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The Daily Bolster: How to Interview Executives

February 29, 2024

Interviewing potential executives is a unique challenge. You’re looking for a candidate who is functionally prepared to execute the role, but you also need someone who fits into your organization and will be a part of its growth. 

The interview process likely won’t tell you everything about a candidate, but there are strategies you can use to get the most out of the process and make the best possible decisions. Several guests on Season 3 of The Daily Bolster have shared their preferred interview strategies and tips for hiring executives. Check out their tips and tricks below!

Know the role you’re hiring for

Quick tip: Be familiar with different approaches to the role you’re hiring for, and get clear on exactly what you need. 

Jessica Schultz, the founder and CEO of Amplify Group, shares her top three tips for hiring top sales talent—something she says startups often get wrong. 

Focus on the behavioral interview

Quick tip: Hiring the right people makes all the difference for your organization. Make sure your hiring team is familiar with behavioral interview strategies. 

Matt welcomes renowned executive coach Janis Machala to talk about their shared dedication to a people-first approach to business. Listeners learn how prioritizing people in your organization leads to business success.

Ask the right questions

Quick tip: The interview process is the beginning of a relationship. Find out what motivates a candidate, what accomplishments they are most proud of, and why. 

What are your go-to interview questions for executive candidates? Founder Charles Bonello joins Matt to share the two questions he always asks potential leaders. Tune in to find out what they are!

Look for intellectual curiosity 

Quick tip: Hire people who are inquisitive and search for answers. It’s one skill that’s almost impossible to teach. 

CEO of Hanna Andersson, Aimée Lapic, shares what she thinks about when interviewing executive candidates. The first tip? Gauge their aptitude for curiosity. 

Spend extensive time with candidates 

Quick tip: Traveling with candidates is a great way to get to know them in a short amount of time. 

In this episode, Capital Factory Founder and CEO Josh Baer shares his strategy for interviewing senior leaders. 

Hire people “better than you”

Quick tip: Hire leaders you’ll be proud to work with, who will help you push the business forward. 

Carolyn Everson is a longtime media sales executive—her notable experience includes time leading Facebook’s advertising business—and a board member. In this episode, she shares the best recruiting advice she ever received: hire people better than you. Tune in as she and Matt talk about how to put that advice into practice. 

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