The Severance Negotiation Framework
Whether you're being pushed out or negotiating an exit, here's how to approach severance strategically.
Know Your Leverage
Your negotiating power depends on:- What you know (sensitive information, key relationships)
- What you can do (walk away gracefully vs. make noise)
- What they need (clean transition, no legal risk)
- What's standard (precedent matters)
The Standard Components
A severance package typically includes:- Cash: Weeks of pay per year of service (2-4 weeks is common, executives may get more)
- Benefits: COBRA coverage or continuation
- Equity: Accelerated vesting or extended exercise windows
- Outplacement: Job search support (often negotiable upward)
- References: Agreed-upon language and contacts
What to Negotiate
Everything is negotiable, but focus on:- Cash amount (the most flexible component)
- Equity treatment (often overlooked, can be significant)
- Release timing (don't sign immediately—you have 21 days by law if over 40)
The Signature Question
Before signing anything, ask: "Is this the best I can do, or am I leaving something on the table because I'm tired of fighting?" Get help if you're unsure.
What This Looks Like in Practice
The Scenario: Alex, a first-time founder who had built a company from zero to $5M ARR, was exhausted. The board wanted to bring in an experienced CEO to scale to the next level. Alex wasn't sure if this was a vote of no confidence or a natural evolution—and whether stepping aside meant failure.
What He Did: Instead of reacting emotionally, Alex created space for clarity:
- He talked to three other founders who had gone through similar transitions
- He worked with an executive coach to separate his identity from the company
- He explored what role, if any, he wanted in the company's next chapter
The Outcome: The conversations revealed that bringing in a scaling CEO was common and often the right move—it wasn't about Alex's abilities, but about matching skills to stage. He negotiated a transition to Chief Product Officer, where he could focus on what he loved (building product) without the CEO responsibilities that drained him.
Two years later, the company hit $20M ARR. Alex was energized again, and glad he didn't let ego drive a reactive exit.
The Lesson: Founder transitions aren't failure—they're evolution. The question is whether you're in the driver's seat of that transition.
What You'll Walk Away With
Our structured session produces concrete artifacts, not just conversation.
Decision Snapshot A clear-eyed assessment of your current situation—what's true, what's not, and what actually matters for your decision.
Fork Recommendation A specific direction (stay, go, or pivot) with the reasoning behind it, so you understand not just what to do but why.
Risk Map Everything that could go wrong with your chosen path, and how to mitigate each risk before it materializes.
Conversation Scripts Exact language for the hard conversations you need to have—with your boss, your partner, recruiters, or anyone else.
14-Day Action Plan The specific steps to take immediately after our session, so momentum doesn't stall.
30-Day Roadmap The longer-term plan for executing your decision, with milestones and check-in points.
These aren't templates—they're customized to your specific situation, role, and constraints.
Ready for Personalized Guidance?
Every situation is different. If you want help thinking through yours—with someone who's seen hundreds of similar cases—consider working with a coach.
What you get:- A structured conversation to clarify your situation
- Frameworks tailored to your specific circumstances
- Scripts you can actually use
- A clear action plan