Building Context in Remote Teams: The Missing Link

The Context Crisis in Remote Work

Here's the hard truth about decentralized leadership: pushing decision-making power to the edges only works when people have the CONTEXT to make good decisions.

You can give people all the authority in the world, but without context, they're just in a dark room, looking through a straw, bumping into the couch.

Last month, our digital team spent three weeks building a feature that the account management team had already decided to deprioritize – all because that context stayed trapped in a private Slack channel.

My bad.

That's when it really hit home: context isn't just "nice to have" in a decentralized organization – it's the oxygen that keeps it alive.

The Traditional vs. Decentralized Divide

The Old Way: Top-Down Control

In a traditional company, decisions flow from the top down. The bosses have the context, they make the calls, and everyone else executes.

The New Way: Distributed Decision-Making

But in a decentralized team (my preferred approach)?

Everyone needs to be a decision-maker.

That account manager?

They need to understand the business strategy to make good choices.

That IT support person?

They need to know what's happening in recruiting to properly set customer expectations.

Just last week, one of our managers made a call to modify a customer's plan on the spot because she understood our retention strategy and pricing philosophy.

In an old-school setup, that would have required three levels of approval.

The Military Parallel: Situational Awareness

Context is the word I like using instead of what military commanders call "situational awareness."

The military spends enormous resources making sure everyone knows what's happening on the battlefield.

Why?

Because without it, people make bad decisions or, worse, no decisions at all.

Your remote business isn't a battlefield, but the principle is exactly the same:

decentralized execution requires centralized context - a common picture of what the hell is going on.

The Remote Context Challenge

When we shifted to remote work, most companies obsessed over tools and schedules.

Zoom for this, Slack for that, status meetings at 9.

But they missed something fundamental: In an office, context happens by accident.

In remote work, all of that ambient information vanishes unless you deliberately rebuild it.

Building Context Deliberately

So what’s the solution?

Here are some of my thoughts - but I’m constantly working on these - that’s how important I think it is.

1. The Buddy System

First, assign working-level onboarding buddies.

Not managers – actual people doing the work.

At Sagan, every new hire gets paired with someone who's been in the trenches.

They spend their first few months not just learning their job, but understanding how everything fits together.

2. Public by Default

Second, default to public communication.

Private channels are where context goes to die.

We try to make everything public except HR and sensitive matters.

When our recruiting team started sharing their challenges in public channels, we saw our sourcing team spontaneously offering insights that transformed our approach.

Public communication principles:

• Transparency builds ambient context

• Findability is crucial

• AI can help surface relevant information

3. Meaningful All-Hands

Third, run meaningful all-hands meetings.

Not status updates – those can be written down.

We do weekly all-hands WITH small group breakout sessions where people talk across teams.

This can feel like “forced fun” but it is very worth it if people get into it.

4. That’s My Job - The CCO

I’m the Chief Context Officer. One of the most important things I do in the company as a leader, is to build context!

I am highest up on the mountain, so I can see the farthest.

In a meeting today about a new project, we spent the first 30 minutes talking about WHY this project was important/useful - and about 5 minutes talking about what it actually was.

Sets the team up to make strong, fast, high quality decentralized decisions.

Future Experiments

We're also experimenting with new ways to build context:

• Internal podcast plans: I want to have a regular podcast/newsletter to celebrate internal wins and challenges, for an internal audience only

• AI-powered knowledge sharing: AI is really good at taking a ton of info, and making it accessible.

• Strategic in-person offsites: Hard with a global team, but worth trying to figure out.

Conclusion

When you're not just building a remote company – you're building a context-rich environment where good decisions can happen anywhere, anytime. That's worth investing in.

Final thoughts:

• Context is a strategic advantage

• Build systems for sharing deliberately

• Make context-building a core value

Yallah Habibi,

Jon

Passage of the Week:

 If a single action was sufficient to stamp the character of any virtue upon the person who performed it, the most worthless of mankind. might lay claim to all the virtues; since there is no man who has not, upon some occasions, acted with prudence, justice, temperance, and fortitude.

But though single actions, however laudable,  reflect very little praise upon the person who performs them, a single vicious action performed by one whose conduct is usually very regular, greatly diminishes and sometimes destroys altogether our opinion of his virtue.

A single action of this kind sufficiently shows that his habits are not perfect, and that he is less to be depended upon, than, from the usual train of his behaviour, we might have been apt to imagine