Leading Across Borders: Expat Wisdom from Tom Roberts
Written by Philip Carrigan
I recently had the pleasure of catching up with Tom Roberts, President of Cranberry Leadership and someone I’ve known from his time in the pharmaceutical industry, on the Morunda Podcast. Tom’s leadership journey—especially as an expat in Japan and Korea—offers valuable lessons for anyone navigating cross-cultural roles.
From Pharma to Cranberry Leadership
Tom spent over two decades in pharma, including 11 years in Asia. He held senior roles, including leading a billion-dollar neurology unit in Japan. Despite his experience, he encountered hard truths early on. One moment that stayed with him was when a Japanese colleague told him, “Tom-san, you’re like a cranberry. You leave a bitter taste.”
That unexpected comment forced him to reflect. He realized he was imposing U.S.-style solutions in a market that required a different approach. That realization became the seed for Cranberry Leadership—a firm dedicated to coaching expat executives.
Learning the Hard Way
Tom calls this learning process “harvesting failure capital.” After leaving UCB, he returned to university at 50 to become a certified executive coach. He didn’t want to rely solely on experience—he wanted tools to truly help others.
During the pandemic, he conducted over 40 interviews with expat leaders, uncovering a common emotional curve. The first six months abroad often feel like a honeymoon. But soon, cultural gaps, pressure from HQ, and communication breakdowns set in. Some executives spiral into crisis; others adapt and grow. The key difference? Seeking help.
Tom’s Three Don’ts for Expat Leaders
- Don’t replicate past wins. What worked in the U.S. might not work in Japan. Context matters.
- Don’t misread silence. Silence in East Asia can mean many things. Don’t assume agreement.
- Don’t let pressure kill empathy. The more pressure you feel, the less you listen—and that leads to mistakes.
Three Do’s That Make the Difference
- Slow down to go fast. “Speed doesn’t equal speed,” Tom said. Patience and reflection lead to smarter progress.
- Manage your energy. Teams look to you for cues. Be mindful of how you show up.
- Push back visibly. Advocating for your local team, especially in front of HQ, builds trust.
The Family Factor
Tom also talked about the impact on his family. His wife, a professional in her own right, put her career on hold for a two-year move that stretched into 11 years. That shift wasn’t easy. They both assumed the other’s life hadn’t changed much—until they realized just how different their experiences were.
It’s a powerful reminder that the expat journey affects the whole family. Communication at home is just as vital as it is at work.
Intercultural Triangulation
Tom introduced the idea of intercultural triangulation—understanding the many cultural forces at play in a single role. At one point, he was an American in Korea, reporting to a Moroccan, in a Belgian company, with U.S. headquarters. It’s a lot to navigate.
His advice? Use cultural frameworks. Talk to people who’ve done it. And most importantly—know you’re not alone.
Final Thoughts
What I appreciated most about Tom’s story is that it’s not about theory—it’s about real lessons, learned the hard way. His message is clear: success abroad isn’t about control. It’s about listening, adapting, and having the humility to grow.
If you’re preparing for—or currently in—a global leadership role, I encourage you to listen to our full conversation. It’s full of hard-earned wisdom that can make the difference between surviving and thriving.
Key takeaways:
- Don’t Assume Past Success Will Translate: What worked at home may not work abroad. Adapt to the local culture.
- Silence Doesn’t Mean Agreement: In Japan and Korea, silence can signal disagreement or discomfort—not approval.
- Pressure Destroys Curiosity and Empathy: Constant urgency blocks your ability to listen and connect with your team.
- “Speed Doesn’t Equal Speed”: Patience and reflection often lead to faster, more sustainable results.
- Manage Your Energy—People Are Watching: Your mood and presence shape how the team feels and performs.
- Visible Advocacy Builds Trust: Stand up to HQ when needed—your team will respect and support you.
- Support Your Family—They’re on the Journey Too: Expat life impacts the whole family. Stay connected and communicate.
- Use Intercultural Tools to Find Your Bearings: Cultural frameworks help you navigate complex cross-cultural expectations.
- Get Help—You’re Not Alone: Coaching, mentors, or peer support can make all the difference.
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