Executive transition checklist
Job changes are when executives accidentally lose benefits, miss deadlines, or make rushed equity decisions. This checklist helps you plan transitions cleanly, whether you're changing employers, negotiating an offer, or leaving a role.
Educational content only. Not individualized financial, tax, or legal advice.
Executive transitions create "moving pieces" risk: you're making decisions while also being busy and stressed.
This checklist helps you slow down the right decisions so you don't miss deadlines or lose valuable benefits.
Use this guide if:
- you're negotiating an offer
- you're considering leaving your role
- you're starting a new executive position
- you're moving from W-2 to consulting/contract work
Transition checklist (before you accept an offer)
Compensation details clarified:
- Base salary
- Bonus structure and timing
- Equity grants and vest schedule
- Sign-on bonus terms (repayment clauses)
- Deferred comp or special plans (if offered)
Benefits clarified:
- Health insurance start date and cost
- HSA eligibility
- Retirement plan match and eligibility
- Life and disability coverage terms
- Any executive-level benefits
Tax planning flagged:
- Expected vesting timing in the transition year
- Any unusually high-income months
- Withholding assumptions reviewed
Equity and job changes (don't rush this)
Equity decisions often have deadlines during transitions.
Checklist:
- What happens to unvested RSUs?
- What happens to vested options?
- What is the exercise window after leaving?
- Are there blackout windows or trading restrictions?
- Are you leaving close to a large vesting month?
The key: know deadlines and rules before you decide.
Retirement plan decisions
Common issues in transitions:
Planning move: confirm what's best for your situation and timeline.
Insurance coverage gaps (common surprise)
Health coverage gaps can occur if start dates don't align.
Checklist:
- When does current coverage end?
- When does new coverage begin?
- Do you need bridge coverage?
- How does this affect dependents?
Build a transition calendar
Include:
- last day of employment
- benefits termination date
- new benefits start date
- equity deadlines and vesting months
- tax checkpoint month after the transition
A calendar reduces missed decisions.
Want your transition mapped before deadlines hit?
If you're changing roles, we can map your benefits, equity deadlines, and tax checkpoints into a clean transition plan.
Book a private callTools and worksheets
What to do next
If you're in a transition, the best next step is to review:
FAQ
Want your transition decisions simplified?
If you're in a transition and want a clean timeline with fewer surprises, book a private call.