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Questions To Ask Startups

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This is something very different. I have had the itch to write again for a while now, but real life has kept me busy enough that I can’t devote enough time to baseball to come up with anything interesting to say about it. So I’d like to write a little bit about my work experience, in the hopes that someone out there may find it helpful in some way.

Some of my remaining dozen or so readers probably know that I’ve spent the bulk of my professional career working at startups in Silicon Valley. Most of my experience has been in middle management, specifically of engineering and technical teams, and along the way I’ve learned a lot about what to look for in a startup as an employer. On my most recent trip through the job market, I made it a priority to join a quality company, so I came up with a list of questions to ask startups to try to evaluate whether they might pan out.

I ultimately decided against joining a startup, but having a framework for what I was looking for and how I was evaluating it helped me engage in better, more mature discussions with prospective employers. Although I specifically had pre-profit, venture-backed companies in mind when I came up with these questions, many of them could apply to any business. Here’s hoping someone out there finds them useful.

1. What does the startup exist to do?
2. Who are the users?
3. Who are the customers?
4. What do they like about the offering?
5. What needs to get better?
6. What can customers get here that they can’t get anywhere else?

1. Who are the investors?
2. How much runway is available?
3. What is the goal of the next round? Is the emphasis to grow and raise, or reduce burn and break even?
4. How transparent are the company’s finances to leadership, and the employee base?

1. What is the CEO’s background?
2. What is the founding team’s role?
3. What are the CEO’s values? What values are shared among the VP/C-level?
4. What is the existing technical and managerial leadership structure?
5. What is the depth of skill and investment in each functional area (engineering, sales, etc)?
6. How transparent is leadership with success metrics, and opportunities and threats to the company?

1. How is the organization structured?
2. Who has the most influence over product and technical decisions?
3. How are key decisions made, socialized, and instituted?
4. How strong is the second layer of leadership?
5. Is any house cleaning needed?
6. Are there candidates for career growth?

1. How ‘mature’ is the product development process?
2. Are successes repeatable and are failures turned into actionable improvements?
3. Are metrics defined? How widely available are they to the staff?

1. What areas are in the most immediate need of improvement?
2. What impact do you expect this role to have on the team, offerings, and company?

1. How many shares are outstanding?
2. What is the strike price of shares issued in the most recent round of funding?
3. What is the vesting period?

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