Creative Interview Questions to Find Your Next Great Hire

by Joan Garry

Here is a question you should ask in interviews that you probably haven’t thought to ask before – and why typical interview questions just don’t cut it.

This weekend I was out to dinner with my family. My daughter (of age) ordered a Bloody Mary, but after one sip she was done.

“I can’t drink this,” she told the waitress, Kim. “It has way too much horseradish.”

Kim’s response –which was not impressive – led me to my first big “AHA” moment of the weekend. It was about hiring staff and a key question to ask in an interview.

This one question can let you know if you’re talking to your next great staffer.

So today I’m going to share with you a question you should ask – one you probably haven’t ever thought to ask before – and why typical interview questions just don’t cut it.


So what did Kim say to my daughter? Her response was quick and final. “Oh, that’s the way the mix is prepared. Sorry.”

At least she said sorry.

Now imagine Kim worked for you at your nonprofit. Is this the way you want your staff members to respond to a problem? I sure wouldn’t. I would never hire Kim to work for a nonprofit. Or for any organization for that matter.

Why not? I want someone creative and nimble and generous. Someone who would say, “You should enjoy your cocktail. I don’t know if we have plain tomato juice on the bar – I don’t think so – but the bartender should be able to fix this drink so it is just the way you like it.”

I was recently taking a long weekend on the beach and trying to unplug. The novel I brought with me was just too sad, complacent and unhappy. So I moved on to Grit by Angela Ducksworth. I highly recommend it.

Grit is a fascinating exploration of the impact of passion and perseverance and effort and how these attributes are critical to success. Even more so than raw talent, expertise, or skill.

How is this connected to Kim? It shows that the usual interview questions are insufficient. They focus on talent, expertise, and skill. But they tell you little about creativity, generosity, commitment to service, passion or effort.

That was my second “AHA” moment.


I’ve been working with a group of teachers recently promoted to department heads, now with hiring and managerial responsibility for the first time.

We embarked on an exercise to describe the ideal classroom experience for a 3rd grade classroom. I asked them to talk about what they would see and hear. What would the teacher do or say that would lead you to know that this was a rockstar educator? What skills and attributes would be needed in that teacher to create that kind of classroom community?

Lots of skills were mentioned, but way more attributes.

The new department heads found my classroom question so revealing that it has shaped how they hold teachers accountable and make new hires. Over time, the classrooms they walk into will be the classroom experiences they all described to me.

This got me thinking. Why can’t we ask what might be considered an off-the-wall question to a prospective hire, asking them about a universal experience, and work with them to tease out their answers in a way that unearths passion, creativity, effort and GRIT?

(P.S. one cool thing about off-the-wall questions? You can’t prepare for them!)

Nonprofits are messy and they demand folks with grit. So here’s my kinda off-the-wall question that could help you make great hires.


Everyone has sat in a 3rd grade class. So here goes. Try it on and see what you think.

We’ve all been in a 3rd grade classroom. Maybe you have kids and have been in their 3rd grade classroom. I find the classroom to be a terrific microcosm for a community of board or staff – a group of friends – because the experience is universal.

Imagine you’re sitting at the back of a third grade classroom observing. Can you describe for me how you know that this classroom experience is one that has the potential to shape those kids in important ways? What is going on? What do you see and hear?

Tell me about the teacher. What is that teacher doing / saying? How is s/he engaging with the students? How is the space organized? Why do you think it’s possible that this classroom has the secret sauce?

After your candidate answers, then the next step:

What attributes and skills are required of that teacher to create that kind of magic?

Listen carefully. Then:

Let’s talk about those attributes. Tell me about which of them you possess and which you need to develop further. Can you give me examples of professional experiences in which you have needed those attributes and how you have put them into play – with your boss, your colleagues, your own staff?


At some level it depends on what you are hiring for. But there are clearly some things you want to hear and tease out in detail. They tie back to my two ‘AHA’ moments at the start of this post.

The very best teachers are gritty. The very best classrooms are often chaotic – lots of noise generated from the excitement of interaction students are having working in small groups. They may, at first blush, even seem a bit messy.

To be a great teacher, you must be passionate, dedicated for the long haul and persevere – be it with tough kids, a tough principal, or tough parents (the most likely scenario.)

These are the things you would like your candidate to talk about and then you can ask the candidate to offer examples of how s/he has exemplified these attributes in her/his professional career.

Or even in her/his personal life. For example, perhaps this candidate has overcome a learning disability that should by all means have precluded the candidate from being a good writing.

In Grit, Ducksworth talks about one of our most renowned and prolific American novelists, John Irving, who was a C- English student in high school because of a learning disability. You’ll have to read the book to really appreciate his grit.


Is there an interview question you find particularly helpful in unearthing the REAL stuff you need to know to make the very best hire? I’d love to hear what you find helpful and how you approach interviewing in a way that reveals not just what experience the candidate has but who the candidate really is.

Let all of us know in the comments below.

39 thoughts on “Creative Interview Questions to Find Your Next Great Hire”

  1. So with one cocktail mistake, Kim is now unemployable? Was the rest of her service terrible? If Kim was under 30, I would cut her some slack. When have you not done “grit” in your lifetime for someone? I love “Grit” but I don’t expect people to live 24/7 by its rules.

  2. I like to ask the question, What are your hot buttons when you’re interacting with colleagues and staff? How do you handle your reaction when something ticks you off? The candidate can’t easily wriggle out of revealing a challenging aspect of her or his personality – those things that irk you about others – and then how she/he answers the second part of the question tells me something about her/his emotional intelligence, the ability to reflect and self-regulate.

  3. Years ago, I worked with an HR consultant to improve my interviewing and hiring skills. She gave me a lot of great tools to work with which I still use today. Her favorite question was: “how are you like your mother? (or father) How are you not like her?” It was a shocking question to everyone but it did bring out some fascinating information about how they see themselves, their values, their work ethic, etc. I no longer use it because it feels inappropriate but I do try to come up with questions that get to these deeper issues of attributes. I like yours and will try it. I’m assuming you wouldn’t use “third grade classroom” for, say, a development director but would rather ask, “what does a successful development department look like?”

  4. My favorite “off the wall” interview question is one I learned from a great boss – “If I made you choose between being perfect and being on-time, which would you choose and why?” Technically, there is no right or wrong answer…it’s all about how the candidate approaches and answers the question. You get some insight into the way their mind works and what they value and think of in terms of success. This question has never failed to surprise candidates!

  5. As I prepare interview questions for the Director of Marketing position currently open at our children’s museum, I find this “out of the box” question inspiring! Thanks for sharing.

  6. Well, it depends what you are looking for. I think Joan explained that she is looking for someone who is creative and thoughtful and generous. So yeah, her response shows how she approaches her job (even if it is as a waitress), which often speaks to the way people approach life. I’m with Joan — I don’t want someone whose response is “that’s just the way it is”, I want someone who sees there is a problem and wants to find a solution.

  7. One of my favorite questions is – You walk up to the copier and it says “needs toner.” What do you do? Says a lot about problem-solving skills, resourcefulness, etc. A similar one is – You walk up to copier and there’s a paper jam. What do you do? This one can get to how they face adversity, deal with colleagues, etc. Nothing like the copier challenge to get to the heart of things. 🙂

  8. When I am feel feisty, I sometimes leave a piece of garbage on the floor to see whether the candidate will pick it up.

  9. We all want people to find solutions to problems. There are 100 or more steps to get there.

  10. My favorite when I hired arts professionals to the teaching staff of a nonprofit was this:
    Can you tell me a time when you failed one of your students? (Then, after they answer: How did that experience change the way you teach?)
    It’s a bit of a shocker in the midst of self-promotion, but wonderful to hear how much great teachers care about all parts of their (adult and child) students’ well-being – and it is clear the ones that are the best and most insightful learners themselves from this question. “Clients” “donors” or even personnel could be substituted for different positions.

  11. It was also the “ah ha” of the moment that was important. In story telling, providing too many details about things that distract the reader from the point can muddle the moral and bog down the article. Joan didn’t want to talk about the waitress’s career trajectory – she wanted to show how one response from a stranger inspired a moment of insight about the value of creating/using every day scenarios to reveal an applicant’s primary tendencies.
    Now, it is also true that people who have not waited tables may not understand the constant judgment or harassment that servers endure. So, if you’re just saying, “hey, give your waitress a break” I can totally get that : )

  12. Sarah. So much better than asking folks about their weaknesses. Everyone has already fine tuned their ‘what do you see as your weaknesses?’

  13. Christine – I was not suggesting that she is now unemployable. Kim was a ‘device’ to make a point. Kim was a perfectly serviceable waitress for quite a yummy dinner. 🙂

  14. I am reminded of my father (of blessed memory) who could not stand going into large hardware stores where he would ask if the store carried X only to be told “If it’s not on the shelf I guess we don’t have it.” That is probably a true statement in many cases but I want more from nonprofit leaders. Donors and those you serve deserve more.

  15. I might use the devo development department look like but i really might ask about a 3rd grade classroom. here i would be trying to unearth values that come out of observations.

  16. I like to ask candidates about traits of the worst boss they ever had, before asking what traits they appreciate in a supervisor. Let’s me know how they handle conflict, whether *I* possess a style that will work for them, and creates a disarming moment of “realness” in what can sometimes feel like a scripted interaction.

  17. I’d really like to thank everyone for these really creative questions & Joan, thank you! of course, tomorrow I have my last virtual interview with a candidate I would hire for the Middle East and you have given me some great last questions to ask.
    One of my favorite interview questions has always been, ‘You can go anywhere in the world– where will you go… & why?’ This question sparks very interesting conversation, and their answer can reveal so much about them.

  18. I was asked whether I preferred cats or dogs. I just laughed (not derisively – I genuinely found it funny). I said, I am a cat person myself but I like dogs and I respect people’s right to prefer whichever one they want. It was one of the best interviews I have attended and led to many happy years in that job.

  19. My favorite question is always the first question I ask….Tell me about yourself….It is always so telling

  20. I use the question “How are you inspired ?” Or “What inspires you?” and then ask “What drains your energy?” But I am stealing Sylvias- “You walk up to the copier and it says “needs toner.” What do you do?”…Brilliant!

  21. Great observations as usual, Joan. I love the storytelling approach to the question. It’s like those word problems in math vs. simple arithmetic. You definitely want people who can listen and think critically about what they hear. Brava! (And I love Grit too.)

  22. I have no idea of what a 3rd grade classroom is like. I have no children, and it was so long ago and I was so absorbed with studying that I remember none of it.
    I don’t even remember what a 3rd grader was like.
    That question makes me feel so alien and out of the loop. I would probably freeze up on it.
    Maybe that is why I always did so terribly on job interviews. Lol.

  23. Being an HR executive for a major part of my career, I’ve got some favorites: 1. Tell me your favorite joke. (Goes to “discretion”) 2. What is the difference between membership service and customer service? (there isn’t any) 3. Have you ever been late to a meeting? 4. What steps are you taking to prepare for your retirement?

  24. I’m so in favor of seeking out attributes rather than skills. My favorite interview questions (which I usually bring up last) is “If you could have one super power, what would it be and why?” It is without a doubt one that allows me to learn the most about the candidate. Do they get excited? Do they hem and haw and act uncomfortable? Do they present a thoughtful answer about why they would choose a specific “power” or do they do an all encompassing and unachievable “I want to save the world” answer? My favorite answer always starts with, “OH, I was just talking (or thinking) about this the other day!”

  25. may be not the most original question, but I still like using, “Describe your desk for me.” It allows me to assess what is important to them, how messy they are, how organized they are, how office work fits into their priorities, etc.

  26. I like to ask: “If you could create an environment in which you would be the most successful, what would that environment look like?” I love the diverse answers that I get to this question.

  27. I am noticing more of the younger professionals coming through are more like Kim. It is a different thing for me as I am one who overextends myself (not always a good characteristic in the NP world when it comes to self care!). What are you all seeing? Am I the only one noticing this generation seems a bit more self focused? I have been told “it is not worth my time” when asked to handle something, and they were serious about saying that to their supervisor and did not understand why they took issue with it. Or when asked to re-do something the comment is they feel micro managed. Looking for a good balance between over extenders and self focused folks – what key question would reveal that in a short interview? Thanks all for sharing, great thread to be following!

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