Exits define culture
There’s no shortage of iconic advice when it comes to hiring.
“Hire slow, fire fast.” “Look for culture add, not just culture fit.” “Only hire A players.”
But ask a founder how they plan for team departures and transitions, and you’ll likely get a shrug.
That’s a problem.
Because every hire is the beginning of a story. And how the story ends matters just as much as the beginning and the middle.
If you don’t design the ending, you’re leaving the story unfinished. Or worse—you’re letting someone else write it for you.
The Founder’s Blindspot
Offboarding gets ignored—not because it doesn’t matter, but because it’s hard to look at.
Founders are wired for beginnings. Vision. Building. Growth. So when it comes time to say goodbye, most leaders freeze, avoid, dealay, or hand it off.
They assume it’s an HR problem. But you don’t need a People Ops team to treat people with dignity.
The truth is, most founders simply haven’t seen it done well. They’ve never been given a playbook. So when the time comes, they rely on instinct or wait too long. And that silence writes a story they didn’t intend.
But leadership isn’t just about the beginning. It’s also about how we end things.
And when someone leaves your team—whether by choice or necessity—that moment becomes a mirror for your culture.
Why This Matters
A. For the Person Entrusted to You
From a psychological and neurological standpoint, exits are a big deal.
Being let go—even with kindness—activates deep fear and pain responses in the brain. Social rejection lights up the same neural pathways as physical pain.
But what makes it worse? Uncertainty.
Ambiguous language. Vague timelines. Delayed conversations. These don’t soften the blow—they increase anxiety.
When someone is let go without clarity or care, they walk away with a fractured sense of identity and no real sense of closure.
Letting someone go well doesn’t mean it won’t hurt. But it does mean they leave with their dignity intact—and with a sense that their time here mattered.
B. For the Team That Stays
This is where the cultural cost multiplies.
When someone disappears without explanation—or with a vague "they're no longer with us" email—the team fills in the blanks:
“Did they mess up?”
“Am I next?”
“Are we not allowed to talk about this?”
This silence creates a narrative vacuum. It erodes trust. And slowly, it rewrites the team’s relationship with leadership.
People stop speaking up. They stop pushing back. They start editing their voice to avoid being the next one out.
As Bill Campbell famously said:
“You can't know how good a leader someone is until you see how they let someone go.”
Letting someone go isn’t just about them. It’s a message to everyone else about who’s safe, who’s valued, and how humans are treated here.
The Quiet Fallout
I once watched a founder handle a team change with what they believed was clarity and confidence. But behind the scenes, the team was unraveling.
No one said anything out loud, but I could see it:
People stopped bringing hard feedback.
Curiosity, play, and wonder started to disappear.
Collaboration began to fade—especially when leadership was in the room.
The founder thought everything was fine.
But the team had lost its voice.
And here's the deeper truth: when leadership doesn’t name what’s happening, the team will. In DMs, in side conversations, in glances across Zoom windows. A new story starts to spread—not the one you intended, but the one you left space for.
These unspoken conversations start acting like tectonic plates. Quiet, slow-moving, and invisible from the surface—until one day, the ground shifts.
The tectonic plates of culture are made of trust.
And when trust moves underground, it reshapes everything above it.
The team is still standing, but the ground under them has changed.
Our Responsibility as Leaders
Let’s be clear: this isn’t about spin or optics. It’s about care.
When someone joins your team, you’re not just hiring a skillset—you’re entering into a relational contract. You’re saying, “We’ll grow together.”
So when that relationship ends, it’s your job to make sure it ends well.
Not perfectly. But with courage. With clarity. With respect.
Because when you lead an offboarding moment with intention, you model something powerful:
That this team is human-centered.
That people matter beyond productivity.
That endings can be just as thoughtful as beginnings.
Culture isn’t shaped by your values on paper. It’s revealed in how you handle your hardest moments.
How to Do This Well
A. Letting Someone Go (With Integrity)
Here’s what it means to let someone go well:
Be clear. Ambiguity breeds anxiety.
Be direct, but not harsh.
Don’t outsource the conversation. Do it yourself.
Honor their contribution. Don’t erase it.
Offer support—recommendations, referrals, a soft landing.
If possible, give them time to process before announcing the change to the team. Let them shape the narrative with you.
Treat the moment as a transition, not an extraction.
B. Supporting the Team
When someone leaves, the team needs clarity too. Don’t go silent.
Here’s what good leadership looks like:
Communicate the change thoughtfully.
Share what you can share with honesty.
Reinforce the values that still stand.
Acknowledge the emotional reality: this affects people.
Create space for reflection and questions.
And—this is critical—ask for feedback.
Invite your team into the process. Ask:
“How did this feel?” “What’s still unclear?” “How are you making sense of this?”
Trust takes time. And especially if it’s not yet deep, don’t mistake silence for alignment. Sometimes the quietest team is the one most unsure if they’re safe to speak.
Rebuild the trust you may have unknowingly shaken.
When It’s Done Right
In 2020, Airbnb faced one of the most emotionally complex moments in its history.
As the pandemic brought travel to a halt, the company was forced to lay off roughly 25% of its workforce. But instead of making the announcement behind closed doors or offering canned PR spin, CEO Brian Chesky did something radically human.
He wrote a long, transparent letter—directly to employees. In it, he named the situation with clarity, outlined how decisions were made, and acknowledged the emotional weight of what was happening. He didn’t sugarcoat. He led.
Then the company went a step further:
They offered generous severance and extended healthcare.
They created a public talent directory to help employees find new jobs.
They gave team members time, space, and support to leave well.
Was it perfect? No. But it was personal. Human. Transparent.
And the result? Airbnb’s culture stayed intact. Their employer brand remained strong. And even those who left carried the story of being treated with respect, dignity, and care.
I know some of you might be reading this and thinking: “Sure, but we’re not Airbnb. We can’t offer generous severance or extended healthcare. We’re barely making payroll.”
And that might be true.
But that’s also a perspective.
Because if you’re too busy launching the next feature, finalizing the investor pitch, or pushing product updates—but you don’t make time to care for the humans building all of that—eventually, you won’t have a team to build with.
You don’t need millions in funding to treat someone with dignity. You need presence, intention, and a commitment to do right by people.
If that resonates, check out my post on being a Human Expert. It unpacks the idea that your most important product isn’t your product—it’s your people.
Offboarding Toolkit
You don’t need a perfect process. But you do need a plan.
Because when the moment comes, you won’t rise to the occasion—you’ll default to your systems. And if you don’t have one? You’ll default to avoidance.
This playbook is your starting point. Not to script every exit—but to build the muscles that make each one human, honest, and aligned with your values.
Reflection Questions (for Founders & Leaders)
What do I want someone to feel when they leave our company?
What story do I want them to tell?
Have I communicated consistently and clearly before this moment—or is this the first time they’re hearing hard feedback?
Am I choosing the honest path forward—or the one that protects me from discomfort?
What would I want, emotionally and practically, if I were in their shoes?
Areas You Need to Cover
The Exit Conversation
Who delivers the message?
What tone are we setting?
Have we rehearsed what we need to say with honesty and empathy?
Support Plan for the Departing Teammate
Can we offer severance, freelance hours, or transition coaching?
Will we write a letter of recommendation or make introductions?
What small gestures can show our care—even without a big budget?
Internal Communication Plan
What will we say to the team?
How can we acknowledge the person’s contribution with sincerity?
What’s the timing for the announcement?
What is the appropriate channel (Slack, email, team meeting)?
Who should the message come from—and how do we ensure consistency?
The Team Debrief
What space are we creating for questions, feelings, and reflections?
Are we asking how this change is being experienced—not just assumed?
Are we ready to listen with humility?
Culture Maintenance
How does this moment reinforce or erode our values?
Are we walking the talk of dignity, clarity, and care?
Will people walk away from this moment more connected—or more cautious?
Technical Offboarding
Have we revoked access to all systems and accounts?
Have we documented and reassigned key responsibilities?
Are we capturing institutional knowledge so it doesn’t walk out the door?
You don’t have to get every step right.
But if you plan for these moments before they hit, you give your company something most never build:
A way to honor people on the way out.
And that becomes a story worth telling.
Note on Harder Goodbyes
Sometimes people leave not because of a business shift or a changing role—but because of harmful choices they made.
In those moments, your responsibility doubles:
To protect your team.
To reinforce your values.
And to still handle the exit with humanity—even if trust was broken.
This is complex—and often charged with emotion, legal nuance, and relational pain. We’ll cover this more in a future article focused on how to lead through those moments without compromising your culture.
Reflection
When someone leaves your company, they walk out with a story.
Not just about why—but about how.
And whether that story is one of clarity, care, and respect—or confusion, fear, and silence—is entirely up to you.
This isn’t about perfection. It’s about responsibility.
It’s about leading in the moment when it would be easier to avoid, to rush, or to outsource.
It’s about making sure that the people who helped build your company—even if only for a season—are treated like humans, not problems.
Because how someone leaves your company doesn’t just reveal your culture. It is your culture.
Note on Legal Boundaries
Of course, there will be moments when you can’t say everything.
There are HR or legal guidelines to follow. Confidentiality to protect. Contracts that shape what can and can’t be shared.
But clarity and care don’t require full disclosure. They require presence, honesty, and the courage to lead with empathy—even when your hands are tied.
