What If Coaching for Real-Life Moments

Doug Fleener is a coach and author of Start With What If, helping leaders and individuals turn perspective into action using the What If Rule.
Doug Fleener is a coach and author of Start With What If, helping leaders and individuals turn perspective into action using the What If Rule.

You don’t need more advice.
You don’t need a long process.
You don’t need to be fixed.

What you need is clarity in a moment that matters.

What If Coaching is designed for people who are capable, thoughtful, and motivated—but feel stuck, reactive, or unsure about what the right next move actually is. Not in general. Right now.

This is personalized support to help you see your situation differently and act with intention instead of default.

What if one conversation changed this moment and what comes next?

When Coaching Is the Right Next Step

Coaching is a good fit if:

  • You’re facing a decision that won’t settle

  • A situation keeps repeating, and you don’t like how you’re showing up in it

  • Something feels off, but you can’t quite name why

  • You’re ready to act, but want clarity before you do

How This Coaching Is Different

Most coaching focuses on unpacking the past or building systems for the future.

This work focuses on the moment.

You start where you are.
No lengthy intake forms. No preparation required. You bring what’s on your mind right now.

You get clarity quickly.
Through focused What If questions, we interrupt the default thinking that’s keeping you stuck and open up better perspectives and options—often within the first part of the conversation.

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.
I don’t prescribe solutions. I help you see your situation clearly so the insight and decision are yours. The momentum comes from you.

This is not therapy.
It’s not long-term unpacking.
It’s practical clarity when it matters.

Not every moment needs the same level of support.
That’s why I offer two focused coaching options.

Two Ways to Work Together

01. The What If Breakthrough

Single 90-minute coaching session

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

This is ideal if you’re:

  • Stuck in one specific situation

  • Circling a decision

  • Ready to move forward, but want clarity first

You’ll leave with a clear perspective and a concrete next step.

"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

Designed for moments that aren’t one-and-done.

This is ideal if:

  • You’re navigating a transition

  • The same challenge keeps showing up

  • You want momentum, not just insight

Over four weeks, we build clarity, adjust in real time, and create consistent forward movement—one week building on the last.

"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."

Ready to Explore the Right Next Step?

No pressure.
No pitch.


Just a conversation to see if this is the right next step.

Because your What If moment might start right here.

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