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BUSINESS

6 Keys to Managing a Remote-First Workforce

6 Keys to Managing a Remote-First Workforce 40
6 Keys to Managing a Remote-First Workforce 41

Kapil Kale. co-founder and COO, Tremendous

I’ve been an executive at both in-person and remote-first work cultures. The former was during my time at AngelList, and the latter at the company I co-founded, Tremendous.

Tremendous has been a remote-first company since its inception in 2011, about 8 years before the global pandemic forced office workers to stay home. Initially imposed as a temporary precaution, remote work quickly became the preferred modus operandi for the majority of the workforce.

According to McKinsey, 87% of workers who have the option to work remotely at least some of the time jump on the opportunity.

But transitioning from an in-office model to a remote-first culture comes with growing pains, because working in the office was pretty good. You had happy hours, a break room with snacks, maybe bean bag chairs to make things feel a little casual and fun.

For a lot of companies, remote-first work is not nearly as productive or enjoyable as it could be. That’s because many companies are trying to retrofit the office experience to a remote-first world.

The way to build a solid remote-first work culture is to create a culture that fits the medium, rather than forcing the medium to fit the culture.

To make the model work, we had to keep a few important considerations in mind. Below are some of the practices that worked for us.

Align protocols around a remote-first work environment

Aligning the expectations of both your leadership team and your employees around a remote-first work environment ensures your teams stay efficient but flexible. 

For example, at Tremendous, we recruit engineers from much of the world to find talent capable of building complex software at scale. Our only rule is that people generally be available online between 12pm and 3pm Eastern Time.

This lax but defined parameter sets a precedent: we want our people to be available to answer questions, communicate over Slack, or hop on a quick Zoom call during peak work hours to foster collaboration across time zones and teams. But as long as the work gets done, it doesn’t matter if they start at 7 and end at 3 or start at 10 and end at 6.

Building these protocols into the foundation of your company from the outset helps to attract the right talent. For us, it’s made it a lot easier to recruit top talent around the world who understand our mission and our way of working. 

This creates a self-sustaining culture of people who believe in remote-first work, want to maintain a healthy remote-first work culture, and know what it takes to keep the productivity machine ticking along under remote-first conditions.

Eliminate practices that don’t serve the team

There’s one area in particular where remote work fails to compete with in-office life: Meetings. Nobody likes meeting online. Long meetings in person can be stimulating and invigorating, but long meetings over Zoom drag on sleepily. It is what it is.

At Tremendous, we limit meetings as much as possible by doing the majority of our communication over Youtube, Loom, Notion, Slack, or Github.

One key guideline we impose on our team is to hold discussions in open Slack channels, public Notion docs, or team-wide Asana boards whenever possible. That way, all communication is searchable and publicly archived.

We also stress the importance of creating project and initiative briefs on Notion, which serve as thorough documentation of all progress and status updates. If we decide to launch a meeting to discuss a project further, we include notes from the meetings in the brief.

These briefs aren’t just for ongoing projects. They’re also for proposals for new services someone may be interested in, a new initiative someone wants to launch, or any other suggestion with reasonably large-scale implications.

To make a proposal, the person with the idea has to first write out the background and logic for the potential move. Then, others can comment on the proposal in the document.

This documentation also makes onboarding a lot easier for new recruits. Rather than sitting through hours of training, they can get themselves up to speed pretty quickly and autonomously by skimming through existing artifacts.

Meetings, of course, still have their place in a remote world. But they’re only used sparingly, and only when there’s a topic of conversation where all participants expect a lot of discussion to take place. 

Hire remote-first managers

Accountability, management, and problem-solving look a little different in a remote world. In the office, you can stick three people in a room, give them a problem to solve, and they’ll organically negotiate, compromise, and iterate until they’ve come to a resolution in a pretty timely manner.

But connect those same people via chat, and things get a bit harried. It may be hard to get everyone online at the same time, response times may lag or occur so instantaneously that it’s impossible to follow the thread of conversation, and one team member may miss half the conversation due to another discussion happening simultaneously in a separate channel.

Asynchronous communication and problem-solving requires a bit more structure. You need to choose a leader to manage collaboration and accountability, communicate expectations, and align the group on goals.

Choosing the right leader (or manager) for a remote-first world is super important. These managers need to be accustomed to a specific method of communication, a certain cadence of checking in with team members, and a structured way of reporting on metrics and tasks that’s suited to asynchronous work.

“If you say it twice, write it down.”

In addition to being a bit boring, meetings on Zoom aren’t easy to revisit for important information. Yes, you can record Zoom meetings and watch them later, but sitting through a meeting and then rewatching it isn’t a great use of time.

At Tremendous, we consciously minimize meetings by encouraging employees to create a paper trail. Our internal rule is, “If you have to say it twice, write it down.”

There are so many ways to do this effectively — there’s about a million collaboration tools designed to  communicate, track, and record ideas so that everyone at your company knows the important stuff. 

We also use broadcast videos and screencasts to share information. This is largely for important, cogent conversations where there isn’t too much back-and-forth.

I put together mini-broadcasts for my team all the time. Instead of holding a lengthy all-hands meeting, typically someone on leadership records a video (which you can watch sped up on your own time) and solicits written questions. 

When we hold the actual meeting, our time together is brief and spent almost entirely in discussion. We also simply cancel all-hands meetings if there isn’t anything pressing to discuss.

Whether you use written communication, video broadcasts, or a combination, having an online record of important information that people can revisit is key to successful remote collaboration. 

Collaboration and writing are critical skills 

 In the same way you should hire managers who have a proven track record of working in a remote-first culture, it’s also important to screen for candidates who thrive in a remote environment.

We do this in two ways at Tremendous. First, we see how well a candidate can move a project forward with minimal direction. We gauge this through a time-limited test assignment.

Second, we test candidates on their writing skills. Effective written communication is an essential skill across departments and roles in a remote-first work environment. We screen every candidate with a writing assessment related to their role to get a read on how well they’d be able to communicate if Slack, Gmail, and Notion were their only options.

For instance, as part of our engineering interviews, we prompt candidates to create an architecture document. The highly-qualified candidates pull in online collaboration tools to sketch out designs, and then transfer those designs into clear documentation that others can comment on without needing to launch a meeting. Those who feel lost without a whiteboard probably aren’t a good fit

We’ve turned down qualified candidates who spoke eloquently but struggled to write clearly. 

Success in a remote-first world isn’t just about raw talent — it’s about collaborating with team members under specific conditions.

There’s value in consistency 

Figuring out how work is going to get done now that your workforce is spread across the country (or the globe) is another key consideration.

The popular hybrid work model can actually create some level of inconsistency across the organization. Those who have the option to come into the office a couple days a week get to have spontaneous conversations around the water cooler that people too far to commute completely miss out on.

More importantly, because thorough documentation is so important at Tremendous, consistently working fully remote across the org ensures everyone understands the value and necessity of recording everything either in writing or on video. 

With some people going in-office and others not, it would naturally feel less important to create a record of certain conversations and ideas for the people who can simply swivel around in their chairs to ask a clarifying question.

At Tremendous, we opted to design the company with no offices to avoid this issue. In fact, until not too long ago, our CEO’s apartment was the official company address.

Eliminating the central office puts everyone on equal footing. Everyone uses the same avenues to build rapport and the same channels of communication to relay ideas. And everyone on a video call participates in the same way.

Company offsites build culture

There are a bunch of benefits to developing authentic, personal relationships. It nurtures trust between team members, builds morale, and fosters a sense of community.

With casual conversations largely stripped from worklife in a remote setting, it’s important to find ways to help people connect and build friendships.

I’ve only found one way to do this, but it works. It involves forcing the entire company to go to the same place and talk to each other for a couple days a year.

The focus of these offsites is firmly fixed on having fun and socializing. It’s like adult summer camp. And when it’s over, everyone feels energized by their new connections with colleagues.

Company off-sites condense all the socialization that would happen in an office setting into two or three team-building trips. We also encourage employees to get together in smaller group settings with their teams at least one other time. They tend to actually involve some work, such as strategic planning, but there’s still plenty of time for fun. 

Is it the ideal substitute for in-office banter? Maybe not. But it’s a lot better than a happy hour over Zoom.

Conclusion

Companies willing to embrace the zeitgeist of the modern workforce have a literal world of talent out there to choose from.

Today’s workers want flexibility and trust from their employers. They want to work from anywhere, and they want their employer to care more about what they get done rather than when they do it. 

At Tremendous, we’ve kept these values at the forefront since the beginning. So far, it’s going pretty well.

About Author:

Kapil Kale is the co-founder and COO of Tremendous. Kapil previously co-founded GiftRocket, an online gift card company that went through Y Combinator and became profitable. Prior to that, he worked as a Senior Associate Consultant at Bain & Company. Kapil has also worked as a Portfolio Team member at Insight Venture Partners. Kapil Kale graduated from Dartmouth College with a degree in economics.

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