Considering Working for a Startup? 34 Questions to Ask Before Signing Up.

Ever thought of working at a startup?  Reading TechCrunch articles and wishing that you could be part of the fun?  Wondering what information you need to make a decision?

When considering joining a startup, here are the questions that I want to satisfactorily answer before making a decision.

Position Questions

  1. Will I be able to effectively partner with the other team members?
  2. Will I get along personally and professionally with the other team members?
  3. Do the other team members have complementary qualities to me or will we all be trying to fill the same? 
  4. Can we develop a shared vision?
  5. Can we disagree in a constructive manner?
  6. How will I get started at the position?  Would there be a trial period?
  7. What will be my roles and responsibilities in the short, mid, and long term?
  8. What will I be responsible for and what will other team members be responsible for?
  9. How much influence will I have over product and company direction?

Compensation Questions

  1. How will I be compensated?  How much cash (both deferred and non-deferred), equity, and bonuses.
  2. Is the equity being offered fair for my position and the state of the company (take a look at this hiring plan equity suggestion from Venture Hacks)
  3. How many outstanding shares are there and how many have been dispensed?
  4. How long will salary be deferred?

Company Questions

  1. Who do you think your competition is, both in the short and long term?
  2. How will the company differentiate itself from these competitors?
  3. What is the marketing plan to raise awareness of the product?
  4. What is the product development plan?
  5. When will releases occur and what will be in them? 
  6. Are the schedules reasonable from both a technology and market view?
  7. What is the upside opportunity for the company?  How likely is that upside to be realized?
  8. How much protectable IP will be available?
  9. How good is the current team?
  10. What gaps exist on the team and when will they be filled in (e.g. VP Marketing)?
  11. Where will the company be located and is there a plan to move as we grow?
  12. How susceptible is the company to changing fads in the VC marketplace?

Financial Questions

  1. What is the financial projections for the company? 
  2. What will the cap tables look like after all investment is in?
  3. What will be my equity position, taking into account preferred shares already granted and those that are planned for future investment?
  4. What are the revenue opportunities and when will we start seeing revenue?
  5. What is the proposed exit time frame?
  6. Who would be potential acquirors?

Introspective Questions

  1. Do I feel comfortable with the timing of taking this position?
  2. Do I have the support from my family?
  3. Am I more scared of failing or of missing a great opportunity?

3 thoughts on “Considering Working for a Startup? 34 Questions to Ask Before Signing Up.


  1. […] meet him: Six Essential Questions Nine Questions to Ask if you are atleast a Senior Programmer The Exhaustive list of 34 Questions. Go through them and see which ones make sense to you and jot them down before you meet […]

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