Issue No. 08 | My Top 5 Interview Questions for Small Business Hiring (and Why I Love Them)
When I first started in HR, I hated interviewing. Hated. It.
I can vividly remember early interviews when I would sound super stiff, overly scripted, and really self-conscious I’d pick the wrong person. And no surprise here, I definitely did make a wrong hire or two when I was just starting out.
Interviewing did not come naturally to me, and if you’re a small business owner feeling the same way, trust me, you’re in good company.
Interviewing is a learned skill, not a personality trait. It’s like a muscle — the more reps you get, the stronger your instincts become. You start reading people more clearly and trusting your gut (yes, your gut matters, and it should absolutely factor into hiring decisions, especially in a small business).
And now, 17 years later? I love interviewing. It’s one of my favourite parts of HR, and I genuinely enjoy offering recruitment support to my small business clients. Because once you get the hang of it, interviewing shifts from stressful, insecure guesswork to a genuinely enjoyable, productive conversation.
After years of fine-tuning my process, these five questions below are the ones I use on repeat. This is obviously not an exhaustive list — just a solid starting point to help you understand the human sitting across from you and assess whether they’ll fit your environment, your leadership style, and your team.
Here are my five all-time favourite interview questions — and exactly why I swear by them.
Interview Question No. 1 | What Do You Know About Our Company and Why Did You Apply?
This question does one very important thing: it shows you who actually cares.
You’ll instantly see who took 30 seconds to look you up versus who is applying to anything with a pulse. Small businesses don’t have the luxury of disengaged employees—you need someone who wants your business, your values, and your vibe.
Why I love it:
It reveals effort, interest, initiative, and whether they can clearly explain why this job fits them—not just why they want a paycheck.
Interview Question No. 2 | How Does Your Past Experience Relate to This Role?
This question sounds simple, but it tells you whether a candidate can connect the dots between what they’ve done and what you need. Can they articulate transferable skills? Do they understand the role? Are they aware of what it actually takes to succeed?
Why I love it:
It’s the quickest way to see if someone is self-aware, realistic, and capable of doing the job—not just talking about it.
Interview Question No. 3 | What’s Your Ideal Work Environment?
Small businesses are… unique. Fast-paced, flexible, sometimes chaotic, and almost always personal. This question helps you find out whether someone will fit into your environment instead of being shocked on day three.
Some people thrive with structure and routine.
Some thrive with freedom and variety.
Some need a quiet workspace.
Some need collaboration.
Why I love it:
Fit matters. If you can’t provide the environment they need, you’re setting both of you up for disappointment.
Interview Question No. 4 | What leadership style do you work best under?
This one is gold. Every employee responds differently to leadership—some love clear direction, others prefer autonomy, some need check-ins, others want to be left alone.
Knowing this upfront tells you:
whether your style matches what they need
how to support them
potential friction points
how coachable they are
Why I love it:
Hiring is a relationship. If your leadership style and their working style don’t align, it won’t matter how great their résumé is.
Interview Question No. 5 | What gives you the Sunday scaries at work?
I LOVE this one — and candidates always answer it honestly. It’s relatable, conversational, and it immediately gets to the heart of their workplace values.
Their answer tells you:
What makes a work environment feel unsafe, stressful, or draining
What they don’t want to repeat
What helps them feel comfortable, prepared, and supported
Whether your workplace will give them Sunday scaries too
It’s also a brilliant way to identify potential misalignments before they become problems.
Why I love it:
This question gets people to open up in a way traditional interview questions just don’t — it’s disarming, relatable, and instantly honest. It gives you real insight into what stresses them out at work.
Why These Interview Questions Work So Well for Small Businesses
These aren’t trick questions or high-pressure “tell me your biggest weakness” cliches (I hate that question). They’re conversation starters — and in a small business, how someone communicates and connects matters just as much as their skillset.
By asking these five simple questions, you’ll learn:
Whether they’ll be a good fit with your company culture.
How they communicate
What support they need
What motivates them
Whether they’re excited about joining your type of team
And that’s exactly the info small business owners often miss when hiring. Use them consistently and you’ll make smarter, faster, better hiring decisions.