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The first time I truly understood how much culture matters in business, I was standing in our Guadalajara office, greeting a colleague the way I'd seen everyone else do it — a hug, a kiss on the cheek. It felt natural. It felt friendly. It felt completely wrong, apparently, for someone in my position.
My business partner took me aside. "You can't keep doing that," he said. "It's not how it works for the CEO." I had been trying so hard to fit in that I'd missed something important: adapting to a culture doesn't mean mimicking everything you see. It means understanding the context behind what you see.
What I've learned from building a company across three countries is that trust doesn't travel with you. The reputation you've built in Portland doesn't automatically land in Guadalajara or Belfast. You have to earn it fresh, on the ground, in the language and rhythms of each place.
In the U.S., trust is often built through results — you deliver, I trust you. In Mexico, it's more personal. People want to know who you are before they decide whether to believe in what you're building. In Northern Ireland, I found a culture of deep loyalty once earned — but it takes time and consistency to get there.
"You can't manage cultural diversity from a spreadsheet. You have to be present, curious, and willing to look a little foolish sometimes."
Over the years, I found a few things that made a real difference. First, I started learning Spanish — not fluently, but enough to give part of my annual company address in Spanish. The reaction the first time I did it was something I'll never forget. People laughed, they applauded, they came up to me afterward with more warmth than I'd ever experienced. A small thing that meant everything.
Second, I started accepting invitations. In Mexico and Northern Ireland, family gatherings are a big deal — and when colleagues began inviting me, I said yes. Those meals built more trust than any team offsite or performance review ever could.
If you're leading across cultures, the most important skill you can develop isn't strategic — it's human. Be curious about the people you work with. Learn what drives them. Show up in their world, not just in yours. Diversity becomes a strength not when it's managed, but when it's genuinely respected — and that starts at the top.