44: From Office to Home: Leading Remote Teams

In this episode I  share my experiences managing and leading a remote team. I discuss the evolution of my firm from an in-person to a fully remote team, the challenges we faced, and the strategies we implemented to overcome them. Key topics include the importance of clear communication channels, leveraging technology, and maintaining personal connections with team members. I also reflect on the benefits of remote work, such as increased productivity and flexible work hours, while providing insights and practical advice for those considering or struggling with remote team management.

Chapters

• 0:00 Introduction to Beth Whitworth
• 0:38 The Evolution of Remote Work in Accounting
• 5:27 Challenges of Managing a Remote Team
• 12:10 Benefits of a Remote Team
• 18:47 Best Practices for Remote Team Management
• 26:55 Future Improvements and Conclusion

Transcript

 I am Beth Whitworth race car driving quilt making CPA firm owning wife, mom, and boss. I'm here to help you build a business you love by sharing all of the good, the bad, the ugly, and the excellent sides of working in this industry. It's not always easy, but after many years, I can finally say it's worth it.

Let me guide you on your journey to accounting with confidence.

Hi, I am welcome to Accounting With Confidence. I'm Beth Whitworth and I am talking today. I was gonna call this episode Managing a Remote Team, but. I realized as I was kind of taking some notes about it, that it is really about leading a remote team Now, I've been in business for a very long time, and I would say 18 years ago when I went out on my own from a firm that was in the financial district of our city where I was going into a office building on the 20.

Sixth floor, whatever I was on, I didn't have in mind any concept really of having a remote team and meaning. Everybody's working from home. There was the rare occasion after we had our daughter where I would, you know, work from home if she had a, a day off or couldn't or was sick. I would kind of set up my computer and sit in the kitchen and, you know, try to get some work done type thing.

But it was. Absolutely expected that you're a hundred percent in the office. And at the time, I was in the office at least six days a week. So when I came out and started my own firm, it was expected that everybody was going to be in the office, and that's how accounting firms worked. We weren't set up to do a whole bunch of remote things and.

If you were taking work home, you seemed to be, you know, kinda shuffling files around and that kind of thing. And so we just weren't, we weren't there. So from 2007 to 2015, we were a 100% in-person in the office firm. And then we changed offices. So we moved our building to a diff or moved to a different building.

And at that point in 2016, some of our people became partially remote. And that was because they lived far enough outside the city that it was, it was kind of a drive. They had young children. And then we also started, we hired. Somebody directly to be remote because we didn't have a seat at the office for them.

We're like, okay, we need them during tax season. They can work from home. And so around 20, it was probably around 2019 is when we hired that first person that was just gonna work from home, maybe come into the office for a meeting or two. And from 2016 till 2023, we were, I would, what? I would say it was partially remote, so.

Obviously the pandemic landed during that time and in 2020 the majority of the team went home. So they, we were set up, we were able to work from home. We were able to, we had finally switched all of our apps to things that were cloud-based or we had a good system in place for a remote access to, you know, our tax information and all of those things.

So. When the pandemic hit, we were, we were ready to be remote, which was great, but we always at that point had kept the administrative person in our office and we had an administrative person working in our office until late in 2024. And that was always just for me, that kept us from being a hundred percent remote.

That was a person who, you know, I would come in and meet with them maybe once a week, but I liked being remote. So when the pandemic came along in 2020 and schools were closed, Sam, my daughter was a senior in high school, and at that point I had been spending about two days a week at home and three days a week at the office.

And when the pandemic came in, I'm like, okay, I need to make a choice. And I chose to work from home and that way I could. Hang out with Sam and knowing she was leaving for college that fall. I just thought that's what I wanted to do. Well, I fell in love with working from home like a hundred percent, but I still had to come in and work with and manage the administrative personnel in the office.

So it wasn't until, like I said, the end of 2024 that we. Hired a remote administrative assistant, so I can say for all of 2025, we have been 100% remote, and I rarely go into the office. I go to the office if I need to meet with a client. I will go into the office 'cause that's our stopping off point or our jumping off point when we leave to go to races.

But I don't spend any time there and I get so much more done at home. And I, my team is really good at being a remote team, but it wasn't all, you know, sunshines and, and rainbows. Um, there's always some struggles there. And our challenges that we had with being remote. Was the first one I would say is defining a clear communication channels.

So when we first went remote, we were using Microsoft Office and we were using Microsoft Teams for kind of managing all of the client communication, internal client communication, I should say. We were using Outlook as our email for going back and forth with clients. There was no centralized point where we could actually, you know, see each other's emails or, or comment on something outside of being something being forwarded to us.

We also had to, you know, deal with that lingering paper. That was coming in. You know, we still had things that were being mailed every month. We still had things that were tax drop offs every year, and so we had to figure out a way to kind of. Really manage that, but the communication channels among the team became really important.

So I've always said over and over to my team that if it's an action item, it needs to be very clear. So when you're messaging me something, if there's nothing on there that gives me an action item, I'm gonna just blow by it. I mean, I, I didn't see something on there that I had to do, so I moved on. So I said, you know, you have to be very clear.

And so we were finding that all of the various channels inside of our team, uh, Microsoft teams was kind of losing things. Were we putting things in there just as FYIs? Were we putting action items in there, but not. Translating that over to our practice management system, you know, as a to-do, were we capturing things still by email?

You know, somebody's forwarding me an email and saying, Hey, address this. It became very cluttered and until we switched, I would say to Canopy Tax as our practice management system, which we. Rolled out in 2023, kind of the last half of 2023. That was when we finally got to a very clear communication channels.

We stopped using teams for all of the individual client communications. We put, put that in canopy. We were able to comment on emails that came in and say, Hey Nicole, could you take a look at this? Could you respond to them without us having to forward the emails to each other? We used teams and are still using teams mostly to chat with each other.

And we, I try not to, but I know I'm, I'm still guilty of putting action items in there, but usually we use teams for more of that. Okay. Quick things. Hey, do you want me to, you know, reschedule this appointment for you? Hey, could you upload this for me real quick? Those types of things. So once we started defining those.

Communication channels and how we were going to use them. It became easier with the remote team. The other thing that's a challenge is that the importance of tech inside of the company was huge. I mean, it, it suddenly took a, a, a bigger role because your level of comfort with tech became really important, that it needed to be a little bit elevated because you were working.

Essentially in your own system, you are not, I mean, yes, you're using all these apps and it's cloud-based and we're logging in here and logging in there, but it also became important that you use the apps as we needed them to be used specifically with our practice management software. So that. When you're remote, you have to have some way of gauging, you know what people have to do and there's no more of this walking into your office and say, Hey, what's on your plate?

Hey, can you help me with this? None of that. There was none of that type of communication, so we really relied on the. Practice management system to tell us what was on everybody's plate. What did they have to get done? Were they getting to due dates? Now, when you have somebody on the team that isn't using the practice management system the way you need them to, which is open it up, leave it up all day, as you finish things, you're marking them off.

It shouldn't be an end of the day, Hey, what did I get done? It should be a real time. We need real time. So it became very obvious at some point we had people on the team that I, I would don't say that they weren't able, they just weren't using it the way we really needed it to be. Good managers and leaders.

So that became a challenge. And then I think the third challenge with a hundred percent remote team is. Just losing touch with the person. So when you're in the office you can read body language, you have conversations, you, all of those things that keep us connected to each other. And it became really clear to me that there are things that it could be very easy to lose touch with people.

And so when we started this mostly remote firm during the pandemic, I didn't have a good system in place other than a weekly team meeting. I had a time where I was talking to each person individually. I just didn't have time. I was, we were very, very busy at that time. We had some really large clients that were on my plate for a good chunk of that and lots of responsibilities.

I didn't have time to keep that connection going, and I realized that, that that needed to change. You know, that is something that I think people find is the hard part about having remote people is that you lose that connection. Now, about half the team currently worked with us when we were. In person.

Actually, maybe not even half anymore, but we had some people who they were in the office with me and had, so we already had that connection. We already know each other. We, so hiring remote after that was something that you needed to just know that you need to work on. You need to create those connections in some way.

So. Those were my challenges, the communication channels, the practice management, and using that tech the right way, and then that challenge of staying connected. But what I found the benefits of my remote team for all of us, and for me, my biggest takeaway was fewer interruptions. So as we defined the channels of communication that gave you the ability to control when.

You're having those communications. Now, when you're in an in-person office, y'all know you get stopped when you're just trying to get to the restroom. You get stopped when you're like, Hey, I'm gonna go grab lunch. Oh, do you have a quick question? You know, you walk past somebody's desk and you get interruptions, or you're deep in the middle of something.

You take a phone call, so you get an interruption, you put the phone back down and somebody hears you hang up the phone and they're running to your office door. Hey, before you start something. Can I ask you a question? So there was a lot of that when we were a hundred percent remote, because that was our easy communication system.

We didn't have, you know, we weren't chatting through teams back then. We were using the stand in the office door, walk up to the desk, stop you on your way past method of communication. And so having the fewer interruptions across the board, I will say. Allows everybody to be more productive because you're controlling your.

Communication within the firm, and hopefully, and I believe my team is really good at it, is they control the interruptions within their household. And that was great. So that was a huge benefit, the more flexible work hours. For a remote team is also great. You have a doctor's appointment. We all know how doctor's appointments work.

Sometimes you just have to take the one they give you, and if it's in the middle of the day, you are have to take it. And so what being remote allows you to do is say, okay, I'm gonna, you know, make up this time later. I'm. Having to worry about, okay, do I need to take the day off so because I need to go to the doctor?

No, I can work up until the time I need to leave for the doctor's appointment, and then I can go to the doctor and then I can come back and start working again. And that's so much easier than when you're driving to your office. And okay, I gotta take this chunk of time off. For me, as a remote firm owner, I am not worried about that life happens and being remote should allow you to be flexible, to take care of your kids, your pets yourself, your car, all of those things that people, you know, used to be so concerned.

Oh, I'm gonna have to take the day off. No, just, you can do that from home and maybe you're getting up. Earlier, maybe you're staying a little late after the kids go to bed, you're gonna go put in another hour and make up for it. That is the benefit of being remote and being completely 100% able to do all the things you need to do remotely.

Of course, with the price of gas that has gone up and down over the last few years, having no drive time. Now I didn't have a long commute, so it's not that big of a deal. But along with that, no drive time is. It kind of goes the, no, get up, get ready, pack your lunch, you know, do all the things, drive to the office, unpack, settle down, get ready to work.

There's a lot of downtime there. There's time where you are not really accomplishing anything except for me getting some podcasts, listening in, or listening to a book on Audible in my short drive. But for people who had longer drives. You're saving so much time. You're getting so much time back in your world to do other things.

You know, maybe it's now, instead of that drive time, you can start your morning working out, or you could start your morning reading a book or listening to a podcast or whatever it is you wanna do, but you don't have to worry about all this downtime of. Packing, unpacking in, out, you know, getting settled into a new environment.

Almost everybody, I believe on the team has a dedicated space so they're not unpacking and repacking every day to set up to work. I'm not saying that when we were in person, that that happened all the time, but think about it, when you came to work, you had to get settled. Okay. You're, you know, you're putting your stuff away, you're putting your lunch in the refrigerator, you're turning on your computer.

You're, you're doing a lot of things every morning that actually take time. And so to eliminate that adds a level of efficiency and productivity. For me. The other thing on along with the fewer interruptions was that we have moved away from being, and me particularly someone who would get tied up in and a little bit distracted by the clock watching, did they come in on time?

Did they leave early? Were they showing up late? Did they show up at all? Did they, you know, I would get really caught up in that. And kind of use that as something that I, I felt I really needed to be monitoring and I don't have to do that anymore. Not on anybody. Everybody on my team is very self-managed.

They are putting in their hours and we are getting work done. And if they need time off, they let us know. They let me know. I used to. Just have I, I remember having text messages with my husband going, Hey, did so and so show up? Oh, nope. Light was off up there. I didn't see him come in yet. You know, it's, and so then I'd be like, ah, you know, they're not showing up and now I don't, that's gone.

That whole kind of, I don't know. It was frustration for me. That's gone. I don't have any of that. And maybe it's been replaced by other things, but not like that. So. For me, I know a lot of people are going back to work. You know, their offices have said, Hey, we need you back. We need you to come back to the office now.

We're no longer going to offer remote, or we're not gonna offer remote for full-time every day, maybe once a week. And so there's some things that I think those companies may or may not have. Gotten to achieve while they were remote. And I, and like I said, communication challenges and lack of connection and those challenges that we have monitoring are, is work, getting done, those types of things.

Um, maybe they struggled with that, but we are making it work. And I would say that the number one thing that needs to happen and at during the pandemic, that wasn't a choice. You were suddenly remote. You weren't hired to be remote. What we do is we hire to it, meaning we are assessing whether or not someone has the skills, the personality, the communication skills to be a remote employee.

We do that in a variety of ways. We, you know, when we're hiring, there are some hidden tests in there. You know, things like, you know, the second step being you need to send me a video of, you need to email me a video and two to three minutes of why you're interested in the job, or whatever that is. No instruc.

And that gives us the ability to assess, are they tech savvy? Because not everybody knows how to email a video to somebody. They may know how to take the video, but they may not know how to get it to you. Maybe the file's too big. Maybe this, maybe that there's some, so, but that helps us assess level of their comfort level with tech.

But we also hire to things like. We don't want to hire our permanent part-time team 'cause we only work with part-time people. It's not a second job. It's not a nights and weekends job. So yes, you're remote, but you can't do it just on nights and weekends. We, our culture is that we prioritize our families.

We prioritize work. So that means that if you're typically, if you're not hanging out with your family and you're not working, you know, maybe you're doing something. I guess I combine the family and the hobbies and self-care and all of those types of things, but. You have to have a culture that prioritizes that in order to get the remote team to work.

But you also need to have team members who value that. So if somebody only values working all the time, then they're not a good fit for us to be remote. You know, that's just the way it is. But our second thing that we do, other than hiring to it, is that we have standing meetings. So we have every Monday morning we have a a team meeting.

During the summer, we do it every two weeks, but the rest of the year, it's every meeting and it is a full firm meeting. It is not just the leadership, it's not just the production, it's not just anything like that. It's the whole team. During that standing meeting, we actually go through everybody's win for the week.

We go everybody through how people give a workload rating. How are they feeling about it? We talk about schedules, we talk about issues people might be having with clients, and it's a time for when people are, especially when they're sharing their wins, for us to celebrate with them and also to hear, a lot of times those are personal wins and that's a connection.

Now. In addition to that, I have a standing meeting with my manager every week. So she's remote and it's, you know, we have a two hours every Wednesday morning that is dedicated to us catching up, finding out what's going on. In addition, she has a standing meeting with each person individually on the rest of the team.

So she is the one, you know, at least every two weeks, she's talking to them to find out, okay, how are they feeling? How are projects going? If there's any concerns about things that are overdue, or projects that might be coming up, or things that we, they need help with or she needs help with, hey, assessing, do they have time to take on some more tasks?

All of those things are happening as well as that personal connection. Hey, what's going on? I saw, you know, I, how are the kids? How was your vacation? All of those things are happening, and that is really important when everybody's remote. Now we are a hundred percent remote and we only have one currently other than myself that is in the St.

Louis area. And we started out as a fully in-person firm. Everybody was in the St. Louis area. And so now we have people all over, all over Missouri. We have somebody in Illinois, we have somebody in Pennsylvania, so. It's not where we can just easily schedule a meeting in person. So what I do with my manager, with Sarah is we actually have planning where we get in person with each other about four times a year.

I also, you know, with the one person that is in St. Louis, Nicole, we try to meet for lunch about once a quarter, you know, so that we have that connection and it's not a standing meeting, but it's kind of one of those things that allows us to see each other in person. The other things that we do that make this work is really lean into our practice management software.

It is very detailed. It is. We use Canopy Tax and like I said, we went to it in 2023 and. We have, everybody's workload is in there. Everything that is due this week, next week, six months from now, people keep track of their time, but not by client. But the practice management software allows us to see what is getting done by who.

I know for some people they say I can't, I don't want remote. I don't know if they're getting anything done. I need them to keep track of time by by client because I need to know how long they spent. We're a little different. We don't do that. We manage the. Outcomes. So if things are getting done on time, the clients are happy, the deliverables are done.

We don't really care how long it took you, and we are not, I mean, we're fine with with that. So, but it's important that that practice management software be set up. So that you can assess how people are doing and what they're getting done and that everybody's using it. Using it the same way. So that means, like I said before, you don't just open it at the end of the day and go, oh, what did I get done?

And remember to click things off or wait and don't click any check anything off until you have the meeting with your manager who says, well, is this still outstanding? Oh, no, I finished that. Okay, well, we want you to have that system open and that is what's driving what you're doing every day. And that is also our visibility into what the remote team is getting done.

So that is key for us on making it work. To having, having a remote team, having those standing meetings, whether you know, the weekly team meeting, the biweekly management meeting, the weekly leadership meeting, having that detailed practice management software in place being used, and then hiring to the skills and the personality to work remotely and be self-managed.

Now it becomes really important that the people that you hire are, they're reliable. But they're also accountable. There are people who are willing to take on the responsibility of these jobs. So obviously a remote team's not gonna work. If you're in a. Production type facility. So like my husband has Nathan who works for him.

He's there actually cutting signs. He's there filling orders, he's there doing shipping. You know it. So that obviously is not a position that can be remote. So this doesn't work for all industries, I understand that. But for service industries or even for people inside your team who. Maybe able to do mostly from homework.

These are things that could help you really make that work is higher to it. Understand that it's not a personality trait that everyone possesses now. Like I said, it wasn't, it's not all sunshine and rainbows all the time, but I am less stressed out over my the team. When are they coming, when are they going?

How long are they gonna be there? All of those things. There are still a couple things I feel that we could improve upon with the remote team, and one I think is to add either an annual or a biannual. In-person event for the whole team. Now, obviously that's a, that's a big budget item, you know, because we've got people coming in from all over and, but I can, I can visualize that being something with a combined training, a social, maybe a client event, maybe team building that everybody gets to kind of spend some time and meet each other face to face.

Because I have people on my team that I have never. Met face to face. In fact, I have one, two, I have three right now of the six that I have never seen in person. But I think that would be something that if we had, I don't necessarily wanna call it a retreat, but some sort of an event that we could say every couple years everybody comes in, we dedicate the budget for it and we dedicate the time to it and maybe take a long weekend.

Either bring everybody to St. Louis would make sense because that's a little central, but. I think that needs to happen, and then maybe some quarterly type of. Remote zoom call team meeting socials maybe around a theme. Maybe we play a game, it maybe it's more of a get, kinda get to know each other type situation.

I think that would be very beneficial to having a remote team. And I know there are some team firms and teams doing great things around that. As well as with in-person retreats or trainings or whatever. And I really wanna get to that point. I think it would is really important for the team to get to know each other and to get to know each other on more of a personal basis and not just a working together on client type stuff.

And then the other area I think we could work on is having some better. Visibility better sh you know, sharing of the wins, the losses, um, the silliness, and maybe it is a dedicated teams channel to posting things regularly. You know, I wanna hear when your kid won the softball championship. I wanna know when you know, your kid got on the honor roll.

I wanna know when you, you know what you. What vacation you went on and, and what you did while you were there that you would recommend. I want those types of things. I talk to my team about all the, I have a lot of hobbies, so they hear about my racing, but I don't post stuff out there very often, you know, and share the video of my fastest run for the weekend.

And I think we're just need to, to do a little bit more of that, just to get to know each other a little bit more, to feel more comfortable to have. Have more fun. You know, fun is something that people don't have enough of inside of their work environment, and when you don't have the ability to be in person in an office where you can say, Hey, let's celebrate Kevin's birthday.

And we bring in lunch or we bring in a cake or whatever, that's not happening anymore. And so I've always been truly terrible at remembering people's birthdays and anniversaries and all the things. And it would be great if I had a better system in place to really celebrate people on my team, even though I'm not seeing them every day.

But to to really know that what's going on in their life is important to me. That is something that as a leader of a remote team, it becomes very important that you make that clear that you still care about what's happening in their world even though you are not seeing them face to face on a regular basis.

So if any of you are either struggling with leading a remote team or considering making your remote team or your your team remote, think about you know, how things are are working. Do you have good communication channels? Do you have standing. Check in times, are you hiring to it? And really look at who's on your team that maybe you hired them in person and since they've been remote, they've really, you've, you felt like things have changed and maybe you're not seeing the productivity or you're not seeing the engagement that you did when they were in person.

It could be that they just. They're not good at at remote, or it could be that you are, you don't have some of these other things in place as far as being able to really have that communication and that check in and all of those things. So things to think about, whether you're considering going remote, struggling with your remote, current remote team, or if you have a phenomenal idea on how to keep your remote team connected.

I wanna hear it. So wherever you're listening to this podcast, or if you're watching on YouTube, leave me a comment. Uh, you can DM me and just let me know, you know, what are you doing to keep your remote team engaged? I'd love to hear it. I'd love to hear ideas and like I said, I, we are not. You know, we are definitely not perfect at this, but we currently have a really strong team and we're getting a lot of work done, and like I said, I love it.

I love not working in an office anymore, so I don't think I'll ever go back. Mm-hmm. Okay, everybody. Remember, I am here to empower you to build a business that you love. So keep listening and I will continue to share whatever I can that I think might help you to do just that. Build the business that you love.

Okay, everybody, talk to you again soon.

Thanks for listening to another episode of Accounting with Confidence. My hope is that my experiences can help you navigate the realities of owning and operating your business. Please subscribe or follow the podcast on your favorite podcast listening platform so that you never miss an episode. Feel free to leave me a text by using the, send us a text message link in the show description