The Offer Evaluation Framework
An offer isn't just compensation—it's a bet on your next chapter. Evaluate it systematically.
The Four Pillars
Every offer should be evaluated across four dimensions:
- Economics: Total compensation (base, bonus, equity), benefits, and future earning potential
- Growth: Will this role expand your skills, relationships, and market value?
- Fit: Does the culture, team, and working style match what you need?
- Risk: What happens if this doesn't work out? How stable is the company?
The Comparison Framework
Don't evaluate an offer in isolation. Compare it to:- Your current situation (including the cost of staying)
- Alternative offers you have or expect
- Your minimum requirements (what you won't compromise on)
The Questions to Ask Before Signing
- What does success look like in 12 months?
- What happened to the last person in this role?
- What's the biggest challenge I'll face in the first 90 days?
- How are decisions made that affect my work?
The Negotiation Reality
Everything is negotiable. Start date, base salary, signing bonus, equity, title, and scope are all on the table. But pick your battles—you can't win on everything.
What This Looks Like in Practice
The Scenario: Marcus, a Director of Product at a mid-size SaaS company, was passed over for VP despite delivering strong results. His manager's feedback was vague: "You're not quite ready." He was torn between pushing harder, looking elsewhere, or accepting that maybe he wasn't VP material.
What He Did: Instead of spiraling, Marcus got specific:
- He asked for concrete examples of what "VP-ready" looked like at his company
- He talked to three people who had been promoted to VP recently—inside and outside his company
- He assessed honestly whether the gap was real or political
The Outcome: The diagnosis revealed two things. First, his company had a pattern of promoting people who were highly visible to the CEO—which Marcus wasn't. Second, the specific feedback about "strategic thinking" was valid but actionable.
Marcus decided to address the skill gap while also broadening his external options. He found a VP role at a smaller company within six months, where his operational strengths were valued more than political visibility.
The Lesson: "You're not ready" is rarely the full story. Dig deeper to find out what's actually being said—and whether it's worth addressing there or somewhere else.
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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.
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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