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Frequently Asked Questions

Quick answers to common remote work questions

Core Concepts

What is remote excellence?

Remote work isn’t a policy. It’s a system.

Most companies treat remote like a benefit. Flexible hours, work from anywhere, no commute. That’s thinking small. Remote done right is a competitive advantage. You hire from everywhere. You operate across time zones. You build a culture of written clarity that scales.

Remote done wrong is isolation, miscommunication, and slow death by video call. The difference isn’t the tools. It’s the system.

Read more: Principle 1 - Remote Is a System, Not a Perk


What’s the difference between remote-first and remote-friendly?

Remote-friendly is a lie.

Remote-friendly means offices exist, and remote workers can dial in. They’re accommodated but not centered. Meetings happen in conference rooms with one remote person on a screen. Decisions happen in hallways.

Remote-first means everything is designed for distributed work. Even people in the same city communicate as if they weren’t. Documentation is the default.

Remote-friendly creates two classes of employee. Remote-first creates one. The middle ground serves no one well.

Read more: Principle 20 - Remote-Friendly Is a Lie


Why do most remote teams fail?

They recreate the office online instead of designing for distributed work.

They meet constantly because they haven’t learned to write. They expect instant replies because they haven’t embraced async. They watch employees because they haven’t built trust. They scatter information across twelve tools because they haven’t picked one place.

Remote that looks like office work done from home isn’t remote. It’s the worst of both worlds.

Read more: Principle 7 - If It’s Not Written, It Doesn’t Exist, Principle 2 - Stop Watching Your Employees, Principle 16 - Pick One Place and Stick to It



Trust & Leadership

How do you build trust in remote teams?

You don’t build it. You start with it.

Give new hires real responsibilities immediately. Full system access. Meaningful work. The message: we believe you’re capable.

Most organizations do the opposite, with limited permissions, probation periods, gradually expanding access. That says: we’re watching. We’re waiting for you to fail.

The rare person who betrays trust will reveal themselves either way. Default to trust. Adjust if needed.

Read more: Principle 3 - Trust Is the Default


What replaces surveillance in remote work?

Outcomes.

If someone isn’t delivering, that’s a conversation, not a software purchase. Tracking tools don’t fix performance problems. They just make symptoms visible while creating new problems for everyone else.

When things go wrong, resist the urge to monitor more closely. Address issues directly. One person failing doesn’t justify surveilling the team.

Tracking software is an admission of management failure. Uninstall it.

Read more: Principle 2 - Stop Watching Your Employees, Principle 5 - Tracking Software Is a Management Failure



Communication

Why is writing the core skill of remote work?

If it’s not written, it doesn’t exist.

Verbal agreements evaporate. Slack threads get buried. Meeting decisions disappear. Writing isn’t overhead. It’s the work.

The discipline of writing forces clarity. If you can’t write it simply, you don’t understand it well enough. Clear writers think clearly. They explain context. They anticipate questions. They make async communication work.

The test: Can someone who joins in six months find and understand this decision? If not, it doesn’t exist.

Read more: Principle 7 - If It’s Not Written, It Doesn’t Exist, Principle 22 - Hire Writers


Why should we kill the daily standup?

Daily standups made sense in offices. They make no sense for distributed teams.

You’re either forcing some people into terrible time zones, or excluding others entirely. Either way, it’s a meeting that could be a message.

Replace it with written updates, posted at the start of each person’s day. What you did. What you’re doing. What’s blocking you. Everyone reads on their own time. Context is captured. Time zones don’t matter.

Read more: Principle 11 - Kill the Daily Standup


When should remote teams meet synchronously?

Rarely.

When you call a meeting, you’re saying: this topic is so complex, so nuanced, so dependent on real-time interaction that async won’t work. Most topics don’t qualify.

Before scheduling, ask: can this be a document? A recorded video? A written proposal with comments?

A one-hour meeting with 8 people isn’t one hour. It’s eight hours of your company’s time. That meeting needs to create at least eight hours of value. Most don’t come close.

Read more: Principle 12 - Meetings Are Toxic, Principle 9 - Real-Time Is for Emergencies



Tools

How do you avoid tool sprawl?

Resist.

Every new tool creates overhead. Another login. Another place to check. Another set of notifications. Teams accumulate tools like barnacles. Someone suggests a new one. It solves a problem. You adopt it. Repeat. Soon you’re drowning.

The best tool stack is the smallest one that works. Before adding, ask: can an existing tool do this? Is the problem bad enough to justify the cost?

A tool you don’t use is better than a tool that fragments your team’s attention.

Read more: Principle 15 - Every Tool Is a Tax


What tools do remote teams actually need?

Fewer than you think.

Pick one place for documentation and stick to it. Pick one place for communication. Pick one place for project tracking. That’s it.

The specific tools matter less than the discipline. What matters is that everyone knows where things live, information doesn’t scatter, and you’re not constantly switching contexts.

Every tool is a tax. Pay it only when you must.

Read more: Principle 16 - Pick One Place and Stick to It, Principle 15 - Every Tool Is a Tax



Hiring & Onboarding

What skills matter most for remote employees?

Writing and autonomy.

Hire writers. Clear writers think clearly. Poor writers create confusion. Every message needs follow-up, every document raises more questions than it answers. A brilliant engineer who can’t communicate in writing will struggle remotely.

Don’t hire people who need babysitting. Remote will break them. Hire people who’ve demonstrated autonomy, who’ve built things without supervision, who’ve owned projects end-to-end. Past behavior predicts future behavior.

Read more: Principle 22 - Hire Writers, Principle 23 - Don’t Hire People Who Need Babysitting


How do you onboard new hires remotely?

Your docs are your onboarding.

If onboarding requires weeks of shadowing, constant questions, and tribal knowledge transfer, your documentation is failing. Good documentation means new people can get productive fast.

Use each new hire as a test. Where do they get stuck? Those are documentation gaps. Have new people improve the docs as they learn. They see the gaps clearly because everything is unfamiliar.

Onboarding should shrink over time. Each hire makes it better for the next.

Read more: Principle 26 - Your Docs Are Your Onboarding



Culture & Connection

How do you build culture without an office?

Intentionally.

Remote work is lonely. You don’t bump into people. You don’t overhear conversations. The ambient human contact that offices provide for free disappears entirely.

So build it. A dedicated social channel with zero work talk. Optional virtual coffees, randomly paired, no agenda. Team channels for non-work interests.

The key word is optional. Create the spaces. Stock them with low-pressure activities. Let people choose their level of participation. Your job is to make connection available and easy. Not to make people connect.

Read more: Principle 27 - Connection Is Infrastructure, Principle 28 - Humans First, Functions Second


Are offsites necessary for remote teams?

Yes. Non-negotiable.

Bring your team together in person at least once a year. This isn’t a perk. It’s essential infrastructure.

Video calls transmit information. In-person time builds relationships. There’s something about sharing meals, walking together, staying up too late talking that video can’t replicate. These relationships sustain remote collaboration for the other 50 weeks.

Yes, it’s expensive. Still cheaper than a month of office rent in most cities. And the return is higher.

Read more: Principle 29 - Meet in Person. Once a Year. Non-Negotiable.



Scaling

What breaks first as remote teams scale?

Everything that was informal.

What works at five people won’t work at fifteen. The informal coordination that felt effortless starts creating confusion. The single Slack channel becomes chaos. The weekly all-hands becomes unwieldy.

Watch for the signals: information gets lost, decisions take too long, people don’t know what others are doing, new hires struggle to ramp up.

When you see these, adapt. Add structure. Create team boundaries. Formalize what was informal. Don’t resist the evolution.

Read more: Principle 31 - What Worked at Five Won’t Work at Fifteen