Creative Interview Questions to Find Your Next Great Hire

creative interview questions

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.