The Strategy of a Handshake
In a remote-first world, the most powerful leadership move you can make isn’t in the cloud. It’s across a table.
A few of my friends had pen pals growing up.
Email and messaging had yet to be invented. Personal computers were still on a Star Trek screen in the future. The world still seemed so big and far away.
I didn’t pay much attention to their letter writing. What was interesting was what came next. Months, sometimes years, of photos and cassette tapes of their voices would finally culminate in a meeting. The person on the other side of the stamp was suddenly real.
I had my own pen pal moment this week.
My colleagues at the American Press Institute have for months been familiar faces in the Brady Bunch grid of my daily Zoom calls. I know their work. I know their Slack emojis. I know their digital mannerisms. In Chicago, I finally met two of them in real life. For the very first time.
There’s a strange moment that happens when a colleague you’ve only known as a square on a screen finally appears in real life. They have height. They have a laugh. They take up space in a way no camera ever captures. The second I shook their hands, something shifted. Something inside our working relationship clicked. It suddenly felt sturdier. More real. More human.
Why a Handshake Still Matters
That little moment was meaningful. But more than that, it was a reminder of something bigger.
The world of work has been completely rewritten over the past five years. Remote work isn’t some temporary experiment. It’s how we operate. It’s efficient. It’s cost-effective. It lets us hire the best talent from anywhere.
But there’s a cost hiding underneath all of that. We’ve figured out how to work from anywhere. What we haven’t figured out is how to stay connected when we’re everywhere. The systems that make our companies leaner can also make our teams lonelier.
That’s why I believe traveling to meet your own team is one of the most valuable investments a leader can make. The water cooler moments that used to happen by accident don’t exist anymore. You can’t hope for connection. You have to plan for it.
My trip to Chicago wasn’t a nice-to-have. It was a deliberate choice with a clear and measurable return.
Break the Zoom Barrier: The power of talking in person is communication in high-definition. It’s layered with body language, energy, and nuance. None of that comes through a screen. And once that connection is built, it sticks.
Trust on Fast-Forward: Trust is the invisible currency of strong teams. You can build it slowly over messages and meetings. Or you can build it over one shared meal. The difference is speed.
A Foundation for the Hard Stuff: Difficult projects and hard conversations get easier when they’re grounded in a real relationship. Meeting someone in person creates a reserve of goodwill you can draw on when things get tough.
But Isn’t That a Pricey Handshake?
I can hear the CFO sighing from here. Plane tickets. Hotels. Meals. It adds up. It’s so easy to treat connection as a luxury instead of a necessity.
But that’s the wrong way to think about it. This isn’t a perk. It’s part of the infrastructure. You pay for Slack. You pay for cloud servers. You should also pay to make sure the people using them are truly connected.
Because the cost of disconnection is far higher. Projects stall. Good people leave. Innovation dries up because no one feels safe enough to take risks.
The real question isn’t whether you can afford to do it. It’s whether you can afford the consequences if you don’t.
How to Engineer Connection: Three Models
So how do you make this part of your strategy? It has to be more intentional than a once-a-year retreat. Here are three ways to start.
The Hub-and-Spoke Meetup: Skip the expensive all-hands trip. Focus on smaller regional gatherings. Get your three Boston-based team members together for a co-working day. Send your two Denver employees out for dinner. It’s low-cost and high-impact.
The Connection Stipend: Put the decision in your team’s hands. Offer a stipend they can use to meet up with a colleague for a couple of days. My trip to Chicago is a perfect example of how powerful that time can be.
The Purpose-Built Offsite: If you’re going to bring everyone together, make it count. Don’t just recreate your weekly meeting in a hotel ballroom. Focus the time on solving a tough problem that requires collaboration and trust. Let the work be the reason and the connection be the result.
We have tools today that make collaboration easier than ever. They save time. They save money. They’re essential. But they’re not the whole story. They’re just the bridge.
And every now and then you have to walk across that bridge. You have to shake a hand. You have to share a laugh. And you have to remind yourself that there’s a real person on the other side of the screen.
Just like those old pen pals, months of conversation can build a foundation. But the real magic still happens the moment you meet.
👉 What’s the most memorable moment you’ve had meeting someone in person after only knowing them online? I’d love to hear your story in the comments.
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