MBA2244 How to Know It’s Time to Upgrade Your Team
2 Feb 2026 · 9 min
Omar Zenhom walks through when to replace team members: imagine firing everyone and rehiring only who you'd keep. He covers one-on-one development plans, follow-up systems, and treating recruitment as ongoing work rather than a one-time event.
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But the mistake a lot of businesses make is that they are stagnant. They don't upgrade their team. They don't on a regular basis to make sure they have the best talent possible to compete in the marketplace. Your team members are what produce the work and create the product and the service that is allowing you to have a thriving business. It only makes sense to have the best talent possible to be the best business possible. And when I say talent, I'm not just talking about skill. I'm talking about attitude. I'm talking about work ethic. I'm talking about the ability to work with others, being flexible and being willing to grow. And of course, skills and talent. But where most entrepreneurs get stuck is knowing, hey, it's time for me to shake things up, to change things, to get better people in place of others. It's not easy, but it's necessary if you want to compete and be around in the long term and have a thriving, growing business. I'm going to show you how to do exactly, how to know when it's time to make a change and upgrade your team and how to use a very simple exercise to evaluate your current team and see if it's time to make a change. Right now. Let's get into it. Let's get down to business. One of my favorite sports is basketball. The reason why I love basketball is because I see a lot of parallels between basketball, the sport and business. You see, let's say you're an owner of a basketball team in the NBA. You might have an okay team. You win some games, you lose some games, you sell some tickets, you have a local fan community or fan base, but you're nothing really special. Some teams, on the other hand, are special and they're competitive. They play in the playoffs every single year. Their games get televised across the country and across the world. They're in contention and they matter. And some teams are absolutely epic. They're dynasties, they win multiple championships, they're expected to win and have countries around the world wearing jerseys with their team name on their chest. What's the difference between these three groups of teams? Well, it's the players, it's what makes up the team, the coaching staff, the management, it's the whole organization that allows them to be an incredible team, a mediocre team, or a just okay team. And if you just want to have a just okay business and hope that you survive year after year, then you're probably okay by just not doing anything or changing anybody on your team. But if you want to move up, if you want to be competitive, if you want to be a dynasty type business, you're going to have to have the best players possible on your team. And you got to be mindful of who to keep and who to replace. This is one of the hardest things as an entrepreneur, as a business owner, because you got to do what's best for the business and what's best for the customers. That's what you really need to do. That's where your loyalties lie. Because without customers, you have no business, you have no employees. You're here to solve a problem and provide a great product or service to the world. And this is why it's really important when you're hiring Somebody to make sure that they're able to grow with the company. Because if they're not able to grow and change and adapt and get better themselves, then they're putting their job in jeopardy. Because businesses only grow when everybody on the team grows and improves. So you might be asking, Omar, how do I know it's time to make a change or to maybe replace a few people on my team? How do I know it's time to change things up? Well, I'm going to share with you an exercise a mentor of mine shared with me, and it's something that he recommended that I do at least once a year. It's an eye opening and simple exercise that you can do right now. And here it is. I want you to imagine that you have to fire everybody on your team, everybody has to get fired, and you have to start all over from scratch. Who from the people that you fired would you rehire? Ooh, that's a good question. Because some of us are, are running teams with half the people on the team. You're just kind of putting up with them. You're maybe a bit tired, maybe you're a bit lazy to find somebody better. So you're just like, they're okay, they're fine, let's just keep the status quo. But now that you imagine you had to fire everybody and now you get to choose who to rehire, you're really saying to yourself, who do I really value and who's really moving the needle in my business? Who do I actually think can help me get to where I want to go in the future of my business? This thought experiment really changes everything because it makes you realize you might have people on your team that are just not cutting it and they're not actually going to fit to build a future you want. Now what do you do once you have that list of people, the people that you said, okay, I'm gonna rehire these people and these people I would not rehire. What about those people that you put down as you wouldn't rehire? What do you do now? Well, your job is to find out if they're in or they're out. You gotta sit down and have a one on one with these people. You gotta ask them, hey, can we have an honest chat? I know you're working hard and you need to sell them on your vision. You need to say, hey, this is where I want to take the company. This is where I want to go. This is the vision for the next year, two years, three years, 10 years. And in order for us to get there. We need everybody on the team to get better. This is what I think you can do to help us get there. And this is basically an action plan, like a professional development action plan. I think that you need to improve your skills. Here, here, here, and here are some courses you can take. Here are some mentorship that you can kind of participate in, whether it's with other teammates or with you personally. This is your professional development plan. Are you willing to do what it takes to get better and improve and become the type of person or become the type of team member that accomplishes great things, things that we just talked about in the vision. People that are enthusiastic, that are like, yes, I'm down for it, this sounds exciting. And they see this as an opportunity. They're people that you want to keep because that kind of attitude is not always prevalent or easy to find. And that's awesome. That means you're going to keep this person, you're going to put them on the plan and you're going to work with them to get them better and better. And it's great because they already know a lot about the business, they know the ropes, they know how to work with you, they know about the product and service, all that kind of stuff. So now they're just going to get better and become the exceptional team member that you need them to be. In that meeting you might have some people say, you know what, this is not for me. And that's an opportunity to part ways. And that's a tough conversation, but it needs to be done because again, you need to do what's best for the business, your customers and all the other people on the team that are working hard and working towards your goal, the team's collective goal of where they want to be in the future. Now you're going to get people that say, yes, I'm down, I'm going to do this plan, I'm going to get better. And don't follow through. They don't do it, they kind of ignore it, they get busy, they don't improve. It's your job to follow up and make sure that you have check ins regularly, whether it's every month or every three months, to make sure that they're on track. And if they're not, you gotta take their actions over their word and you gotta actively look for people to fulfill their position. A buddy of mine who was a president of AppSumo, Ayman Abdullah, who was also a great, great extended interview here.
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USAA knows Dynamic duos can save the day like super superheroes and sidekicks or auto and home insurance. With usaa, you can bundle your auto and home and save up to 10%. Tap the banner to learn more and get a'@usaa.com bundle restrictions apply. Mentioned to me once that as a CEO of any company, big or small, your job is really recruitment, is really finding great people to fill the roles you need. So essentially, you're always recruiting because you're either finding new people to be added to your team or people to come in and step in in place of other people on your team that are just not going to make it. And this is what I Learned the last 20 years. This is going to happen all the time. Meaning it's very rare that I had the same team, the same team members. Every single one of them didn't change for five, six years straight. No, there's going to be changes because you're going to have different goals, you're going to want to grow. And some people are great at some stage of the business and some people are great at other stages. That's just the facts. And that's why it's so important to always be on the lookout for great talent, to find them, to insert them, to make them a part of your mission and your goal and part of your team. Of course. So this thought experiment is really, really good. Who would you rehire if you had to fire everybody today? I want to make something clear. You don't have to be a heartless CEO. I'm not saying that you just cut people off and say you're out of here. You're just not good enough. I'm a big fan of loyalty. I'm a big fan of people that work hard and have a great attitude. I'm a big fan of people that care. If they care, it's very hard for them to lose their job. But it's on you to make sure you give them an opportunity to get better that you give them the skills, you give them the actual knowledge or training they need to get better, to become who you want them to be, and you put the ball in their court. If they get better with all the resources you offer, awesome. If they don't, that's a sign that this is not a mutual relationship. Meaning you are expecting one thing and they have different expectations of how they want to work. And by the way, that's okay. Maybe it's just not for them. It's a new season in their life and they're going to move on and you can part ways with your team members that are just no longer a fit in a polite, courteous, friendly way. I've done it before several times with teammates where they just reach the point where it's time to say goodbye and we still have a very friendly and positive relationship. That wraps up today's episode. Today's lesson on the Hundred Dollar VA show if you love what you hear and you want to hear more of it on the regular hit, follow on your favorite podcast app. Whether it's Apple Podcasts or Stitcher Radio or Spotify. Hit the top right hand corner, the triple dots and you will see a menu that says follow. Click that follow button and you'll get our next episodes automatically and you'll get access to our archive link Lessons in our back catalog. Over 2200 business lessons for you to devour Before I go, I want to leave you with this. I'm a big believer that in business and in life there is no stasis. Meaning there's no just staying the same. You're either growing or you're dying. So if you're not actively getting better as a business, you're not actively doing things to improve, then you're declining. That's just how it works. That's how it works in life, that's how it works in business. So you gotta actively make the effort to grow and improve your team. Always. Thanks so much for listening and I'll check you in tomorrow's episode. Q and A Wednesday. I'll see you then. Take care. A KFC Tale in the Pursuit of Flavor the colonel made his $10 Tuesday bucket so full with eight pieces of juicy crispy chicken or tenders that it might just last you till Wednesday if you've got that kind of self control. I mean some people want leftovers, others are mourned. To right nowers, the Colonel lived so we could chicken 10 bucks 8 pieces. One big deal with KFC $10 Tuesdays prices and participation may vary taxes, tips and fees extra.
