The interview questions that tell you more than a resume ever could

Thinking of whinging the interview?

Most small business owners walk into an interview with a rough list of questions in their head, a copy of the resume on the table and a vague plan to just… see how it goes.

Which works fine, until you’re three months in and realising the person you hired interviews beautifully yet doesn’t actually fit your team, your culture or the reality of the role.

The interview is your best chance to find that out before you make the hire — yet it only works if you’re asking the right questions, the ones that go beyond what someone has done and get to who they actually are.

Here’s what I recommend instead of winging it.

Start here

the one question I recommend every small business owner asks 👇🏽

💚 “Tell me about your ideal day at work. What does it look and feel like?”

It sounds almost too simple, yet the answer tells you more than almost anything else you could ask. Someone who describes a day full of variety, spontaneous problem-solving and constant interaction — in a role that’s heavily systems-based and largely independent —is telling you something important about fit. A mismatch like that is worth knowing about before day one, not after.

Someone who lights up talking about focused, quiet, deep work, in a fast-paced, people-first business that runs on energy and collaboration? Also worth knowing, for exactly the same reason.

The best hire isn’t always the most experienced candidate. It’s the person whose natural working style actually fits the reality of your business right now.

A few more worth adding to your toolkit

Once you’ve asked the ideal day question, here are a handful of others that cut through the rehearsed answers and get to the real person sitting across from you.

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💚 "Tell me about the best team you’ve ever been part of. What made it work?"

This tells you what they value in a team environment — and whether those things exist in yours. Listen for whether they talk about people, culture and connection, or process, autonomy and results. Neither is wrong, you just need to know which one you’re hiring.

💚  "Tell me about a time you dropped the ball at work. What happened and what did you do?"

This one cuts straight to self-awareness and accountability. Someone who owns the mistake, explains what they did to fix it and reflects on what they learned? That’s someone who will handle your inevitable hard conversations with maturity. Someone who deflects, minimises or blames everyone else? Worth noting.

💚 "What do you need from a manager to do your best work?"

Most small business owners don’t have a lot of time for hand-holding, so this question helps you find out upfront whether the person you’re about to hire needs constant direction, or whether they can run with a brief and check back in when they need to. Both styles exist in the world — you just need to know which one fits your reality.

💚  "Why us and why now?"

Simple, yet so revealing. A candidate who has done their homework — who knows something real about your business, your values or what you stand for — is telling you something important about how they approach things generally. The candidate who gives a vague, generic answer is also telling you something.

How you ask matters as much as what you ask

The best interview questions don’t work if the room feels like an interrogation. The candidates who are right for your business perform better in areal conversation than in a formal Q&A, so create the conditions for that.

Start with something easy to settle nerves. Tell them a bit about the business and what you’re looking for before you dive into questions. Be honest about the challenges of the role, not just the good parts — the right person won’t be put off by honesty. They’ll appreciate it.

What you’re actually looking for

Skills can be taught and systems can be learned, yet what’s much harder to change is someone’s working style, their values and the way they show up for a team. A great interview isn’t a test to see how well someone performs under pressure — it’s a conversation designed to help you understand who this person actually is, and whether who they are is a fit for where your business is going.

Take your time, ask the questions that matter, and trust your instincts.

Want to go deeper on the full hiring process? The Bold Hire is a live 90-minute masterclass where I walk you through everything — from scoping the role to making the offer and onboarding your new person properly from day one.

$29. Date dropping very soon.

Jump on the waitlist here

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