What remote work taught me before remote work was a thing.
What Remote Work Taught Me Before Remote Work Was a Thing
I started my career in 1990 — before laptops were common, before we had cell phones, and long before “remote work” became a trending hashtag.
Back then, many of us in sales worked from home by default. My “office” was a desk in my tiny studio apartment. There were no Slack channels or Zoom meetings — just phone calls and paper.
We got weekly mail packages from head office. That’s how we received our memos, meeting invites, printed plane tickets, and how we submitted our reports and expenses. (Good, I feel old just typing that.)
Most of our managers didn’t live in the same city — sometimes not even the same province. But still, we found ways to feel like a team.
Here’s how connection showed up back then — and what I still carry with me today:
1. Routine Creates Reliability
We had monthly breakfast meetings — pre-scheduled, always in-person. Senior reps would run them, we’d share what was coming up, trade appointments, and ask questions. Everyone showed up because we needed each other.
2. Presence Over Proximity
Our managers only visited once a quarter — but when they did, they sat in every single meeting with us for 2–3 days. It was intense (terrifying, honestly), but it mattered.
They also showed up in small ways.
One Winnipeg manager had a standing lunch table at DeLuca’s on Portage. No matter how your day was going, you knew there was a seat for you. That kind of presence can’t be replicated in an email.
3. Connection Can Be Simple
When I started leading teams, I tried to recreate that sense of connectedness in my own way.
Instead of weekly mailers, I held weekly team calls and regular 1:1s. But those check-ins weren’t always about work — I discouraged it. I wanted to know what else was going on in their lives.
And while I didn’t have big budgets for fancy retreats or elaborate team-building, I always prioritized shared meals — or even just shared snacks. Sitting down to eat with someone changes the dynamic. It reminds us we’re human first.
What Remote Teams Can Still Learn Today
Technology has changed, but people haven’t.
We still crave consistency.
We still need to feel seen.
We still connect best through shared experience — even when the work is hard.
You don’t need more platforms or dashboards.
Sometimes, you just need a seat at the table and someone who’s willing to listen.
Honest stories from thirty-five years of leadership, what I got wrong and what it taught me.