Mom said, don’t talk to strangers.

Turns out, doing the opposite upgraded my business life

Sometimes, the biggest breakthroughs come from unexpected connections. One bold message to a stranger transformed my professional life, proving that stepping outside your comfort zone can lead to extraordinary opportunities.

It was January – one of those mornings when I found myself at my kitchen counter in Cascais, scrolling LinkedIn with coffee in hand. (Living in Portugal while working abroad, LinkedIn has been essential for staying in touch). That’s when a ‘suggested connection’ caught my eye: a former colleague from a major Life Sciences multinational.

Though we’d never met, we’d worked at the global HQ of the 40bn CHF company in Basel in our ‘past lifetime’. He’d had a C-level role there and had recently completed a board program I’d been considering for some time. I decided to reach out about the program.

Here’s how our conversation unfolded:

10:44 AM
“Good afternoon, Stefan, I am reaching out as a former colleague. I would like to know if the IMD board director program is something you would recommend. It would be an honour to connect. Many regards.”

10:45 AM
“Hi Anna, thanks for your message and yes, happy to share some insights on the IMD Board program and viewing your impressive CV maybe we find some further areas of common interest. All the best Stefan. My coordinates (email, mobile no).”

12:39 pm
“Thank you for this. Very kind. Will reach out on WhatsApp!”

I had no idea that my business life was about to get a massive upgrade.

In the Zoom conversation that followed, Stefan quickly impressed me. Around my age and highly accomplished, he spoke about his business purpose with clarity and conviction. Despite many achievements and contributions across multiple boards, he was both modest and generous in sharing insights. I immediately liked him.

At the close of our first discussion, I took a step that did not come naturally. I spontaneously asked Stefan to have another 30-minute call in the next few days. I simply said:
“If we have another call, I promise to pay it forward and mentor someone who needs it.”

Worst case? He’d say ‘No’. But to my delight, he said ‘Yes’.

One conversation led to another, and so over the next two months, Stefan – a stranger from the internet – mentored me on various sophisticated nuances of board governance and contribution. With a mix of insight and kindness, he proved to be a great sounding board and discussion partner. That alone was invaluable.

But then came the real game-changer: a single comment that shifted my perspective – one of those rare ‘aha moments’.

Stefan shared that he dedicates eight hours a week (!), every single week, to speaking with new people – strangers he’d otherwise never meet.

Boom. What? Is this accomplished C-level guy already on five or six boards setting aside a full day a week to talk to strangers? But wait, he doesn’t have to. Yet he chooses to and is super intentional about it!

Stefan explained that this disciplined practice exposes him to new ecosystems, keeps him sharp, brings fresh ideas, and sometimes even leads to new board positions.
Imagine how this process compounds over time…

My next step was crystal-clear: emulate.

Fast forward to November 2024:
I now aim for four to eight hours of weekly ‘stranger exposure’. When I run out of new contacts in Lisbon, I turn to LinkedIn:
“Hello X, I am reaching out to schedule a call. I recently met an accomplished board director who dedicates eight hours a week to connecting with new business people he’d otherwise never met. It inspired me. If you have 30 minutes, I would love to say hello and explore how our business interests might intersect. Warmest regards.”

The ROI from this approach has been unbelievably satisfying. I’ve grown my network, gained new professional friends, mentored people and was mentored in return. I landed a new board role, engaged in collaborations and communities, and even found my voice on LinkedIn which boosted my visibility here in Portugal.

The mindset shift has been both profound and practical. So, yes – go ahead and talk to strangers on the internet!