going to bring it up? The one on one is the safest place for honest feedback. Use it.
Why 20 minutes works
Thirty minutes invites padding. People fill time. Give them 30 minutes and you will get 15 minutes of content and 15 minutes of awkward filler. Twenty minutes creates urgency. Both people come prepared because they know the time is short.
I manage teams across multiple markets. If every one on one ran 30 minutes, I would lose half a day every week. At 20 minutes, I can have six meaningful conversations in two hours and still have time to do my actual job.
The one on one is the smallest unit of leadership. If you cannot run a good 20-minute conversation with one person, nothing else in your management practice is going to work either.
About Khary Penebaker
Khary Penebaker is Division President at MetalMaster-RoofMaster, the Upper Midwest division of Wolkow Braker Roofing Corp. He previously built Roofed Right America from startup to $35M+ in revenue with 180 employees (2014-2025) and founded Penebaker Enterprises, growing it from $1.5M to $15M. A gun violence prevention advocate and former Everytown for Gun Safety Fellow, Khary brings two decades of leadership in commercial roofing, architectural sheet metal, and civic engagement.
Common questions
How often should managers have one on one meetings?
Weekly or biweekly for direct reports. Monthly for skip levels. The frequency matters less than the consistency. A 20 minute meeting every week beats a 60 minute meeting once a month.
What should you discuss in a one on one meeting?
Three things: what is going well, what is stuck, and what do you need from me. That is it. Save project updates for team meetings. One on ones are about the person, not the tasks.
What mistakes do managers make in one on one meetings?
Doing all the talking, canceling them regularly, and turning them into status updates. The best one on ones are 70 percent the employee talking and 30 percent the manager listening and coaching.
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Last updated: June 28, 2026