How we moved from work from office to remote work and the mess it created

"I don't know what's happening in my company anymore."

That's what my CEO told me in my first meeting as Chief of Staff.

Not ideal is it?

But in our shift from in office to hybrid to remote during covid,

we'd unintentionally created a digital maze that was suffocating productivity:

- Slack for chats (but only some teams used it)

- Clickup for project management (used by exactly one team)

- WhatsApp for "urgent" updates (everything became urgent)

- Email threads that went nowhere

- Google Drive folders within folders

- Zoom calls to find information that should have been documented

The real problem wasn't the tools

- it was that information lived in silos.

Need to find something?

First find the person who knows where it's stored.

Then hope they're online.

Everyone knew this was broken.

Yet no one was fixing it.

Here's our messy journey of fixing it:

1. FIRST ATTEMPT:

The "Simple" Solution -

Tried consolidating to Slack for communication and Clickup for projects.

Failed because:

We were still splitting information across tools (including good old email).

Just fewer of them.

2. THE CEO CHALLENGE:

My CEO pushed back: "Keep looking. It needs to be simpler."

He was right. Adding tools wasn't solving our core problem.

3. THE BASECAMP DISCOVERY:

Found a single platform for everything: chats, projects, docs, files.

But then came the real challenges:

4. THE REALITY CHECK-

- Teams were comfortable in their silos.

- Some resisted the transparency.

- Private DMs were easier than public discussions.

- "Just one quick WhatsApp" kept creeping back.

5. THE SMALL WINS STRATEGY

Instead of a big bang rollout, we started with one simple habit:

Daily attendance logging - something everyone already did in Slack.

Moved it to Basecamp.

Small? Yes.

But it got everyone logging in daily. (eventually ended this practice)

6. THE SEQUENCED ROLLOUT

Started with internal teams first:

Week 1: Content team (our early champions)

Week 2: HR & Finance

Week 3: Product team

Week 4: Customer-facing teams

Why this order?

We could afford some chaos with internal teams.

But customer experience couldn't take a hit.

7. THE TRANSPARENCY CHALLENGE

The biggest pushback? "Everyone can see everything!"

Exactly. That was the point.

But it was uncomfortable.

Teams used to hiding work in DMs now had to communicate openly.

8. THE CHAMPIONS STRATEGY

The content team surprised us - they loved the transparency.

Used their examples to show others what good looked like:

- How they documented decisions.

- Where they stored files.

- How they turned meetings into actions.

9. THE IMPERFECT PROGRESS

Four weeks in:

- Most teams were active.

- But WhatsApp hadn't died completely.

- Some still hoarded information in DMs.

- Old habits kept sneaking back.

But we also heard:

"I don't get dizzy anymore trying to find stuff"

"Finally, no more app switching!"

"I can actually see what other teams are doing"

10. THE ONGOING REALITY

After Six Months: Was it perfect? No

Were we still finding the occasional rogue WhatsApp group? Yes

Had visibility improved dramatically? Absolutely

Could the CEO see what was happening? Yes

11. THE REAL LESSONS?

- Perfect solutions don't exist - but better ones do.

- Change happens in small steps, not big bangs.

- Transparency is uncomfortable but necessary.

- The simplest tool is usually the best.

- Tool consolidation is about people, not features.

MOST IMPORTANTLY: Sometimes you need to go slower to move faster.

What communication challenges is your remote team facing? Let me know if this resonates.

P.S. As of today, 3 years since this move, we are happily a largely remote first company. Removing communication silos is JUST ONE aspect of building a healthy and thriving remote company. I'll share deep dives on other aspects soon.