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Why Trust is the Key to Your Remote Work Strategy

At different points in my career, it’s felt like there exists an underlying belief that “time in office” correlates to “work effort” — such as one manager’s guidance to “be aware of the bad optics of leaving before five” or leaders suggesting that “the people who tend to get into the office earliest are usually the ones who get promoted.”

At one former company, a quarterly “Grinder” award was given to the sales rep who got into the office the earliest and stayed the latest. The underlying message was this person was in the office the longest, and therefore is the hardest working and most committed.

Over time, I noticed the reps selected for the “Grinder” award weren’t at the top of sales leaderboards, which made me question the validity of “time in office” as a cultural tenet. It turned out I wasn’t the only salesperson to come to this realization, and the award was viewed in a negative light. This recognition that was meant to be inspirational became de-motivating across the broader sales team.

Another company eventually parted ways with its highest-achieving sales rep when that person moved out of state. Even though there was genuine interest in retaining this star employee — and the average cost of replacing a sales rep is $115k — the fear of remote work won out.

I’ve heard managers say “My reps would be on YouTube and ESPN all day if they didn’t come into an office.”

Despite the rise of remote work, there remains a pervasive and genuine fear that allowing teams to work from wherever they choose will result in a dip in effort and production across the team. The truth is, those fears are well founded. 

When you start from a lack of trust — if you believe people will be less productive when you’re not around to look over their shoulder — your team will inevitably perform worse than teams with greater independence. 

Lack of trust is the real issue.‍

Thriving remote teams start from a place of trust‍

Google’s Project Aristotle found that psychological safety is the most important trait shared by high-performing teams, and that autonomy, respect, competence, and social status are critical inputs to build psychological safety. 

When the manager of a team believes their team is incapable of meeting a baseline level of productivity without his or her physical presence, it’s readily apparent there’s a breakdown around employee autonomy, perceived competence, and ultimately respect. 

People have a tendency to gravitate toward the expectation you’ve set for them, and when a manager sets the bar too low, it can become a self-fulfilling prophecy that the team will underachieve as a result. 

Plus, it’s no fun being on a team like that — either as an employee or a manager. 

When you search online for “remote work,” it’d be easy to assume we’ve figured out remote work from the multitude of thought pieces and best-practice listicles. Yet the majority of remote work thought leadership misses the key blocker that holds most companies back from embracing a remote setup: trust. 

Not all jobs can be done remotely, but for those that can, the biggest blocker — more so than any tip or tool — is the fear surrounding the question: “Do I trust my employees to be effective when we’re not in an office environment?

Further Reading

5 ways to build trust when your teams are working from home indefinitely — Fast Company

How to Build Trust With Remote Employees — Gallup

The 5 Ways We Build Trust on a Fully Remote Team and Why It’s So Valuable — Buffer

This Is How Leaders Build Trust With Remote Teams — Forbes

Modern tools make trust easier

When I worked as an investment banker a decade ago, our VPN connections were so unreliable that you couldn’t be nearly as effective when you were away from the office. The software we have available to us now simply didn’t exist, so it was hard to stay connected and truly engaged with coworkers the way you can today.

Today, we have remote access to our work via laptops and cell phones. Chat tools like Slack, video conferencing tools like Zoom, and video messaging tools like Loom make telecommuting easier than ever before.

That isn’t to say remote work is a piece of cake — doing it well requires a shift in mindset, tooling, and technique. But if you’re willing to give it the benefit of the doubt and lead with trust, there’s zero indication that people are more effective working in the office than elsewhere. 

The ability to work remotely, at least some of the time, is something 99% of employees desire. With that kind of morale at stake, it's worth exploring remote work with an open mind, even if it means parting with relics of workplace culture from a time when remote work wasn't a viable option (e.g., “you don’t leave your desk until 30 minutes after your boss leaves”).

To make remote work effective, we have to let go of some of these long-held ideas.

Related: A Curated List of the Best Remote Work Resources

Making the switch from the office to remote

Before there was broad understanding of how COVID-19 would affect us, or the Bay Area imposed a lockdown, I asked my CEO if I could work from home — my wife was newly pregnant and I wanted to work from home as much as possible. Still, given my conditioning, I felt a pang of anxiety bringing it up with him. I told him I was happy to come into the office when we have important meetings or candidates onsite, and that I was open to discussing alternative paths if he had any concerns.

Joe, who is a thoughtful leader and is known to take his time with responses, didn’t miss a beat.

“I am 100% supportive of you working from home, and I have zero concerns about this.”

Boom. Just like that. 

What happened next? I worked from home. My wife felt better about me working from home. I felt better about it. And — to my surprise — I got a lot of work done. Work that I was super proud of, work that required deep collaboration with teammates in different states and countries.

So did the rest of the Loom team, including releasing a Herculean effort across all parts of the organization to make Loom Pro free for teachers and students as a response to the global crisis. Seeing our ~70 teammates band together to produce such an impactful effort against a tight timeline bolstered my conviction that remote work can be incredibly collaborative and effective, and that you don’t need to be co-located to do something incredible.

Screenshot of Slack channel for COVID-19

A screenshot from the Slack channel dedicated to Loom’s COVID-19 response

For veteran remote workers, these may not be revelations. When you have a team committed to effective distributed work using best-in-class tools, remote work isn’t a lofty goal. Effective and impactful remote work is 100% achievable, even for a relative newbie like me. 

The key theme that I saw throughout this project was clear and intentional communication, and demonstrating trust in each other throughout. 

Screenshot of Slack channel for positive reaction to COVID response

Lead with trust, early and often

Trust is at the root of every fear associated with remote work. A lack of trust is the reason that company created a “Grinder” award to incentivize more time spent in office. A lack of trust is the reason that company didn’t make a remote exception for it’s star rep, because it feared less productive reps would push for a similar arrangement. And a lack of trust was the reason I had a pang of fear when asking my CEO to work from home more often a few months into a new job. On some level, I didn’t trust my ability to perform at the level I hoped to. 

Luckily for me, my latest manager didn’t feel the same way, and this hasn’t been the case. It’s easy to talk about leading with trust and expecting people to rise to the occasion, but it’s another thing to practice it. Joe’s reaction to my request made me feel trusted, supported, and motivated to do my absolute best work. 

This is a feeling all leaders hope to evoke in their team, and supporting remote work a meaningful way they can demonstrate trust in employees. There are a number of best-practices and tools to make the shift to remote work easier and teams more productive, but all successful remote works begins with trust.

Oh, and baby Prowitt is due in October 2020. You can trust that Mommy and Daddy are pretty stoked. 

(If you thought you’d get through this without a dad joke, you were wrong, my friend.)


Pete Prowitt family photo


Apr 9, 2020

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