Hi there, it’s Jill!

If you’ve been job hunting recently, you’ve probably wondered:

🤔“Is there something I could ask during coffee chats that would actually improve my chances of getting the job?”

Surprisingly… there is.

But before we get to the question, let me take you back to the moment I discovered it…

When I was exploring a move from data science into product management, I scheduled coffee chats with senior PMs across multiple retail product lines. I wanted a full picture of what each team valued and needed—and whether I could be a fit for that team.

Unsurprisingly, every PM had a slightly different understanding of what a data science manager could bring to a product role. Some saw immediate alignment. Others… had doubts.

Here’s what I heard:

You get the idea.

These comments weren’t personal. They were simply people articulating their mental model of what someone like me might lack—based on their own experiences and biases.

But here’s the critical insight:
When people share their perspective, they’re also revealing their concerns.

And that means we can intentionally surface those concerns rather than guessing in the dark. That’s where the golden question comes in.

This is the question that changed everything for me:

💡“If a role opened on your team today, what concerns would you have about candidates with my background?”

Ask this in a calm, curious, non-defensive tone—and you’ll be amazed by how honest people become.

Whatever they say next, whether you agree with them or not, are exactly what you should address first in future interviews.

Because once you know the mental hurdles someone might have when evaluating you, you can walk into the interview room already disarming those concerns proactively and strategically.

This one coffee chat question has helped me, and many others, increase interview success dramatically.

When you’re switching functions, industries, or career paths, you will inevitably face bias.

Not malicious bias, just the natural limitations of how people understand roles outside their own. What’s obvious to you about your capabilities may not be obvious to someone else.

At first, this frustrated me. It felt unfair.

But later, I realized something freeing:

People can interpret your past experience however they want, but you can shape the narrative.

It’s our job to make our value easy to understand.

If you want a deeper dive on navigating hidden bias in job hunting, I wrote a post specifically on that. You can check it out here: [Link]🎯

Once you know the concerns, you can prepare to speak to them head-on. Here are a few approaches that worked incredibly well for me:

1. Acknowledge your transition openly.

“While I come from a different background, the transferable skills I bring—like X and Y—will help me ramp up quickly.”

2. Show you’ve done the thinking most candidates never do.

“Here’s my 1-year plan if I joined your team. At the 1-, 3-, 6-, and 12-month marks, here’s what I plan to accomplish. I’d love your feedback on how to refine this.”

This not only shows ownership—it reduces their perceived risk in hiring you.

3. Name the concern before they do.

“Before coming to this interview, I learned that one concern people often have is X. I want to share an example from my previous role that strengthened that exact skill.”

By addressing it upfront, you flip a potential weakness into evidence of your readiness.

The job market is competitive, but it’s also full of people who genuinely want to help —if you ask the right questions.

That one coffee-chat question not only reveals what others see in you (or don’t yet see), but it also gives you the information you need to position yourself effectively and confidently 🤗.

— Jill

Founder of Anchor Growth Newsletter

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