3 Favourite Questions to Ask Candidates

Read this article
⸻ Beyond Data

What makes a person tick and what environment will get the best out of them are as important as their technical skills.

This post is a follow-up to the last one, my favourite three questions to ask interviewers. That covered general questions that I’ve used time and again when I’ve been interviewed. This time, we’ll focus on questions to ask candidates that give me a lot of information typical interview rounds can miss out on.

Interviews are hard

It’s no secret that I think the whole hiring process is pretty broken – it’s very hard to get the right information without grilling candidates and if your process is too cumbersome you won’t stay competitive. Someone with a process quicker and more streamlined than yours might land the best candidate while you’re still working through grading your umpteenth rounds of questions.

How do you get the most insight with the fewest questions?

When it comes to the technical parts, I have tried and seen a lot of different approaches. I prefer project walkthroughs, pair programming, and take-home tests to whiteboard coding and brainteasers.

Once you’ve ascertained that they can deliver the role from a technical perspective, I’ve found these three questions really help me in understanding what they’ll be like on the job, no matter the role.

1. What has to happen in this role in the next nine months to make joining our company the best career decision you’ve made?

Answers to this question carry a lot of information. I almost always ask this in every interview process because it tells me so much. You’ll get a feel for what they want and what they truly seek from the role. They’ll often give insights into how they want to work and what kind of management they work best with.

They might take a team/culture/social slant on the answer – which can make or break for some people. They might talk purely technical, allowing you to ensure their expectations are aligned with the reality of the role at hand.

This can also highlight red flags and misaligned expectations. You never want to trick someone into working with you – if their answer points to something reasonable but not achievable at your company, you should tell them to avoid pain and disappointment down the road.

2. What kinds of people and teams do you work best with, and what do you work worst with?

We often don’t ask about the teams and people directly in an interview. We spend all of our precious little time checking the technical delivery over and over again and maybe checking the people stuff right at the end – if we remember.

This question asks them to not only outline, clear as day, what the best setup would be for them but also to spell out for you when they clash with folks and what teams don’t get the best from them. You can then use this information to ensure you’re setting this person up for success and not putting a technically brilliant person into an environment that won’t work for them.

Be wary, sometimes candidates will try to reflect the type of environment they think you have – this is usually quite obvious so you need to tell them there’s no right answer and you really just want to hear about what they prefer.

3. If you could change anything, with no constraints, at your current organisation, what would it be and why?

This is a great one for understanding what they really care about. Answers will vary wildly, but you’ll get some insight into the deeper parts of what makes them tick. If they point out things like delivery processes or culture similar to yours – there’s a chance they might not be happy that they’re going into a similar environment (unless you’re willing/able to change that environment for them?!).

I’ve found this gets them thinking about why they want to move on and drop the mask a little bit to give you some honest insight into their motivations and what drives them.

Final thoughts

Much like my favourite questions to ask interviewers I’ve used these questions over and over again to get a deeper insight into what a candidate is like to work with and what they want.

I’m always looking to sharpen my interview process and skills – if you have any gems I’d love to hear them.

As always, feedback is greatly appreciated. Please let me know if you have requests for content you’d like to see.

All the best,


If you enjoyed this, consider sharing this newsletter with others that would find value from it or follow what we’re doing at Hypercube


When you’re ready, there are a few ways I can help you or your organisation:

What do you think of this issue?

I’d love your feedback to ensure I’m writing about the topics you want to read, let me know if this one hits the mark

Want to write for Beyond Data?

Have something you want to share? Interested in writing an issue or working with our team?