Remote management: Advice from a career flex worker

In the last few days, I’ve seen a lot of excellent advice for first-time teleworkers, from online tool recommendations to suggested actions and behaviours, to ensure maximum productivity.

What I didn’t see much of are tips on managing remote workers. So I wanted to share some of the practices I’ve collected over the years, as I’ve been a “flex worker” in one form or another since 2009: a part-time remote worker, a digital nomad, a gig worker, and a manager responsible for remote workers (while doing it remotely myself sometimes).

These points may be particularly useful for first-time managers who may have found themselves in the midst of a management style that requires as much flexibility as network bandwidth.

Establish a list of activities or expected deliverables you would like to get from your teleworker for each day.

This may seem like micromanagement, but it is not. It lays out expectations ahead of time, and allows both parties to agree on what is reasonable and attainable without the need for constant check-ins over emails, project management tools, etc. This also helps you understand what the team will be delivering at the end of each week, so you can brief up as needed.

I usually ask my team to provide me with the list of things they’d like to deliver on the day before they’re teleworking (if it’s a daily arrangement). This allows me to see if their priorities are aligned with the team’s or the organization’s, and I can course-correct ahead of time. At the end of the day, I usually know what they were able to do, and can also measure the effectiveness of the teleworking arrangement over time. The same approach applies to long-term remote workers, except it tends to be more of a weekly list, with milestone deliverables on certain days.

The other benefit to this approach is that each employee is taking ownership of their productivity, and is responsible for what’s on the list they’ve provided. It’s been my experience that those who believe they are responsible for their work tend to deliver on time, and feel personally responsible for the quality of the work they are producing.

Do not send emails or schedule calls at lunch, or after stated working hours.

I know from my own personal experience that plowing through something to get it done feels much better than pausing for a break and picking up the work later. But when you’re managing others, it’s very important to set healthy boundaries and stick to them. Your team may feel the need to stay behind and respond to each message right away, and in doing so, they forego their own lunch hour or breaks. I learned from one of my former teams that I caused undue stress by bombarding their mailboxes on my telework day. They felt a needless sense of urgency as I did not communicate that I was simply going through my list, and there is no expectation for immediate responses. Now, I schedule emails to go out either after lunch or the next day. I’m also clear on what is something they need to respond to soon, and what can wait.

If you’re managing a whole team remotely, do a morning check-in with everyone.

Managing a few employees remotely for a short period of time is quite different from having a whole team that works remotely. Taking the pulse of the group in the morning helps you better plan the day based on the fresh data you are able to gather in those first few minutes. This is especially important at times like these, where our own personal anxiety is present and sits right next to us. This quick virtual gathering (which can also be done through texts or chat) is also a signal that you are available to discuss any issue that may have surfaced overnight, because you are allocating the first part of your working hour to your team’s needs.

Check your personal biases at the door.

You may have previously worked in environments where telework is uncommon. You may have also been discouraged from asking for remote working opportunities because it wasn’t a “serious move”, or the company culture considered teleworkers “low performers on vacation.” Of course, the last few years have provided us with enough studies and data to know that remote workers are more productive, and cost less in overhead.

When I joined a more skeptical environment a few years ago, I made a point of collecting data about my own productivity for two years to quantitatively gauge how much work I was doing. My average rate of performance was 140% more than my regular output on any given day (I used numbers of emails, phone calls, and plans or content developed as my performance indicators). That put a stop to some of the commentaries on telework.

Let me say that again, for the cheap seats in the back: check your biases at the door. If you don’t, you are not going to be an effective remote manager.

I still encounter modern-day skeptics who equate telework with an opportunity to binge watch Netflix. And after a few minutes of conversation, it becomes apparent that their previous working experiences included a manager or a culture that was against telework, so they learned the behaviour and inherited the bias.

Let me be clear, it’s not your job to defend your remote workers or telework itself all the time, but it may be part of your work to document what is working and what isn’t, and help push for slight tweaks in culture. I once gave up an office to prove a point about remote work.

Build in the mechanism to address unproductive remote workers.

This is a difficult one, and is not applicable in times like this, but it is worth remembering for the future. You need to create a process or policy for remote work that allows you to pull the plug on telework arrangements that are unproductive for your organization or team. In most of the cases I’ve encountered, it comes down to an employee who does not know their own working patterns, is unable to cultivate better remote work habits or mimic their office tempo, and needs your help because they are drowning. Remote work — that doesn’t arrive because of extraordinary circumstances like the current one — is not for every personality. Having a mechanism to talk through expectations, work on milestones, and end an ineffective telework arrangement is the best thing you can do for your team and your organization.

Ultimately, managing remote workers is a matter of trust. They need to trust your ability to communicate priorities and expectations clearly, see that you are open to emerging tools and workflows, and believe that you are available to them when they need help. You need to demonstrate trust in your team’s ability to do the work, and know when to spot an issue and have tough conversations about shortcomings (yours or theirs).