I’m A Hiring Manager—Here Are Five Questions I Always Ask Job Candidates

With the right questions, there’s a lot you can tell about a candidate in just half an hour.

I’m A Hiring Manager—Here Are Five Questions I Always Ask Job Candidates
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Job interviews can be really unpleasant for interviewers and candidates alike. A 30-minute chat sandwiched between a busy hiring manager’s afternoon meetings isn’t always the best way to get to know somebody, let alone judge their fit for an open role.


But over my past few years in the hiring seat, I’ve developed a set of five go-to questions that are easy to ask within the space of a half hour and still lead to revealing answers. Together, they give me a pretty comprehensive idea of who an individual is, how well they know their craft, how quick they are on their feet, and whether I’d be happy to see them every day.

And over time, I’ve found that asking this same set of questions has helped me get a sense for how everyone is performing against the same criteria, which means I can make apples-to-apples comparisons. The people who knock their job interviews out of the park are invariably the ones we hire, and who go on to thrive. Here are the five questions I always ask:

1. What’s Your Greatest Career Hit And The Role You Played In It?

Why it works: This question allows you to get a sense of the individual’s working process, whether they can lead and contribute, and how enthusiastic they are. It also lets you know their perception of quality. They might choose to talk about a student project (if they’re just starting out), a global integrated campaign, or a startup that they founded or contributed to.

I tend to spend the most amount of time digging into a candidate’s answer to this question–usually I’ll allot 10 minutes to discussing it, whereas the subsequent four only take five minutes apiece–probing for the specifics, and pulling up the work they’re talking about on the internet.

Related: These Are The Worst Answers To The Most Common Job Interview Questions 

Answers that work: A detailed walk-through of the project that outlines their sources of data, inspiration, challenges and triumphs, along with a clear explanation of why it was successful and why they were proud of it.


Answers that suck: An inability to explain their processes, or an eagerness to say that the thing that didn’t happen was the fault of the client/the creative director/the universe–anyone else but themselves.

2. How Your Discipline Is Changing? What’s One Company That’s Adapting Well?

Why it works: The world is changing quickly, and we want people who understand and embrace new opportunities.

Answers that work: A CRM strategist once described the way Glossier is inventing a new model for digital commerce and community-building. A visual designer told me about the way GE made machines brilliant in the smaller spaces of Instagram, and a copywriter gave a blow-by-blow account of the Twitter beef between Wendy’s and Hardee’s.

Answers that suck:Has it changed?”

3. What’s The Last Thing You Read, Saw, Or Listened To That You Wanted To Tell Someone About?

Why it works: I look for curiosity. I legitimately don’t care if the answer is Game of Thrones, as long as they have an interesting take and an ability to communicate it clearly.

Answers that work: There are too many to list, but here are some great examples from our recent hires:

  • A strategist who described an article about the CEO of Scotts Miracle-Gro investing in hydroponics products that seem geared to the burgeoning cannabis industry
  • A designer who pulled out a book about interface design in science fiction
  • A creative who talked about Big Little Lies, and how Reese Witherspoon’s production career was an empowering response to the lack of roles for older women in Hollywood

Answers that suck: Someone who mentions something they haven’t read properly, or only have flicked through when they were at the airport.

4. What’s A Current Cultural Phenomenon You Want Nothing To Do With?

Why it works: Because we want them to have opinions and not be afraid to express them.

Related: 7 Ways To Talk About Your Athletic Experience On A Job Interview

Answers that work: Anything, just as long as they can explain why. Here are some examples we’ve seen persuasively argued: Coachella, cyber-bullying, the word “xennial,” internet outrage, transparent jeans, identity politics, Twitter, dressing children up as animals, the coopting of the term “self-care” by marketers.

Answers that suck: Saying you don’t like “politics,” for instance, without being specific about what you find disconcerting.

5. What Do You Do For Fun?

Why it works: Because we work hard, and maintaining a life outside of it is important. I want to hear how they stay grounded and what makes them happy.


Answers that work: Their own genuine answer.

Answers that suck: Not having an answer at all.

Jess Greenwood is R/GA’s SVP, Head of Strategy, North America, and co-runs strategy, social, and content over six offices. She’s always looking for ways to do more in less time.