Why we fear networking — and how 50 cups of coffee can change your career

When I ask my clients to do informational interviews, many of them look at me like I’ve just suggested skydiving without a parachute.

They freeze.

They say things like:

“I don’t want to bother people.”

“Why would they talk to me?”

“I don’t have anything valuable to offer.”

“Who the hell am I to ask?”

Sound familiar?

You’re not alone. So many smart, capable women tell me they feel uncomfortable reaching out - as if asking someone for a chat is imposing, awkward, or needy. But here’s the truth: this single activity is one of the most powerful career research tools you can use.

It’s called informational interviewing - or as I like to call it, The 50 Cups of Coffee Strategy.

The 50 Cups of Coffee Strategy

There’s a great article about this approach by Peter Thomson, who was laid off and committed to having 50 coffee conversations. Read it here https://www.inc.com/peter-thomson/50-cups-of-coffee.html

He spoke to anyone willing to share insights about their industry - no agenda, no “please hire me,” just genuine curiosity.

By cup number 50, he’d gained a deep understanding of his new field, a powerful network, and even negotiated a job offer in a completely new industry.

Why I love this strategy

You cannot do too many informational interviews.

They’re like gold-mining for your career — this is where the hidden insights, unadvertised jobs, and real stories live.

Job boards only show a fraction of what’s out there. But when you talk to people, you uncover:

• The day-to-day realities of a role (beyond the polished job description)

• The good, the bad, and the ugly of an organisation or industry

• The skills that are actually valued and how people really got into those roles

• The culture, flexibility, and unspoken expectations you won’t find online

It’s real, human, and invaluable.

What an informational interview really is

Think of it as a conversation, not an interrogation or sales pitch.

You’re not asking for a job — you’re asking for insight. In fact, if you're asking for a job you're doing it wrong.

Here’s what you’re doing:

• Fact-finding: What’s this career actually like?

• Testing fit: Does this align with my values, energy, and long-term goals?

• Gathering insider knowledge: What’s changing in the field? What challenges are people facing?

• Building relationships: These chats often lead to referrals, introductions, or job leads down the line - but that’s not the goal. The goal is understanding.

And that understanding gives you confidence and clarity.

Because suddenly you’re not guessing - you’re informed.

Why women especially struggle with this

Many of my clients (brilliant women in their 40s and 50s) have spent years being the person others come to for help - not the one asking for it.

So the idea of reaching out to a stranger and requesting their time feels… uncomfortable.

But here’s the reframe:

You’re not taking from someone. You’re giving them an opportunity to share their experience — something most professionals actually enjoy doing.

People love to talk about their career journeys.

They remember being where you are now.

And most will be flattered that you asked.

How to Reach Out (Without Saying “Can I Pick Your Brain”)

Never use that phrase. It feels vague and transactional.

Instead, craft a simple, sincere message like:

Hi [Name], I came across your profile and I’m really interested in learning more about [industry/role]. I’m exploring a possible career transition and would love to hear what drew you to this work and what your experience has been like. Would you be open to a quick 20-minute chat over coffee or Zoom?

Keep it light. Keep it real.

It’s not a pitch. It’s a conversation.

Your Challenge: 50 Cups of Coffee

Try committing to the 50 Cups of Coffee challenge yourself.

It doesn’t need to be literal coffee — it could be a short Zoom, a phone call, a walk, or a LinkedIn message exchange.

Each conversation will:

• Expand your perspective

• Build your confidence

• Bring you one step closer to the career that truly fits

My Favourite Part

I call informational interviews the reality test in the career change process.

They’re how you find out whether your dream role is really your dream once you get behind the scenes.

Before you make any big career move, talk to the people already living it.

You’ll save yourself time, stress, and possibly a major wrong turn.

If you’ve ever done an informational interview - or tried the 50 Cups of Coffee approach - I’d love to hear what you learned.

What surprised you? What changed for you after those conversations?

Drop your thoughts in the comments - or tag someone who’s your next “coffee.” ☕️

P.S. Most people never find their dream job because they don’t know how to look for it. I'm running a 90min workshop on Thursdsay 30th Oct 2025 at 12pm NZT to help you learn how to find it. It's called "Research Your Career Ideas" I'd love to see you there. Register here