Cover of the book Start With What If

Immediate Change and Growth. Now.

For life. For leadership.

I’m Doug Fleener — author of Start With What If and creator of The Better Leader Now.

Most change fails in real time. Pressure rises. Old habits take over.

I help individuals and leaders create better perspectives and options in the moments that matter most.

The Better Leader Now
Not leadership theory. Leadership in the moment.

An action-oriented leadership experience that improves how you think, respond, and lead when it matters most.

See the 4-Week Program → Here

Doug Fleener and his wife Joanna

About Me

I didn’t arrive at this work through theory.

My path has included success, failure, rebuilding, and starting over.

In my early years, addiction nearly took everything from me. Recovery reshaped how I think about responsibility, leadership, and relationships. It taught me that real change happens one decision at a time — often in the smallest moments.

Professionally, I went on to lead teams across the country, serving as Director of Retail for Bose Corporation and later running a national company as CEO. I have worked with executives, entrepreneurs, and frontline managers who want leadership that works in the real world — not just on paper.

Real life has been my greatest classroom. The most important lessons rarely come from a boardroom. They come from how you show up at home, at work, and in the moments no one else sees.

Joanna, my wife and partner in this chapter of life, reminds me that growth is not about perfection. It is about awareness, ownership, and doing the next right thing.

Doug’s Insights Have Been Featured In

Logos of The Boston Globe, Business Insider, The New York Times, WSJ, and Fast Company.

And hundreds of newspapers, magazines, and podcasts.

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    WHAT READERS AND AUDIENCES SAY

    What If You Connected with The What If Rule Today?

    SPEAKING

    Turn your event into a catalyst for real growth and transformation. Learn more about booking Doug Fleener.

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    Audience

    THE DAILY WHAT IF

    The Daily What If is a quick daily prompt that helps you pause, think differently, and move forward with intention.

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    Daily What If sample

    COACHING

    What if one question sparked your next big change and growth moment? And what if we can do it in a single session?

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