In this episode of Chasing the Insights, I talk to Doug Fleener.
Doug talks to us about Using What If questions.
Doug Fleener is a coach, speaker, and author who helps entrepreneurs and leaders create better perspectives and options as they navigate decisions, change, and everyday complexity.
His work is grounded in a simple belief: one well-asked question can shift how you see a situation and what you do next.
Doug’s journey to this work was shaped by real turning points. He moved from addiction and business failure to becoming Director of Retail for Bose Corporation, where he led teams and learned what actually drives sustainable growth. Those experiences taught him that clarity often comes through action, not endless analysis.
He is the author of Start With What If: Weekly Questions to Spark Immediate Change and Growth, which introduces The What If Rule: Pause. Question. Go. The framework helps entrepreneurs interrupt default thinking, simplify decisions, and move forward with intention.
Doug works with business owners and leaders who want practical tools that fit real life, not abstract theory. His style is direct, human, and grounded in lived experience, shaped by decades of leadership, recovery, and coaching.
He believes meaningful change starts with asking a better question and being willing to take the next step.
You can connect with Doug here:
Website: https://dougfleener.com
Listen to the episode here.
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