Work Together Anywhere
Entrepreneurs
DropRegion · Lessons from Work Together Anywhere · Lisette Sutherland and Kirsten Janene-Nelson

What Entrepreneurs Can Learn from Work Together Anywhere

A founder who just closed a small seed round sits at her kitchen table studying a hiring plan. She has budget for three people, none of whom will share an office with her. Her only management experience was running a college project team, and most culture advice assumes a room where norms are absorbed by being present. She hires her first engineer, a stranger from another city, and spends the month unsure how often to check in, what belongs in writing, and whether he is quietly struggling. Her calendar fills with ad hoc calls, and a rushed message soon reads as a rebuke. Building a company, she realizes, means building a way of working first.

01 · The Book in One Minute

The whole book, compressed

01Setting Communication Norms From
02Building Rituals Before There Is
03Choosing Tools On Purpose
04Onboarding People You Will Barely

This edition works through 4 core lessons — take them one at a time, not all at once.

02 · Where Are You Now?

What's different for your conditions

Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.

No existing culture to lean on, so every norm has to be invented, not inherited.
Cash and time pressure push founders toward whatever tool is fastest, not fitting.
Hiring and culture decisions land in the same week, with no runway to correct.
A founder plays every role at once, so personal habits become team habits by accident.
Early hires judge a venture's stability by how confusing the first weeks feel.

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03 · Core Lessons

The core lessons, applied to you

Setting Communication Norms From

Setting communication norms from the first hire

The idea

A founder who decides, before the first hire starts, what belongs in a quick chat message, a shared document, or an actual conversation saves the new person weeks of guessing. This is cheaper to set with one employee than retrofit with ten, since habits calcify fast and every later hire copies the first. A short, plain list of channel purposes turns an implicit expectation into something a stranger can follow on day one.

What it looks like

The founder ignores her own norms under deadline pressure, sending urgent decisions through whatever channel is open, teaching new hires the real rule is unpredictability.

Try this

Write a one-page channel guide before the first hire starts, covering chat, documents, and live conversation, and revisit it after thirty days.

Building Rituals Before There Is

Building rituals before there is a team to bond

The idea

Founders often assume rituals are a luxury for larger companies, but a distributed team of two or three needs deliberate rhythm even more, since no hallway lets trust accumulate by accident. A short recurring check-in on blockers and wins, held at a consistent time, gives a scattered handful of people a shared heartbeat. Skipping it because everyone is busy building is exactly when trust is least likely to form on its own.

What it looks like

The founder treats rituals as optional overhead and cancels them whenever a deadline looms, precisely when the team needs the anchor most.

Try this

Protect one recurring, short check-in each week that survives the busiest sprint, and use it for connection as much as status.

Choosing Tools On Purpose

Choosing tools on purpose, not by default

The idea

A founder under pressure reaches for whatever tool is already open, letting a call handle a decision that should have been a document, or a chat channel absorb a policy new hires later hunt for. Deliberate choice means asking what a piece of information needs, permanence, discussion, or speed, before deciding where it lives. Left unexamined, this drifts into a patchwork where nothing is findable.

What it looks like

Tools accumulate one at a time, each chosen to solve one afternoon's problem, until the stack itself becomes confusing.

Try this

Once a quarter, list every tool the team uses and its one job, and retire anything duplicative.

Onboarding People You Will Barely

Onboarding people you will barely see

The idea

For a founder, onboarding a remote hire is founder-led trust-building that happens in the first weeks or not at all, not a checklist handed to someone else. Stretched thin, it is tempting to skip structure, but a hire without early clarity on norms, rituals, and tools spends months guessing rather than contributing, and may leave before the investment pays off.

When the clusters compete

A founder juggling norms, rituals, tools, and onboarding feels the pull between speed and structure most sharply. Every hour spent writing a guide or scheduling a check-in feels like an hour not spent on the product. Skipping structure to move faster tends to produce a scattered team that spends more total hours untangling confusion later, since investors and customers watch only the visible output, never the infrastructure underneath it.

04 · Choose Your Priority

Name one thing, honestly

What caused the most confusion for your team this month, and which channel carried it? If a new hire started tomorrow with no access to you for a week, what could they not figure out? Which tools would you keep if limited to three?


Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.

05 · Put It Into Practice

The practices from this edition

Write a one-page channel guide before the first hire starts, covering chat, documents, and live conversation, and revisit it after thirty days.
Protect one recurring, short check-in each week that survives the busiest sprint, and use it for connection as much as status.
Once a quarter, list every tool the team uses and its one job, and retire anything duplicative.

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06 · Small Experiment

Run this for seven days

Once a quarter, list every tool the team uses and its one job, and retire anything duplicative.

07 · Remember This
If you remember only 4 things
01Setting Communication Norms From. A founder who decides, before the first hire starts, what belongs in a quick chat message, a shared document, or an actual conversation saves the new person weeks of guessing.
02Building Rituals Before There Is. Founders often assume rituals are a luxury for larger companies, but a distributed team of two or three needs deliberate rhythm even more, since no hallway lets trust accumulate by accident.
03Choosing Tools On Purpose. A founder under pressure reaches for whatever tool is already open, letting a call handle a decision that should have been a document, or a chat channel absorb a policy new hires later hunt for.
04Onboarding People You Will Barely. For a founder, onboarding a remote hire is founder-led trust-building that happens in the first weeks or not at all, not a checklist handed to someone else.
08 · Your Next Step

What will you do differently because you read this?

Founders wanting a deeper, more systematic treatment of these habits will find it in Work Together Anywhere by Lisette Sutherland and Kirsten Janene-Nelson, a book built around making distributed collaboration a repeatable practice rather than improvised guesswork. Reading it early can save months of trial and error most small teams otherwise pay for in confusion and turnover.

Also in this series — Lessons from Work Together Anywhere
1. Entrepreneurs
2. Leaders & Managers
3. Teachers
4. Parents
5. Students & Young Adults
6. Career Professionals
7. Creators & Innovators
8. Coaches & Mentors
9. Sales & Customer-Facing
10. Everyday Life