How to conduct an interview that actually tells you something

I love hiring. Interviewing most of all.

But nobody taught me how to do it. I learned the way most people do, by getting it wrong, reading too much about it, and cornering other founders who were scaling teams fast and asking what worked for them.

Here’s the conclusion I keep coming back to. Most interviews don’t measure what you think they measure. They measure how well someone interviews. The candidate who rehearsed, who’s done forty of these, who’s comfortable on camera, walks out looking strong. That’s a real skill. It’s just rarely the skill you’re hiring for.

A useful interview is different. It’s built to surface evidence of how a person actually works, and it holds every candidate to the same bar so you can compare them honestly. That’s harder than it sounds, and most of the work happens before anyone sits down. This post is about both halves: what to do before the interview, and how to run the conversation once you’re in it.

Great interviews start before the interview

A mistake I see all the time, usually from leaders who came up at bigger companies where they only ever saw the interview stage: they decide interviews are the problem. “Interviews are a waste of time. I can tell in five minutes when someone’s a bad fit.”

If that’s how your interviews feel, the candidates aren’t the issue. Your screening is. If the wrong people keep reaching the interview stage, your filters aren’t doing their job, and no amount of clever questioning fixes a bad shortlist. You’re just running good interviews on the wrong people.

So before you touch your interview technique, fix what gets someone an interview in the first place. Put real qualification questions in the application. Ask for the one or two things that actually predict whether a conversation is worth your time, not “years of experience” but the specifics of the work.

This is the lane candidate screening software sits in, Truffle included. Truffle is a candidate screening platform that combines resume screening, one-way video interviews, and talent assessments. Use one on its own or stack all three. You can ask candidates to record short video answers to questions like “What are you looking for in your next role?” or “What are you learning right now?” and layer in assessments that read for personality tendencies, situational judgment, and how someone fits the realities of the role. AI transcribes the responses, scores each one against the criteria you set, and surfaces summaries and match scores so you can see who’s worth a live slot before you ever schedule a phone screen. The AI doesn’t pick for you. It just gets you to a shortlist you can trust faster.

One question I always ask: top strengths, and one thing you’re actively working on. The thoughtful, self-aware answers are the ones that catch my eye, and those candidates almost always show up strong in the live interview too. That’s the tell. Good screening doesn’t just save you time. It loads the room with people worth talking to.

Run the conversation with funnel questions

Once someone’s earned the live slot, the job changes. Now you’re trying to get an honest, unrehearsed picture of how they think, and that takes both good questions and a setting where they’ll actually open up.

I start broad and open-ended. It lets the candidate talk freely, and it keeps me from steering them toward the answer I’m fishing for.

I always start with broad, open-ended questions, which allow the candidate to speak freely and help me avoid leading them in any direction.

Then I funnel. Open with something wide, like “Tell me about a challenging project you worked on.” Once they’re talking, narrow in. What was your role specifically? Where did it get hard? What did you actually do when it did? Each follow-up tightens the focus until you’re past the rehearsed summary and into the real decisions they made.

The funnel does two things at once. It gives you a fuller picture of their experience, and it lets the conversation breathe instead of feeling like an interrogation. People tell you more when it feels like a conversation, because it is one.

What separates a good interview from a great one, though, is treating it as a two-way decision. Most candidates experience hiring as a black box. They work hard, they wait, and they get a rejection with no idea why. So I pull them into the call itself. I tell them what I’m seeing, I name my hesitations out loud, and I give them room to think.

A while back I interviewed someone who looked great on paper but seemed uneasy about stepping into a role managing a much bigger team. Halfway through I stopped and said, “You’ve done incredible work with small teams. What excites you about leading a bigger one?” She paused, then admitted she wasn’t sure she was ready for that jump.

That turned the interview into something better than an interview. We stopped performing for each other and talked honestly about what she wanted, and we both landed in the same place: the role wasn’t the right fit right now. She thanked us for the clarity. Nobody walked away with a bad taste, and I didn’t make a hire that would have unraveled in three months.

That’s the upside of asking questions that invite reflection instead of a pitch. The interview becomes a joint exploration, not a one-way test. You get a clearer read on fit, and the candidate leaves respected whether or not you make an offer. That matters more than it used to, because the candidate you pass on today talks to the candidate you want to hire next year.

How do you conduct an interview that assesses skills and values

Two things decide whether someone is right for the team: can they do the work, and will they thrive in how your team actually operates. They’re different questions, and you assess them differently.

Assessing hard skills is more straightforward. I ask the candidate to walk me through specific examples of work they’ve done, digging into the how and why behind their choices.

Say a candidate tells me they’re great at SEO. I don’t take the claim. I ask them to walk me through a recent project where they improved a site for search. What was the strategy? How did they measure whether it worked? What moved, and by how much?

This does more than test knowledge. It exposes thinking. Can they explain their approach clearly, or does it dissolve into buzzwords the moment you push? Do they have real numbers, or just adjectives? Someone who actually did the work has the details ready. Someone who watched it happen doesn’t. The gap shows up fast once you ask for specifics, which is the whole reason to ask.

Values fit is trickier. You can’t put it on a spreadsheet or pull it from a portfolio. It’s about how someone works, what they expect from the people around them, and whether they’ll do well in your environment specifically.

So I ask about motivation and behavior. “What does your ideal team dynamic look like?” or “Tell me about a time you had to work through a hard situation with a coworker. How did you handle it?” Answers like these show me how a person actually operates under friction, not how they’d like to think they do.

My favorite move is to be candid about what’s hard right now. I’ll describe a real obstacle the team is facing and ask, “How would you approach this?” It tests problem-solving with a live problem instead of a hypothetical, and it shows me whether their instincts line up with how we work. It also tells the candidate something true about the job, which is only fair.

The point is to weigh the technical and the personal together, because a strong hire needs both and a great answer in one column rarely makes up for a weak one in the other.

Make it repeatable, then trust it

Here’s the part that took me too long to figure out. None of this works if you do it differently every time.

If one candidate gets the easy version and the next gets grilled, you’re not comparing two people. You’re comparing two interviews. The structure is what makes the comparison fair: the same core questions, the same bar, the same things you’re listening for, run consistently enough that the differences you see are real differences between candidates and not just differences in how the conversation happened to go. A simple interview schedule template goes a long way here, locking in who asks what and in what order so every candidate gets the same shot.

That’s also where good screening and good interviewing start to feel like one system instead of two. The application questions, the video responses, the assessments, the live conversation, they’re all collecting evidence on the same person. When they’re consistent, each layer makes the next one sharper. When they’re improvised, you’re back to trusting your gut and hoping it was right.

You won’t get this perfect. I still don’t. Some of the best people I’ve hired interviewed unevenly, and I’ve been wrong about candidates I was sure of. But the more your process leans on evidence over impressions, the less often you’re surprised, and the easier it is to look a hiring manager in the eye and say exactly why this person and not that one. That defensibility is worth as much as the hire itself, and it’s the thing a box-ticking interview can never give you.