Rosie The Riveter

Rosie the Riveter is a cultural icon representing American women who worked in factories, shipyards, and other industrial jobs during World War II, many of whom replaced male workers who had gone off to war.

Beyond the propaganda, Rosie represented a real shift: millions of women entered the workforce, proving they could perform skilled, demanding jobs. Though many were forced out post-war, Rosie’s legacy represented the long-term trend toward women’s increasing workforce participation.

Covid and Remote Work

Just as World War II transformed who entered the workforce, COVID changed when and where we work. The traditional 9-to-5 office model gave way to flexible, location-independent schedules.

Is remote work here to stay and will it follow the same path as women in the workforce post World War II?

There’s been some return to pre-pandemic office norms because:

• Remote-async doesn’t fit all roles

• Some prefer in-person work

• Empty offices remain a challenge for companies and communities

However, the remote/hybrid model appears here to stay. Why?

• Generational comfort: Younger workers embrace digital-first connection.

• Real estate correction: Surplus office space will normalize over time.

• Net benefits: For companies and employees alike, remote work delivers more value—if we actively design for its unique challenges and strengths.

I have been remote or hybrid since 2016, four years prior to COVID.

Since then I have worked exclusively with companies that are remote first or mostly remote across multiple time zones in the US and around the world.

The following are best practices I’ve experienced and observed from companies successfully managing remote teams.

Remote Teams

Clarity over Control

Documentation

A common problem across all companies is undocumented institutionalized knowledge.

In person, it’s easy enough—although not ideal—to stop in and ask “Deb from accounting” or whomever you think possesses the knowledge you need.

Remote companies require institutionalized knowledge to be well documented and easily accessible.

Clear Metrics

Your OKRs (Objectives and Key Results) and KPIs (Key Performance Indicators) should be clear, widely known and understood so everyone knows what success looks like.

Promote Transparency

The most effective companies I’ve worked with provide the ability to keep up with the day-to-day of major initiatives.

For example, key projects will have their own Slack channel where all participants communicate openly around tactical and strategic issues for the project.

Async-First Culture

Asynchronous Check-ins

When working in the corporate world I often thought, “This meeting could have been an email.”

Most meetings can be replaced with written updates or shared docs.

Video Documentation

Platforms such as Loom—a screen recording video capture platform—are life changing.

Here are a few examples of how I’ve used it to either replace meetings or make them 10x more productive as a prep tool:

• Documented end-to-end monthly accounting close processes

• Provided walk-throughs of complicated financial models

• Explained new product ideas so teammates have time to formulate questions and thoughts ahead of the synchronous meeting

Focus on Process Not Tools

Online debates rage around the best team communication tools. Be it Slack, Teams or any other platform the tool matters less than the process.

The best remote companies I’ve worked with proactively:

• Thoughtfully design and manage channels and their purposes

• Set expectations for proper use

Deliberate Culture Architecture

Company or team culture is by design, not by accident.

Non-work Channels

The virtual equivalent to the water cooler are non-work channels in Slack or Teams. Consistently, the ones I notice that get the best engagement across all team members are:

• #Food

• #Holidays (or seasonal)

• #Travel (or vacations, etc.)

• #Random

In-person Events

Humans are social creatures and face-to-face time is essential. If you’re company is remote, a portion of savings otherwise spent on physical space should be reallocated to in-person meet ups.

A common cadence I’ve seen work well is:

• Company wide—1 to 2 times per year

• Team level—2 to 4 times per year

If you have clusters of team members in proximity to one another, more frequent happy hours or other social events can be organized as well.

Onboarding

Whether your new hire is a contractor or full-time employee, integrating them to the culture and processes ASAP will improve performance and retention. The best practices include:

• Assigning them a peer buddy or mentor

• Keeping a descriptive org chart or roster accessible. Include photos of each team member, their background and non-work related information

• Maintain excellent documentation on company processes and procedures

Output Over Optics

I used to work at a big company where certain employees would brag about the vacation they had accumulated, ie not taken. I never heard them talk about accomplishments or output, just “effort”.

The best teams essentially ask the question, “Did the work get done?” As importantly, they track real metrics to answer the question.

Further, the metrics are highly visible and everyone knows who is contributing. When done correctly, there is no where to hide.

If your company is considering implementing keyboard or mouse tracking software, reconsider.

Are you running an adult daycare or a company?

Set clear output metrics (customer satisfaction, project timelines, etc.) and allow people to manage themselves to accomplish the goals.

Support Well-Being Proactively

Remote work comes with many downsides including:

• Isolation - One of the strongest indicators of employee retention has always been whether or not someone has a “best friend” at work. A decade ago, “co-worker” was a top answer to “Where did I meet my spouse?”

• Always on - The only thing I enjoyed about my commute prior to going remote was the “mental commute” or shift from work to home. Remote workers often feel they are somewhat always at work since both share the same location.

Creating a deliberate culture as discussed above will help offset feelings of isolation.

Favoring output over optics will lessen the pressure of remote employees feeling like they need to answer Slack messages at 10:30pm.

Here are other well-being practices that are employee favorites:

• Meeting-free days

• Home office budgets

• Personal development stipends

• Dedicated personal development days

• Robust and flexible PTO

The Next Step

I hope your reaction to reading this was something like:

“Aren’t these best practices ideas all companies should use?”

If so, you would be correct.

I am neither a remote-work Pollyanna or an in-office purist like Elon Musk.

However, I do believe much of the so-called benefits of in-person work—the ability to pop-in for a quick chat, better monitoring of employee productivity, etc.—are crutches supporting poor management and workplace practices.

Remote work eliminates those crutches so you MUST utilize these best practices or it will fail.

How could you improve your own team—remote or not—by beginning to implement these practices into your own organization or team?

My goal with The Leap is to provide you each Saturday with the knowledge, tools and lessons learned to help you get started and keep going toward building your future. 

Whether you are making the leap to startups, solo-entrepreneurship, freelancing, side hustles or other creative ventures, the tools and strategies to succeed in each are similar.