What York Zucchi taught us about asking, honesty, and being human

“One of the greatest skills to have is the ability to ask.”
– York Zucchi

We often think strength looks like having all the answers. A bold pitch. A confident stance. But in my interview with York Zucchi (entrepreneur, mentor, and investor) the conversation flipped that idea on its head.

What really creates movement?

Being vulnerable enough to ask.

In York’s world of startups and entrepreneurship, vulnerability isn’t weakness. It’s a strategy. A way to build trust, open doors, and create momentum – especially when you’re trying to lead something new.

Let’s explore what that looks like in practice.

The courage to ask for help

When York was mentoring thousands of entrepreneurs, he noticed something consistent: the ones who progressed weren’t the most polished or best-funded. They were the ones who weren’t afraid to reach out.

“We are all one message away from an opportunity.”
– York

He told the story of someone who wanted to connect with a big name in healthcare. Instead of waiting to be ready or perfect, they simply messaged the person on LinkedIn and asked for a chat. It wasn’t smooth or rehearsed. But it was real.

And it worked.

Vulnerability signals openness

This is especially relevant for those of us working on courageous communication as leaders.

When we admit we don’t know something, or that we’re unsure and want input, we don’t lose respect. We earn connection. People stop performing and start engaging. They get curious. They want to help.

“When you ask with sincerity, people love to help. It’s in our nature,” York shared.

In fact, many of the opportunities York gets involved in now don’t come from pitch decks. They come from people reaching out with a short, vulnerable message. “Here’s what I’m working on. I’d love your thoughts.”

That kind of communication isn’t weak. It’s powerful.

What this means for your leadership

If you’re in a leadership position or growing into one, try this:

1. Start small but specific.
Don’t wait to have it all figured out before reaching out for feedback or support. Use something as simple as your WhatsApp status. York recommends putting something like:

“Exploring how we can make team meetings more energising. Got 5 minutes to share what works for you?”

It invites dialogue. It opens doors.

2. Ask with honesty, not polish.
Professionals often feel they have to present requests with perfect grammar, logic, and structure. But York has found that when someone is too smooth, it feels like a pitch. When they’re real, people lean in.

One entrepreneur York helped simply said:

“I’ve got this idea. I don’t know if it makes sense, but can I get your take on it?”

It sparked a 30-minute conversation that led to a key introduction.

3. Share your intent, not your fear.
Being vulnerable doesn’t mean dumping your doubts on the other person. It means being clear about what you’re trying to do, and why. A message like:

“I’m testing a new leadership workshop and would love to run it by someone who’s led change in tough environments. Would you be open to that?”

That kind of message is human. And generous. And it works.

Why it matters

Vulnerability makes room for collaboration. For ideas to grow. For people to want to be part of your journey.

It’s a reminder that leadership isn’t about pretending to be bulletproof. It’s about being brave enough to invite others in.

“If you’re too proud to ask, you miss out.”
– York

So if you’ve been holding back from reaching out (because it’s not perfect yet, or you’re unsure how it will land), ask anyway.

You might just be one message away from the opportunity you’ve been waiting for.

Want to improve your ability to speak up and ask for what you need with confidence? I offer private coaching to help professionals communicate more courageously and lead with impact. Book a Readiness Session here to explore how we can work together.