How to Manage a Remote Team as an Online Entrepreneur

As a freelance writer, I’ve been a part of more remote teams than in-person ones. Some of them were in the formal setting of a content agency or company I’d work for. Others were informal groups, with the main goal of online creators to support each other.

Whenever I’m a part of a remote team, it’s a peculiar experience. On the one hand, it seems like I just interact with a computer — type in messages, send emails, and get responses. All along, I’m alone in the room. It doesn’t feel like I’m interacting with another human.

But then it strikes me: All those messages go to and come from real people! The way I communicate over digital channels matters. I’m still collaborating, even if that’s hard to grasp due to the physical experience of solitude.

This makes remote work tricky — but what’s even trickier is managing a remote team as an online entrepreneur. A remote leader needs to maintain a sense of that human element, even if it’s not directly accessible. They need to account for the feelings and motivations of their team, even if those are hidden behind the Zoom window or a Slack message.

At the same time, they need to ensure things get done and business moves forward.

To understand how to manage a remote team effectively, I spoke to Shelley Prevost, a psychologist and co-founder of Big Self School. Together with her husband and business partner Chad Prevost, they’ve been building a 100% remote startup to help people with mental health and provide psychological education. All of this in a pandemic — which made remote working the only feasible way to make it happen.

Apart from leading and managing the Big Self School team, Shelley is an educational psychologist and coach. That’s why I was particularly interested in her perspective on managing remote teams. How does someone with such a vast knowledge of the human psyche handle this complex challenge?

Here are the five key insights I took away from our conversation.

1. Know what to delegate and what to do yourself

It’s one thing to shift to remote work when you already have your business up and running. But it’s a completely different one to start from scratch 100% remote.

Shelley and Chad did the latter. When the pandemic hit, they knew they wanted to offer mental health support and psychological education by sharing their work online. As they started building Big Self School, questions arose around what they needed to do themselves — and which tasks should be delegated.

Here’s how Shelley told me they dealt with that:

“When deciding who to hire, I start with these two questions:
1. What’s our core value proposition and what product or services need to be created from that?
2. What work should I not be doing and who can I hire to help with that?
Thanks to these questions, I have more clarity around where we need to go as a company, what I should and should not be doing in that, and a deep trust in my intuition when it comes to finding and hiring the right people.”

Key Lesson: When building out a remote team as an entrepreneur, it’s important to know what you shouldn’t be doing and what tasks need delegating. It may be tempting to try and do it all by yourself — but that’s usually not the best use of your skills and time. Once you know where you’re headed, identify a few key areas where you need professional help and then, get it.

2. When hiring, trust your gut and values

When I asked Shelley about the biggest challenges of hiring remotely, she told me that “it’s harder to build that trust and cohesion when you’ve never met the people you work directly with.”

When hiring remotely, you miss a lot of information and cues that would otherwise help you make the decision. For example, you can’t see the candidate’s body language or how they behave in a group. Their experience and portfolio they present you with are also hard to verify. After all, anyone can type in anything in their LinkedIn profile, can’t they?

That’s not to say that you shouldn’t interview your remote staff and try to get as much information about them as you can. But in the end, you may need to also just listen to your gut — and, look out for whether the person you’re planning to work with “vibes” with your business in terms of values.

When Shelley and Chad set out to find psychologists to work with on the Big Self School curriculum, this approach did the job. Even though most of those people were from outside their network, Shelley says:

“The first person we hired was a friend here locally. She helped with marketing coaching services. But as we started building out more workshops, it was clear that we needed help so we set out to find subject matter experts in psychology. Almost everyone we worked with (besides our first employee) was a stranger. And, luckily, they’ve all been effective, smart, and capable people.”

Key Lesson: Knowing what drives your remote employees — or, what their core values are — can tell you a lot about them. Together with your intuition, this can help you decide which people are a good fit for your remote team.

3. Understand what motivates your people

As I continued to speak with Shelley, I realized she holds quite a unique mindset when comes to managing a team. She doesn’t just expect people to do the job for her. She also wants to ensure that working for Big Self School aligns with their path and supports their growth.

This is huge, especially when your business hires a lot of freelancers and independent contractors. Those people’s professionals lives are often quite fluid, which means they may stop working for you when they get a better gig or need holidays. Knowing what motivates them to work can help you keep them engaged and contribute their best to your business.

That’s why it’s so important for Shelley to understand what drives her remote team members and where they are on their journey. However, she also acknowledges that people coming and going is inevitable to some extent:

“This is part of owning and building a business, and we try to keep a growth mindset around turnover. What can we learn? How can we help people stay who want to stay? I try really hard to find out what motivates every person and what their goals are for their work — if we can be a part of helping them to create that, that’s awesome! If they evolve in ways that don’t sync up with what BSS is, that’s ok, too.”

Key Lesson: A part of managing your remote team is understanding what motivates them and where they currently are in their career. If you can align your business objectives with helping employees find fulfillment, you’ll have a happier and more productive team. Working for you won’t be just another job for them. They’ll also see it as a place for their personal and professional growth.

4. Know your communication tools

To keep the work meaningful for your team and profitable for you as a business owner, you need to be flexible. For that, excellent communication is a must. But how do you ensure this when your team is spread across the country — or even around the world?

There are many actions you can take to keep everyone in the loop and engaged. Regular check-ins, proving time and space for socializing, emotional support, and mentoring — these are some that experts recommend the most often.

Whatever you do, Shelley says it’s important to know which communications tools you use for what purpose. This doesn’t just apply to communication across the team. It’s also about keeping track of your entrepreneurial ideas, breakthroughs, and plans — i.e. communicating with yourself.

“I start and end every day with my Full Focus Planner. Unresolved tasks or tasks I need to delegate go to the appropriate person — sometimes in Trello, sometimes in Slack, sometimes I get on a call with someone. I rely on Trello for long-term project management and Slack is our go-to for quick check-ins and questions.”

Shelley also mentioned a lot of brain dumping and sharing of Google docs as a way to record ideas or simply ease the entrepreneurial mental load. It’s important for her to know which type of communication happens where and what tools she needs for which parts of her work.

Key Lesson: Be intentional about the use of both digital and analog communication tools to stay on top of things. As a bonus, it’ll also help you manage your remote team because it’ll set clear expectations around what type of information they can find in which communication channel.

5. Keep the knowledge when people are gone

If you’re running an online business, a big part of your team likely consists of freelancers. As mentioned before, this may mean your staff turnover is higher than in a company with a more traditional employment model.

Shelley and Chad understood this early on. That’s why they make sure to record each employee’s contribution and save knowledge about the project they work on. Shelley told me, “We try to keep the knowledge bank of everyone’s content in Google Drive so that if they leave the team, we can continue the work with someone else. “

Additionally, Shelley and Chad try to use those and other data to make better business decisions in the future:

“One thing we’re learning is to slow down and look at the data instead of plunging into whatever idea we’ve fallen in love with. Chad and I are both passionate people and get excited about our work, so learning to slow down, look at the data and insights, has been extremely hard, but helpful for us.”

Key Lesson: As an online entrepreneur, you have at least two good reasons to record the contribution and content created by your remote team members. First of all, it’ll preserve their knowledge even when they quit working for you. Secondly, it’ll provide you with relevant data to make better business decisions in the future.

Closing Thoughts

Effectively managing a team is a complex task in any circumstances. But as an online entrepreneur, you have an even bigger challenge in front of you:

You need to lead and manage a group of people you’ve never met — and who haven’t met one another.

However challenging, that’s not impossible. With the technology we now have, you surely can do it. To manage your remote team effectively and, at the same time, empathically, remember these five tips:

  • Be clear on which tasks are yours to do and which you should delegate.
  • Involve your intuition and values in the hiring process.
  • Align your business objectives with the motivations of your team members.
  • Know which communication tools serve which purposes.
  • Record the knowledge and contributions of your remote team for future reference.

Apart from that — enjoy the process and be proud of yourself! It’s quite something to bring together a bunch of people who live all over and enable them to create something together.

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