MBA1760 Q&A Wednesday: How often should I do 1:1’s with my employees?
2 Feb 2026 · 8 min
Omar Zenhom answers how often to meet one-on-one with employees. He recommends short 15-minute video calls scheduled into the calendar, at least once a year, letting the employee do most of the talking. Cadence depends on your business tempo and whether someone is new.
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Hey O welcome to the $100M Favorite Business podcast for practical business advice every single day with our daily 10 minute business lessons for the real world. I'm your host, your coach, your teacher Omar Zenholm. I'm also the co founder of Webinar Ninja, an independent software company I started with my partner back in 2014 and today's episode is Q and A Wednesday. On Q and A Wednesday, I answer a question from one of you, one of our listeners. If you have a question you want to ask, just email me over@omar100mba.net Today's question is from Craig and Craig asks, hey Omar, Love the podcast. I have a small team of seven people. Everybody works remotely and many of them are outside of my country. We all talk to each other via chat and a project management tool. But in the three years I've been in business, I've never conducted one on ones. How often should I be doing one on ones with my team members to check in and see how they're doing? Any help with this would be amazing. Thanks so much Craig. Great question, Craig. Sometimes when we're running our business, things get busy. Everybody's doing their job, everybody's working hard and we never kind of make the time to sit down and just catch up with our teammates individually. In today's episode, I'll answer your question and give you a simple system to make sure you do have time for one on ones that you don't forget and it just happens in an automated fashion. Let's get into it. Let's get down to business.
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So in today's Q and A Wednesday, Craig asks how often should he be doing one on ones. He's been in business for three years and he hasn't done one yet. And I say that with a chuckle, not because it's a bad thing, but because it's such a common thing. You know, I remember when I started running my businesses, I didn't even know I had to do one on ones. So before we answer the question, let me just explain what one on ones are really. One on ones are not really evaluations. They're not a chance to evaluate your team members. Those are separate. One on ones are just a chat that you can have with each team member to get feedback about how they're doing, how they're feeling, just catch up. It's a chance for you to understand how you're doing as a leader and how the company can serve your employees better. These don't need to be long. They could be 15 minutes. And there doesn't need to be a formal structure. It could just be an informal conversation where you catch up and touch base with your team members. Now, Craig mentioned that his team is a remote team. Many of his team members are abroad. And I can totally relate to that, Craig, because I run a remote team and our team is across four different continents. So when I do one on ones, I'll have to accommodate for that. Now, if you've never done one on ones before, don't feel bad. That's totally fine. You can just get started. And you have a team of seven people, so it's totally doable. You could probably get it done in a couple days. So here's my recommendation. Just put it in the calendar. Now, you want to schedule these one on ones maybe back to back in a couple days, 15 minutes apiece. And you may want to choose a time of year when things are not so hectic in your business, where you and your team members are not busy to the point where this is an inconvenience or it's holding them back from hitting their deadlines. So one on ones are good when you're winding down. I often do them between Christmas and New Year's that week. It's kind of slow for me in the world of business. And then I try to do them again sometime in May or maybe even in Easter, depending on My schedule, but we literally just plug it into calendar in advance so I know that it's going to happen. And it's in my calendar. There's no way I can avoid it. I don't have anything else. I'm not going to double book myself with something else because, hey, it's already reserved. It's in my calendar. It's in the team members calendar as well. And you can do this with a Google Calendar invite, or you can have your virtual assistant or, you know, executive assistant to do this for you. And it's literally just a video call. I like to start the call by telling my team member, hey, this is your call. You should be doing most of the talking. I want to hear from you how things are going. So I'll be asking some brief questions and feel free to ask me questions. Ask questions like, how are you enjoying the work you're doing? If they've taken on new responsibilities, I'll ask them how that's going. I'll ask them maybe their work life balance or how much is this job a part of your fulfillment in life? I'll ask them for some feedback too. What are some things we can do to improve the business? Improve your department or the way we do things? Or maybe if we have a little bit of budget, how can we spend it? Do you want to be able to order some books or courses or a way to attend some local meetups? It's a great way to touch base and also for you to be honest. Whether your business is thriving or is in a rough spot. You can just say, hey, we're in the spot right now. I want to be honest about it. You know, we're doing everything we can and we appreciate everybody's effort. As we get through it, people will appreciate your honesty and your transparency and will have a sense of comfort that you're telling them things as they are. I also just emphasize this is not an evaluation that's separate from these one on ones and to put them at ease, that they can just speak freely and they're not being evaluated on their answers. Now, I personally like to run one on ones minimum once a year. Okay. I might be moving that to twice a year every six months. Or I might do a hybrid where I'll do it every six months for new hires. But after the past one year, I'll do it once a year. Believe it or not, a year flies by and a year is not a bad cadence. I just wrapped up a bunch of one on ones I did back in December, but I didn't do all for all our teammates. I'm going to pick up where I left off with the rest of our teammates now in April. I know some companies or some entrepreneurs that run one on ones once a quarter. Personally, I think that's a little bit too frequent, but my advice to you is that more is not necessarily better. I would start with at least once a year since you haven't done them yet. So once a year. If you feel that you want to do more, do twice a year and ask your team members if you want to meet more regularly. If they say so, try it out. You can always kick it back. This is your business, your rules. But one on ones are healthy. They allow you to connect with your employees, allows you to connect with your team members and get a pulse on how people are feeling. It also helps you not get blindsided by somebody who may not be so happy in what they're doing in the company. They might need a change. And instead of them just surprising you with saying, hey, I think I'm going to leave, you can suggest or preempt before that happens to they move into a different role, take on different responsibilities so they can be re energized so you can get the most out of that hire.
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To wrap up today's Q and A Wednesday's question from Craig, start off with once a year with your one on ones. Then you might want to work up to twice a year. It's up. But keep them short. Schedule them in advance so both you and your team members know them. They know that's going to happen and they can see it coming up in their calendar. Keep it informal, keep it flexible and allow it to be a chance for you to get feedback so you can learn. They should be doing the talking, not you. Thanks so much for listening to the $100 MBA show. If you love Q and A Wednesday and you have a question you want to ask like Craig asked today, go ahead and email me@omar mba.net I can answer your question here on Q and A Wednesday. Before I go, I want to leave you with this. One of the best things you can do for your company is have a happy team. To have a team that loves what they do, that work hard. Not because you tell them so. It's because they want to, because they feel a sense of ownership of the company. You can't buy that kind of culture and you can build that culture by getting to know them with these one on ones. The ROI is incredible because you have a team that has your back so you know your business is a well oiled machine. Thanks so much for listening and I'll check you in tomorrow's episode. I'll see you then. Take care. From athletic stuff like a full court pickup game Swish. To athletish stuff like a half mile stroll. Get those steps in. Head to sierra or sierra.com for the brands you want at the prices that let you do it all. From athletic to athletic. Sierra's got it.
