Does your small business offer a lot of flexibility in terms of scheduling and paid time off? If not, then it might be time to reconsider. Flexibility is one of the most sought-after qualities that people look for in potential employers and offering this type of benefit will give you a competitive edge during our current labor shortage. In this episode, Jon Aidukonis and Gene Marks discuss how small business owners can develop a flexible scheduling policy that will effectively serve both themselves and their employees.

Podcast Key Highlights

  • What Benefits Should My Small Business Offer To Help Motivate My Employees?
    • Flexible Scheduling
    • Health Insurance
    • Retirement Plans
  • How Do I Develop a Flexible Scheduling Policy that Serves Both My Business and My Employees?
    • Instead of aiming for an absolute, steadfast policy, such as a four-day workweek, establish a system that enables employees to request paid time off whenever they need it.
    • Be upfront during hiring and let your potential employees know that all paid time off needs to be approved first.
    • Start off by providing your employees with an accommodating schedule and then, give them the opportunity to earn even more flexibility each time they complete their work in a timely manner.
    • If your employees think they may require extended leaves of absence, develop a plan with buy out and rollover opportunities for unused days off.
  • What Are the Disadvantages of Implementing A Four-Day Workweek?
    • If you own a service-based business, it may not be possible for you to stay closed three days a week.
    • A four-day workweek may not be convenient for your customers.
    • Sometimes your employees’ needs shift and it may actually be better for them to work more than four days.
  • What Are the Disadvantages of Offering Unlimited Paid Time Off?
    • This format will only work if your particular industry is more focused on the product or service output, rather than the actual amount of hours that your employees work.
    • In most cases, business owners find that their employees are less likely to take paid time off when it’s unlimited.
  • How Can I Make Remote Work Possible at My Small Business?
    • First, make sure working from home is actually feasible given your industry.
    • Because it can be difficult to find a clear balance in hybrid workplaces, it’s best to either have a completely remote setup or have your entire staff return to the office.
    • If you do opt for a hybrid situation, you need to make sure that all your employees will have equal opportunities for growth and engagement regardless of whether they work in person or remotely.
    • Establishing a clear set of protocols will also help you keep your daily operations running smoothly in a hybrid environment.



The views and opinions expressed on this podcast are for informational purposes only, and solely those of the podcast participants, contributors, and guests, and do not constitute an endorsement by or necessarily represent the views of The Hartford or its affiliates.

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Jon: Welcome back to another episode of Small Biz Ahead. This is Jon Aidukonis. I’m back with Gene Marks. Hello, Gene.

Gene: Hi, Jon. We’re talking about employees today, aren’t we?

Jon: Yeah, we are talking about how to keep a staff motivated and retain them, especially when there is a labor shortage.

Gene: Yeah, there’s a lot to talk about there. And I got to preamble this conversation with just saying that I actually do a radio show with this other guy and he always accuses me of always being so negative on employees. And I want to be clear, I am not negative on employees at all, but it’s just my aspect of all these conversations is as a business owner. So I like to talk about what can we do to be fair to employees, but also to be fair to employers as well.

Jon: I think that’s fair. And I can speak from the employee perspective as both someone who has led as an employee and been led in the past four years.

Gene: And one of the hardest working employees of The Hartford itself.

Jon: Oh, thank you.

Gene: Yes.

Jon: All right. So I guess first thing, when you think about motivation, we tend to talk a lot about I think company culture and pay and benefits, which I think are all parts of things, right? I think that those expectations have risen over the past couple years and I think employers have gone way above and beyond-

Gene: They have.

Jon:… to address them, right?

Gene: They have.

Jon: But I think it’s time for a level set, right? So I think maybe start just with time off. We’ve gone through these yo-yos of-

Gene: Have we gone too far with all this? We have four-day work. Because from the employee perspective, and I’m the employer perspective, what’s your take on four-day work weeks? It’s a hot topic.

Jon: So I feel like whenever you put the system in place for everyone, there’s someone who’s not going to work out with it, right? And-

Gene: Fair enough.

Jon:… either because it doesn’t make sense for them, the composition of the company workforce, maybe it doesn’t make sense for the company. So I think you got to be careful with all of those absolutes.

Jon: And I think I had an experience recently where I actually have to use a lot of time. So I tend to be someone who never uses the time off that I’m given and I give a lot back at the end of the year, which is funny because I feel like that’s a polarizing concept. Y’all get criticism on both sides for that. It’s kind of like it’s your time, you should use it.

Gene: Yeah. It’s a mental health issue, the whole… Right?

Jon: Right. And I don’t personally look at it that way. So one, I’ll own the fact that I’m probably not the norm when it comes to work/life separation, and I don’t say that from a balance side, but I’m a person who gets a lot of pleasure from the job or jobs that I do. I look at work as part of my DNA, kind of gets me wired. It gets me going.

Gene: Yeah. And your workday isn’t a 9:00 to 5:00 work day anyway. I mean it varies in-

Jon: Right. And there’s times where I work multiple jobs. The notion of producing something is what gets me excited.

Gene: So the four-day work week for a guy you is kind of irrelevant because you’ve got-

Jon: I would do something else.

Gene: Yeah, yeah.

Jon: I’m not like the sit down and stop kind of person. So I don’t mind. And people talk about unlimited vacation. I think that’s kind of a weird one too. But what I have noticed recently, and I think I can finally articulate it better, is the notion of flexibility in general has been really important.

Gene: Yes.

Jon: I had some family health issues lately. I’ve needed to be absent for a while, and it was without a question that I had the time that I needed to take care of things that took a massive demand on kind of my person. I had the team around me to carry it through. I could never be more grateful for that. But that wasn’t because of a policy or cultural decision or I should say a benefit decision.

Gene: I disagree. Yes, it was. I think the Hartford have their vacation and their PTO policies. They have a culture of a team culture here. You went through some deeply, well, hard stuff. The company’s benefits allowed you to take the time off that you needed, and the company’s culture provided you with people.

Gene: I mean, I saw you talking to Sarah before this conversation about the supports she was providing. She’s a colleague of yours and a fellow employee. So I do think that’s important for a company to provide those things for their employees. And by the way, I will also say to you that, I know this is fairly recent, but months from now, you will look back and you will be like, I am really appreciative of-

Jon: Oh, for sure. Yeah. I didn’t mean call… So I should have said benefits.

Gene: It’s okay.

Jon: But my kind of point on that is I don’t think I can even express the amount of appreciation and gratitude I have for these folks, but I think it was because of the notion of flexibility. It wasn’t because it was X amount of… I mean I used my time, but had that been I think a defined thing or not, I think the culture would’ve figured out a way to kind of give the access.

Jon: So I say that because I don’t know if it’s really about do you need to have unlimited time off? Do you need to compete with the most days? Or is it just like we’re going to work with you at an individual level to make sure you have what you need?

Gene: Okay. And so a couple comments on that because again, this is for small business owners that are listening to this, right? One of the biggest advantages that you have as a small business versus The Hartford, which is a big business, is that you can allow more flexibility with your employees, and it doesn’t necessarily have to be by the book. It can be based on an employee situation or something that they’re going through.

Gene: And that’s a cultural thing, is you don’t have to have an official four-day work week policy. You don’t have to buy into some of these narratives that you’ve got to have this kind of program or that program. It’s a matter of just providing, like you just said, Jon. You come and work for me, we’re flexible. Okay, you need to take time off, you have personal issues or whatever, or if you need to take just even time for a vacation and your supervisor’s okay with that, we can be okay with that. I think that’s a big plus for working for a small business.

Jon: I think so too. And I think even if you’re managing in a larger small business where you might not have that kind of direct relationship with every single person, but I think it’s a mutual obligation, right? So I think that that’s where it comes to… To me, it all starts with the hiring because you need the person who’s going to kind of complete the transaction.

Jon: So if you think of the relationship like a debit account, eventually if you take all the money, I think there’s nothing left, right? So you have to be able to put things in as you take things out. And I think that part of it is, you build up the credibility, the trust, the ability to get your job done over time, you get more flexibility, and that might be kind of old fashioned.

Jon: I do think the employer has an obligation to understand that there’s probably much less separation and formality between work and life the way there have been historically because the rest of the institutions we have right now have not fully gone back to where we were say in 2010. The world functions differently.

Gene: It is a different workplace right now. So I have a couple questions for you. First of all, you just mentioned earlier about you saw the unlimited paid time off as kind of a weird… Right? I mean, you said that, right? I mean, why?

Jon: So I think it goes back to labels, right? So you can’t give someone 365 days of paid time off because that implies they’re not working 365 days but getting paid.

Gene: Okay.

Jon: I think it’s the notion of flexibilities. If you can get your job done, if we’re paying for the job versus the hours, if you can think about it that way.

Gene: And that’s what’s behind the four-day work week concept, right?

Jon: And then it could be a two-day one. But for some people, that might be a seven-day one because to be honest, there’s some parts of the year maybe where I’d like to work half days, seven days a week and then be done at noon every day because I have other things to do and I’m happy to work a Saturday or Sunday, right?

Gene: Yeah.

Jon: I don’t think that most people probably feel that way anymore. But I think you also have to think about your industry and nature, and can you be closed for a day?

Jon: So I think about… This is an interesting one more from the customer side. I had to run an errand the other day. It was a national chain store. They close for lunch. Apparently, part of the store closes for lunch from 1:30 to 2:00.

Gene: Okay.

Jon: I was unaware of that, but I also didn’t research because I thought the store was open. I couldn’t get the one thing that I needed in the half hour, so I had to come back. But I see six people behind the counter. So in my head, I’m like, okay, I could get that if it was a single… You need to let someone take a break, but there’s also multiple people-

Gene: It’s like, come on guys, right?

Jon:… where you could schedule more effectively, and so now you’re not negatively impacting the customer.

Jon: And I wonder, I don’t know, but part of me, I’m like, well, maybe this is an employee cultural play. We’re going to reward and give you this time to be together. But I’m like, most people don’t want to sit down and have lunch together every day or at the same time. And are they all coming at the same time? It didn’t feel like that. This is a 24-hour thing, so I’m assuming they’re staggered shifts. They don’t close for dinner.

Jon: So it felt like a little bit of a performative act, and I think that’s where we get into the risk in a lot of kind of benefits conversations. I shouldn’t even say benefits. I should say perks, right? Because they’re meant to appease what people say they want, but is that what they actually want?

Jon: So if you think about wedding planning, right? Trying the burlap. People would come in like, “Oh, I want burlap napkins at my wedding.” It’s like, I know you think you want that. Have you ever wiped your face with burlap? No. Have you ever smelt it? No. You want something textured and soft and that looks like it.

Gene: People say they want… Unlimited pay time off, you say that to an employee like, “Oh wow, that’s sounds like an incredible perk to have in a company.” And then studies have shown that companies… Like Facebook did this big study that they started implementing unlimited paid time off and they found out their employees were taking less time off then. Because it’s getting back to what you said, it’s like what people say that they want, but then what they actually… It’s not necessarily what they want.

Jon: And it’s perception versus reality. If you are thinking, if you’re in a state that has accrued paid time off and in your mind it’s something that you earned. I’ve earned these five days and the only way I will realize the value of five days is if I take them away from work, then I think people are more apt to use them.

Gene: Yes.

Jon: Because it’s like money they’re leaving on the table, right?

Gene: Yes. It’s like a flex spending account. If you don’t use it, you loose it.

Jon: And there might be worlds where it makes more sense to offer a partial buyout or a rollover kind of save your days for a big vacation you want to take. I think people’s lives change every day, let alone every year.

Gene: But don’t you think if you’re an employer and you’re a small employer and you say to a prospective employee, we offer an unlimited pay time off plan… And again, everybody’s desperate for employees. Don’t you think that that’s a selling point? I mean-

Jon: I think it’s a selling point. I would reposition it though if I was talking. So if it was my business, I would say like, “Hey, we don’t have a maximum on the days you can take off.”

Gene: Okay.

Jon: If you need flexibility in your schedule, we’ll talk about that and we’ll work through it. Because I think there needs to be some parameter on what that means because you still have a business to operate and this person still needs to know what to expect.

Gene: So I’ve got a couple comments on that. I mean, I have clients that have unlimited PTO plans. They’ve learned a couple things. Number one is that you got multiple PTO plans at a company. It doesn’t have to be. So you come and join us, you work for us for two years, you might be eligible to join our unlimited PTO plans. So it’s sort of like a carrot that you hang out there.

Gene: They all make it where you can’t take time off unless it’s approved by your supervisor. So we’re saying it’s unlimited PTO, but don’t come to me and say like, “Oh, I’m going to go surfing in New Zealand for the next six months.” The supervisor’s got to approve the time off to make sure that it aligns with the business’s priorities. Does that make sense?

Jon: It makes sense. But that’s where I think you’re kind of-

Gene: Back on the unlimited PTO thing, right?

Jon: Right. It’s sort of like, why is it there.

Gene: There is a potential deceptive part of that.

Jon: Theoretically, if I work in a world where three months out the year I’m just kind of going through the motions, should that job be scoped the way it is?

Gene: Right. Right.

Jon: Right? And maybe yes, but if I could be gone for three months, nobody notices then good on me for figuring out how to do that as the employee. And then awesome. That’s what you’re offering as the employer. But I think when you start to say things, because they sound like the right cultural thing to say, but with the hidden terms and conditions, then just be transparent.

Jon: If I was looking for a job and someone’s like, “Hey, we don’t really have a max on PTO days because as long as you let your manager know and we can work around it, we’re good,” that’s the same thing. But you’re setting the expectation fairly-

Gene: I see.

Jon:… so you’re not then dealing with a blowback of like, “Well, I’m going to go leave and get somewhere else because I thought they had this.” So I think it comes back with really kind of being fair and honest.

Gene: Working from home. You and I were talking about this before we started recording or whatever, but just generally give me your thoughts. I mean, everybody has got thoughts on working from home. You’re an employee of a big company with very generous programs and perks, whatever. If you were running your own business, what would be your thoughts as far as a work from home policy for your employees?

Jon: I go back and forth on it personally.

Gene: Okay.

Jon: So this is me speaking.

Gene: Just you speaking, right.

Jon: I think that The Hartford’s actually been really generous to your point and very flexible.

Gene: Yes.

Jon: A lot of people have kind of been able to pick what works best. I think everyone’s kind of been able to pick what’s work-

Gene: Worked best for them.

Jon: I’m going to cut that part out because I totally lost it.

Gene: I think we get the point.

Jon: So this is me speaking as me, but I think it depends on… are you in an industry where people can work from home?

Gene: True.

Jon: You can’t really host at a restaurant or bartend from home.

I think in some instances it makes a lot of sense. I think that if you’re in a role where it’s a individual contributor based role and you don’t really need to interact with people or everything can kind of be done usually over the phone, yeah, great, go for it. That doesn’t impact your bigger operations.

Jon: I do think that we need to be better about balance and what that means and rigor around when we talk about hybrid workplaces. So I think that people who’ve really found it easiest from my experience and people I talk to are people who’ve gone full, full remote or are in office. And when I say people, I mean the business owners or businesses who have adopted a one or the other.

Gene: Wait, so are you saying that either you’re either all in on full remote or full in the office and with no in between? That’s preferable to you than say a hybrid approach?

Jon: Yeah-

Gene: That’s interesting.

Jon:… I don’t know that it’s preferable, but I feel like those are the two who figured it out because they’re a little bit more absolutes. So when they build in rules and procedures and operating routines, they’re kind of doing something that makes sense for everyone in those roles.

Gene: Makes sense. Okay.

Jon: Doesn’t mean that it works for everybody, but it means you can have a set of norms when you’re in office and norms when you’re fully remote. I think where people are still struggling or in these kind of hybrid worlds. So I think the universal belief and what people purport is that we want you to work where you’re more productive and more efficient and what works best for you.

Gene: So it’s funny that you bring… It’s funny because I’ve been talking about how most of my clients are doing something hybrid, and this gets back to the PTO thing and the unlimited PTO thing, and you’re making me think that people want rules to follow. That’s like a human nature thing. We might rebel against them, but we want rules. And when you leave the choice up to people, it tends to create more stress.

Jon: I think. So I think there’s a whole bunch that goes into it, especially in the hybrid world. So I think there’s things that, whether real or imagined, are believed to happen when you’re in person.

Jon: So there was a lot of conversation around pay equity and promotion. At the beginning of the pandemic, those were big kind of news cycle things. Can you advance your career if you’re not present? And people are. And how do you now give people who chose in most instances to work remote in office level of engagement or experience?

Jon: And we put the ownership of that task on the business leaders and institutions and decision makers. And I don’t know that that’s right or wrong, but I also feel like as a human, if I make a choice, then I have an obligation to make that choice work if I’m given the opportunity to make it.

Jon: And I feel like that’s where there’s still kind of this seesaw happening in these hybrid cultures of can you be equitable? Is my question. Because I don’t know that you can. I think you can do things to be more equal, but if you’re in a situation where there’s people at home and people in a room, you’re going to get hallway chatter from the people who are walking down the hallway together.

Jon: And I don’t know the way to say that for someone who’s working remote in that instance, or make them feel more included if you’re in a conference room or at a meeting location or a co-working space and one person is gone. But now the expectation is that everybody feels like a camera square. It’s like the tiles-

Gene: Just for that one person, right.

Jon: Right. Now you have three people sitting at a table, but they’re not even looking at each other because they’re trying to interact through a device. So you almost lose the effectiveness of the… Which would make the argument should everything be full remote.

Jon: But then you start talking about time management. There’s a benefit to being able to walk by someone’s office or pop in and say, “Hey, I have a quick question for you. I’m going to drop this by” versus let me schedule a formal meeting 30 minutes two weeks from now because now everything has to be calendared because we don’t know where anyone is. Where you do you lose some of that kind of in-person interaction. And I don’t know the way to solve that. And I’m speaking as someone who tends to be more of an in-office person-

Gene: Yeah, as am I.

Jon:… but you hear it from the other side too, and I don’t know how you bridge that gap.

Gene: I think first of all, I’ve learned everything is, it depends, right?

Jon: Right. Yeah.

Gene: Because it depends on the person. There are some people that can work great remotely. There are some people that are terrible working from home. And then the same thing in the office.

Gene: And what I’m seeing is that people that are doing these hybrid solutions, that the more they leave the choice up to the employees, the more trouble that they get into because then they have the one person that’s not there. They chose to take that time or give a moment to three other people in the office.

Gene: So it almost seems like you have to establish set rules. You’re not going to please everybody, but you know say, “Okay, yeah, we’re going to have a hybrid environment, so Monday and Fridays are your day, but everybody’s got to be in the office on these days, whether you like it or not, that’s just what we’re going to do. So that way if you want to have meetings, you want to do things face-to-face, that’s when it is. So maybe it’s just heading in that direction of just being where you’re having a hybrid, but with just more stringent rules around them.

Jon: I agree. I think you do kind of have to set the kind of lanes.

Gene: And some people are going to complain.

Jon: Right. But people are going to complain about everything. You go full remote and someone likes to be in office, they’re going to complain about that. You go back in office, people enjoy being remote, they’re going to complain about that. I think to your point, nothing is going to be universally pleasing. The counter to that is remaining flexible when it’s needed on the employer side, but also on the employee side.

Gene: Sure.

Jon: If your point of wanting to work from home is… I don’t know. I mean, if you didn’t do it before, and not to say you shouldn’t have access to something now, but is two days better than nothing? Or has your life changed so much? And maybe you had a child or a life change or something where now remote makes more sense.

Gene: Sure.

Jon: But I feel like there’s also a lot of options now on then maybe that means you should work in a company that is more full remote or that is more in office. I think sometimes we’re looking for existing institutions to change when maybe we need to change the institutions we kind of engage with, right?

Gene: Right. I agree. I agree. And spending 20 minutes on talking about motivating your employees and out of… Just as a wrap, I mean, obviously health insurance is important and retirement plans are important, but we’ve been talking about flexibility.

Gene: And would you, as an employee, and also as somebody who works all the time with small businesses and small commercial customers, would you agree that flexibility has now become the type of, what do you want to call it, a benefit or a perk, but something that every employer has to have along with health insurance and retirement? Is that important now?

Jon: I think so. And I even look at those as subject to it, right?

Gene: Yeah.

Jon: So I think when you’re thinking about your employee strategy more broadly, it is figuring out where you can meet them and where they can meet you. And that might look like… To some people, supplemental benefits might be much, much more important now than they were maybe six years ago when it was like, “Hey, do you have a ping pong table in your office, right?

Gene: Right.

Jon: Because the notion of

Gene: Beanbag chairs, I think those were popular, too.

Jon: I need more of a notion of certainty, right?

Gene: Yeah.

Jon: I want accident insurance, I want something for hospital injury, or I want additional flexibility with my 401(k).

Gene: Yes.

Jon: I mean, there’s a lot of things now where I think to me the conversation would be to go back to all of your vendors or providers and say, “Is there a range of things so people can build packages and platforms that are right for them?” And that doesn’t mean you have to pay for them. That can be things that come at supplemental costs. Those can be things that just give people the access to the tools that they might want, but really making sure that you understand what those are and kind of communicating them with you.

Jon: But I think the great thing about that is we all, if we’re worrying about retaining and motivating employees, we probably have them. So we could ask them like, what is it that you need to stay motivated and how can we play a role in that, right? Because most people will tell you how to make their life better and easier if you ask them.

Gene: That was Jon Aidukonis. My name is Gene Marks. You’ve been listening to The Hartford Small Biz Ahead podcast. Thanks everybody for joining us. If you need any advice or tips or help running your business, visit us at or and we’ll see you again soon. Take care.

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