Offer red-flag checklist

The default 90 days forces you to find the strike cash (and possibly a tax bill) within 3 months of leaving, or vested options vanish. Extended windows of 5–10 years exist and cost the company little.

Ask: “How long is the post-termination exercise window?”

Your spread — and the tax when you exercise — depends on the gap between strike and current fair market value. A grant issued right before a big 409A jump is worth much more than one right after.

Ask: “What's the current 409A price per share, and when is the next valuation?”

If investors hold >1× or participating preferences, common stock can be worth little even in a decent exit. Late rounds at high valuations often carry protective terms that come straight out of employee upside.

Ask: “Are all preferred rounds 1× non-participating?”

Without double-trigger acceleration, an acquirer can lay you off post-close and your unvested equity evaporates with the deal that made the company successful.

Ask: “Is there double-trigger acceleration for employees?”

A few companies reserve the right to buy back your vested shares at their price when you leave. It defeats the point of vesting; treat it as a serious red flag.

Ask: “Does the company have any repurchase rights over vested shares?”

If the company dies at month 10, your equity conversation was fiction. Founders expect this question from serious candidates.

Ask: “What's the current runway, and what assumptions is it based on?”

10,000 options means nothing without fully-diluted share count. Any company that refuses to tell you the denominator is telling you something else.

Ask: “What percentage of fully-diluted shares does my grant represent?”

A company that has run employee tenders has actually let employees turn paper into money — the single best evidence that equity there is real.

Ask: “Has there been an employee tender offer, and is another planned?”

An over-broad non-compete or an IP clause claiming your side projects can cost more than the equity is worth — especially outside California, where non-competes are enforceable.

Ask: “Can I see the full PIIA / non-compete text before signing?”

"We're visa-friendly" is a sentence; LCA filings are records. Check what the company has actually filed — takes 30 seconds with our lookup.

Ask: “Will you sponsor H-1B transfer / new filing and green card, and at what stage?”