How We Make Remote Work, Work

I did not set out to have a remote workforce.

Pre-2020, we were an in-office company with just a handful of remote employees spread across the country for a variety of reasons. Like most people, March of 2020 came with a six-week plan. We would move home, get the virus contained, and return to normal.

Six weeks became six months. Six months became a year. And year-end made it very clear we were not going back anytime soon.

Meanwhile, something interesting happened.
Our team adapted.
Some moved.
Some reimagined their days.

And the idea of asking people to spend two hours a day in the car (the average Seattle metro commute) started to feel less like leadership and more like habit.

After a lot of conversation and a few anonymous surveys, we made the call. We would transition to a fully remote environment. That decision, made in early 2021, still comes up in conversations with other business owners today. Usually in the form of questions like:

“How do you make that work?”
“How do you train people without that osmosis learning you get in an office?”

Or statements like:

“We tried that. It did not work for us.”
“No way. I could never…” (insert a long list of things here)

Here is the thing.
Can remote work work? Absolutely.
Is it the only way? Absolutely not.

If you know remote work will not work for you and your team, you can stop reading now. No hard feelings.

But if you are in the I want it to work, I just cannot figure out how camp, this one is for you.

This is our blueprint.

Set Clear Ground Rules

Remote work does not eliminate the need for structure. It actually increases it. Here are a few of our non-negotiables:

• Cameras on.
  If you are at your desk and not camera-ready, go get ready. You would not show up to an office unpresentable. The same expectation applies here. If we need to talk to each other, we also need to see each other.
• When you are working, you are working.
  Remote work is not compatible with being the primary caregiver for another human during the workday. If you would not leave them alone while working in an office, you should not be responsible for them at home either.

A less common, but more serious, issue is a second job. It happens. It has happened to us. Performance, availability, and schedule conflicts tell a story. When something feels off, we address it directly.

• There is still a dress code.
  It is relaxed, but camera-visible clothing needs to be work appropriate. One step up if you are on a client call.
• Everyone has a schedule.
  Published schedules matter. Clients need to know when you are available. Coworkers need to know when they can rely on you. Remote work does not mean whenever work.
• If you are sick, you are sick.
  Just because you cannot get us sick does not mean we want you powering through a Teams meeting. Rest is still part of doing your job well.

These rules are not complicated. The difference is that we actually uphold them.

Retrain Your Leaders for Remote Leadership

Most remote work failures are not employee failures. They are leadership failures. Leading remotely is not harder than leading in person. It is just different.

Here is what we focus on:

• Intentional connection.
  Each PayNW team starts the day with a 15-minute huddle. That daily rhythm matters. I recently interviewed someone seeking a new remote role. Her number one reason for leaving? She only saw her manager about once a week. Connection cannot be accidental.
• Cross-team connection does not just happen.
  We hold bi-weekly all-hands meetings with breakout rooms and simple human questions. Not work updates. Not metrics. Just space to connect with people outside your department.
• Clarity becomes non-negotiable.
  When you are not watching how someone works, you must be crystal clear about expectations, priorities, and what “done” actually means. Strong training supports this, which we will get to next.
• Do not only show up when something is wrong.
  Remote managers who only reach out to correct quickly become invisible until something breaks. Review tickets. Read client feedback. Call out good work publicly. Let people know they are seen.

Remote leadership is still leadership. It just leaves less room for assumptions.

Build Rock-Solid Onboarding and Training

A new remote employee without a plan will float. And floating feels a lot like failing.

Here is what we do:

• A welcome box that says, “You matter.”
  Before day one, equipment arrives. So does PayNW swag and a welcome sign. The message is simple: you are not an afterthought.
• A full calendar on day one.
  No one should log in wondering what they are supposed to do. Meetings and training are preloaded for the first two weeks so new hires can focus on learning, not guessing.
• Intentional introductions.
  Every new employee meets the full leadership team within their first four weeks. Faces become familiar. Departments make sense. Connections form early.
• Mentors and shadow time.
  This is where the osmosis question comes in. Training is often better when both people are looking at the same screen instead of one person squinting over another’s shoulder. New hires shadow multiple teammates and have a dedicated mentor responsible for their success.

Done well, remote onboarding builds confidence faster, not slower.

Design In-Person Time That Actually Matters

Remote does not mean never together.

Once a year, we bring everyone together for a highly curated in-person experience. Themes. Sessions. Connection. Development. Fun with intention.

We just wrapped our 2025 event in Nashville, and it deserves its own post. When you only get a few days together, they need to count.

Remote work is not a magic fix.
It is also not a doom sentence. It is a choice.

If you choose it, choose it fully. Set clear expectations. Retrain your leaders. Invest in onboarding. Design in-person moments that actually matter.

Your team is already telling you what is working and what is not. The real question is whether you are willing to listen and adjust.

What is one change you are willing to make so remote work truly works for your team?

Gratefully,