The Leadership Habit

The Leadership Habit


Latest Episodes

How to Navigate Conflict and Set Boundaries at Work with Dr. Jen Fry
November 14, 2025

Conflict is part of being human, but many leaders still struggle to approach difficult conversations in a healthy, productive way. Whether it shows up as tension on a team, discomfort around identity-based issues, or uncertainty about when to speak up, ma

How to Drive Results as a Leadership Coach with Will Linssen
October 31, 2025

The latest episode of The Leadership Habit Podcast welcomes globally recognized leadership coach Will Linssen to discuss how leaders can drive measurable results through better coaching. Hosted by Jenn DeWall, this conversation explores what separates goo

How to Prepare for High Stakes Conversations with Dia Bondi
October 17, 2025

Every leader faces those moments that can make or break an opportunity. It may be asking for a raise, pitching a big idea, or addressing a room full of decision-makers. These high-stakes conversations

How to Make a Purpose Pivot: Finding Balance and Fulfillment with Melissa Gonzalez
October 03, 2025

In this episode of The Leadership Habit Podcast, host Jenn DeWall talks with Melissa Gonzalez, retail strategist, experiential designer, and author of The Purpose Pivot. Together, they explore how pro

How to Lead People Who Are Not Like You with Stephanie Chung
September 19, 2025

On the latest episode of The Leadership Habit Podcast, Jenn DeWall sat down with aviation executive, trailblazer, and author Stephanie Chung to discuss one of the biggest challenges leaders face today: how to lead people who are not like them.Stephanie i

Emotional Intelligence Still Matters in the Age of AI with Caroline Stokes
September 05, 2025

What will it take to lead in the year 2030?In this episode of The Leadership Habit Podcast, Crestcoms Jenn DeWall speaks with leadership strategist and author Caroline Stokes about the critical mindset shifts leaders must make to stay relevant in a worl

Leading the Multigenerational Workforce with Karen McCullough
August 22, 2025

It’s Not Personal It’s Generational!Managing a multigenerational workforce is one of the biggest challenges facing leaders today. With five generations working side by side, the workplace is more diverse than ever. From Traditionalists to G

Pitch, Sketch, Launch Your Team’s Creativity with John Krewson and Rob Kutner
August 08, 2025

Leaders know that keeping a team innovative is easier said than done. The pressure to deliver results, stick to timelines, and avoid mistakes can stifle the very creativity that sparks breakthrough id

How to Overcome Burnout by Aligning with What Matters Most with Michelle Niemeyer
July 25, 2025

Burnout is more than just feeling tired. It is a signal that something deeper needs to change. In this episode of The Leadership Habit Podcast, Crestcoms Jenn DeWall sits down with keynote speaker, coach, and former attorney Michelle Niemeyer to explore

Why Employee Ownership Matters More Than Ever with John Abrams
July 11, 2025

What happens to a business when its founder is ready to step away? Too often, legacy companies are absorbed, shuttered, or changed beyond recognition. But what if there were a better wayone that preserves the companys culture, protects jobs, and gives e