Learn how to navigate difficult conversations, manage risk, and lead with integrity in legal settings by building courage as a practical skill. In this conversation, Stephanie Everett is joined by Jim Detert, professor at UVA’s Darden School of Business and author of Choosing Courage: The Everyday Guide to Being Brave at Work. 

Together, they explore why speaking up at work is so hard, how fear and stress shape behavior, and what lawyers can do to build confidence over time. Jim introduces tools like the “courage ladder” to help professionals take small, strategic steps toward more effective and values-aligned leadership. 

Legal professionals will gain: 

• Skills to manage fear and prepare for high-stakes conversations 

• A framework for building everyday workplace courage 

• Insight into the cost of silence in legal practice 

• Guidance on how to align personal values with professional conduct

Ideal for lawyers, firm leaders, and legal professionals who want to take more intentional action in their work and leadership. 

Listen to our other episodes on personal leadership: 

 Episode 491: Crafting Your Purpose-Driven Leadership Vision, with Leticia DeSuze Apple | Spotify | LTN 

Episode 494: How to Stop Procrastination and Conquer Your To-Do List, with Paul Unger Apple | Spotify | LTN 

Episode 499: Conquering Self‑Doubt, with Tim Atler Apple | Spotify | LTN 

Episode 508: From Retreat to Rebrand, with Patricia Mancabelli Apple | Spotify | LTN 

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you. 

Access more resources from Lawyerist at lawyerist.com. 

Chapters/Timestamps: 

0:00 – Contranyms & Clarity in Legal Language 

2:39 – Meet Jim Detert: Leadership Professor & Author of Choosing Courage 

3:18 – Why Speaking Up at Work Feels So Hard 

4:56 – Courage Is Not a Personality Trait: Debunking the Myths 

6:28 – Practicing Bravery Like a Skill: The Importance of Reps 

7:30 – Fear, Physiology, and Mindset: What’s Really Holding You Back 

10:40 – From Performance to Growth: Reframing Stress and Risk 

13:18 – How to Start Tough Conversations Without Fluff 

16:39 – When Courage Gets Risky: Speaking Up in Politicized Professions 

20:20 – Values vs. Aspirations: What Do You Really Stand For? 

26:51 – The Long-Term Costs of Staying Silent 

28:49 – Building a Courage Ladder: Start Small, Scale Up 

32:34 – First Steps to Practicing Everyday Courage 

33:34 – Final Reflections: Leading with Bravery at Work