Three Leaders Asked Me the Same Question (Without Knowing It)

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IN THIS ISSUE:

• The Question Every Leader Gets Wrong – Why "Is it time to leave?" is keeping you stuck (and what to ask instead)

• The 3-Question Framework – The decision-making tool I teach Microsoft leadership teams (get the diagnostic)

• Free Download: The Wrong Question Detector™ – A 2-minute diagnostic that tells you if you're asking the wrong question (and what to ask instead)

• Your December Challenge – Calculate what staying is actually costing you and win a Decision Clarity Call

Three leaders asked me the same question last week.

They just didn't know it.

A reader from Chicago asked: "How do I weigh stability against opportunity?"

Someone in Paris framed it as: "Is it time to leave Microsoft?"

A leader on the West Coast wanted to know: "How did you transition from full-time work to speaking?"

But they were all really asking:

"How do I know when it's time to go, make the pivot, take the leap?"

The Framework Nobody Teaches

Last month at a Microsoft leadership workshop, a director told me:

"I've been asking the wrong question for two years."

She'd been asking "when is the right time?" instead of "what's it costing me to stay?"

That one shift changed everything. She made her move three weeks later.

Here's the framework I teach leadership teams before any major transition:

The 3 Questions:

The right time is never going to feel right

But there's a difference between "not ready" and "not comfortable."

The leaders who move forward aren't more confident than you.

They just stopped asking "when" and started asking "what's the cost?"

Want to know what question you should be asking?

I created The Wrong Question Detector™ - a 2-minute diagnostic that reveals:

• Which wrong question you're stuck on ("When should I leave?" "How do I know if I'm ready?" "What if I'm making a mistake?")

• What question you should be asking instead

• Your specific cost pattern (Energy drain / Growth stall / Impact gap / Identity drift)

• Your decision-making style (Certainty Seeker / Permission Waiter / Analysis Paralysis / Fear Avoider)

• Your exact next move (not generic advice—your specific next action)

Your challenge this week:

Take The Wrong Question Detector™.

Be honest with your answers. Don't overthink it.

Then reply to this email with:

1. Your wrong question (the one you've been stuck on)

2. Your cost pattern (Energy / Growth / Impact / Identity)

3. One thing that surprised you about your results

I'm giving away 2 complimentary Decision Clarity Calls (15 minutes) to people who complete the diagnostic this week.

I'll pick 5 winners on Friday and announce them next Tuesday.

No pitch. No agenda. Just 15 minutes to help you see what you've been avoiding.

"Transitions: Making Sense of Life's Changes" by William Bridges

If "The Body Keeps the Score" helped you understand how trauma lives in your nervous system, this book will help you understand why you're actually stuck in career limbo.

Here's the part that broke my brain:

Bridges says every transition has three phases:

1. The Ending (what you're leaving behind)
2. The Neutral Zone (the uncomfortable in-between)
3. The New Beginning (what comes next)

Most people think they're stuck because they haven't found the "right" next thing.

❌ Wrong.

You're stuck because you're trying to skip the Neutral Zone.
You want to jump straight from ending to beginning.
But the Neutral Zone—that awful, uncertain, "I don't know what I'm doing" phase?

That's what I call the messy middle.

And it's where the transformation happens.
That's where you calculate the real cost of staying.
That's where you name the actual fear.
That's where you see what becomes possible.

The line that hit me hardest:

"It isn't the changes that do you in, it's the transitions."
Change is external (new job, new city, new relationship).
Transition is internal (who you're becoming in the process).

Most leaders manage the change brilliantly.

And completely ignore the transition.

Then they wonder why they feel lost.

Because they're trying to skip the messy middle.

The place where you're no longer who you were, but not yet who you're becoming.

The place that feels like failure but is actually where the real work happens.

This book taught me: The question isn't "when is the right time to make the leap?"

The question is: "Am I willing to sit in the discomfort of the messy middle long enough to get clear?"

That's the real work.

(Not an affiliate link—just a book that rewired how I think about career decisions)

Know someone wrestling with "when is the right time?"

Forward this to that leader who's been asking the wrong question.

Or send them here: [email protected]

Want a little thank you? Forward this to 3 people who need it by Friday of this week and reply with their first names—I'll enter you to win one of 3 $50 Amazon gift cards.

I'm picking winners on Saturday and announcing them in a future issue. 

Sometimes the best thing you can do for someone is show them they're asking the wrong question.

That's it for this week.

Two actions:

✓ Take The Wrong Question Detector™

✓ Reply with your results (to win a Decision Clarity Call)

This is the simplest decision-making diagnostic I know.

And December is when you have the reflective space to actually use it.

Don't wait until January when the chaos returns.

See you next Tuesday.

Ways I Can Help You:

1. The Activated Leader 1:1 Coaching
Navigate your transition with personalized support and accountability.
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2. Keynote Speaking
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3. Activate your sales organization
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4. Fractional CRO Strategic sales leadership for organizations who need executive-level expertise without a full-time hire. I help tech companies build pipeline, close enterprise deals, and activate their revenue teams. Explore fractional support →