The Mistakes I Made When Managing Remote Team Members

The Growing your Team Podcast: Episode 158

I’ve made some big mistakes when managing remote team members—both in corporate and within my own business.

Like many leaders, I had to learn through trial and error, and this is not the most comfortable place to learn. 

Learn from my mistakes so you can successfully manage your remote employees.  

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Episode Transcription:

This podcast episode transcription might be edited for clarity and conciseness.

Hello, Jamie Van Cuyk here, and welcome back to the Growing Your Team podcast.

Last week in episode 157, Jody came on the podcast to talk about how to keep a remote team connected. He shared so many great tips on things you can do to make sure your team is fully connected and even interacts a lot like they would if they were in the office.

When going back and preparing to get this episode out and market it, it made me think a lot about myself managing remote teams. And it made me think about how I failed at managing remote teams. So that’s what I want to talk with you about today – Getting real honest about how I failed when I was managing remote team members. This is going to include examples from when I was in corporate and then also with my own team.

00:02:46 – My first remote employees

Way back when I became a first-time manager, I ended up having two remote team members on my team. One was in a satellite office, and the other one was working from home. With the team member that was working from home, this was really abnormal during this time. Pretty much all employees worked at one of the company’s offices. And then, my team member that was working from the satellite office originally had been in an office where there were lots of team members. They had their own manager and everything, and slowly and slowly, some of those team members were let go. or relocated, and as positions became open, they were refilling them there at the headquarters where I worked. So eventually, this team member was the only person doing what she was doing in this office and reported to me many, many states away.

00:03:47 – My first mistake: limiting people’s potential

One of the things that I noticed with my management style, which actually was passed down to me from other managers, was this mindset that if someone’s not in this office, their current position is really all that they’re capable of doing. This person can’t help out with special projects. This person’s probably not going to get promoted, so it was about figuring out how they function in their role and everything that they do there to be good in their role but knowing that they’re never really going to move beyond their role unless they move.

And let me tell you, that was a horrible, horrible mindset to have. Because at the same time, these employees needed to have goals like other team members, which also included talking about their goals on where they wanted to go in the organization. And it was just really weird as a manager to know that the organization didn’t necessarily approve of them being promoted into higher level roles, yet we were supposed to have these conversations with them about how do you prepare yourself for higher level roles.

So that, I’ll say, was mistake number one. That is, being in this mindset that not working in the same office, whether it’s working remotely, whether it’s working from a satellite office, means limited opportunities. We now live in a space where a lot of people work remotely. There are a lot of communication tools out there that make it so people can communicate just as effectively without actually being in the same place. You don’t have to be in the same place as your manager. You don’t have to be in the same place as everybody on your team that you work with day-to-day in order to make things really effective.

00:05:34 – My second mistake: ignoring workloads

Mistake #2 that I will say that I made with one of these team members as they were extremely overworked, working very long hours, and I did nothing about it.

Now when this team member first started, the role was an hourly role. I saw their timesheets every time I went to go approve them, but I still didn’t do anything about it.

What really turned out to be the case here was this team member was not drawing boundaries for herself. This team member was letting themselves be pulled in by that next e-mail. They were afraid to leave their desk during the day to go for lunch or anything like that because what if somebody reached out? What if I, as their manager, reached out? So they were working extremely long hours, not taking a break, and kept working throughout the evening because they’re like, I got to get this done.

I let that go on way too long.

We didn’t have conversations about what was driving those hours. We didn’t readjust workloads when we said, hey, this might be a little bit too much for one person. We just kept right on at it.

That was the 2nd mistake. It was not being aware of your employee’s workloads, how many hours they’re working, and then when you are aware, not doing anything about it just because the work’s getting done.

But I can tell you I had an employee in my office that was always working really long hours. I could see the stress. I could see that they weren’t staying late just because they wanted to but rather that they were really overwhelmed. I could visually see what was going on, so we had conversations. I didn’t have those conversations with my remote team member.

I knew as a manager that managing remote teams at that point in time with the way things were set up in corporate and with my skills and expertise, I really didn’t want remote team members. But of course, I was transitioned to lead a different team, and that team came with a remote team member. And I will say. With this team member, I made multiple mistakes.

00:08:00 – My third mistake: putting them on an island

The first mistake I made with this team member was that I never really connected with this team member. She was doing different work than the rest of my team and I kind of contributed to her feeling like she was out on an island. We didn’t do a whole lot to make her feel like a part of the team. It was us and then her. Even when we had her come into our team meetings, nothing ever applied to her. We were taking her time to talk about stuff that didn’t apply to her, but we were never taking the rest of the team’s time to talk about stuff that did apply to her.

So that was the first thing I contributed to this person feeling like they were all alone on this island. To feel like they weren’t a part of the team. You need to put effort into making your remote team members feel like they are part of the team. Otherwise, no wonder why they distanced themselves or possibly decide that they don’t want to work here anymore and go find new jobs.

00:09:04 – My fourth mistake: no proactive communication

The other thing that I did wrong with this team member was that I wasn’t good about being proactive with any communication except when things were going wrong. This poor team member was in a position where if things were going wrong, she was the one to catch those things. It was her responsibility to see when things were out of the norm and report it. So once again, she was always involved when things were going wrong. While there were some slight performance issues that we needed to work on, we only ever communicated when we needed, and that meant we only ever communicated when something was going wrong. Which made it so our entire relationship was about negative things.

This team member, to this day, I want to say thank you. One day we were having a conversation. It was myself, the executive director that I reported to, and this team member. We were talking because we wanted to see some changes in performance, and during that conversation, we were laying out what we wanted to see as the leadership team, and we were getting her input and her opinion. And during that conversation, she had the guts to sit there and say that she thought the relationship between her and me was extremely negative, all we talked about was the negative, and it was just really draining.

As I said, she had the guts to do this because how many people, when you’re on a call that includes their boss, are going to say anything negative about your boss? You might want to say it, and you might say it behind your boss’s back to a lot of other people, but to sit there on a call with your boss and have the guts to say that takes a lot. And I am so thankful that she did because it allowed me to sit there and really realize that she was right.

Every conversation we had was around some negative topic, and we never had positive conversations. We never talked when things were going well. We never talked about what she was doing right in her role and the things that she caught that saved us money and saved us issues. It was all negative, and because she had the guts to say that, I was then able to change my behavior as a manager and start focusing on the positive. I started reaching out to her to see what she needed and if there was any support that I could offer her instead of just reaching out, saying, “hey, I hear there’s this problem going on. Fill me in on all the details you know.”

I was able to realize that it is super important to build that connection with your remote team member just as you would with a team member in the office. With a team member in the office, you have those water cooler conversations. You see each other in the hall, and you talk about random things like what they did that weekend, their kids, and everything.

With remote team members, you need to do the same. You need to build those connections and not just talk shop all the time.

Luckily we were able to really turn our relationship around and have it be a much more positive conversation.

00:13:10 – My fifth mistake: excusing poor performance

All right, so now I want to f to my team within Growing Your Team. One of the team members that I had, at the end of the time that they were with me, their performance really started to slip. And guess what? I chose not to do anything about it.

Now for me, I use the justification that this team member is leaving anyway, so why rock the boat and end on a bad note? There’s always a chance that once team members turn in their notice or you tell them their position is ending that they will kind of check out a little bit. But, I realized that this person hadn’t just checked out once we had those conversations, that it was kind of something that’s been going on for a while. This team member really wasn’t performing the way that I wanted them to perform. And the problem was I never addressed it. I didn’t address it before this person was on the way out, and of course, I didn’t address it once this person was on their way out; I just kind of left it. I picked up the slack throughout many moments in the relationship. In the end, this team member wasn’t doing what I was paying them to do, and as a manager, I started resenting them for it, but I had no one to blame but myself.

It’s something that I tell you all the time. If you don’t set expectations with your team members, your team members will. And so I made the decision not to address it, which meant things never got better.

You need to address performance issues with your team members, even with your remote teams. You need expectations, and you need goals. You need check-ins to ensure this person is performing as they should be.

00:15:25 – My sixth mistake: making the position 100% flexible

There’s one last remote team member mistake I want to share. One of the mistakes I had was making the position 100% flexible in terms of the time that they worked. This is actually something I think I talked about in the last episode with Jody. It became an issue because I didn’t know when my team member was working. I didn’t know if she was on when I was on, so I didn’t know if I should reach out or send a text because I had a quick question. If I had a question, I sometimes would take the time to figure it out myself or do it myself because I needed something now.

While I like that there was flexibility, and with future positions, I want there to be some sort of flexibility, I realize that in order to really build a true team and be connected, there needs to be some sort of consistency with schedules. I need to know the times and hours of the day that person is working. So even if there’s flexibility where this week might look different than next week, I am aware of when my team member is working. This is not so I can monitor their behavior but more so that we can have those connections and work together as a team when needed.

00:16:46 – Be the manager your remote team members need

So these are some of the ways that I kind of screwed up and learned by trial and error as a manager of remote team members.

With remote team members, you’re going to make mistakes. But guess what? Even with employees in your office, you’re going to make mistakes. I’ve made other mistakes with employees that have physically been located in my office, even a desk away from me. It’s just about learning from our mistakes. It’s sometimes about getting that coaching and guidance and everything that will help you become a better manager. Because that’s what’s important, taking steps to become a better manager, recognizing that we are not perfect, and growing as a leader.

Even the most seasoned leaders out there are not perfect. There are things their employees will put them through that it’s like, oh, that’s new. What do I do in this situation? So you want to make sure that you’re taking steps that help you grow as a leader who does things well for your team, who is always managing better the next day than they were the day before.

So, learn from my errors here, and if you realize that you’re performing some of these errors in your business as well, take the time to start changing things so you can start off being the leader your team and business need you to be when you have remote team members.

Related Episodes:

Ep14 – Why It’s Smart for You to Embrace Remote Work

Ep63 – How a Wedding Surrounded by Sharks Taught Me to Be a Better Leader

Ep157 – How to Keep a Remote Team Connected with Jody Grunden

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