Effective interviewing: How to conduct an interview like a pro

I really love hiring—especially interviewing. My years of experience scaling teams from 0 to hundreds of people has taught me that interviews are opportunities to connect with wonderful people. 

However, no one ever specifically taught me how to conduct an interview. It was something that I learned through trial and error, reading as much as I could on the subject and listening to podcasts, and talking to other start-up leaders tasked with rapidly scaling their teams. 

In this article, I’m going to try and distill down the principles that make up effective interviews. I’ll touch on how to create a strategic interview schedule template, use advanced questioning methods, and assess those all-important soft skills and cultural fit. 

You’ll be an interviewing expert in no time.

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Ask more questions as part of your application

Before diving into interviewing, it’s important to talk about screening—because great interviews start with great screening.

A big mistake I see hiring managers make is thinking recruiting is just about interviews. They come from larger companies where they only saw the interview stage, not the entire process. So, they’ll say things like, “Interviews are a waste of time; I can tell right away when it’s a bad fit.”

But if your interviews feel like a waste of time, it’s not the candidates—it’s your screening. If the wrong people are making it to the interview stage, your filters aren’t working. That’s on you.

One simple tool for better screening? One-way virtual interviews. Ask things like, “What are you looking for in your next role?” or “What are you learning right now?” A messy answer is a good indicator the interview might go the same way. These quick questions can give you a ton of insight before wasting time in an interview.

For example, I ask candidates about their top strengths and one thing they’re working on. The thoughtful, self-aware answers are the ones that catch my attention—and those candidates tend to shine in interviews too.

Good screening means better interviews.

Use advanced question techniques

To conduct interviews like a pro, it’s essential to blend advanced questioning techniques with a collaborative approach that puts the candidate at ease and invites honest, open discussion.

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

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

A great technique here is the funnel method—start with something general like, “Tell me about a challenging project you worked on,” and then drill down into specifics about their role, the obstacles they faced, and how they overcame them. This gives a fuller picture of their experience while allowing the conversation to flow naturally.

What really sets the process apart is taking a collaborative approach during interviews. Most candidates feel like the hiring process is a black box: they perform, wait for feedback, and often get a rejection with no real understanding of what happened.

Instead, I make a point of inviting candidates into the decision-making process by addressing concerns directly and creating space for reflection. For example, I once interviewed a candidate who seemed confident but hesitant about stepping into a role that involved managing a larger team.

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Midway through, I paused and said, “I notice you’ve done incredible work with small teams—what excites you most about leading a bigger one?” The candidate hesitated, then admitted they weren’t sure they were ready for that level of responsibility.

We shifted the conversation from selling themselves to having a real dialogue about what they wanted. This led to a collaborative discussion where we both realized the role might not align with their current goals, and the candidate expressed gratitude for the clarity we reached together.

By listening deeply and asking open-ended questions that foster self-reflection, interviews can be transformed into a shared exploration, not just an evaluation. This approach not only helps assess fit but also leaves candidates feeling respected, regardless of the outcome.

Assess soft skills and cultural fit

When it comes to assessing both hard skills and cultural fit, I take a similarly direct and thoughtful approach. These two areas—while distinct—are equally important in determining whether a candidate is right for the team.

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. For example, if a candidate claims to be proficient in SEO, I’ll ask, "Can you take me through a recent project where you optimized a site for search? What was your strategy, and how did you measure success?" This kind of questioning not only tests their technical knowledge but also reveals their thought process. Are they able to articulate their approach clearly? Do they have metrics to back up their claims? A well-prepared candidate will have these details ready to go.

Cultural fit, on the other hand, is trickier. It’s not something that can be measured on a spreadsheet or demonstrated in a portfolio. Instead, it’s about shared values, work ethic, and whether or not someone will thrive in your environment.

To get a sense of this, I lean on questions that explore motivations and behaviors, like, "What does your ideal team dynamic look like?" or "Tell me about a time when you had to navigate a difficult situation with a coworker—how did you handle it?" These answers give me insight into how the candidate operates in real-world scenarios, and whether their style will mesh with the team.

One of my favorite ways to probe cultural fit is by being candid about our company's challenges. I'll share a current obstacle the team is facing and ask, "How would you approach this?" Not only does this test their problem-solving skills, but it also reveals whether their mindset and approach align with the way we do things.

At the end of the day, it’s about marrying the technical with the personal. A candidate might tick all the boxes on paper, but if their approach or attitude doesn’t align with our values, it’s a no-go. Likewise, a culturally aligned candidate with a passion for learning can sometimes make up for gaps in hard skills with the right support. The key is in asking the right questions to uncover both—and being upfront with the candidate when it’s not a match.

Conclusion

You’re here because you wanted to improve your interviewing technique.

It’s taken me years (and way too many hours thinking about hiring) to land on an approach that works consistently. But don’t worry—no need to go down the rabbit hole quite like I did. The basics are all about blending thoughtful screening, strategic questioning, and reading between the lines when it comes to both hard skills and cultural fit.

Start with refining your screening process to avoid wasted interviews, use collaborative techniques to dig deeper, and remember—sometimes it's as much about cultural alignment as it is about technical skills.