In this candid and energizing conversation, Kevin Rice sits down with Deena DePhilips, CIO of Red Robin, to explore how becoming a mother transformed her leadership, her relationship with time, and her definition of success.

Deena shares the raw reality of stepping into the CIO role just five weeks after giving birth and the crash that followed when the old “workhorse” playbook stopped working. She opens up about rebuilding from burnout, trading perfectionism for presence, and shifting from doer to strategist by empowering her team.

Together, Kevin and Deena dig into parenting as a mirror for leadership, breaking generational patterns, and creating boundaries that protect what matters most. Deena lays out the three lessons that changed everything for her: deep focus in short windows, falling in love with fluidity, and embracing “done is better than perfect.”

Whether you are navigating a big promotion, new parenthood, or both at once, Deena’s story offers practical tools and hard-earned encouragement for leading with clarity at work and at home.

In this episode, you’ll learn:

• Why motherhood can be a launching pad, not a pause
• How to compress deep work into focused 60 to 90 minute sprints
• Tactics for choosing presence when work never truly turns off
• Why fluidity beats rigid routines in high-pressure seasons
• How to move from workhorse to strategist by empowering others
• Ways to protect sacred family time, especially bedtime rituals
• How parenting sharpens empathy, patience, and listening at work
• Why legacy is built through daily deposits in the connection bank

Top Takeaways:

• Presence over perfection creates more impact in both roles
• Focus and discipline matter more than long hours
• Let go or be dragged is a powerful mindset for change
• Done is better than perfect keeps momentum moving
• Work can be a passion, but family is the purpose that sustains it

About Deena DePhilips:
Deena DePhilips is the Chief Information Officer at Red Robin, where she leads enterprise technology and digital transformation. Known as both a workhorse and a visionary leader, she has built a reputation for simplifying complex systems and empowering high-performing teams. Deena is also a devoted mother who believes that work is her passion and her daughter is her purpose.

• (00:00:00) - Introduction
• (00:02:23) - Balancing Executive Responsibilities and Parenthood
• (00:03:29) - Lessons Learned from Burnout and Work Ethic
• (00:05:10) - The Effects of the Burnout Experience
• (00:08:11) - Done is Better Than Perfect
• (00:09:25) - Staying Present with Family Whilst Under the Pressure of Career
• (00:13:02) - The Tug of War Between Work and Home
• (00:16:57) - Shifting from Doer to Leader
• (00:25:22) - Empathy and Patience: Parenting as a Leadership Tool
• (00:27:47) - Creating Meaningful Family Rituals
• (00:31:08) - Instilling Work Ethic in Children
• (00:35:41) - Lessons on Work and Purpose
• (00:39:23) - Lessons and Values to Share with Your Children
• (00:40:34) - Legacy and Impact as a Parent