MBA1437 Lessons Learned From a 1:1 with Every Team Member + Free Ride Friday
2 Feb 2026 · 13 min
Omar Zenhom explains how to run effective one-on-one meetings with your team. Schedule 20-30 minute sessions, ask open questions, take notes, and act on what you hear. The payoff is better retention and a company that actually improves.
Questions this episode answers
Diamond Fields
Free access to the EasyCourse 30-day course (retail value $500)
November–December 2019
20 minutes (sessions were scheduled as 30 minutes to allow a 10-minute break)
About 15 hours to set up and implement
Chapters
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Hey O. Welcome to the $100 NB. Welcome to our business pleasure every 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 the Hundred Dollar mba, a complete business training and community online. And in today's episode you will learn what I learned from doing a one on one with every team member. One on ones are exactly what they sound like. One on one meetings with your team. It's recommended that the leader or the CEO of the company does regular one on ones whether it's once a year, once a quarter Obviously, that depends on the size of your team and time, but you should do it at least once a year. One on ones gives you a chance to talk directly with each teammate privately to learn how they're doing in your company. Are they enjoying the job? Do they have job satisfaction? Do they have any feedback to give you? Are they excited about the future? How are you doing as a leader? Or what are some things that the company can do to improve their work experience or their work satisfaction? This is in no way an evaluation for the team member. In fact, this is more an evaluation on the company and yourself. One on ones are incredibly helpful for you as the leader of your company to get an insight on what you're doing right and what are some things you can improve. It also gives you some insight on what are some of the gaps of communication, what are some things that maybe your team don't fully understand and that they need a little bit of training on, or maybe you just need a better job communicating on a regular basis those ideas. In today's lesson, I'm going to show you how to schedule your one on ones with your team, how to run your one on one meetings, what questions to ask and what you should try to pull out of the conversation, and then what to do with all this information once you've done all your one on ones. So let's get into it. Let's get down to business. The first thing we did to set up our one on ones between me and each team member was to make an announcement in our team project management software basecamp. Uh, rea. Romina made an announcement, said, hey, Omar is going to be meeting with each one of you and described exactly what this meeting is all about, what we're trying to do here. This is not an evaluation. Be as honest as possible. It's only going to take about 20 minutes. She included a link to my calendar. I created an appointment type in my calendar called one on ones. And I had a and a deadline. I wanted to make sure I get them all done by the end of 2019. So I had the window of November and December for them to book some time with me to do the one on one. It's only 20 minute, so the sessions were 20 minutes apiece, or actually made it 30 minutes. Give me 10 minute break in between. And every single person on the team would click the link and reserve a time for the one on one. Now some people needed a few reminders to make sure they book a time. And that's what Rina did. Our ea, she was Fantastic with that. And she just followed up with everybody, make sure that everybody's on the calendar. She has access to my calendar so she could see who's booked and who's not. So that setup was pretty simple. Now, once we got on the call, I reiterated for the first minute, thanks for taking the time to speak with me. We are very busy during our working days. We never really get a chance to catch up and talk about how work itself is. We talk about the tasks we have to do and the deadlines and the projects we're working on, and it's go, go, go. So this is a chance for us to hit the pause button and say, hey, how things are going. I also let them know that, hey, number one, be as honest as possible. This is not an evaluation I'm trying to learn here. The next thing I say is, you should be doing most of the talking in today's meeting. I should be doing most of the listening. So keep that in mind. It's good to say that in the beginning so they understand that you're asking them to talk and to elaborate on their answers. And then lastly, I say, I will be taking some notes just for my own reference so I can later on refer to this meeting. The first question I ask is just basically a recap question. You've been with us, for example, two years now. How have the two years been? What are some of the challenges? How has things been since, you know, when you started versus now? And it gives them a chance to kind of reflect on their time in your company and talk, about, you know, their growth and how things have changed. I also ask them some, you know, off the wall type of questions just to hear what they have to say. And I just say, when you have to describe to your friends and family what you do, what do you say, and where do you say that you work and how do you describe your job? And I just want to hear the language that you use to describe the company and is it aligned with what the company actually is, our vision, our values, all that kind of stuff. This allows me to know, hey, do they actually understand the company and what we're trying to do here and all the things that I've tried to communicate. If not, then I know I need a better job with that. It's an indirect way for me to find out how much do they actually know about the company they work for? Because, hey, they have to kind of explain that to other people when they're asked. Another question. I ask on these one on ones is, name your favorite thing about working for our company, and what is the one thing you'd like to change? So usually they'll mention something that will indicate what are some of the things you're doing as a company, right, in terms of the value of working there, Whether it's their autonomy, whether it's. They're inspired by the product itself. They might say, I love the challenge. You know, I love the challenge I get every day working in my department. The next question, what is one thing you'd like to change? It gives you a chance of knowing where you can improve. This is usually something that's annoying to them, something that really bothers them, something that really gets under their skin about the company or their job. And it could be something small, but it also could be something quite significant. But a lot of the times it's something that you can easily change and you can really help them improve their situation. Very rarely is it like, I wish I was being paid more. You may get that as an answer. And you can address that, which is great. Where you can have some sort of plan or timeline or milestones where they can hit the goals that they need to hit so they can get compensated the way they want to be compensated. But some of the answers I got were like, I would love some sort of budget for personal development, so I could take some courses online or go to a conference. Some of them are just procedural things, like, I wish there was a better procedure for this. And that's something that could be implemented very easily. Another question I like to ask in these one on ones is, where do you see yourself professionally in the next three years? Three to five years or so? And I preface this by saying, hey, we want to make sure that there's a place for you to grow here at the company, that we understand what your goals are professionally. So hopefully we can be able to cater to those goals as we grow as a company. And I'd love to hear, and I'd like to hear what people are dreaming of, what they want to see in their future in their career. Now, don't worry if somebody says, really, I'm happy in my job and I want to continue to do it just better every day. That's a valid answer. Not everybody wants to be a manager. Not everybody wants to advance in their career. Some people love their job and love what they do, and they're satisfied with that. And by the way, not everybody could be a manager. You don't have the positions for it, right? So it's good that there are people that are happy to just be really excellent at what they do. I also like to ask questions on work life balance. If they're a relatively new hire, I ask them, you know, what attracted them to join us in the first place. But I also leave a healthy amount of time to ask them if they have any questions, to allow them to ask any questions, say anything that's on the table. Ask me any questions you have. Some people ask me questions about the future of the company. Some people ask me questions about blog posts I've published. Hey, what did you mean by that? I read that blog post. I wasn't so clear on that. Some people ask me, you know, questions about the origin story of the company or maybe even what are your plans for growth and that type of thing. And of course, I give them time to give any feedback, any kind of advice or feedback they want to pass on something they've been thinking about for some time. And most people come prepared because we say in the announcement, I mentioned earlier that I'll be looking for these things. So they come to the meeting knowing that I'll be asking for feedback, that it will be their chance to ask questions. And that rounds off the meeting. It's about 20 minutes. I thank them for the time and say thanks so much for all the info. I take my notes during the meeting. I kind of write down my gut feeling at the end and I save that file so I can refer to it and read it for the next one on one that I do. So see if there's any change, see if there's any transition or improvement. Some of the feedback that I got after doing the one on ones really surprised me. People saying, this is incredible. I've never been asked to do this in any company I've worked for and I've been working for 20 plus years in my field. And it shows that you actually care and you actually are taking the time to hear what I think. You're actually interested to know if I'm happy at my job. And I heard that from many people and I was actually quite taken aback by that because I felt like, man, I should have been doing this a long time ago. So glad I'm starting to do this just to learn how to get better from you. It's just an education, but they felt it was a token of appreciation. They felt like it was good for them as well. And even though it's a short meeting, I get a chance to know them a little bit more on a personal level, understand their personality, understand how they think and how they feel, and Just a little bit more about who each person is and their quirks and their interesting qualities. This is great, especially if you haven't met that person in person yet. If you have a remote team and we do a team retreat every year and a lot of the team members that are on our team haven't been on that team retreat yet and it kind of is a primer to meeting in person. So it gives me some insights about who they are. Now after it's all said and done, I do pass on some of the feedback for improvement, some things that they'd like to see in their departments to the department managers. And I usually just kind of give it without even giving a name unless it's specific to that person and it's no harm, no foul kind of thing. It's like, you know, this person made a great suggestion. They would like to see more of this in their job. And this is super helpful for the managers to understand how they can get better, how they can improve, how they can make their team's life a little better and enjoyable. I am so glad I did these one on ones because it really allowed me to connect closer to my team members, understand how to improve as a company and as a leader of the company. Sometimes you're going to hear some feedback that's hard to swallow, but you got to be receptive. You got to realize this is how we get better. This is how we allow people to feel comfortable, to be transparent and honest. You can't put the walls up, you can't keep the feedback out because that's when you keep innovation out. That's when you keep improvement out. Swallow that pride a little bit and enjoy doing these one on ones with your team members.
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To wrap up Teddy's Lesson. Taking the time to meet with your team at least once a year, one on one with each person is going to make a tremendous difference in their job quality, in your retention rate. You're going to save money and time for, you know, rehiring people that are unhappy. You're going to find out how you can improve your company and your work satisfaction levels at a greater level quickly before it gets too much of a problem. Now, I'm not going to kid you. This took some time. It took some concentration. Took about 15 hours to put all together and implement, but it's time well spent. That wraps up today's lesson. But today's episode's not over. It's Free Ride Friday. Let's see who won this week's Free Ride. And the winner is Diamond Fields. Diamond Fields says this show gave me the courage and the tools to launch five stars. I found this podcast through a Google search. I wanted to start a business and listening to it daily gave me the courage to do it. Eight months in, I have my little business and it's slowly growing. I listen to it daily, I take notes, I read the books that are recommended. I've added the other podcasts that are mentioned and suggested. This podcast is a must listen for anyone who wanting to be in business. Thank you Diamond Fields for that great review. You are a free Art Friday winner. Your mission is to email me at omar00mba.net so I can hook you up with the free ride, the free access to our $500 course easy course over at EasyCourse Co if you want to win. If you're listening right now like, hey, how can I win access to EasyCourse? Just leave us an iTunes rating and review and you enter our weekly random draw. Listen in on Friday to see if you want. It's that simple. Thanks so much in advance for doing that. Before I go, I want to leave you with this. No one builds an empire alone, right? No one builds a great business, a great product, a great success by themselves. They do it with a team. So it's a good idea for you to spend time understanding who each person is, how you can make their life a little easier, improve their job satisfaction so they can get you to the promised land so they can help you reach your goals as a business. Thank you so much for listening and I'll check you in Monday's episode. I'll see you then. Take care.
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