5 key essentials for leading a remote team

I take care of the remote Onboarding team here at Timely, and I’m incredibly proud of this group of people – not just because of the results they deliver but of how they interact as a team.

Building and leading a remote team isn’t for the faint hearted. There are a bunch of obvious technical barriers to overcome when you start out as a remote company, but they’re generally very easy to solve.

The biggest and most difficult challenges relate to people. Looking after a group that is geographically removed from you is a different ball game to working in the same office space.

There are five key things I’ve learned on this journey so far, which by sharing I hope will help others to grow remote crews that are happy, thriving, and smashing it out of the park:

1) Hire amazing people who will rock the remote life

Obviously, one of the first questions you’ll ask someone when hiring for a remote position is whether or not that’s actually something they want. It’s easy for them to give a token answer and gloss over the point, but there’s nothing more important than how they react here.

Do they answer like this?

“Yes, I’ve thought quite a bit about this aspect of the role – I think I’ll be fine working remotely. I quite like my own company and have a spare bedroom with a desk, so…yes, I’m sure I’ll quite enjoy it.”

Or like this?

“Are you serious? Working remotely will be AMAZING. I’ve had a taste of it before with some freelancing work I did, and the flexibility it gave me was perfect. Being able to work remotely is one of the big reasons this role and your company really jumps out at me. Yep – amped about it.”

They both said ‘yes’ to the remote work aspect, but only one of them really understands and means it. The first person may well have enjoyed working remotely – but they didn’t actually know at that point, and neither can you. That’s a big punt to take.

These are both actual answers from interviews I had with candidates at Timely. Guess who got the role and went on to absolutely rock their work-life blend?

Remote working is not for everyone, and you need to be very sure early on that the people you hire will thrive in this unique environment.

2) Obsess over writing ability and attention to detail

90% of the communication you’ll have with your team will be written – whether it’s via email, your project management tool, support tickets or team chat. The Onboarding team at Timely get together face-to-face regularly (at least once every fortnight), but aside from a couple of Google Hangouts here and there the rest of our communication is written.

Clear, concise written communication is key.

There’s nothing more frustrating than being part of a team discussion that degenerates into confusion and misdirection because someone drops their writing guard and explains something poorly. There’s no body language, no sound, no visual clues at all to contribute context. What should have been a five-minute conversation has turned into 20 minutes of untangling. It’s inefficient, frustrating, and completely avoidable.

The ability to clearly and concisely communicate a point in writing is the single most important skill a remote worker can possess.

3) Create an environment of trust and transparency

Obviously you need to trust the people you hire, but it’s arguably more important to put this spotlight back on yourself. Does your team trust you?

Leaders are born from the trust of their team. Before that’s given they’re just a person with a title. Trust is earned, and it can be hard when you’re not face-to-face with people every day. Your team can’t hear your voice, see your face and mannerisms, feed off your confidence, watch what you obsess over, shout out questions from their desk as they learn, or grab you for a quick chat on the way to the coffee shop. All of that in-person stuff normally defines how quickly rapport develops, or not. Working remotely removes many of these opportunities, and building trust becomes infinitely harder.

But – we can still take those general principles and apply them to remote.

Live loud in your role. Be open, honest, confident in your convictions, and be available.

Be awesome at the day to day tasks your team work on. Muck in, lead by example. Never is this more important than in a remote team. Let your work be your voice, particularly in the beginning. People will listen to you because you’re their boss – they have to – but they’ll start to trust and follow you if they’re inspired by your work.

They’ll also start trusting your opinion on that work, and your ideas for direction as a team to make things better. They’ll start trusting you as a person.

It is no trivial thing to gain the trust and support of a group of people sitting miles and miles apart on the other side of the city/country/world.

It’s also worth pointing out while we’re talking about trust that good remote workers are never a slack-off risk. Quite the opposite. If anything, they’re a burn-out risk.

If someone is slacking off that’s my mistake, because they clearly weren’t ready for a remote working lifestyle and yet I still offered them a role. The right people remove that concern completely, and in almost three years at Timely I’ve never once questioned the productivity or dedication of someone on the team. It’s almost unfathomable as a concept.

I’ve questioned focus, sure – but that’s different and not related to dedication and responsibility in any way. More on that next.

4) Foster a continual feedback loop and course correct, course correct, course correct

You’ve hired great people who are going to wake up and smash it out of the park each day, but when you’re not there to see what they’re doing how can you be sure they smashing the right things? Are they placing value on the most important metric-movers, or are they getting bogged down in stuff that isn’t adding value? Are we all on the same page?

Make sure you all talk. Foster openness and discussion in team chat throughout the day.

Ask questions. Check in on little things regularly via DM – not for a productivity status update (your team is smashing it, remember) but just to touch base.

Encourage your team to be vocal in chat. To share what they’re working on, what they’re struggling with, where they’ve had success, what made them laugh, what they’re eating for lunch…stay tuned to all of it, and grab the chance to course correct on focus whenever you feel it straying from the team’s main goals. Your crew usually won’t have the visibility, context or experience you do – they’re relying on you to be vocal with those course corrections. You’re the focus safety net – if your team knows they’ll be subtly course corrected and kept on target, they’ll speak up sooner rather than later with where they’re at.

No one likes to feel directionless and lost, or that they’re working on something that doesn’t add value. Create an environment where feedback is constant and your team will always be pushing towards common goals.

5) Regularly get together face-to-face – and make the most of it

The Onboarding team at Timely gets together at the office here in Dunedin City every fortnight. We chat, joke, plan, scheme, and work alongside each other physically for a while. It doesn’t feel all that different to any other day – more, an extension of a normal remote day. It’s a rich experience we all get a lot from because we know it’s a bit out of the ordinary. We soak it up and make use of every second we’re together.

It’s also my chance to sit down with each of the team one-on-one for an hour or so in what is probably my most important role – a sounding board. We talk about dreams, passions, career goals, life struggles, workload, professional development ideas, random half-formed thoughts on how our team could do something differently, the quality of the coffee we’re drinking, how awesome the surf was in the weekend…

We leave those catchups – both the 1:1s and the overall team day – feeling refreshed, excited, and heard. We leave as a stronger team who can’t wait to wake up the next day and smash it for each other all over again.

It’s not always feasible to get together face-to-face or as regularly as every fortnight, but make it happen whenever you can. Bonus points for regularity. You’ll be amazed at what a day together can do to strengthen trust and focus in a team.

Leading a remote team has its own unique set of challenges, and it’s not for the faint of heart. Most of the time you can’t see your team – their faces, body language, moods or screens – and it’s not hard to start feeling in the dark. Is everyone working on the right stuff? Are they doing ok, or feeling lost? Did I really get across the importance of that thing we talked about last week? There’s way too much to get through today, they must be feeling swamped…are they getting bogged down? They know I’m here for them, right?

All that’s on you. Hire people ready to rock the remote life, obsess over the quality of written comms, foster an open, supportive environment and build trust with and among your team, and never, ever stop leading by example.