12 Interview Questions Every Small Business Owner Should Ask

You don’t need a formal hiring framework to interview well. You need a short list of good questions, asked the same way every time, so you can compare candidates fairly instead of going on gut feel.

Here are twelve questions worth asking, grouped by what you’re trying to learn. Pick the eight or nine that fit the role - you don’t need all twelve in a single conversation.

Questions about how they actually work

Past behavior predicts future behavior better than hypotheticals. These get candidates talking about what they’ve really done.

1. Walk me through a typical day in your last job.

An easy opener that quickly shows whether their real experience matches the resume - and how clearly they can explain their own work.

2. Tell me about a time something went wrong at work. What did you do?

You’re listening for ownership. Strong candidates describe the problem and their part in fixing it. Weak ones blame everyone else.

3. What part of this kind of work do you enjoy most? Least?

The “least” half is the useful one. If their least favorite thing is most of your job, that’s important to know now.

4. How do you handle a busy day when everything needs doing at once?

Especially important for retail, restaurants, and trades. Look for a real method - prioritizing, asking for help - not just “I work hard.”

Questions about fit with your business

A small team feels every hire. These questions test whether someone will thrive in your specific environment.

5. What do you know about us, and why did you apply?

You’re checking for genuine interest. A candidate who looked you up and has a real reason will usually stick around longer.

6. We’re a small team, so everyone pitches in beyond their job title. How do you feel about that?

Be upfront. Some people want a narrow, defined role - better to learn that before you hire, not after.

7. Describe a manager or workplace where you did your best work.

This tells you what they need to succeed. If it’s the opposite of how you run things, that’s a real mismatch worth weighing.

8. Tell me about a time you dealt with a difficult customer or coworker.

Almost every small-business role touches people. You want calm and level-headed, not someone who gets dragged into conflict.

Practical, deal-breaker questions

Boring but essential. Skipping these is how you fall in love with a candidate and then discover they can’t work the hours.

9. The schedule for this role is [be specific]. Does that work for you long-term?

Spell out exact days, hours, weekends, and seasonal crunch. Get a clear yes - not a hesitant “probably.”

10. What are you looking for in terms of pay?

Ask early so you don’t waste anyone’s time. If you already posted a range, confirm it still works for them.

11. When could you start, and is anything else on your plate?

Timelines, notice periods, other offers in play. Useful for planning and a quiet read on how in-demand they are.

12. What questions do you have for me?

Never skip this. Thoughtful questions about the role or the business signal genuine interest. No questions at all can mean the opposite.

How to make these questions count

The questions matter less than how you use them. Three habits make any interview better:

• Ask everyone the same core questions. It’s the only honest way to compare candidates side by side.
• Take notes during or right after. By the third interview, the first one is a blur. Write while it’s fresh.
• Listen more than you talk. If you’re doing most of the talking, you’re selling, not learning. Aim to listen for roughly 80% of the conversation.

If more than one person on your team interviews, those notes become the whole decision. Keeping them attached to each candidate - instead of scattered across texts and memory - is what an applicant tracking system is for.