MBA894 Are You a Terrible Boss?
2 Feb 2026 · 14 min
Podcast episode 'MBA894 Are You a Terrible Boss?' (The $100 MBA, host Omar Zenhom) explores how founders and new managers can evaluate and improve their performance as bosses. Main claims: avoid trying to be liked or feared; set clear company-wide and individual expectations; maintain consistent communication; regularly praise good work; conduct exit interviews to learn why people leave; and develop leadership skills via biographies, mastermind groups, and journaling. The episode includes brief ad reads interspersed with the host's monologue.
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So who's going to evaluate you? It's going to have to be yourself. And this is what this episode is all about. How to evaluate yourself and make sure you're not a terrible boss. When you're building a business, your team is your biggest asset. This is something I learned the hard way, something I really saw really to be true when I built Webinar Ninja, our software company. The better our talent has become, the better the product has become, the better the business has become. And I'm talking about in all facets of the business, whether it's sales or marketing or development or content. And if you want to attract a great team and keep a great team, you got to be a decent boss. You got to be a decent manager and a decent leader. So in today's episode, we're going to find out if you're a terrible boss and how to make sure you're not one. So let's get into it. Let's get down to business. So are you a terrible boss? Chances are you're probably neither a fantastic boss or a terrible one. And this is where I want to start. Often we're very hard on ourselves, especially at the beginning when we see our teammates or even just our vo. If we have one employee, if they make any kind of mistake, they're not on the ball. We often blame ourselves. We often feel like, am I not telling them what to do properly? Am I a bad boss? Am I not hard enough on them? Am I too soft on them? This is completely normal, completely natural. We all go through this. And I want to start by saying that you're not going to be a fantastic boss from day one. You need to try it out for a while. You have to get some experience. I saw this firsthand with Nicole, my co founder, now Nicole, when she became an entrepreneur, where we teamed up in 20, 18 and 12, it was the first time for her to be a manager, to be a boss, to manage other people. And she had all these doubts and she was going through these things. And I've seen her progress over the years. It's been great to see her become such a great boss, such a great manager, knowing how to balance that, making sure that they're doing a great job and that they're supported. I love that progress she's made. It's been really an honor to see, and I'm so proud of her. But I also got to see what experience really does for you. Not only in her own experience, but in mine. When we would talk about things at the start, I would say, you know, this is just normal. This happens because I was a manager before I was an entrepreneur. I was a head of department in the college and the high schools I worked for back when I was an educator. So I would lead a team of 33 teachers and run meetings and evaluate them and do classroom observations and have to have, you know, those uncomfortable talks with them when they came late to work or they would call out sick every Monday. Yes, that did happen. But the point is, is that I was very young when I was doing that, and I had those doubts when I was a manager, when I was a boss, and I had to get it out of my system. So now that I am an entrepreneur, when I was doing entrepreneurial things and I was hiring people and managing people, those butterflies were out, those doubts were out. And it's kind of like a rite of passage. You have to understand you're not going to be perfect at the start, and you're going to fall into some traps. And they fall into a lot of traps. One of the biggest traps people start to get into when they're becoming a manager or they're managing other people is they either want people to just fall in love with or to fear them. One of the other. And obviously you need to shoot for neither. Right? But a lot of people Fall into this trap. Like, I just want people to really like me and I want people to really like to work for me and be the cool boss. Or they say I want them to just do things and they do it immediately. I want them to fear the hell out of me and never to cross me. So I mean, obviously the former is more prevalent than the latter, but they both exist and both are disastrous. Your job is not to to be liked. Your job is not to be feared. When you're building a business and managing a team, your job is to make sure you do what you can to make sure they succeed. There's an onus on them to do the work because you need to make sure they succeed so the whole company succeeds. So that's pitfall number one. To make sure you stay clear from don't worry about being liked, don't be worrying about being feared. Do they fear me enough? Worry about making sure you do what you can so they do a great job. They do the job. You need to support them, give them the right information, be supportive. Some people think that answering every single question somebody has is supportive. No, they have to be resourceful. Some questions they can answer themselves. Most questions they can answer themselves. So just keep that in mind. The next tip I want to give you is make sure you have consistent communication. I'm not saying every single day you have to communicate and have a meeting, that's fine. Some people do that. They do stand ups, 10 minute standups and that works. But if you don't have time to meet with every single team of yours every single day, that's fine. But as long as it's consistent, so say for example, you meet once a week or twice a week. Consistency is key. They need to know that they have a time where they can ask questions or they can seek advice where they can get updates on new things that's happening in the business where the role is evolving. Consistency is key. So make sure you have regular ways for them to communicate. This can be online, it could be a video call, it could be via Slack channel, and of course it could be in person. Now another thing I want to pass on to you as a warning, something I really struggled with and it has to do with expectations. You have to have company expectations and individual expectations. What I mean by that is that what I would do for my business is going to be different from what somebody who has joined our team, as you know, employee number 50, for example, and they're coming in with an understanding that they're going to be compensated in this way, you know, don't really have a stake in the company. They like it, they find it interesting, and they're, you know, kind of. They're bought into the idea, but they're not you. So you need to have company expectations. Like, we expect you to put this kind of effort, to have this kind of care. This is unacceptable. This is not acceptable. Sort of like a guidebook, a rule book. Right. And they can be a simple list of key values. Don't even have to be a whole bunch of rules. But the point here is, is that these values, these rules apply to everybody in the company. And that's kind of the standard of what we expect from everybody. Now, you as the founder, you're probably going to go way above and beyond those expectations and those rules because your heart is so much into it, your livelihood is so much into it. How well the company does often affects your lifestyle versus somebody who's getting salary, you know, they're getting paid versus somebody who's getting a salary. They're not directly impacted, their life is not directly impacted by what happens with the growth of the company, the evolution of the company, the improvement of the company. Yes, of course, if the company does well, they keep their job and they have a little bit more security, of course, but it doesn't hit them on a daily basis. They don't really feel that as much as you do. So therefore, you're going above and beyond every single day. But you can't expect everybody in the company to do the same. That's not what they signed up for. You know, they got to work hard, they got to do their job. They got to do their job to a level of excellence. But I can't expect them to work every single weekend for the past, you know, 12 months. Right. That's what I've been doing as a founder. That's what happened. This last 12 months. I've been working every single weekend. I haven't had a weekend because this is my company, and I want to put the extra time and the effort and there's certain things I'm just trying to push forward. My reality is different than theirs, so I can't accept expect them to do the same. Now, sometimes some of our teammates do work on weekend. Our friend and developer, Eugene, he's been working almost every weekend for the last couple months because he's working on some important stuff for Webinar Ninja. He's really working hard on certain aspects of a feature set that we're working on, and I highly respect that. I really appreciate that from Eugene, but I don't expect him to do that every single weekend for the rest of his life working for us. No, I may say that to myself. I may do that to myself. Can't expect other people to do that. So be aware of that. The reason why I'm highlighting these things is because when you violate these things, this is where you fall into the terrible boss kind of territory, where people start to be like, what's wrong with this person? You know, they're a slave driver, or, how can they expect me to do that? In business is all about expectations. Your job as a boss is to tell your employees to tell your teammates, hey, this is how you win in my company. This is what doing a good job looks like. People need to know they're doing a good job. Doing a good job looks like this, this, this, and this. Are you in? If they say yes, great. Hold them accountable to what a good job is. For example, in customer service, it's very clear to them what a good job is. To make sure that their customer service rating is at a certain percentage. To make sure that, hey, if it's the end of your shift and there's one or two tickets still left in the queue, finish those tickets up. Leave it@inbox0. Even if it means going over time a couple of minutes or maybe even 10 or 15 minutes, that's how they know they're winning. They say, yes, I'm doing a good job because I was told this is what being good at my job looks like. And I mentioned communication. But praise is just as important. Make sure that you recognize when people do a good job, when they do their job, believe it or not, that's very important. A lot of people forget that you have to praise even when they do their job. People think, well, they're just doing their job. Why am I going to praise them? There's nothing to be praiseworthy about doing your job. No, that's praiseworthy. Doing what you expect them to do. Doing a great job at what they do. That requires praise to keep them going. Because there's plenty of people, trust me, I've been around in different sectors and especially education, that are just coasting. They're not doing a good job. They're not doing the things that make them a, you know, a great employee. They're doing below the bare minimum. So when somebody does the job right, you gotta praise them on a regular basis. And, hey, it's not gonna cost you much. It's gonna cost you a few seconds of your life. Just give Them a thumbs up or a smiley face or by the way, you're doing a fantastic job. I look through some of your work. Thanks for your hard work. Now, I know you might be thinking, so I kind of understand what I need to do as a boss. If I don't do these things, I'm going to fall into terrible boss kind of territory. But how do I really know if I'm terrible at what I do? Am I a horrible boss? Do people hate me? What if people start leaving? What do I have a lot of turnover? Well, if you have a lot of turnover, you need to be concerned. Either your style of management is really not meshing with these people or they're just a bad fit for your company. Some of us by nature are just really driven and really like to drive very everybody else along with us. Really push them to the limit. If you look at somebody like Steve Jobs, the lead Steve Jobs, he was one of those leaders. He wasn't for everybody, but a lot of people loved working for him because they brought out the best out of him. A lot of people couldn't work for him, but a lot of people could and loved working for him because he brought out the best in them. He pushed them to become better. He had such high standards that they met those standards because he enforced those standards. Now, his interface was not great. A lot of people thought he was a big jerk. And that's not for everybody. So be aware of who you are and if you can be less of a jerk, try to be. There's no reason to be rude or obnoxious to get your point across. You know, Steve Jobs is a brilliant man, an innovator, one of my heroes, really. But he has flaws and those were one of his flaws. His interface was garbage. So keep that in mind. Even if you're going to drive people, you could do with a smile, with encouragement. You don't have to be a jerk about it, right? But if you are having a lot of people leaving your company, you need to reevaluate how are you managing. Maybe you're not managing them at all. Maybe they have no direction. Maybe it's an HR problem, maybe it's compensation, maybe it's how the company is performing. Maybe, you know, the product's not inspiring. Whatever it is, you need to pinpoint it and find out. And maybe it's you. So you have to look at all the options. There's a good chance it's not you, it's other factors. And this is why an exit interview is great. And I highly Recommend if you have a small enough team that when people leave your team to ask them these questions, find out why are they leaving? What are some pieces of feedback they can give you as a boss, as a company leader? Feedback for the company itself. This is going to be great value for you and you can just be frank with them. Hey, I'm not going to hold you accountable. There's no hard feelings. I need to learn. Tell me your honest opinion of how the experience was working for our company and working for me in particular. This is super valuable stuff. So as you can see, being a terrible boss is actually quite hard to do. But if you want to improve, you need to follow things I'm mentioning in today's episode. Need to be on top of things. You need to communicate with your team. You need to communicate with those people that leave. And you also have to develop yourself as a leader. You have to do your own professional development. You have to train to become a great manager, a great leader, a great boss.
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So how do you develop yourself as a better boss, as a better leader, as a better manager? I'm going to give you the tips that have helped me, things that have worked for me. Number one Biographies. There are plenty of biographies of great leaders, great managers, great business leaders. Some of my favorites are Ashley Vance's Elon Musk. That book is fantastic. Shoe Dog by Phil Knight, the founder of Nike Total Recall by Arnold Schwarzenegger. Yes, he is a fantastic leader and actually business person. He was a business person before he was even a bodybuilder. Of course he was a governor of California, so lots of leadership there. Reading Biographies really gives me perspective. It gives me different ways to solve different problems. Even though these are big companies, they started small and they had to go through a lot of decisions that I have to go through as a small business. And this really is a great way to develop your skills. Learning from the greats. They've been through it. Learn from their mistakes, learn from their failures, learn from their successes. So that's number one. Read biography. They're great. I actually love Audible. I listen to audio books. I listen to the gym. I listen when I'm in the car. Sometimes I listen before I fall asleep in bed. And, you know, it's just a great way to hear some great stories on how to become a better manager. Number two, be part of a mastermind. When I say mastermind, it's just a group of other entrepreneurs that are probably in the same place you are, same level of business, maybe a little higher than you are. And you're just meeting on a regular basis, whether it's once a week or once a month, maybe for an hour. I'm part of a mastermind group. It's just three people, but I've been in mastermind groups that are larger. 15 people, 10 people. You find your sweet spot. But the point here is that when you're in a mastermind group, you get to hear about other people's challenges and how they solve them, or you can hear the feedback of other entrepreneurs, how they would solve them. Sometimes it's easier for you to solve problems when they're far removed. So you can help people solve problems and then realize, hey, I just solved that problem. And maybe later on the line, your company has the same problem, and you can just refer back to your own advice. So masterminds are great in that respect. Make sure you find a great group that you get along with, that you can be consistent with. This is so important. So many mastermind groups just dissemble because people can't be consistent to actually meet every week or meet every month. Again, this could just be a few of your friends that are entrepreneurs trying to find those people. Go to a conference, meet up with people, get some contacts, and be the organizer of a mastermind group. You don't have to join one. You can create one. I've created one before, many times. And learn through other people's experiences as well as your own. Lastly, this is a hard one. A lot of people have difficulty doing this, but journaling is a great way. Document what's happening in your business, in your life. Sometimes just writing out your problems allows you to solve them. Seeing them in black and white can allow you to be objective. It's also great to read back and say, hey, wow, look at all these problems I've solved in the past. I think I could solve this one that I'm having right now. You have the confidence because you've solved problems over and over again. You realize, hey, I'm a problem solver. That's why I'm an entrepreneur. Of course. Again, journaling requires consistency. Whether it's daily journaling for five minutes a day or even journaling once a week on a Sunday morning. Those are my tips. I hope they help. I hope you find that no, you're not a terrible boss, but you're not the best boss in the world either. You're somewhere in between and you're working towards becoming better and better every day. Guys and gals, I hope you enjoyed today's episode. Let us know in an itunes rating and review what you thought of it. By giving us a review, we get to hear from you, we get to know what we're doing right. And it also allows other people to learn more about the show. Also, if you don't know, if you don't hit subscribe, you don't have access to any of our backlog of episodes. We have over 900 episodes for you to listen to. By hitting subscribe, you have access to all those episodes. So do that right now. Alright, that's it for me today, guys. But before I go, I want to leave you with this. One of the most important things that I learned when I first became a manager, became a boss is that just being present does a lot. Just being around, being accessible, that people know that you're around, that you're here to answer questions, to help, to supervise. That alone can help you become a better boss. Checking in with your team, letting them know that hey, I got your back and that we're here trying to do this together. All right, I'll see you in the next episode. Take care.
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