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The Conversation You Should Have on Your First Interview

Published By

Tom Millington

Aug 21, 2026

A lot of first interviews are basically two sales pitches happening at the same time.

The candidate is trying to convince the business that they’re right for the position, while the hiring manager is trying to convince the candidate that the opportunity is worth taking.

There’s nothing necessarily wrong with either side wanting to make a good impression. The problem is when you spend the majority of that first conversation selling to each other and very little time understanding whether you’re actually aligned.


Before you get too deep into technical capability, salary expectations, benefits and everything else that comes with the hiring process, there’s one question both sides should be trying to answer:

Should we actually be working together?


On this Week’s Toolbox, here’s a framework you can use to turn your next first interview into an alignment discussion:

1. Understand what they’re moving towards

Most interviews ask the candidate: “Why are you leaving your current company?”

There’s nothing necessarily wrong with that question, but it only tells you what they’re moving away from.

Instead, ask:

“What are you trying to move towards?”

Everyone is motivated differently.

Some people want leadership. Some want to stay technical. A Project Manager might want to step into larger projects, while an Engineer might want to become a technical expert without ever managing a team.

Ask questions such as:

  • Where do you want your career to be in 12–18 months?

  • What type of work do you actually enjoy?

  • What projects excite you?

  • What skills do you want to develop?

  • What would make you want to stay with a business for the next three to five years?

Don’t interrogate them. Listen.

Ideally, you should be doing around 70–80% listening here because you’re trying to understand the decisions they’ve made throughout their career and what is driving the next one.

2. Put your cards on the table

Once you understand what the candidate wants, it’s your turn.

Tell them what they’re actually walking into.

Explain:

  • Why the role exists

  • Where the business is struggling

  • What skill gap you need them to fill

  • What will be exciting about the role

  • What will be difficult

  • What success actually looks like

If you’re backfilling someone who didn’t work out, there’s also nothing wrong with explaining where that person fell short and what you need differently this time around.

You don’t have to make the business or opportunity sound perfect.

The goal here is transparency. Give the candidate enough information to understand the opportunity properly and decide whether it actually aligns with what they’re looking for.

3. Explore the alignment together

Once both sides have put their cards on the table, ask:

“Based on everything we’ve discussed, do you think this is somewhere you could genuinely make an impact?”

Now you’re asking whether they can see themselves solving your problems, working within your environment and succeeding against the expectations you’ve just laid out.

And you need to ask yourself the same thing from the other side.

Can this business genuinely give this person what they told me they’re looking for?

Alignment works both ways.

Because someone can have the right experience for the job, but that doesn’t automatically mean your business is the right next move for them.

And if you want a more in-depth discussion on alignment, listen to Episode 5 of Leader Scout wherever you get your podcasts.


Here’s my challenge this week:

Before your next interview, take a look at the questions you normally ask and think about whether they actually help you understand what that person wants from their next move.

Instead of relying on the standard “Tell me about yourself” or “What are your strengths and weaknesses?”, ask about the decisions they’ve made throughout their career.

What made them take their previous roles?   What are they looking for that they don’t currently have?  What type of environment helps them perform at their best?

You don’t need to fire ten questions at them. Pick two or three and actually listen to the answers.


Remember, you’re not trying to catch someone out. You’re trying to understand whether what they want from their next move aligns with what your business can actually offer.

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