Open-Ended Questions for Your Start-Up Interview

Ask the Right Questions

to assure yourself of a profitable future

In the next few weeks, we’ll be giving general advice for women (and men!) about the right questions to ask when having an early interview with a start-up. Our experience in advising managerial employees as well as VPs, SVPs and executives taking C-suite positions is that every start-up employment conversation begins with the founders’ vision and hopes, proceeds to interviewee questions about the total compensation package, including base, bonuses, equity and all the extras, continues with career-path discussions and ends with negotiation over compensation.

The questions below are early diagnostic questions geared toward learning about the opportunities and challenges of joining a start-up as well as the interests of the founders - their needs, desires, challenges, preferences, priorities, values and predictions for the future.

  • If you were in my position what would you most want to know about Startup?

  • If you were in my position what would incentivize you to leave my position and salary and benefits at Current Employer and take the job with Startup?

  • What specific opportunities for career growth during the next 1 or 2 or 3 years will be made available to me at Startup?

  • Why is $____ K the highest base Startup could offer?

  • When does Startup expect to be in a position to pay market rates?

  • Why does Startup believe its grants of stock options or RSU’s will close the gap between the offered base salary and the market rate for comparable positions?

  • What other benefits does Startup believe will close the gap between the total compensation offered to me and total compensation packages in established businesses for this same or similar position?

  • What do you see as the career path for the person who takes this position What are the chances that Startup would bring in someone above me in the next 1 to 5 years?

  • What does Startup base its equity interest offers on?

  • What’s the current total value of the company?

  • What are the current number of outstanding shares of stock ?

  • What level of employee if any are given stock grants instead of stock options or restricted stock units?

  • How does Startup protect its equity holders against dilution, of share value?

  • How liquid are the stock and option grants?

  • What is the order of payout on equity interests What is the vesting schedule for equity interests?

  • What does Startup hope my department (position) will produce in way of revenues in the next one to five years?

  • What is Startup’s “burn” rate?

  • How many additional rounds of funding does Startup believe it will need to raise before it can support itself on revenues generated?

  • What is startup’s exit plan (IPO? Acquisition)?

  • When does Startup believe it will likely exit?

  • Is there a market for my equity interest before IPO or acquisition?

  • What are Startup’s greatest challenges and competitors?

  • What is Startup’s “secret sauce,” i.e., why will it beat its competitors?

  • Startup is offering ___% in bonuses in addition to the base salary. Has Startup been paying bonuses at that percentage for similar positions to the one we’re discussing and are they performance or profitability based? Any other metrics used by Startup to decide on bonus awards at year-end?

This list is by no means comprehensive. It does provide, however, questions that are important to ask to ascertain the risks and benefits of leaving legacy employment to throw the dice on a startup enterprise.

Victoria PynchonComment