The Comfort of an Uncomfortable Question

People sometimes ask me how I manage to connect with such different people, on and off stage.

I think it starts for me with an almost unstoppable curiosity. Not the voyeuristic kind. I genuinely want to understand people. What makes them tick? What shaped their thinking? What do they care about? And what lies beneath the person we see on stage?

When a subject interests me, I can become almost obsessive about understanding it. And when I don’t know something, I want to find out as much about it as I possibly can.

I’ve always found it strange how many conversations, especially interviews and panels, become exercises in broadcasting. The interviewer has an opinion to deliver. The guest has a message to get across. Everyone is talking, but is anyone actually listening?

When I moderate a conversation, I don’t necessarily have to agree with the person sitting opposite me. I do need to understand them. And actually listen. I need to consider the people in the audience who might see things very differently.

Because my job isn’t to make the conversation about me. It’s to connect the people on stage with the people in the room.

I once asked a very well-known international fashion designer a simple question on stage:

“What was your biggest failure?”

She wasn’t particularly happy with that question. At least, not initially. But something interesting happened. The audience came alive. That uncomfortable question opened up the conversation.

And that’s an important distinction for me.

Making someone feel safe isn’t the same as making them feel comfortable all the time.

Sometimes the most interesting conversations begin exactly where the rehearsed answers end.

I often think about hosting as welcoming people into my own home. If someone were sitting at my kitchen table, how would I make them feel comfortable enough to be themselves? To share something, to disagree, to be vulnerable without feeling exposed?

That doesn’t mean avoiding difficult questions. It means creating an environment in which those questions can actually be asked.

Ultimately, I think it comes down to empathy. Being able to sense what’s happening between people, reading a room, understanding different perspectives and knowing when to push a little further or when to give someone space.

Humour plays a big part in that. A little Rotterdam humour, to be precise.

Not to make light of something important, but sometimes a well-timed remark takes the sharp edge off a moment. It creates breathing room. You can move from something serious to something playful and back again, without losing the substance of the conversation.

There’s also something interesting about ego.

Let’s face it, standing on a stage requires a certain willingness to be seen. Whether you’re the speaker or the moderator, there’s probably a little ego involved. But when you’re hosting, you have to know when to step out of the spotlight.

You’re there to guide the conversation, not become the conversation.

And that curiosity doesn’t stop when I leave the stage.

It’s just as important in design, education, coaching and personal branding. Before I can help someone communicate who they are, I want to understand the person behind the title. The student. The maker. The CEO. The keynote speaker.

Who are they, really? What fascinated them when they were eight years old? Where did their playfulness go? What still makes their eyes light up? Because how can you translate someone’s identity into a visual language, a strategy or a story if you haven’t taken the time to understand the human being behind it?

For me, it all comes back to the same thing: genuine curiosity, empathy and the willingness to really listen. Not just on stage, but in the way we interact with each other every day.

Perhaps the question isn’t whether we’re asking enough questions.

Perhaps it’s whether we’re genuinely interested in the answers.

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