What “Fit” Really Means in Hiring

In this mini-episode of the Extraordinary Pursuits podcast, we're joined by Kristian Schwartz, founder of Montgomery Group Executive Search. Drawing from decades of executive search experience, Kristian shares how to think beyond resumes and reference calls to identify the right leader for the right moment.

He unpacks why chemistry matters, how to surface areas of support (instead of just gaps), and what a working session can reveal that no interview ever will. The conversation is a candid look at the intersection of leadership, context, and conviction—and what it takes to make the right hire when the stakes are high.

Timestamps:

• 00:38 | Art vs. Science in Hiring

• 01:41 | Understanding Areas of Support

• 02:28 | Why Final Working Sessions Matter

• 04:06 | Fit vs. Technical Skills

• 05:10 | Matching Leaders to the Moment

Points of Wisdom:

• “Interview questions have predefined answers. But a whiteboard doesn’t.”

• “Some people interview well—and some don’t. An interview isn’t real life.”

• “You’re not hiring for perfection. You’re hiring for alignment and possibility.”

About Kristian Schwartz: Kristian Schwartz is the founder of Montgomery Group Executive Search, a retained executive search firm that helps high-growth companies hire transformational leaders. With a background in strategy and organizational design, Kristian has built a reputation for matching companies with executives who deliver more than what’s on their resumes—they deliver the right kind of change.

• Montgomery Group

• Kristian Schwartz on LinkedIn

BIP Ventures

• Website: www.bipventures.vc

• LinkedIn: BIP Ventures

• Podcast: Extraordinary Pursuits