Great leadership doesn’t begin with better answers—it begins with asking better questions. In this episode, Dean Newlund and Ashley Jablow explore how design thinking can help leaders create intentional cultures, embrace uncertainty, and make better decisions through empathy, experimentation, and purposeful action.

In this episode, Dean Newlund and Ashley Jablow discuss:

• Applying design thinking beyond product development
• Why organizational culture should be intentionally designed
• Innovation, leadership, and navigating uncertainty
• Creativity within organizational and personal constraints
• Designing meaningful careers and life transitions

Key Takeaways:

• Start every challenge by understanding the people involved before jumping to solutions. Ashley explains that designing with empathy leads to more effective decisions for employees, customers, and leaders alike.
• Favor small, fast experiments over waiting for perfect plans. Ashley encourages leaders to learn from each attempt, iterate, and build confidence through continuous experimentation.
• Building innovative teams requires creating enough trust and psychological safety for people to contribute ideas, take healthy risks, and learn from failures without fear.
• Constraints such as limited time, resources, or existing commitments can become productive design tools by narrowing focus and encouraging more creative problem-solving.
• When facing uncertainty, Ashley recommends asking, “What is the smallest, fastest, cheapest thing that I could do or try today to learn the most?” to identify low-risk actions that generate valuable learning and momentum.

“You kind of have to build the plane while you’re flying it.” — Ashley Jablow

About Ashley Jablow:

Ashley Jablow (Jab-lo, pronouns: she/her) is the founder of Wayfinders Collective and creator of Life Design School, a creative studio for people in career and life transition. A seasoned facilitator, speaker, coach, and design strategist, Ashley blends design thinking and innovation, emotional intelligence, and creative tools to spark clarity and action for teams and individuals navigating change. She’s also the artist and author of 100 Days of Designing My Life, a guided journal series for reflection and reinvention.

Connect with Ashley Jablow:  

Website: https://www.wayfinderscollective.com/ & https://www.lifedesignschool.co/

LinkedIn: https://www.linkedin.com/in/ashleyjablow/

Instagram: https://www.instagram.com/ashleyjablow/

See Dean’s TedTalk “Why Business Needs Intuition” here: https://www.youtube.com/watch?v=EEq9IYvgV7I

Connect with Dean:

YouTube: https://www.youtube.com/channel/UCgqRK8GC8jBIFYPmECUCMkw

Website: https://www.mfileadership.com/

The Mission Statement E-Newsletter: https://www.mfileadership.com/blog/

LinkedIn: https://www.linkedin.com/in/deannewlund/

X (Twitter): https://twitter.com/deannewlund

Facebook: https://www.facebook.com/MissionFacilitators/

Email: dean.newlund@mfileadership.com

Phone: 1-800-926-7370

Audio production by Turnkey Podcast Productions. You’re the expert. Your podcast will prove it.