3 Big Challenges in Managing Remote Employees (And How I Solved Them)

Everything I know about managing remote employees, I learned the hard way.

From my first taste in the ’90s, which nearly scared me off remote workplaces for good, to a recent experience in which I had no choice but to manage from a distance, I’ve had decades of practice figuring out what works and what doesn’t.

But as challenging as it may be, remote work is here to stay. According to Gallup, 63% of millennials would change jobs for flextime, and most workers would choose remote work over a raise. In this environment, if you don’t learn how to effectively manage remote teams, your company will suffer.

So as we adapt to this brave new world, here are three challenges I faced managing remote employees and the lessons I learned from them. Hopefully, you can learn from my experiences (instead of learning the hard way).

1. The Challenge: Seeing Your Remote Employees as Stick Figures

In the late ’90s, I was living in Orange County, California, and managing a team in Indianapolis. For a while, it seemed like everything was fine. The work got done, and my key leaders on the ground gave me a good sense of who the “problem children” were.

But it only took one trip to Indianapolis to make me realize how very wrong I’d been. When I sat down face-to-face with the team members I had dismissed as bad apples, I realized to my horror that I didn’t know them at all. Hearing their stories firsthand put them in a totally different context than hearing about their problems thirdhand.

Without understanding their context, I had seen these people as two-dimensional stick figures. But after 20 minutes of eye contact and close conversation, they sprung into three-dimensional human beings with hopes and dreams. I realized that I couldn’t possibly support them without this close-up look at their lives and their challenges. After that trip, it was obvious that my attempt to manage remotely wasn’t going so great after all. Soon, I moved to Indiana full time to be with my team.

The Solution: Simulate Proximity with one-on-ones

As I learned the first time I tried to manage a team from a different time zone: without the benefit of proximity, it’s easy to see people in two dimensions. But if you can’t move to Indiana to be closer to your team, then you have to simulate proximity. The best avenue for this type of relationship building, context-finding, and problem-solving is the one-on-one meeting.

One-one-ones are indispensable for nurturing the seeds of accountability, loyalty, and dedication to a shared company culture. Without regularly scheduled reinforcement, team members feel like hired guns. And as legendary venture capitalist John Doerr said: “we need teams of missionaries, not teams of mercenaries.”

If you want people to believe in your company and your product, they first have to believe in you as their leader.

You earn that belief in the work you do in one-on-ones. You earn it by helping a team member work through a difficult issue, guiding them to success in their professional goals, and sharing laugh or a personal story that brings you together as human beings.

Your team members crave this kind of interaction, even if they’d never tell you so. HBR’s survey of remote workers found that the single most important quality in a successful manager was checking in frequently and consistently. Having a standing one-on-one appointment with each team member, in which they know they’ll have your full attention and can share what’s going on, is absolutely essential. If you’re waiting for these conversations to happen organically, you’ll be waiting for a long time.

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2. The Challenge: Trusting Your Remote Employees

After my California-to-Indiana experience, I shied away from managing remote employees altogether. Then, in the late ’00s, I had an opportunity to bring two guys into an important project I was leading. I suspected they’d be incredibly valuable to the team, but there was one big problem. They were based in Florida, and I wasn’t sure I could trust them to prioritize my project over their other work.

Despite my reluctance, I eventually relented and through intentional communication, we developed a close, productive, and long-lasting working relationship. This collaboration helped me reconsider the benefits of remote work, since it gave me the opportunity to work with the best people! It also highlighted a common issue managers experience with distributed teams: trust.

The Solution: Extend Faith, Expect Honesty

I don’t think of myself as a suspicious person or a micromanager. Even so, I used to struggle to trust my remote staff to stay on task when they were at home. It was easy to imagine them doing anything or nothing at all.

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But as Uptick’s Head of Growth Michael Probert pointed out on a recent episode of our podcast, if you can’t trust people to get work done when they’re at home, you probably can’t trust that they’re not watching Netflix at the office when your back is turned.

At the end of the day, if I can’t trust my team members, then they shouldn’t be on my team, remotely or otherwise.

Not every employee will thrive in a remote environment, and it’s important to recognize that as early as possible. When I’m weighing whether to let an existing employee go fully or partially remote, I ask questions in one-on-ones. I about a candidate’s experience working off-site, their time-management skills, and their tendency toward distraction. If your workplace is fully remote, then you should build those questions into your interviews, so you know at the outset if someone will be a good fit for the remote model. But the issue here still comes down to trust. You have to trust that your team members are being honest about their strengths and limitations.

When you’ve built solid remote work processes, you can relax, knowing that you don’t need to constantly look over everybody’s shoulders.

For example, a few years ago I I was completely laid out by an illness for a few weeks. I couldn’t make it into the office, (in fact, I couldn’t even get out of bed!). Still, I had one-on-ones with every key member of my team. The meetings were short and sweet, but they kept work going forward as planned. And I never worried that things were falling by the wayside just because I wasn’t there.

3. The Challenge: A Skewed Perspective of Your Remote Employees’ Status

In my experience, there are two dangers to relying on remote team members to self-report: you only hear the bad or you only hear the good.

I saw the “only the bad” problem in my first remote management experience. Remote leaders only brought me problems, so I never got to see what was going right. I couldn’t even make idle chitchat around the water cooler. But that’s why it’s so important to develop formal processes to celebrate victories, both in one-on-ones and in public channels,. For example, in every one-on-one agenda, you should ask your team member to share something that went right that week.


Then there’s the opposite problem: remote team members who promise that everything is fine, even when they’re quietly drowning in quicksand. The danger is that if managers can’t check on work, they don’t learn about problems until they’ve really gotten out of hand.

The problem is widespread. An HBR study found that when remote workers encountered challenges, “84%” said it took them days to resolve. And 47% said it took weeks. However, it’s important to note that this disconnect in communication isn’t usually because employees are being deliberately evasive. It’s because they don’t know how to say they’re in trouble.

The Solution: Deep Conversations, Probing Questions

In the old days, working remotely meant that all you knew of your employees was an email signature or a voice on a conference call. Back then, getting a real sense of their issues was nigh on impossible. But thankfully, today’s technology has made it possible for managers to have meaningful one-on-ones with their reports.

The advent of video conferencing tools like Zoom and Google Hangouts has fundamentally changed my ability to manage remotely. They allow for one-on-ones where I can make eye contact and read my report’s body language and tone of voice. These are cues I can use to sniff out a problem that might go unnoticed through email.

Of course, remote software can help managers, but you still have to practice the fundamental skill of asking the right questions.

When an employee is having a problem, I know now to search for the root cause instead of just slapping a fresh coat of paint on a broken-down car.

Again, one-on-ones are the ideal time to ask these probing questions since the same questions take on a totally different tone when asked in an intimate, conversational setting. If you send an employee a Slack message asking, “Why is this late again??” they’ll feel defensive or demoralized. But if you have a video call to probe into why something is going wrong and ask how you can help them, they’ll feel cared for and listened to.

Managing Remote Employees with Heart

My favorite part of being a manager is nurturing relationships. I love watching my team members grow, guiding them through hard times, and celebrating their victories. For many years, I thought the only way I could do that was to keep my team close at hand. But these days, part of supporting my team means letting them work in the way that makes sense for them. I can let an employee stay home with a sick kid without them worrying they’re being judged for it. I can respect an employee who finds the office distracting and works better on their own.

I’ve built the skills–and at Uptick I’m helping to build the tools–to ensure that we can continue to have the kind of meaningful relationships that make work worthwhile, wherever we are on the globe.

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