MBA2344 Q&A Wednesday: What’s the best way to train new leaders in my business?
2 Feb 2026 · 12 min
Podcast episode (MBA2344) from The $100 MBA Show hosted by Omar Zenhom answering listener Josh’s question: how to train new leaders as his business expands. Omar emphasizes first securing buy-in from prospective leaders, modeling leadership behavior, using shadowing and sideline coaching, scheduling dedicated training time, and running book clubs. He recommends leadership resources including John Maxwell (The 7 Laws of Leadership), Gino Auriemma’s MasterClass on Leading Winning Teams, and Dale Carnegie’s How to Win Friends and Influence People. The episode also contains multiple sponsor ad reads (Intuit QuickBooks, Dell Tech Day, Amazon docuseries, UnitedHealth Group, Fidelity, GEICO).
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I'm also the co founder of Webinar Ninja, an independent software company I started back in 2014. Today's episode is Q and A Wednesday where we answer a question from one of you, one of our listeners. You. If you got a question you want to ask, go ahead and email me over@omar00mba.net Today's question is from Josh and Josh asks, what's the best way to train new leaders in my business? Josh's business is expanding. He's promoting, he's got some talent that are going to move into leadership positions. For many of them, it might be the first time they're being asked to be a leader in an organization. So how do you train these teammates to Become great leaders to help you, your team and your business thrive. That's what we'll discuss in today's lesson. There's a lot of great resources out there, but if you don't know how to implement them or roll them out to your team, they're kind of useless. I'm going to share with you the resources I recommend how to present this to your team, how to create a structure so that they're trained up on leadership and a way for you to measure results and check in back with them to see how they're doing. The good news is that leaders love to learn. So if you got a plan in place, learning, they'll eat it up. So let's get into it. Let's get down to business. When I was thinking about this question today on Q and A Wednesday, I was thinking to myself, what made me a good leader? What were some of the trainings I got when I was younger, when I was moving up, back when I was an educator, when I was in schools, when I became a head of department, I vividly remember asking myself, how do you become a leader? How do you be a great leader? What's the difference between a leader and a manager? How did I learn and what was the things that really helped and what are some of the things that didn't help? So I'm gonna walk you through how I recommend doing this, what I try to do in my own team with my own leaders, and a few things you should avoid. The first thing you need to keep in mind is if you want to train your team members to become leaders, you gotta get buy in, meaning you gotta make sure that they're on board, that they actually want to be a leader. So as simple as this might sound, or maybe you might think, oh, can I just skip this step? No, don't skip this step. What's really helpful is to just have a meeting with this person, whether it's one on one or with the group, with a group of people that are going to become leaders in your team. The purpose of this meeting is to make sure they understand this only works if both of us want this. I want you to be a leader, but do you want to be a leader? Are you in? Is really what you want to ask. And it's okay to ask them why. Why do you want to be a leader? Why do you have this ambition? Get them to question these things and think about it for a moment. And the reason why we do this is because you want to basically get permission to lead them, to show them hey, this is how you become a leader. And when people say yes to something, it kind of gives you a blank check to say. And the thing is that when people say yes to something and say, yeah, yeah, I want this, then it kind of gives you a blank check to basically give them what they need and train them and give them a little tough love when they need it. It also gives them a chance to get out, get to say, hey, maybe this is not right for me. And this is why this meeting is important. It's gonna say like, hey, I think you'll all be great leaders. This is why I think you'll be great leaders. This is what my vision is for you. But I can't do this alone. You gotta want it too. So now is your chance to tell me if you want in or out. Because if you're out, there's no problem. You'll always have a place in my company. And I'll respect you more for saying that. Now instead of us investing in something that you don't want. But if you're in, I want you all the way in. I want you to make sure that you are 100% committed to, to the path ahead. Get commitment from everybody. This is a huge step. Second, I can give you all the resources in the world, books, courses, trainings, and we're going to get into that. But the number one thing that's going to impact their ability to lead is you. Actually, as human beings, we learn most by watching other people. You're going to model what leadership is. They're always watching. They're watching what you're doing, and they're also watching what you're not doing. For example, let's say you have an employee that walks in late and they see you seeing them walking in late, and it happens more than once, and they keep seeing you kind of just letting it slide. What they're learning here is it's okay to let people break the rules and really not talk about it. Listen, I'm not saying you gotta be this harsh, harsh leader, but you have to address problems. If you have a policy where people are not supposed to be late and people break that policy, then you should have have a word with this person. Most of the leadership skills I gained were me just watching my own supervisor, my own managers along the way. And by the way, a lot of it was great, but some of it, I picked up some bad habits, some bad management skills, because that's what was in front of me. That's what I had to learn from. So just keep that in mind, the better leader you are, the better leader they're going to be. Now, knowing that one of the best ways to teach people leadership is, is just to have them around. You have them shadow you, get them involved in meetings. If you're working on something, pull them into your office, pull them into your, you know, room virtually and say, hey, listen, I'm working on xyz. I want you to watch me do this because I want you to do this next time around, or I want you to learn how to do it on your own. Let's say, for example, you right now are approving all the leave requests from everybody on your team. Now that you have some managers and leaders, you can now start to ask them to do that for their departments. So you might say, hey, come and watch me approve these leaves. This is what I do. I get into the system, I take a look at the notes, I click this button. This is what I do. Sometimes I gotta approach the employee and say, hey, this is actually a bad time to take leave. Is there any way you can move this around? Because we're doing a launch or we're doing something really important, and you're training them on this right then and there. They're not only gonna learn how to do the task, but they're also gonna learn how to train other people. And that's what leaders need to know how to do. And not specifically this task, but any task. One of the things that really works is called sideline coaching. Think of a coach of a sports team. The coach is not in the actual game, right? He can't step onto the court or the field and score for the players. There's a great technique called sideline coaching, and it's a metaphor of what coaches do in sports. Now, the coach can't step onto the court or the field and score for the team, but he or she can be on the sidelines and help them score, coach them through it. But you gotta let the team try to figure it out on their own, to try to score on their own. And that's what you do with your leaders. You give them a task. You tell them, hey, this is the outcome I'm looking for. This is what I want you to do. And I'll be here if you need me, if you got questions, and I'll even chime in if I feel like you need some help. For example, when. When I was 22, I had to lead my first meeting in front of the department that I was managing. I was so nervous, I was looking to the Floor. I had an agenda. I was prepared and everything like that, but I didn't feel very confident. My manager was in the actual room in the meeting, amongst other teachers, about 20 teachers. And as I was going through the meeting, sometimes he helped me out and said, hey, don't forget, guys. We gotta do xyz. He would mention something that I forgot to say. He would give me encouragement. He would, you know, maybe end the meeting, say, hey, let's give it up for Omar leading his first meeting. And I felt supported, but at the same time, I had to jump into the deep end and just do it myself. Now there's a bunch of resources that you can dive into when it comes to leadership and management and you can recommend to your team. But let me just mention a few. John Maxwell. John Maxwell is an author that writes a lot of great leadership books. He's got one called the Seven Laws of Leadership that's very, very powerful. What I would recommend is, is handing out this book to everybody in your group or other leaders in your team and doing a book club, you know, syncing up once a week and talking about the last couple chapters they read that week. If you don't hold them accountable, they're just not gonna do it on their own. This is what I've learned when it comes to these types of trainings. They gotta feel like, hey, I'm gonna show up next week. I gotta say something about what I've learned. It could be something simple where you're sharing a lunch together on a Friday. There's another great online course you can find@masterclass.com by Gino Arima. Gino is a women's basketball coach in the U.S. i believe he is a coach that has won the most titles in women's basketball. And he's got a great, great, great masterclass called Leading Winning Teams. And it's not really about basketball. It's about how to lead and how to help others get what you want out of them. So this is a great course for you, but also for the leaders that you are training. And one more book I want to recommend. It's a classic. Dale Carnegie's how to Win Friends and Influence People. Listen, at the end of the day, business is about managing people. And the best leaders know how to manage different types of people, how to get the best out of them, and winning friends and influencing people. This book is a masterclass in this and understanding human psychology, understanding how to get the most out of people, how to win them over, how to understand everybody's different. Everybody ticks in a different way, and your job is to understand that and to react to that. This episode of the $100 NBA show is brought to you by this Is Small Business Next Generation, a new docu series from Amazon. I've jumped in and listened to a bunch of these episodes of this series and I want to share with you a bit about episode one, where host Andrea Marquez meets her new host, Mitch Gilbert, who is the founder of Oya Femtech Apparel, who's also a former winner of the Rice University Business Plan Competition and is one of the first 200 black women to raise a million dollars in venture capital. Andrea and Mitch walk you through the journey of raising capital, pitching to investors and how to polish up your business plan so that you can get the best value for your business. This is Small Business Next Generation is out now. Go listen to it wherever you get.
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I really love Josh's question about how to train leaders in your business, but here's the key. You gotta make time for it. Listen, I know that you're busy. I know that the company's busy and your leaders that you're training are busy. But you gotta literally make time for it in the calendar for the trainings, for the shadowing, for the sideline coaching, for the book clubs, for the whatever. If you don't put in the calendar, it's just not going to happen. You're going to have good intentions, but your actions are not going to follow. You got to plan for success and you got to just follow through. Trust me, this is an investment in these people that are going to help you build an incredible company. The return investor is going to Be incredible given the fact that you know you're spending a bit of time and a bit of effort, but you might be 10xing your results by improving each of these team members tenfold. And because they're leaders, they're influencing the people that are being led by them. Pretty, pretty cool. And remember, be patient. These people are beginners. They haven't been through everything you've been through. They haven't seen what you've seen. They haven't really endured the challenges you've had to get to this point. Remember when you got started, Remember when you started to learn how to be a leader? Harness that curiosity, those feelings, so that you can remember how to approach them in a gentle and kind way. Because at the end of the day, you want them to feel that you have their best interest in mind. You want them to feel that, hey, I care about your well being. I want you to improve not just for the company, but just for you to be better. Because when you do that, when they feel that they're going to give their best and you're going to get the best result. Thanks so much for listening to the $100 MBA show. If you got a question you want to ask here on Q and A Wednesday, go ahead and email me over@omar100mba.net and don't forget, hit subscribe, hit follow on your favorite podcast app, Spotify, Apple Podcasts, Overcast, whatever it might be. Go ahead and subscribe or follow so you get our next episode automatically and get access to over 2,300 episodes and our archives. Before I go, I want to leave you with this. I've been teaching pretty much all my adult life and I really see that leadership and training is basically teaching other people how to be better. It's incredibly rewarding. It's one of the things that people don't talk about enough in business. You get to see people grow, you get to see people improve. You get to see people become better people. There's no real price tag you could put on that. It's priceless, really. So enjoy the process and remember, you once were a beginner too. Thanks so much for listening and I'll check you in Friday's episode. I'll see you then. Take care. Of. We've all been there. You hold on to a coupon, but forget about it and suddenly it's Expired. Expired in 2012. Dang it. Fortunately, by switching to Geico, you could save about 900 on car insurance without ever touching a coupon. It feels good to save big. It feels good to Geico.
