Stories · Career

The tempting offer

You're a senior backend engineer at a big tech company, five years in, earning $180k a year. A Series B SaaS startup wants you as head of engineering: $215k cash plus stock options. They want an answer within two weeks. You've arranged to talk with their CTO, Ethan Lin.

Who you're talking to

Ethan Lin, startup CTO.

(stands up to shake your hand, beaming) Finally! We really need someone like you here. Ask me anything.

Questions to start with

• “Why are you in such a hurry to hire?”
• “Who had this role before?”
• “What should I fix first if I join?”

Ethan Lin won't volunteer everything. Some of what matters only comes out if you ask the right follow-up questions.

Questioning habits this story trains

• Ask about the downside they skipped. For example: “What's the worst that could happen?”
• Look for another explanation. For example: “Could something else have caused it?”
• Pin down vague words. For example: “How soon is "soon"? How much is "mostly"?”
• Get the story behind a number. For example: “From what to what? Compared with what?”
• Find the unspoken premise. For example: “For that to hold, what else has to be true?”

The decision

When you've heard enough, you give Ethan Lin your answer face to face. The choices include:

• Accept the offer as is
• Negotiate the cliff, cash mix and deadline first, then decide
• Decline and stay
• Use the offer to negotiate a raise at your current job

Then you read what happened a year later, see how sound your decision was, and get notes on the key moments of your conversation with a better way to say each.

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