How We Work Now: 5 Keys To Effective Remote Leadership

Patrick Holly
Patrick Holly
January 26, 2023
January 26, 2023
How We Work Now: 5 Keys To Effective Remote Leadership

While I may lead a global, remote team now, that wasn’t always my reality. I used to work in an office. When that was the only way I knew work to be, it felt fine. Productive, normal, comfortable.

Like lots of people, I first started working—and leading—remotely in the spring of 2020. And at first it felt…uncomfortable. New. Different. But as I settled into a remote workflow, I discovered that I could work creatively—and build a team—better and more effectively than ever.

The process of getting comfortable in this new, remote environment, wasn’t something that happened overnight, though. It took intentional effort on my part to cultivate a rewarding and functional remote-first culture for my team.

Sure, it might help that I now work for Upwork, which has been facilitating and supporting remote work for over 20 years, but I still had to unlearn some of what I thought I knew about management and embrace a new way of growing and interacting with a team.

Through this process, I've looked closely at what made the "old" way of working—being in an office where we're all together—functional. And I focused on the key elements, the core essences, that can apply to just about any team, remote or not:

These are universal, human concepts that you already know—it’s just a matter of adapting them to the way we work now. By focusing on these elements, you can improve the way you manage remote teams, hone your creative output, and create a virtual work environment that simply works.

Five ways to succeed

1. Kindness

One of the most insidious things I’ve ever encountered in the workplace is a lack of trust. If people don’t trust each other, remote work (or in-person work, for that matter) won’t be successful.

Bonds of trust can be built through acts of kindness. And we don’t need face-to-face interaction or water cooler conversation to be kind to each other. We just need to be a little more intentional about creating opportunities to cultivate kindness and build trust with our remote team members.

Here’s an example for you: my team does a sync every Monday. This isn’t unusual in itself—I know many of you start your weeks this way too. But what’s unique about our syncs is that we don’t just talk about work. Instead, we take time to share things that we appreciate about each other.

The first time I tried this with my team, to be honest, I could hear crickets in the background. Me, spouting my thanks and appreciation for my team members, followed by total silence. This is how it progressed for the first ten or so attempts—it was like pulling teeth from an alligator.

But then, it all clicked. I logged on for a team meeting and everyone began giving thanks for each other, without me starting the process. It feels natural now.

Cultivating kindness takes practice. It might take 10 or 20 tries. It might feel awkward. It might feel uncomfortable. But once you make it a regular part of your workday, you’ll find that it unlocks new levels of trust and communication in your teamwork.

2. Communication

This brings me to the second essential element leading remote teams: communication. Communication goes hand-in-hand with kindness.

By making it a point to push your communication beyond simply discussing the next work deliverable, you can begin to learn more about your team members as people. What are they like? What motivates them? Do they have unique interests? How do they communicate best?

I try to start work-related conversations the same way I would if I were meeting someone for coffee. If I were meeting a colleague in person, I wouldn’t swing open the door and immediately start talking about work. Instead, I’d say hi, ask them about their day, and engage in conversation.

I make a point to do this with virtual team meetings and one-on-one video calls, too. It helps to reinforce the fact that we are all people with unique lives and interests—not just boxes on a screen.

I also remind my team that we need to assume good intentions. Sometimes, nuances that we’d pick up on in face-to-face communication are lost when communicating in a remote setting with tools like Zoom or Slack.

In these mediums, someone might say something that seems, at first glance, curt or short. Rather than bristling, assuming good intentions helps you remember, “Hey, wait, no. That’s just Dave. Dave is cool, Dave has my best interests at heart. Something might be going on in Dave’s world today, so I’m going to check in with him and see how he’s doing.”

3. Craft

Better communication allows you to create elevated work.

We might risk limiting ourselves creatively if we always work alone. But working to improve communication within our own teams and cross-functionally, we improve our craft together. This requires approaching the idea of collaboration differently than in an in-person environment.

In an office, you might throw all your ideas up onto a board and let it stew, adding to it as colleagues drop in to share new perspectives and ideas. You might not be able to recreate this exact experience digitally. When working remotely, though, you can leverage technology to create a collaborative space in which you execute your craft with others.

This might look like using collaborative document editing tools, making Loom videos to put a face to feedback versus just sending an email, or working in a shared whiteboard space. And above all else, it involves putting trust in each other’s craft.

As a team leader, I love knowing that I can go to bed and wake up to find that my team members in different time zones have been working on new ideas and contributing to projects while I’m asleep. I have trust in them and their craft; I know that I can rely on them to do good work.

4. Humility

For all of the above to work, though, you’ll need a healthy dose of humility.

Humility in remote work involves understanding that in some ways, we’re all making this up as we go along. Our teams grow and change, project goals shift—and we all keep learning new ways of working together.

I think that when the pandemic hit in early 2020 and remote work became the norm overnight, a lot of us tried to force our in-person company culture into a remote model. It’s understandable—it’s the way most of us knew how to work. And as I think we can all agree, it wasn’t the best environment for an introduction to remote work, and it didn’t lead to the best work-life balance.

Now that many professionals are settled into working remotely, we can focus less on output and more on exploring new avenues. This means accepting that sometimes we’ll be wrong, sometimes we’ll hit a friction point, and sometimes we’ll have to go outside of our comfort zones.

We have to be open and accepting not only of our colleagues, but also of ourselves—we’re going to make mistakes. We just need to have humility (and humanity) about it.

5. Drive

Finally, a strong drive to do great work is essential when leading a distributed team.


While drive can be a very personal, internal thing, you can help to foster it among your team members by supporting them, providing clarity around roles, setting clear expectations, and actualizing ideas in ways that foster accountability.

This doesn’t mean that cultivating drive involves micromanagement. If anything, I’d say it’s the opposite of that. Creating drive on your team involves leaning on the bonds of trust and healthy communication you’ve created and saying, “Here’s what we need to do, here’s your part in it, and here’s when we need to have this done.”

The process should be empowering and give agency to your team members by letting them work in the ways that suit them best—all while driving toward a shared goal.

There are three things that I feel really help my team create both an individual and a shared drive to do good work:

  1. We have creative flexibility to do our heads-down work how and when we see fit, but when we’re in a virtual brainstorming session together we’re all aware of what we need to bring to the table and when.
  2. We have a dedicated member of our team who documents our collaborative work and idea generation. This makes it easier for us all to remain accountable and driven.
  3. When someone new joins the team, they know exactly what their role is within the team and the larger organization as a whole. We can communicate these details to them during onboarding with just a few sentences—not pages and pages of documentation. This keeps communication streamlined and roles aligned, so everyone can focus on bringing their best work to the table.

Taking the complexity out of leading a remote team

You don’t have to come in and, in a single day, completely overhaul everything about the way you work remotely. But by starting at the top of this list and working down, you can begin cultivating a healthy and productive remote work environment.

And remember that effective remote leadership isn’t just about supporting your team—it’s about getting the support you need, too. This starts with finding the right professionals for your remote workforce and using tools that help you implement processes effectively without spending too much time on all the back-end details.

Upwork can help with the unique challenges faced by large remote teams. From staffing support to full-service solutions provided by Enterprise Suite, there’s help for building your high-performing remote team. Learn more about the many ways to use Upwork and explore what’s right for how you work now.

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Patrick Holly

Patrick Holly is a multidisciplinary creative whose career has run the gamut from agencies like R/GA and AKQA, to brands like Apple and Uber, to serving as Steph Curry’s creative director. At Upwork, he leads a team of writers, art directors, designers, and strategists who are changing how the world thinks about work. Prior to joining Upwork, Patrick was the brand director at Harley Davidson, overseeing content, PR, social, and brand partnerships.

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