Interview Like Charlie Rose

Tips for talking with your next design candidate


Growing your team is the best and the worst decision you can make for your company. Making a good hire can be like a Mario mushroom for your group’s productivity and vibe. Conversely, bringing a bad fit into your team can be dismally awful, and not easily reversed. Finding the right people at the right time is key, and interviewing candidates in-person is usually the best (and final) step in deciding on hire or no-hire.

Despite the importance of the in-person interview, there are a lot of people, and companies, that under-consider how they’ll approach them. Having been on both sides of numerous interviews in these past few years, here are a few tips that could help you interview at your best…

A Good Conversation

Before the interview, identify a few key questions or points you’d like to hit:

  • What’s the candidate’s past work like?
  • What kind of teams have they worked on and how did they contribute?
  • Which products do they appreciate? Which designers? Why?
  • How do they communicate? How do they want to work?
  • What’s brought them to your company?

It’s not important that you touch on each one, but it is good to have a path to guide your discussion and keep it flowing should a particular subject run out of steam. If you don’t touch on a topic, another person on your team could. You and your co-interviewers might even talk ahead of time on what things everyone will try to cover.

Start the conversation by being a real person, try to connect over something to establish a rapport.

Make eye contact, smile, and listen to what your candidate says in an interview. Have a natural conversation. Don’t present a verbal questionnaire. Conversations can fall flat if interviewers don’t care or aren’t interested. If this describes you, by all means exclude yourself from the process.

Don’t interview the candidate from behind a laptop or iPad, that’s rude. If you’re having a genuine conversation and paying attention, you need not be taking copious notes.

It’s exciting to have the chance to meet someone who could one day do awesome work with you and your company. You may pass on more people than you accept, but the opportunity alone is valuable and worth your positive energy.

Don’t Judge

The last thing a candidate should hear about during a visit to your company is how much those other companies suck. Don’t tell them that another option they’re considering is a bad one. Instead, talk about the things that make your company great on its own.

Chances are if your candidate has made it to an on-site, they’re qualified enough to evaluate potential jobs for themselves – pooh-poohing something they’re interested in is a turn-off.

Be Charlie Rose, not Alex Trebek

Treat candidates like welcome guests, don’t try to stump them, “catch them”, or otherwise befuddle them intentionally. Gotcha-interviewing is not an effective way to gauge someone’s skills, weaknesses, or experiences. You have the high-ground in these conversations: if you’re out to trip someone, you’ll probably just succeed.

Think of yourself like the Charlie Rose of your company, dive into a person’s personality and work, see what makes them tick. Challenge yourself to suss out that one thing your candidate is best at, and all the things they’re passionate about. It’s okay to ask tough questions… actually, it’s critical. Tough questions give your candidate an opportunity to express themselves and show their skills in important ways, but even tough questions shouldn’t be mean-spirited.

Finding weaknesses is important, too, but better candidates will often offer those up openly, and the inexperienced ones usually have obvious areas for improvement. It’s up to you to judge if those aspects are deal-breakers – but remember: everyone has them, even you.

Be Open

Ask yourself and the others on the candidate’s interview loop to answer “What can we learn from this person? What can she learn from us?” Don’t assume you or or the candidate are expert-ninja-firefighting-jedi. Put yourself in a position to learn from your candidate just like you would a fellow co-worker. Never be defensive with someone whose strengths are similar to yours, there’s plenty of room for both of you to thrive.

Problem Solving

Design exercises are often a bad idea. They’re difficult to execute well from the interviewer’s point-of-view, and encourage summary judgements of a person based on a small window into their working habits.

There are times, however, a design exercise can be used to explore how you and the candidate might work together, When creating these exercises, keep these points in mind:

  1. Choose neutral ground. Avoid asking candidates to design something that you have unequal domain knowledge over. If you’re a productivity company, don’t ask candidates to design a task list.
  2. Collaborate, or leave the room. Don’t watch-and-judge-arms-folded as your candidate sketches, thinks, or ideates – give them space and time to work. Or better yet, engage with the candidate like you would a co-worker, and use the conversation to drive the exercise forward.
  3. Remember, you’re not proctoring an exam. Don’t treat your candidate like a pupil or a contestant. Engage with their solutions even if they’re not what you expected.

Finally, keep in mind that someone’s performance during an exercise might not reflect their actual working style or abilities. If you hope to get even a hint at someone’s working style, its critical to help your candidate feel at ease.

The Sell

If all goes (really) well, and you and your team have decided to move forward the conversation often enters the sell phase. If you’ve played your cards right, your next designer is already pretty amped to accept, but sometimes they need that extra push. A great way to do that is to have open and honest conversations about the advantages and disadvantages of the various opportunities before them – they’ll appreciate that you’re interested not only in filling a position, but also in helping them make the best decision.

Set your candidate up to talk to people in different areas of your company that have things in common with them. Make Mr. or Ms. Right feel like they’re already part of a great team, and excite them about all the work on the horizon.

Sorry, Charlie

Giving someone an offer is awesome! You’ll feel great to have found someone you’d like to work with, and they’ll feel happy to be accepted. Sadly, not every loop ends in a yes – in fact, the majority probably don’t. While it’s your responsibility to pass when the match isn’t right, it’s also good to share some constructive feedback with your (former) candidate. If you can, share with them the highlights and the depths of the interview, and why the fit wasn’t right. You’ve both invested many hours in the process, and providing a little closure (directly or through a recruiter) is good karma. You might also express a varying degree of finality depending on the reason for the pass: should you leave the door open to talk again in a year, or weld it shut with a smile?


At the end of every interview, Charlie closes with either a hard cut-to-black or a warm “It’s been a pleasure to have you here.” Charlie interviews writers, heads-of-state, dictators, villains, and TV actors – and he does so with respect and interest every. single. time. We’re not all well-educated southern gentlemen, but we all owe our candidates at least a warm smile and a genuine conversation. That’s the key to a great interview, and to hiring the best designers.


Thanks to Julie Zhuo, Robyn Morris, Luke Woods, and Noah Levin for the thoughts.