10 Essential Questions for Hiring Awesome Employees
An unofficial guide to finding the right human, not just the right resume.
Buried in a subfolder of my notes app is a note I’ve been editing for the past three years called “Good Qs to Ask.” Stupidly titled but ever-useful, the note contains a list of every good behavioral interview question I’ve heard or come up with.
When I say “good,” I don’t mean most helpful for assessing a skill. IMO, skills are always best measured through simulations and case interviews instead of meandering “tell me about a time when” rallies. The questions in this newsletter are designed to aid in the most challenging and arguably most important part of hiring: understanding who a candidate really is and how they’ll show up on your team.
Over the years, I’ve revised and refined this list, trying all permutations of questions, but this is my current go-to curation. It might not be your perfect list, depending on what qualities you hire for. But if you’re looking for an ambitious, autonomous, self-aware employee with an internal locus of control, these questions might make an excellent addition to your current interviews.
1. What are you better at than 90% of people?
One of the things I’ve come to value in an employee is self-awareness about their strengths. When someone knows what they’re great at, it sets them up to identify where they can add value and lean in with confidence. People with confidence and awareness about their strengths are also more likely to enter a team and coach or upskill others around them.
I love this question because it helps me understand what skills employees will lean into and what part of their capabilities they’re most sure about. It’s also best paired with the follow-up question, “How do you know you’re better at it than others?” to understand whether their confidence is grounded in fact or fiction.
2. What’s the hardest thing you’ve ever done (personal or professional)?
The first time I heard someone recommend this question, I was stunned by how smart it is. What people consider “hard” is so varied and unique, and asking a candidate to tell you what “hard” means to them can be incredibly helpful in predicting what will motivate and challenge them at work.
When I ask this question, I explicitly suggest that the answer can be personal or professional. While this prompting can lead to some heavy conversations, I recommend giving people the space to share their personal challenges with you. So much of our character is formed outside of our day jobs, and you can learn a lot about where people’s resilience and drive come from by giving them the opportunity to open up.
3. Tell me about a mistake you made multiple times before you truly learned the lesson.
Of all the ways to ask about a person’s weaknesses, this has become my favorite. I came up with the question while reflecting on a lesson I was having a hard time learning, and I realized that often, our repeat mistakes reflect the shortcomings we have to work hardest to outgrow.
After adding it to my interviews, I’ve been impressed by how much this question helps me understand candidates. It also helps you gauge someone’s growth orientation and allows them to demonstrate that they can do the work to overcome their stickiest bad habits.
4. What’s one process, framework, or common way of doing things that you think is overrated?
Because I hire a lot of early-career generalists, I’m particularly wary of people who have solved a problem exactly once and their propensity to become overly attached to the mental tool they used to solve it. I suspect this is true for all disciplines, but in strategy and operations work, there are many overrated frameworks and practices. When hiring for a role that demands strong first-principles thinking, this question helps me assess whether someone has thought critically about the tools they’ve been taught to use and if I’ll be able to throw them at the types of problems that no playbook can help you solve.
Tip: Give people ample time to think about this one. Many don’t have an immediate answer, but you can get amazing insights by asking them to walk you through what they’re considering, even if they don’t land on one solid answer.
5. What’s the most motivated you’ve ever been to achieve something (professional or personal)?
Good interviews should be fun. Sure, you can’t take away a candidate’s nerves entirely, but blending hard questions with ones that let candidates talk about things that excite them can uplift interviews and help make people more comfortable.
This question does just that. I love asking it because it’s a direct way to understand what motivates a candidate, and it lets you see what they’re like when they’re excited. Try asking this, and tell me it didn’t make the whole interview more comfortable after they lit up about something they’re passionate about. I also open this one to personal or professional answers because I find people’s motivations are pretty consistent across spheres of their lives.
6. What’s something that worked for you at your last job that you don’t think will work here?
One of the hardest things to assess in an interview is whether the candidate understands the company they’re interviewing with. I tend to dislike when candidates spend time telegraphing that they’ve read the company website (I don’t need to know — it doesn’t make you a better hire), but it is valuable to understand that they get what they’re walking into.
I love this question because it helps you gauge how well the candidate grasps your culture (and where you might need to fill in gaps) while challenging them to identify which of their ways of working are unique to a past job. Employees who join teams thinking their way is the only way can create friction. Asking this question lets you assess if someone is reflective enough to avoid causing that friction and gives you a read on whether they’ve done their homework.
7. Who is the most challenging stakeholder you’ve ever had to work with, and how did you handle it?
Regardless of whether “stakeholder management” is one of the named skills in your job posting, I highly recommend asking questions that help you understand how a candidate works with others. For me, this question has been the most effective way to get to the root of that.
Understanding what type of people a candidate struggles to work with can give you early insight into where they’ll face challenges in their role. It also gives you the opportunity to understand how they’re likely to work through that struggle on their own. This isn’t one of the more challenging questions, but I’m often impressed by how much it reveals about humility, cleverness, and patience in dealing with difficult colleagues.
8. What’s something at your last job you really wanted to work on or build but never got around to?
Brief origin story: when I was a debate coach, a fellow coach once asked me who my “one student” was. Every good educator, they told me, has at least one student who haunts them (in a healthy, well-adjusted way) because they just couldn’t reach that kid and help them succeed. That sentiment stuck with me. People shouldn’t be tormented by their failures or missed opportunities, but I find that people truly committed to excellence are keenly aware of the times they came up short.
Fast-forward to hiring talented problem solvers, and my working hypothesis is that exceptional problem solvers are acutely aware of many more problems than the one right in front of them and have particular awareness of the issues they couldn’t get around to addressing. This question gives you so much mileage in figuring out if a candidate is the type of person.
It helps you understand if people can spot problems (not just execute on the ones you point them to), assess intrinsic motivation, and give you insight into what types of obstacles they’ve faced and may continue to face.
9. What would your peers tell me it’s like to work with you?
I’ve been in a lot of interviews that ask some flavor of this question, but my personal recommendation is to specifically ask about people’s peers instead of their managers.
Many people are great at managing up while simultaneously being nightmares to collaborate with. Asking someone to really consider their peers’ perspectives and think about their reputation with the people they work closely with gives you a better read on what it will be like to work with them on your team.
10. Tell me one story from your career that best illustrates who you are as an employee.
From what I’ve gathered, this is the hardest question I’ve ever asked in an interview. However, it’s also my favorite question for establishing a clear line of sight into who the candidate is at their best. People often need a bit of time to come up with an answer, but their responses paint such clear pictures of who they are and want to be.
My recommendation: save this question for last. It lets the candidate close the interview on a high note, where you’ve given them the freedom to make the impression they want to make. It always gives the interview a satisfying sense of closure.
Wishing you happy hiring!
p.s. If you’ve got a favorite interview question that I should add to my note, I would love to know!