MBA1772 How Much Time Off Should You Give Your Team? + Free Ride Friday
2 Feb 2026 · 12 min
Omar Zenhom covers time-off policies for small and remote teams: vacation, sick leave, holidays across time zones, and parental leave. He uses Basecamp as a case study and explains why contractors and employees need different rules.
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Hey O welcome to the Hunter R and B A show. Real world business advice and strategies every single day with our daily 10 minute business lessons for the real world. I'm your host, your coach, your teacher Omar is at home. 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 Free Ride Friday. If you're new to the show, Free Ride Friday is the day we give away a free lifetime membership to one of our programs. We're giving away easy course. You want to build your own online course? We'll take hours and we'll show you step by step how to do it. It retails for $500 over at EasyCourse Co or you can win it for free. Just leave us an Apple podcast rating and review and you enter our weekly random draw we call Free Ride Friday. Listen in on Friday to see if you won. It's that easy. Stay tuned to the end of the episode to hear this week's Free Ride Friday winner. In today's lesson you will learn how much time off should you give your team, your employees, your teammates? This is a question a lot of entrepreneurs struggle with because they're not really sure how many vacation days, sick days, maternity leave, all that kind of stuff they're not really sure how much of each they should give to their teammates. It can get really complicated, especially when you have a global team, teammates from around the world, where they have different local holidays, where they have different standards for vacation. You might be wondering, what about freelancers? What about part timers? What is the deal? How do you set up your rules? How do you set up your policies for time off? Well, I'm going to share with you what we did in our company and give you some solid advice. Regardless of what kind of you run, how many employees you have, whether they're part time or full time, whether they're all local or they're around the world. Remember, when it comes to your employees and when you hire, time off is part of their compensation. And it's one of the things you don't want to mess with. People need a break. So let's get you set up. Let's get you organized. Let's get into it. Let's get down to business.
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Having a clear and definitive policy on time off for your teammates is super important. We've tried all different kinds of things in our business. Having a policy, not having one, limited leave, unlimited leave. And we learned a lot of lessons along the way. And I'll share some of those lessons in today's episode. But before we begin, I want to give you a little case study that I thought was really interesting. The team over at Basecamp, they run a software company. They have a team of a little over 60 employees. They had an unlimited leave policy in place, meaning you can have as many days off as you like. Holiday sick, it doesn't matter. And they implemented this policy to say, hey, we want to make sure that you are taking the time off you need and we trust you. The problem is, is that it didn't work. In fact, people took less time off than when they had a policy when they had a limited number of days. If, for example, you have an unlimited policy and somebody had 15 days off and then somebody else had seven days off in one year and the other person had three days off in one year. That person who took 15 days off just by nature feels guilty, feels like I took too many days, and can't help but feel self conscious about the time they're taking off, versus if they had a leave policy where they can't take 15 days, they would have felt like, hey, I used the days that I was given and I didn't do anything wrong. So it was interesting when Basecamp shared this whole case study, this whole experience that people do need parameters, people do need a policy. Now, our team at the $100 MBA and webinar ninja, they're based around the world. We have people working on four different continents, 20 plus numbers. It's really interesting because we're all somewhere different in the world, meaning we have different local holidays, different national holidays, and different standards for time off. In the U.S. for example, some companies don't even give two weeks. Some people give one week in your first year of employment, then two weeks in the year after, versus some other countries like in Europe, where they're given five and six weeks of vacation. So you need to figure out what's best for your company. So if you have a global team like us, you might want to consider allocating a number of days to local holidays. This is what we did. We don't have many holidays where the whole company's off. I think the only exception is Christmas and New Year's. And we do that because business is slow anyway during that time. So it's a good time for us all to take off and make the announcement to, you know, our customers that will be off these days and will be back these days. Other than that, every country will have different holidays. So instead of trying to accommodate for people who are celebrating Diwali versus celebrating Memorial Day in their country or their own Independence Day, we allocate five local holidays to each person and they can choose when to use those days depending on their local holiday. Next is sick leave. We want to make sure that people take their sick leave. Okay? If you are not feeling well, we don't want you coming into work. We want you to rest, get better, and get back 100%, or at least close to 100%. So no matter how many days you give for sick leave, 2, 3, 4, 5, 6, whatever it is, my advice is to make sure those days do not roll over, meaning that if they don't use them, they don't like roll over and they can use them the next year. This is reserved for when you're sick, and if you're not sick, awesome. Now let's get into the meat and potatoes of actual holidays figation days. We like to actually just say the days of work. So we allocate 15 vacation days. So essentially that's three weeks, plus, of course, at the local holidays, again, no matter what the number is for your company, we enforce the rule that these days do not roll over. We want people taking a break, okay? We want them to use these days so they're well rested and they don't burn out. And if you allow rollovers or cash outs, then people will burn out. Okay? People will go for that alternative now of you don't want everybody taking off at the same time. So what we like to do is we like to have a policy where people apply for leave and then the line manager, the manager of that department will approve that leave or negotiate that leave with that person to make sure not too many people are off during the same time. This is super, super important in departments like customer support or engineering, where, you know, things need to get fixed or things need to be solved. Now, I highly recommend when you set up these policies to use an HR software. Why? Because you want to make simple for your team members to apply for these leaves, apply for sick leave, so there's no confrontation. They don't have to call somebody or message them. You just want to make sure it's streamlined and easy for you to keep track. And of course, you want to make sure they keep track that they have a certain number of days for their contractual year. So say, for example, you're giving X amount of vacation days. It's not on the calendar year, but the year that they've worked with you. And everybody will have a different start date. So this is where software is super, super helpful. So there's a lot of different HR softwares out there. There's bamboo hr, there's HR Partner. We use HR Partner. My advice is just use something that is simple and does the job, does what you need. Don't go overboard and get something that has every bell and whistle and it gets super complicated for your team. That's why we chose HR Partner. It's not perfect, but it does the job and it helps our team apply for leave and makes it seamless. They can go into the portal, they can see who's off when, they can see how many leave days they have left, all that kind of stuff. Now when you're deciding the numbers of how many days for each type of leave is allowed or allocated, you got to keep in mind what type of work they're Doing, you have to keep in mind as well, what type of work environment does your business encourage or allow? So in our company, we have a very flexible work environment, meaning that people work from home. They have the flexibility of working from home or working from wherever their laptop is. So for example, we have an engineer that is a nomad. He travels the world. As long as he's got his laptop and he shows up for work and he's around and communicating, we're happy. This is a huge advantage if you have remote workers because it's a huge perk. If your team members have to go into an office if they ever want to go somewhere but they still want to work, that's kind of hard. You know, they have to go into the office every day. They would have to apply for leave if they want to go somewhere. What about part timers? What about freelancers, people that on your team that maybe are not full time? In our company we made a decision that our leave policies are only for full time employees. If you're a part timer and you're working hourly rate, then you're going to be compensated for that time you work. Part of your compensation package is not the days off. You're going to have to manage your own burnout. That's kind of our policy and that's why we kind of have minimal part time freelancers on our team. We have a few which are usually part of what we do. They have great important roles, but about 90% of our team is full time. Some of our part timers are on retainer, meaning they get paid a certain amount every month to do certain tasks. And it's up to them how they want to do these tasks in terms of the time, how they manage their days off and all that kind of stuff is up to them.
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To wrap up today's lesson. You want to make sure your leave policy is fair and covers all the bases. One thing we didn't mention is maternity paternity leave. I highly recommend, recommend you have a policy for when people have children and make it clear how many days are paid, how many days are half pay beyond that and how many are Unpaid. Some companies, they do this, they do like one month of paid leave and then a month of half paid and then a month of no pay. The reason why they do this is because it's much cheaper to do this than to find somebody new to replace them. Turnover is expensive. And by the way, that was just an example of maternity leave. It's up to you how much you want to give. That's the nature, that's the perk. That's the wonderful thing about running your own business. You make up the rules. Now, having said that, you need to make sure that your rules are in compliance with any mandatory local government rules. And if you're not sure about that, you can easily speak to a lawyer or even some accountants know this and they can figure out if your employee contract should be contractors or full time employees. It's different for every place in the world. But for many online companies, what they do is they just say all their employees are contractors and all the policies I just described today are kind of like perks. They're not really rights. They're a way for you to run a smooth organization. And at the end of the day, a contractor just signs a contract and signs an agreement based on what is on the contract, right? So if the contract says X amount of days, that's the days they agree to speak to a lawyer about this. It's different in every country. Just to make sure you're in the clear. The other thing I want to mention before we wrap up is there are different types of freelancers or part time workers that work through a service like you hire a freelancer through Upwork or Freelancer and you're actually paying upwork or that, you know, gig site like Freelancer and not the actual person directly. Many people go down this route because there are some protections on your end because you're kind of separated from the person. Every site like upwork or Freelancer will have their own policies. Read them when you sign up for them. When you're hiring somebody, are you actually hiring Upwork or that person? In my opinion, if you're trying to figure out how many days and you know the minimum you need to offer, it's okay to be a little bit generous. Most people do not abuse it. Most people are actually quite conservative. It's better for them to know they have enough days off than not to have enough in the back of their mind, right? To know that, hey, if I need them, they're there. 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. Arianna Rosa. Arianna Rosa says brilliant advice. Five stars. I feel so blessed. The $100 MBA exists and it's so easy to access. The information is practical and it gives me daily hope. Omar and his team deserve every good thing they receive. Thank you so much, Arianna Rosa, for that great review. You are our Free Ride Friday winner. Your mission is to email me at omar00mba.net so we can hook you up with a lifetime membership to Easy course over at EasyCourse Co so you can build your own online course in 30 days. If you want to win a free ride, just leave us an Apple Podcast rating and review and you enter our weekly random draw. We call Free Ride Friday. It's that easy. Go ahead and do that right now and listen in on Fridays to see if you won. Before I go, I want to leave you with this. The good thing about having a leave policy that everybody knows where they stand. They know how many days they can take off. They know how to do it. They know how many they have left. It's just easy and transparent and it makes something that's very precious people's time, easy to use, easy to take advantage of that time off that they really deserve. Back in the day when I was in teaching, I worked at some places where they made it so hard for you to call and sake. They made it so hard for you to take some time off. They actually deterred you from calling in sick when you're tired and when you're. They actually deterred you, made it difficult for you to call in sick when you're not feeling well. It would make it really confrontational. You have to call somebody and get approval and then send the work for somebody to do when you're gone. You know, like you're a substitute and it's a horrible feeling for you as an employee. Don't do that to your teammates. Make it simple, make it easy, make it pain free. 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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