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What Questions Should You Ask Before Joining A Startup?

By Richard Harroch

Before joining a startup as a new employee, you should have a clear understanding of the role, the company’s culture, and the company’s prospects. You don’t want to jump into a financially troubled startup or into a problematic work environment.

After you have reviewed the company’s website, press coverage, online reviews, and Google search results, you should consider which of the following questions will make sense to ask to help you make a decision on whether to accept or reject the job offer. But make sure you aren’t asking questions already answered on the company’s website or materials provided to you. And consider the appropriate time to ask these questions (some questions you may want to ask only after you have gotten a job offer).

1. Job-Specific Questions

You will want to inquire about the specific role and opportunity, with questions such as the following (tailored to be relevant to you):

  • What are the responsibilities of the position?
  • What is the title of the role (Senior Manager? Software Engineer? Customer Support Assistant?)
  • What is the company culture like?
  • What is the work from home policy?
  • What is the paid time off (PTO)/vacation policy?
  • Who will I be reporting to?
  • How often will I get a formal review of my performance?
  • What happened to the last employee in this role?
  • What types of opportunities for advancement will there be?
  • How much travel is expected?
  • What do you think are the most important qualities to have to succeed in this role?
  • Can you tell me more about the team I will be working with?
  • What is the No. 1 priority coming into the job?
  • What will constitute success in the role?
  • When would you want me to start?

2. Compensation and Benefits Questions

Before joining a startup, you will want to have a clear understanding of compensation, bonus, and benefits for the job, so consider the following questions as relevant to you:

  • What is the base salary?
  • What signing bonus may be available?
  • What performance bonus/commissions/additional compensation is available in addition to the base salary?
  • What kind of stock option or equity incentive plan does the company have?
  • How many options will I be granted? And what percentage of the outstanding capitalization of the company does that represent?
  • What is the vesting schedule for any stock options?
  • Will there be accelerated vesting of stock options in case the company is sold or there is a termination of employment by the company without good cause (senior executives often negotiate this, but it’s harder to get for lower-level employees)
  • What health/medical benefits are available for employees?
  • What other benefit plans does the company have? (For example, does it offer a 401(k) program or provide employees with equipment such as cellphones and laptops?)

3. Capitalization and Financial Questions

You will want to understand the company’s financial situation, so consider the following questions. A company with a great culture can still fail if it has financial viability issues.

  • How much in venture capital, angel, or other financing has the company raised?
  • How much of that funding does the company still have?
  • How long will the remaining funding last before the company has to seek another round of financing? (This is in essence asking what the company’s “burn rate” is—the amount the company is losing each month, taking into account its revenues and expenses)
  • Who are the major investors in the company? (prominent individuals or venture funds certainly will help)
  • Will I be able to see the company’s latest investor pitch deck describing the company?
  • What is the company’s revenue-growth rate?
  • What was the valuation of the company at the last round of financing?
  • How big is the market opportunity for the company?
  • What key traction has the company gotten? (Traction could include increasing revenues, marquee customers, strategic alliances, venture financing rounds, PR, etc.)

4. Company Mission, Vision, and Positioning Questions

When you are contemplating joining a startup, you should get an understanding of the company’s mission, vision, and plans for growth, so consider asking these questions:

  • What is the company’s mission and vision?
  • What are the company’s plans for growth?
  • What are the key milestones for the company to meet in the next year?
  • What is your favorite part of working for the company?
  • What are the biggest opportunities for the company?
  • What are the biggest challenges for the company?
  • What is particularly unique about the company?
  • Who are the company’s principal competitors?
  • Do you see the company ultimately being acquired or going public? When do you think that might happen?

5. Legal Questions

For anyone planning on joining a startup, a few key legal questions may be appropriate, as follows:

  • If an employee is terminated without cause, what is the severance policy?
  • Is the company involved in any litigation or government/regulatory proceedings?
  • Will I be subject to any non-compete or other restrictions after my employment ends? (some states allow non-compete agreements)

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About the Author

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Richard D. Harroch is a Managing Director and Global Head of M&A at VantagePoint Capital Partners, a venture capital fund in the San Francisco area. See all his articles and full bio on

Copyright © by Richard D. Harroch. All Rights Reserved.

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