Questions to Ask Before Joining a Startup

A friend asked what I’d want to know about a startup, even a late-stage one, in order to better evaluate a job offer. Here’s the short list of less-obvious questions I’d ask before joining a startup.

The role

  • If you could make one impact in the business in your first 6-12 months, what what would it be (according to them)? This is as much to understand the metric they chose – revenue? product usage? features shipped? employees hired? – and why it’s important as it is to understand the amount.
  • Where do you see the company in 3 years? What internal or industry changes might make you cut the vision short or significantly change the goal?
  • Is there an employee who everyone thinks of as very connected and savvy, who you could use as a mentor for a few months to learn the communication style? If you’re remote, ideally this person will be too.

The offer

  • Get enough understanding of the company’s cap table to have an idea what your offer represents. At a minimum, ask what percent of the shares currently outstanding your options would be, if they were vested.
  • What happens to vested options if you leave? Have they solved this problem? If not, it dramatically decreases the value of the options; you basically have to stay until IPO (or some resale event) or acquisition, or take a risk that few people would (exercising illiquid options), or leave without the vested options. 7 years is great. 3 years is okay. Given how long companies remain private, 1 year or less make the options basically toys.


  • Is the company forthcoming with the answers? Best case: the company not only answers the questions thoroughly, but also gives detailed reasoning behind their answers. If it seems like they’re reluctant to answer (or worse, dismissive of your need to know), that may be a hint how important employees’ concerns are, how much they’ve thought about the role you’d be doing, or how savvy other recent new employees are.