I really love hiring—especially interviewing.
My years of experience building teams from the ground up have shown me that interviews are a chance to meet great people.
However, no one ever specifically taught me how to conduct interviews. I learned through trial and error. I read a lot about the topic, listened to podcasts, and talked to other start-up leaders who were scaling their teams quickly.
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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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 fixating on the question "how do you interview someone". 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.
Conducting an interview with advanced question techniques
To hold interviews effectively, it’s important to mix good questioning methods with a friendly approach. This helps the candidate feel comfortable and encourages honest conversation.
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 good technique is the funnel method. Start with a broad question like, "Can you tell me about a challenging project you worked on?" Then, ask more specific questions about their role, the challenges they faced, and how they solved those issues.
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. Many candidates see the hiring process as unclear. They work hard, then wait for feedback, only to face rejection without really knowing why.
I invite candidates to take part in the decision-making process. I encourage them to share their concerns and give them time to think. For example, I once interviewed a candidate who seemed confident but hesitant about stepping into a role that involved managing a larger team.
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 discussion where we both saw that the role might not match their current goals. The candidate thanked us for the clarity we found together.
By listening carefully and asking open-ended questions that encourage self-reflection, interviews can become a joint exploration instead of just an assessment. This approach not only helps assess fit but also leaves candidates feeling respected, regardless of the outcome.
How do you conduct an interview to assess skills and culture 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 says they are good at SEO, I would ask, "Can you explain a recent project where you improved a website 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?"
This not only checks their problem-solving skills but also shows if their mindset and approach match how we work.
At the end of the day, it’s about marrying the technical with the personal.
How to interview takeaways
You’re here because you're searching for tips for job interviews.
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.
