How to have an informational interview that actually helps

Why most informational interviews fail

You find someone on LinkedIn who has made the career change you are considering. You send a polite message. They agree to a 30 minute call. And then you ask: so what is it like working in product management?

That question, and ones like it, is why most informational interviews produce nothing useful. They are too broad, too polite, and too focused on the destination rather than the journey.

Ask about the transition, not the job

The most valuable information is not about what they do now. It is about how they got there. The messy middle. The moments of doubt. The things that surprised them.

Here are five questions that actually produce useful answers:

What was the hardest part of the transition that nobody warned you about?

This gets past the polished LinkedIn narrative. Everyone has a version of their career change story that sounds clean and intentional. The real story is messier. You want the real story.

What skills from your previous career turned out to be more valuable than you expected?

This helps you see your own transferable skills more clearly. Career changers consistently underestimate what they bring from their previous role.

If you could go back to the moment you were deciding, what would you tell yourself?

This surfaces the emotional reality of the transition. Was the fear justified? What turned out to be easier, or harder, than expected?

What did the first 90 days actually look like?

This grounds the conversation in practical reality. Not the six month view or the three year view, but the immediate experience of starting something new.

What is the one thing about this career that would make someone NOT want to do it?

This is the question most people are too polite to ask. But it is the most important one. You need to know the downsides from someone who lives with them every day.

How to find the right person

Do not just look for someone with the job title you want. Look for someone who made a similar transition to yours. The finance to UX designer journey is different from the teaching to UX designer journey, even though the destination is the same.

After the conversation

Write down everything within 24 hours. Not just the facts, but how you felt during the conversation. Were you energised? Scared in a good way? Confirmed in your doubts? Your emotional response to the conversation is data.

A better way

Informational interviews are valuable but limited. You are relying on the goodwill of strangers, the conversation is often surface level, and there is no structure or follow-up.

That is why we built Veerd. Every Twin call is an informational interview, but with someone specifically matched to your situation, prepared to have an honest conversation, and supported by 30 days of structured exploration before and after.