Everyone gets an onboarding plan.
Almost no one has an exit strategy.
Introducing Leave Well™ — the first strategic exit framework built for leaders who have something to lose.
Use this checklist to build your exit strategy — before you need it.
THE PART OF YOUR EXIT MOST PEOPLE OVERLOOK
The High-Stakes Window No One Prepares For
You’ve made the decision to leave. Now comes the part no one talks about.
Most people treat it like a formality: an awkward conversation, two weeks’ notice, a few handoffs.
Few treat it like the strategic opportunity it is.
This stretch—between “I’m leaving” and “I’ve left”—does more than wrap up your role.
It quietly shapes what gets remembered and what happens for years to come.
This window is too short—and too visible—to improvise.
FROM A FORMER CHIEF PEOPLE OFFICER WHO'S SEEN BOTH SIDES
Why Leave Well™ Exists
I created Leave Well™ after years managing high-stakes exits—my own and others', from VPs to C-suite executives.
When leaders leave well, teams stay stable and relationships endure.
When they leave badly, organizations pay for months—in project delays, team destabilization, lost institutional knowledge, and investor confidence.
This isn't about encouraging departures. It's about reducing damage when change is already in motion.
These are the decisions that shape how you're remembered.
The Decisions That Shape Everything
These aren't intuitive decisions. They're strategic moments that shape how you're remembered. They happen faster than most leaders expect. And they're emotionally charged.
Who to tell first—and in what order (your boss, HR, your team, key stakeholders—sequence matters)
What to say when they ask why you're leaving (and whether to say where you're going)
How to handle the counteroffer (without burning bridges on either side)
How much notice to give (and what happens if they walk you out early)
How to tell your team (all at once? individually? by level?)
How to handle their reaction—and yours (when your boss gets angry or tries to guilt you into staying)
What goes in your resignation letter (it's not a thank-you note)
Most leaders assume they'll figure it out as they go. But this isn't something to "get through"—it's something to get right.
That's why exits need a system, not just good intentions.
Knowing what to worry about isn't the same as knowing what to do.
A TALE OF TWO EXITS
The Exit They Remembered (for the wrong reasons)
He hadn’t planned to say anything yet. But in a quiet moment, he told a close colleague—someone he trusted.
“Just between us. I haven’t told my boss yet.”
By the next morning, someone else had heard.
By lunch, his boss asked:
“So… is there anything you want to tell me?”
He tried to explain.
But it didn’t matter. The trust was already cracked.
From there, things got messy. The whispers started. And just like that, the story of his exit wasn’t his anymore.
His last few weeks were awkward—for everyone.
He didn’t mean to cause tension.
He just didn’t realize how quickly the story starts writing itself—and how hard it is to rewrite.
The Exit That Made Them Remember Her (in a good way)
She knew her departure would raise eyebrows—so she planned for it.
She mapped who to tell, in what order, and exactly what to say.
She wasn’t managing impressions; she was managing the transition.
Her boss appreciated her foresight—and the way she brought him into the plan instead of dropping the news and disappearing.
She didn’t overshare or overstay. She stayed steady, handed things off cleanly, and left people feeling prepared—not abandoned.
And when another exec said, “I can’t believe she left. You must be devastated. What are you going to do?” He didn’t hesitate:
“I’m excited for her. She left things better than she found them. The team is ready. Thanks to her.”
Your exit writes the story people will tell for years.
FOR RECRUITERS & REFERRERS
How to Share Leave Well™ (Without Awkwardness or Overreach)
If you work with leaders during transitions, you already know: The exit is where things wobble.
You've seen offers implode because someone overshared too soon. You've seen brilliant people damage relationships they didn't need to lose.
Here's the language recruiters use when they share this page:
“This isn't outplacement—it's strategy.”
“It helps people protect what they've built while stepping into what's next.”
Sharing this resource isn't meddling. It's leveling the playing field.
Most Companies Don’t Offer a Playbook for This Part
They're focused on minimizing disruption to the organization.
You need a strategy for protecting what you've built.
That's why your exit is yours to lead.
The story gets written whether you lead it or not.
WHAT YOU GAIN WHEN YOU LEAVE WELL
Most people leave quietly and professionally.
Fewer leave in a way that strengthens their reputation.
When you leave well:
The manager who mentored you stays in your corner
The team remembers how you finished—not just why you left
Former peers become future partners, references, and champions
New opportunities come through the people watching how you handled the hardest part
The story people tell isn’t just how you left.
It’s what kind of leader you were at the end.
The Three Phases That Determine How Your Exit Is Remembered
1. Before You Announce
→ Architect your exit. Time the announcement. Map who to tell and in what order. Prepare for the counteroffer conversation.
→ Without this: You're winging the highest-stakes conversation of your tenure.
2. The First 48 Hours
→ Control the narrative before others write it for you. Manage the resignation conversation. Handle your manager's reaction without fumbling. Know exactly what to say when they push back.
→ Without this: The story gets told in rooms you're not in.
3. Your Final Weeks
→ Finish strong when your brain has already moved on. Stay engaged. Cement relationships that matter. Make your final act your finest leadership moment.
→ Without this: People remember how you coasted, not how you led.
The Leave Well™ Framework walks you through all three phases—with specific scripts, behavioral techniques, and strategic guidance for high-stakes exits.
You’ve Planned the Next Role.
Now Lead Your Way Out.
Most leaders improvise their exit—and spend years repairing what they lost in two weeks.
This checklist helps you protect your reputation, relationships, and future trajectory—before you walk out the door.
What You’ll Get:
The Exit Readiness Checklist
10 smart, strategic questions that shift your exit from reactive to intentional.
Bonus: The Logistics Checklist
The practical steps—files, benefits, contacts, tech—that most people forget until it’s too late.
This isn’t about quitting. It’s about leaving in a way that strengthens everything you’ve built—because your last impression becomes your lasting impression.
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Most leaders wing it. You don't have to.
IMPORTANT NOTE
If you've experienced discrimination, harassment, or other wrongful treatment, consult an employment attorney before resigning. Quitting before exploring your legal options could mean leaving compensation or protections on the table.
Leave Well™ is strategic exit support, not legal advice.
A SYSTEM FOR FINISHING STRONG
Need Help With a Specific Decision?
For leaders navigating a high-stakes exit, a 50-minute strategy session focused on your biggest challenge:
The boss conversation (what to say, how to handle their reaction)
Counteroffer decision (should you take it, how to decline)
Communication strategy (who to tell, when, what to say)
Or the decision that's keeping you up at night
Investment: $500
Lead your exit. Protect what you've built.
AS SEEN IN
Featured Writing on Leadership Exits
How to Quit Your Job the Right Way (Without Burning Bridges) (Medium)
The tactical playbook for finishing strong and protecting key relationshipsEveryone Talks About Making a First Impression — But What About Your Last One? (BioSpace)
Why your exit matters more than your entrance.
How to Resign Gracefully (U.S. News & World Report)
Expert guidance on timing and communication during high-stakes transitions.How to Leave Without Burning Bridges: Transition Smoothly and Build Supporters
What people remember most isn’t how you start — it’s how you leave.
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