How To Lead From Home (Not Just WFH)

Chris Litster
The Helm
Published in
6 min readMay 28, 2020

I recently joined 75 of our employees on a Zoom call for something we called Morning Coffee at the Buildium Cafe. To be honest, it was a little chaotic. No one was talking about work. Some people were playing music. Some were in their pajamas. A couple of babies and several pets were even present.

And, from a leadership perspective, it was the best possible way we could have spent company time.

Plenty has been written about working from home but not about leading from home. As the head of a 200-plus person property management software company adapting to fully remote working during COVID-19, I’ve been thinking a lot about this. I’ve wrestled with the same hurdles as everyone else — getting the technology right, juggling time with family, and, yeah, fighting the urge to wear pajama pants all day. But for leaders, there’s an added challenge: motivating people, deepening relationships and getting sh*t done at a distance during a crisis.

To be sure, there are so many serious issues that businesses and individuals are shouldering these days, especially as the economic and health fallout from COVID-19 grows. To work for a great company and have a great team is a privilege in itself right now.

Being Boston-based, we’ve had some “dry runs” working remotely due to snowstorms and had some process in place; however, a prolonged period of working from home for all of our employees across the globe is something altogether different. Here’s some of what we’ve learned (so far) for leaders out there on leading from home:

It’s still business … but not business as usual.

A critical job for leaders right now is to establish continuity, from an emotional perspective and from a business one. We’re still doing our regular meetings — morning standups, code reviews, weekly check-ins — albeit, via Zoom. This is what businesses do. And there’s something reassuring about this continued routine.

But, really, nothing is normal. For leaders, it’s equally important to allow space for that strangeness and the emotions bubbling up. We’ve got dedicated Slack channels for WFH questions and oh-my-God-how-do-I-teach-my-kids-algebra panic moments. We know people are adjusting to new circumstances and need extra time, emotional outlets, and even a virtual shoulder to cry on.

It’s just as important to model that vulnerability yourself as a leader. I didn’t intend to tear up during one of our daily exec stand ups recently. But, all at once, it hit me: Boston was being shut down. Traditions like my son’s high school graduation were being cancelled. And I knew my colleagues — my friends — were also struggling with their own stresses and challenges.

But my team didn’t even blink at my emotional moment; they rallied around me. That support and empathy allowed me to get back on my feet so that I could turn to them and say, “Now, how can I help you?”

Virtual “bumping-into-each-other” moments are priceless.

Back at the office, I don’t have an actual office. Instead, my stand-up desk is in the middle of everyone, and it means I’m always accessible. I live for the in-the-moment chats (“Christina, did I just hear that they accepted the role?”) and personal check-ins (“Hey, how’s your grandpa feeling?”) that don’t ever make it onto a formal meeting agenda.

These random encounters are the farthest thing from wasted time. Small talk is proven to support rapport and trust. It’s how relationships are built, ideas exchanged and loyalties cemented, and it’s an essential ingredient in any strong team.

So even in this WFH world, it’s important for leaders to make time and space for people to “bump into each other,” outside of scheduled meetings. Though bars were closed and the parade cancelled for St. Patrick’s Day (a pretty important day here in Boston), we got dressed up in green and met for a virtual video-chat happy hour. We have a casual group check-in over “morning coffee” on Zoom. And aside from project and team-based Slack channels, we’ve got fun ones, too, like #push-upalooza, where one of our customer support leaders gets us (including me) to hit the floor every hour.

The butts-in-seats approach to leadership never really worked — and it really doesn’t work now

Now more than ever, it’s not a leader’s job to (virtually) stand over people’s shoulders monitoring “workscreen-time” (the new twist on the old “butts-in-seats” metric). Instead of making sure people aren’t watching Netflix, energy is far better spent helping employees find ways to meet their goals and ensuring they have the support needed in this new environment. This has always been the essence of good leadership, and it’s really the only way to lead at a distance.

Of course we’re still checking in on performance metrics and KPIs, as we always do. But the onus has shifted more to employees to manage their own time, communicate challenges, and find solutions together. Yes, things have changed. Boundaries between work and home have blurred like never before, bringing new challenges in terms of time management, focus and productivity.

But what doesn’t change is trust. If you’ve hired right and built the right culture, that trust extends beyond office walls. It means you’ve got capable people who take pride in what they do and do it well. It means you’ve set realistic performance goals and empowered your team with the independence to achieve them. And it means you’ve built real relationships in the office, not just transactional ones — so people are there for each other and for customers, rather than just clocking in.

With a dispersed team, having a single source of truth is more important than ever

This is a time of change, rumor and uncertainty. People are worried about getting sick. They’re worried about their jobs. Our mental health is vulnerable. As we work from home in physical isolation from our work support network, it’s incumbent on leaders not to allow an information vacuum to open up.

And the reality is your teams are looking to you for support. Edelman’s 2020 Trust Barometer shows employees trust their leaders more than they do the government or the news media — and this applies doubly in times of crisis. Being that one-stop source of info — even if you don’t have all the answers (and you should be up-front about that, too) — is a key way to keep everyone on the same page and relieve anxieties.

I’m emailing my team regularly with a summary of updates that impact our immediate lives — from colleagues affected by the crisis to critical customer relationships, the health of the business overall and even news on new hires. These emails are a chance to distill what really matters from all the noise and reiterate that we’re aligned and in this together. Critically, this isn’t a unilateral decree from me. These messages come from speaking with leaders throughout the company and getting their buy-in, first.

There’s one subtext for all these suggestions: leading from home really isn’t possible unless you’ve fostered trust, and built strong relationships, from the start. If your culture is founded on foosball and snacks, that’s going to fall apart pretty quickly once your team has scattered into their home offices. Caring about your team, and ensuring they care about each other, is a cornerstone of effective leadership — whether you’re in an office together or working miles apart.

This article was originally featured in Business Insider. Stay up to date with my latest by clicking the “Follow” button above or follow me on Twitter.

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