10 questions I love asking when hiring creative people
1. “Send me a link to the article you most loved writing, ever. It can be a professional, work-related piece or a personal piece. The lone rule is you feel it’s your best writing ever.”
Why this question: It helps you skip formalities and get right to their very best work. It also helps you shape the conversation when you ask follow-ups. Why this piece? What’s the backstory? What did you love about it? If it was awhile ago, why haven’t you written anything you love more since that time? (Plus, receiving the link to this article is proof they can write, versus a description they can write, as with a resume or LinkedIn bio — largely useless.)
2. “Send me a link to any side projects you’ve launched, whether it’s currently being updated or not.”
Why this question: We should hire tinkerers, regardless of the role. If someone takes initiative on the side to pursue their curiosity and interests, without letting any gatekeepers stop them, and they find the time to create stuff regardless of how busy their lives get (i.e. they make making a top priority), it reveals a profound and intrinsic desire to create and learn. (Personally, side projects have been like slingshots to my career. I remember my first interview for my very first full-time job after college, when I wound up working for Google, multiple managers asked me about a sports blog I wrote on the side. They wanted to understand my thinking and my process, and how I navigated ambiguity and pursued things when I wasn’t simply instructed to do so. I was surprised at the time. Now it makes perfect sense in my mind that they’d ask me.)
3. “Pretend I could give you two years’ worth of money to live comfortably, and you didn’t need to work anywhere else. But there’s a catch. To receive this money, you’d have to write a blog about literally anything you want, anything at all. What would you write about?”
Why this question: This helps you understand whether someone has that all-important intrinsic desire to create, that motor and that imagination and that relentless pursuit of curiosity. Additionally, it helps you understand who the person is when they’re not trying to impress someone. What are they interested in? Ask why that topic, because it’s another way to understand who they are, where they came from, and what they want to do in life. (Note: It’s useful to weed out people who pander, too. For instance, when hiring for a past editorial team that I ran inside a big tech company, some people replied that they’d write about SEO or marketing, because that’s what we wrote about, in part. While I applaud anyone who truly loves what they do for their day job, it always felt like they were pandering to me. They said what they thought I wanted to hear, rather than what was true. We all harbor these weird but wonderful quirks and interests, and we all wonder at some point in life, “Wouldn’t it be great if…” If I felt someone was burying that and trying to pander to me instead, I replied by assuring them I wanted to know their deepest, geekiest answer, not something superficially relevant to the job. They’d often get excited, drop the pretense, and give me their real answer next.)
4. “Who or what inspires you? What are your go-to sources to get excited? What do you read, watch, or listen to?”
Why this question: (a) You get to see whether they’re going outside their echo chamber to learn and get inspired, in order to avoid rigid, conventional best practices and become a well-rounded thinker and maker, and (b) the people they admire will heavily influence what they enjoy doing and creating, and how. You’ll learn a ton about the person and their innermost aspirations with this question, and you can envision what it would be like to have a distant echo of their hero(es) at your company.
5. “How did you prepare for this interview?”
Why this question: How do they prepare for things in general? Do they go beyond the superficial to dig deeper? Did they actually put in the time to research and prep, or are they winging it? Do you want that type of person on board and working with you, or not? (When you ask them if they have any questions for you, you’ll also learn if they actually did their research.) This is a sort of “attention to detail” question which isn’t a weird brain teaser but actually knocks down any professional facade by asking for the story of what they really did.
6. “Where do you disagree with my/our team’s thinking and opinions?”
Why this question: Personally, I want to know that we aren’t hiring people who think the exact same way we do. While shared beliefs and values are important, so is cognitive diversity, especially in the minutiae of how we execute. (In other words, they have to believe in what we are building towards, but have opinions, ideas, and challenging questions about how we get there.) A bonus benefit of asking this question is you’ll learn how they prepared for the interview, too. They can’t answer unless you really spent time with your work. (Note: I often find I have to reassure them that we want disagreements and won’t hire someone who never challenges me or us. Then they open up more.)
7. “Of all the things required of you in your work, what gives you energy?”
Why this question: It helps you understand what they truly get excited about and thus want to lean into more in their career. Rather than ask about “passion,” which is a bit nebulous and not always aligned with what they’re good at, asking what gives someone energy in the work they’ve done is how you better understand how they feel about their various projects. Where do they find flow in their work? When people get lost in the process, they seek out that type of work more often, and they proactively find ways to improve it. That’s the kind of response you want your team to have towards their work. That’s how they find fulfillment, too. So this is not only revealing information to you, the interviewer, but it helps you wonder to yourself, Is this job going to provide them what they need to thrive?
8. “Of all the things required of you in your work, what drains you of energy?”
Why this question: The inverse of #7 is equally as important, and while it’s hard to talk about what you dislike during an interview for a job, this is vital information to know. To ensure I get honest answers, I often start this question by saying something reassuring like, “We all have these things in our work, and I certainly do, so please feel free to be honest. If you can’t describe anything, I’d actually be worried you were putting on face here. We value transparency, and we want to ensure the job molds to the person, too.” This gives them a kind of “permission” to answer openly. If it doesn’t work, and they’re still too formal, I may give an example from my work, but I hesitate to start with that because it anchors them to the category of topics I’ve just shared, or maybe even exactly my example. (I’ve gotten too many answers that sound like, “Yanno, I’d actually say the same thing as you.”)
9. “Can you explain the process behind your assignment?”
Why this question: I always assign a small project before I ever talk to someone one to one. I let them know it is indeed time constrained, and that if I ever use any of their work for our company, I will pay them. But I front-load the project assignment because (a) I want to ensure they can really do the work before we go any further, and projects are the best way to do that, and (b) I want to remove my own biases from the process early on. We often flip this, putting a project at the end, because we think the project must be huge. Unfortunately, you may have missed someone who was brilliant at the work because you focused on the wrong things early, like where they went to school or whether they made you laugh. Logically, a first filter is the more objective question of whether or not they can do the work, and to what degree, and in what ways they make the work their own. Then, once you have a smaller group of people in mind who can indeed deliver, you can focus on the surrounding things, like interpersonal stuff, communication, challenging each others’ thoughts, and so forth. So, lead with the objective stuff (a project) and get more subjective later. (Who cares if Mary is less charming than Sally, or that I lived in the same city as Mary, or we attended the same school? Who cares about any of that if Mary is amazing at the work compared to Sally? We shouldn’t let biases weed out great candidates any more than we should let superficial but less-important things advance a candidate further.)
10. “What questions do you have for me?”
Why this question: Again, it shows you what they think about and whether they’ve done their homework. I often lace this with some qualifiers when I ask it: “It can be about me and my work, the company, our content, the job itself — anything.” A bad sign is if they shrug and go, “Yanno, I don’t have anything,” or if they ask some generic question because they think they’re supposed to. Given how revealing and important this question is, I’ve started asking it first over the last few weeks, and I’m leaning towards always opening with it.
Although there’s no one right way to run an interview when hiring, I think we tend to cling to the wrong way more forcefully than in most things we do. We copy the conventional wisdom and “best practices” of interviewing and hiring. We ask rote questions and proceed with the phases of resumes/cover letters, then phone calls, then projects, then deeper conversations or meeting the team, and so on. It’s not our full-time job to hire, so we just default to what one is “supposed to do.”
But who we work with and how we work together are among the most crucial things in our entire careers. That stuff makes or breaks any venture. Why not master it the same way we master anything? By questioning best practices and thinking for ourselves.
In the end, not only do we learn more about others, we learn how we can better help them, too. That’s the difference between hiring an employee and hiring a colleague … between top-down control that stalls out, and creative collaboration that makes things better.
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