Questions To Ask Before Quitting Your Job To Work At A Startup

Twice in my career I have left corporate jobs for startups. The first time I left was because I wanted to be in an innovative work environment where we would be inventing and creating technology that never existed. I tasted what it was like to work in a fast moving amazing technology company. I felt alive and the energy from my team was amazing. Before joining the startup here are the questions I asked myself:

Questions I Asked:

  • How much money was being raised through venture capital?
  • What was the burn rate?
  • How much equity would I be getting? How many total shares were there?
  • Do I believe in the CEO’s vision for where the company is going?

In hindsight were these good questions?

  • We raised $21M.
  • We burned through that money in less than 12 months. You’d think $21M would last a long time. It doesn’t when you’re hiring like crazy. I was one of the first few hires and we ended up hiring 90 people at our peak. Hiring and growing can mask how a company is really doing. From the outside it looks like you’re successful. The burn rate was out of control.
  • I got a ton of stock options. Worthless if the company doesn’t survive. The initial job offer had two options A) Higher pay, lower stock options. B) Lower pay, high stock options. I counter offered and asked for option C) Higher pay, higher stock options. If you think you’re worth it, ask for it.
  • I met and believed in the founder and CEO, I drank the Kool-Aid. I was in the inner circle.

Today I would ask a different set of questions:

  • Would I personally invest in this startup?

Joining a startup is akin to investing in a startup. You’re about to put a ton of your time into building up this startup. You’re investing more than what an investor is putting in. This question leads to more questions such as market potential, addressable market size, competitive landscape, founders’ backgrounds, customer validation, etc. If I wasn’t ready to invest money into the startup, I would’t want to go work there.

  • What are the credentials of the founding team?

If I don’t believe in the people that started the company, there’s no way I would go work for them. This is actually more important to me than what the startup actually does. Startup will shift direction and for lack of a better word, pivot. There are people that I would work for where I don’t care what the idea is, I would just join them because I believe in them.

  • What are the core values of the company? Do my core values align with those of the founders?

This question is more important to me than ever. If we don’t align here there’s no way I could go work for that startup. Startup pressure is so intense and when the founders are facing the darkest moment only their core values will stand the test. Who are they when they hit the wall. Is that something you want to be associated with. Is that something that you will be proud of their decision making. If not, don’t even bother working for them.

  • What kind of work culture do I want to work in?

You will be spending most of your day with the people in this startup. What’s the culture like? I want to enjoy working with the people I’m around all day long and the work environment. I personally want to work with people that have a goal crushing attitude, love to serve their coworkers and customers, and are always learning. We all have a choice in what type of work culture we want to be in.

  • Will this be a demanding, learning environment?

If you’re the smartest person in the room, you’re in the wrong room. I want to work really hard, that's the only thing I know how to do. I also know that I have a ton more to learn. If I’m not in an environment where I’m always learning, I don’t want to be there.

What are some questions that you would ask?

If you’re looking to make the jump from corporate to startup and have questions like these, you should attend and register for our event “Emerge from Corporate to Startup” on August 14, 2014 at 6pm.

Olivier Poulin

Head of Sales Europe at Ibex Medical Analytics

9y

The most important thing is that you do whatever you do with passion. This gives you the energy, creativity and happiness to do a great job without being stressed. I would exchange all the procedure related to corporate jobs for the excitement of a start up company any day. Look at my profile on the 20th of august for my next challenge.

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Pinaki Ranjan Mukherjee

Senior Program Manager, MBA, CSM, SAFe

9y

Thanks for this article.

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Joseph Hacker

Maintenance Planner & Scheduler at The Clorox Company Retired

9y

Everyone, is looking ,for the young, go getter, when the true background person, who stable, maybe older, doesn't hit the radar, because they achieve, without a fanfare. The average person thinks, they will be noticed, with diligent work esthetics, and personal drive. Not often so. The aggressive social person, that talk a good show, but has no real skills, is usually placed above, the qualified. Why, because people want, to be around upbeat people, not qualified people, sad but true. Let your light shine, so others may find you.

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Paul Gornell

Sales Team Manager at biBERK, a Berkshire Hathaway Company

9y

Two additional questions worth asking - albeit more difficult for some start-ups to answer than others - is: "What is our time to market and how long before we are profitable?" Of course, when you get the answer, multiply that timeline by 3 and that's more likely the correct answer. Then go back to the question of "how much capital have we raised?" and re-evaluate.

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