Fiona Chorlton-Voong, Co-Founder and COO, The Portfolio Collective

Fiona Chorlton-Voong is the Co-Founder and COO of The Portfolio Collective, the world’s fastest-growing online community for portfolio professionals. The first fifteen years of her career were spent developing brand strategy in high-end fashion houses and teaching sales processes to tech engineers. As her leadership skills evolved, she shifted focus to the world of startups, taking on a role sourcing tech startups for an ultra-high net-worth individual and launching HighNetWork, an enterprise app for professional service firms. In 2020, she was inspired to help shape a new future of work, so she and Ben Legg launched The Portfolio Collective, ensuring continuous learning and collaborative support for thousands of portfolio professionals around the world.


Several years ago, I was on a business flight to LA and the mood was a bit tense. There we sat, strapped into our respective seats as I stared out the tiny window at the same, unmoving view of a static runway. We were grounded. Delayed. And there was no indication of when things would change.

It was the perfect recipe for human conflict. One that many of you reading this would be all too familiar with. Tensions were high. Legs were numb. And the alcohol was flowing.

Before too long – and after a few tasty pre-flight cocktails – I struck up a conversation with the man sitting next to me.

It was awkward at first. He wasn’t too sure why I was asking so many questions. But as we shared life stories, we forged a fast friendship. The conversation continued throughout the flight and we even agreed to stay in touch. That man turned out to be a Senior VP at Sony, which eventually became a big client of mine. Not too long after, my new friend reached out to me with a job offer in California.

Why you should always be open to new encounters

Now, it’s not totally unheard of to chat with someone sitting next to you on a plane, but these days it’s more common for us to shut the world out with screens and noise-cancelling headphones than say hello to someone we don’t know.

So, what would actually happen if you embraced a bit more curiosity and opened yourself up to the insights of strangers? And how would that affect the way the wider world perceived you and your leadership style?

As COO and co-founder of The Portfolio Collective, an online community for portfolio professionals, I’m constantly building relationships. I speak to people who want to shake up their careers, professionals who are struggling to define their stories, and industry disruptors who need a bit of help articulating what makes them unique.

But I also carve time out of my busy schedule to speak to at least three strangers a week – that’s people who have absolutely nothing to do with my company or career. Why? Because it’s a brilliant way to build a network and, in turn, cultivate my personal brand.

The benefits of embracing curiosity

According to a recent study focused on commuters in London, people are held back from speaking to strangers because they assume that starting a conversation will be more difficult than ending one and they aren’t confident that people will actually be willing to talk to them.

I began engaging in this practice when my old mentor challenged me to step outside my comfort zone and approach three completely random people a week. This was pre-COVID and I wasn’t intentionally going to industry events, so I wasn’t sure where to start. At first, I didn’t think I could do it. Then I watched in awe as my mentor chatted with a guy in an elevator on our way to dinner.

She was so organic and smooth about it. It didn’t feel targeted or calculated at all, and that’s because it wasn’t. This guy had no connection to her whatsoever. She didn’t know what he did or how he could benefit her network – that is until she got to learn more about him. She simply complimented something he was wearing and it turned out he was the managing partner of a huge legal firm. This man went on to be one of her biggest clients.

Talking to strangers helps us humanise one another. Even the simple act of making eye contact with someone makes them feel more connected, and we often underestimate how positively a compliment can be received.

What’s important about this example is that my mentor built up trust and established a relationship before even thinking about business. Human connection matters. So does your reputation.

The other side of building a network

When I speak to a stranger, I want them to walk away with a feeling of enthusiasm or hope. It’s such a tiny thing, but it’s incredibly energising to know that someone loved a conversation you initiated.

Of course, not everyone reacts the same way. Sometimes they look at me like I’m a weirdo – many think I’m hitting on them. But once we get into it, they’re often delighted and surprised by what we end up talking about. It’s all part of reinforcing my brand as a helpful person who supports others.

When you’re establishing yourself as a leader or entrepreneur, you have to remember that your reputation is more than just what you put out there in the digital world. Your network goes beyond a list of LinkedIn connections. And that wider, physical network is very much a part of your brand.

If you have a rich black book of interesting individuals, it means your brand is organically growing. I’m bad at social media, but I’m great at building my personal brand. The most powerful thing for any brand is what people say about you when you’re not in the room. The circle is much smaller in the world of CXOs, so you want to make sure those people are saying primarily good things.

So why should you start speaking to more strangers?

I do it for two reasons. First, I love talking to new people. I love learning their stories and seeing how excited they become when you ask them genuine questions about themselves. The other reason is because I want to build a more diverse and rich network full of people who can solve problems.

I don’t just reach out to people who do what I do or look like me. I want to be able to find someone who can do something I can’t so I can connect them with a friend or colleague and expand their network as well. That’s the best way to discover surprising opportunities.

If someone in my network needs a plumber, I want to be just as confident in recommending a brilliant person for the job as I am when I recommend an accountant or lawyer.

So set yourself a goal. Mine is three strangers a week, but yours might be even more (or less) than that. My advice is to be bold about it. If you speak to one new person a month, you’re probably not going to build a lasting habit. Step out of your comfort zone and start widening your circle. You’ll be amazed by who you meet and the knock-on effect it has to your personal brand.

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