Remote Team Management for the Modern Company

By Chris Arnold

Over the past half decade-plus, the remote culture has steadily crept its way into everyday business conversation. From large corporations to smaller team outfits, we commonly see at least some form of the work from home option, or even a work from “anywhere” option when considering remote travel opportunities that may also arise.

It would seem as the traditional rules and expectations of the work/life balance continue to evolve, we’re primed to observe this growth only continue in an upward trajectory. As remote work environments grow, so too will the need for understanding management of such teams.

At our company, every team member is not only 100% remote, but we’re also entirely dispersed. From coast to coast, our team is built on — and relies upon — a strict diet of clear expectations, targeted outcomes, and communication tools.

For business owners and team managers, how can you, too, be prepared for this change? Perhaps you’re already seeing the transition take place.

After 10 years working remotely, and managing a variety of small teams throughout that time, these are a few select big ticket items to remote team management success.

Setting Expectations

Being remote begins in the interview process

Managing remote teams should begin early and often; starting with the interview process. Asking pointed questions right away will give you a sense of the candidate’s ability to work in an environment that requires a fair amount of autonomy.

• What is your definition of a work/life balance? Explain what that looks like for you during a typical work day/week.
• Have you worked remotely in the past? If so, was it entirely remote, or some other form of working remotely?
• What is your biggest struggle with working remotely, and why?

By immediately getting into a candidate’s head from the onset, you start to learn about how they may or may not be successful in your particular work environment.

For example, our small digital studio requires that we’re available when our clients are available. We’re not building a product for ourselves, but rather building various websites and web products for clients who require our attention when they’re at the office.

Unlike some businesses, we can’t work odd shift hours and still maintain strong relationships with paying customers. Consider how schedules impact your bottom line, and be clear about your high level expectations starting from day one.

Tracking Progress

Scheduling routine checkins to follow progress and results

When there isn’t a water cooler to loiter around, or company lunches to connect over, making the time to check in over a video call becomes paramount. In my experience, even the most independent employees appreciate being communicated with under more casual circumstances.

The purpose of tracking progress is multi-fold. Not only is it an opportunity for management to step in and provide a more private assessment (what’s been going well; areas of improvement), but it provides a clear space for the employee to shed light on how it’s been for them, too.

During these progress checkins — usually monthly for at least the first few months — we set up a call to informally chat about recent experiences. What questions are we asking? Most aim to get the employee to open up about their experiences, positive or negative.

• How has your working experience been in the past (time period)?
• Are you coming up on any challenges with your (home office, co-working office, etc.) setup?
• What can we do to better support you and the projects you’re working on?
• How can we be better at communicating in any area of our day to day?

These checkins allow us to casually discuss how things have been going on both sides of the proverbial coin. There’s no sense in getting stuffy about these meetings — not at our company, at least — but we don’t hesitate to be honest.

What is going well and what needs improvement can be objective at times, so do your best to remain open to transparent conversation. On rare occasions you may not be expecting the feedback you receive, but it’s better to have a clear sense of the employee’s situation versus being in the dark.

Communication Tools

Touch-points for a remote team to feel less remote

There are plenty of tools posts floating around these days, so the focus here is less about exact app recommendations and more about what tools, in a general sense, should be in place.

At a high level, anticipate most work environments will need tools similar to these to cover the main bases. I make a brief note about what we’re using at Authentic and why:

1. Macro level communication:

• Email for more privacy and high level conversation

2. Client communication and project management:

• Basecamp for project updates

3. Team communication:

• Slack for dialogue
• Calendars for meetings

4. Tasked communication:

• Asana for assignments and deadlines

5. HR communication:

• 15Five for the company pulse
• Harvest for time tracking

It’s important to know where someone is physically, what they’re working on, and what the next step is for their particular workload. Whether that’s a casual chat to check in, or taking a peek at deadlines in a todo app, knowing where employees stand is important. Otherwise, how will you know what is happening and when things are getting done?

Much more goes into the finer points of managing team members using this outline of tools, but speaking for our team, it’s important to have a strong understanding of where time goes and when things are checked off the list.

This extends to employees, too: they always know what they’re working on and what is expected of them that day, week, and month.

Scaling Management

For teams in the 10’s or larger

We have a small, sub-10 person team. Even though the team is lean, the management of that team still feels like a big-team task at times. What then is the model for growth beyond a small team?

My experience in this realm is admittedly light, but from what I’ve read on the topic, and through the observation of larger remote teams, it comes down to replicating process from within.

In other words, if the team is 24 people strong, dividing the greater team into sub-teams of eight makes sense. Each team operates in the same way, and yet tackles different projects at the same time, and within the same process.

Company structure, process documentation, and actually executing in your particular industry will certainly evolve with this growth. But the business model of deploying the “same” team 3x in this example allows for continued refinement of your process, and the ability to nip/tuck on a team-by-team basis to further hone your execution.

Remote teams at the corporate level are an entirely different beast, and something I’m not qualified to speak on. Teams like Zappos and Amazon have experimented in and around remote the past few years, and with varying levels of success.

It takes quite a few hands to transition a corporation to a remote culture; a greater experiment that I’m not sure we’ve seen banner success with yet.

Taking the Leap

Embarking into remote management

Managing a remote team isn’t a one size fits all proposition. Depending on your company size, culture, and relationship to product or clients, things may be quite different.

And yet, in the end, it comes back to being clear with your needs as a business to those you bring on board. Clarity with your expectations, purpose, and mission, all equate to a team that better understands not only what they’re doing, but why they’re doing it.

Team dynamics on the remote level are ever-evolving, and as a manager of a dispersed team, it’s up to you to think outside of yourself, and of your business, to make sure your team is poised to produce the best outcome possible.

Chris is a Partner at Authentic Form & Function, where design captivates and technology converts. He went remote 10 years ago for the work/life balance unattainable in the traditional workplace. You can follow him at @chrisfarnold on Twitter.

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