What If One Conversation Changed Your Next Six Months?

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Doug Fleener in Puerto Rico

Maybe you know exactly where you want to go but can't see the path to get there. Or maybe you're not even sure what direction to head—you just know something needs to change.

Either way, you don't lack capability. What you need is clarity and a breakthrough that helps you move forward with confidence.

You might be:

  • A leader who knows something needs to shift but can't pinpoint the highest-impact move

  • A business owner struggling to scale, delegate, or break through revenue plateaus

  • Facing a career decision and weighing your options

  • Building momentum in one area while seeking clarity in another

  • Overwhelmed by responsibilities at work and home, looking for a clearer path forward

  • Ready to act but want to ensure you're focusing on the right next step

Who Doug Works With

  • Leaders navigating transitions, tough decisions, or team challenges

  • Business Owners struggling to scale, delegate, or break through revenue plateaus

  • Professionals ready to level up their career or impact

  • Entrepreneurs stuck between ideas and action

  • Parents and partners feeling overwhelmed and looking to show up better at work and home

  • Anyone facing a turning point and ready to move forward with clarity

A Different Kind of Coaching Experience

Most coaches spend months unpacking your past or building elaborate systems you'll never use.

Doug's approach is different:

You start where you are. No lengthy intake forms. No prerequisite work. You bring what's on your mind right now, and we go from there.

You get clarity fast. Through What If questions, Doug helps you see the situation from angles you haven't considered—often within the first 20 minutes.

You leave with action. Every session ends with a clear next step you can take immediately. Not theory. Not homework. Real movement.

You stay in control. Doug doesn't prescribe solutions. He helps you discover your own answers by asking better questions. The insights are yours. The momentum is yours.

Whether you need one powerful conversation or four weeks of focused momentum, you'll walk away knowing exactly what to do next—and having the confidence to do it.

Not everyone needs the same level of support to create momentum. ‘

That’s why I offer two flexible coaching options—both designed to help you shift perspective, gain clarity, and take meaningful action.

You choose what fits your moment.

Two Ways to Work Together

01. The What If Breakthrough

Single 90-minute coaching session

A powerful conversation to help you move through a challenge, make a decision, or act on an opportunity you don't want to miss.

Whether you're stuck or ready to move fast on something new, this is the moment to shift perspective, get clear, and take action.

"I had a session that started with my mind all over the place. Ninety minutes later, I had a clear path forward and the confidence to take it. Doug didn’t just help me think differently. He helped me move."


02. The What If Sprint

4-week coaching experience with one focused session per week

Ideal if you're navigating a transition, rebuilding motivation, or ready to make meaningful progress with guidance and accountability.

This format gives you time to explore, shift, and take consistent action, with each week building on the last to create real, forward movement.

Perfect for: Anyone ready to create significant change with structured support and momentum

"In just a few weeks, I went from circling ideas to making real moves in my business. The clarity and momentum were exactly what I needed."

Specialized Coaching

  • Designed to help district and regional managers strengthen their store leaders, drive consistency across locations, and grow their leadership capacity.

    → Let’s talk about how coaching can support you in leading multiple locations more effectively.

    Text or call 617-340-9041, or use the contact form below.

  • Focused on you as a leader — sharpening your perspective, strengthening decision-making, and building the confidence to lead with greater clarity and influence. This coaching is about your growth, not just the role you hold.

    → Schedule a conversation to explore how coaching can help you grow as an executive and elevate your leadership impact.

    Text or call 617-340-9041, or use the contact form below.

  • Tailored to owners who want to balance growth with focus, improve sales and profits, and lead their teams with greater impact.

    → Reach out to discuss how coaching can help you grow your business while leading with clarity.

    Text or call 617-340-9041, or use the contact form below.

Ready to explore what’s possible?

Let’s talk. No pressure, no pitch, just a quick conversation to see if this is the right next step for you.

Use the form to the right to get started. Because your What If Moment might start right here.