by Patrick Newman (patorick002@gmail.com). Originally written in 2017, revised 2023-November.

Prior to joining my first big tech company in 2017, I spent 11 years working at startups. I fully expected to spend my entire career in startups, and I interviewed at several that I didn't wind up joining. These companies tended to be ones that had attracted venture funding, but weren't yet household names, and when interviewing I spent a lot of time assessing how likely they were to survive and thrive. Over time I developed a set of questions to ask to help with that task. In essence, what I wanted to learn was whether the company has something (production, roadmap, vision) that a customer base is willing to pay for, and whether they have enough assets (technology, talent, revenue, cash) to reach their potential. Of course, I also wanted to get a sense of whether I was the right person to help move the business forward. I don't think there are any precise 'correct' answers for these questions, though there are probably some wrong ones. Different companies at different stages of maturity will have these figured out to varying degrees, so there is some judgement involved with assessing the answers. I don't think I ever asked all of these questions in a single interview, that would have been overkill. I tended to focus a little more on one area or another depending on what I was observing.

I have used questions from this list in interviews at multiple startups over the years, though not as much recently. The startup I interviewed with that went on to get the biggest was Palantir. The two that I was the most sure about were Auth0 and Narvar. The one I incorrectly disregarded was Chewy. The one I correctly declined was OnLive. Palantir has since IPO'ed, Auth0 was acquired by Okta, Chewy was acquired and later IPO'ed, and Narvar is still in business. OnLive dramatically went out business a few years ago. Ironically, I didn't wind up working at any of these places, for various reasons.

I wrote these questions from the perspective of an engineering leader, but many of them should be reusable accross different roles.

PRODUCT AND CUSTOMERS

1. What does the company exist to do?
2. Who are the users? Who do you want to delight with your offering?
3. Who are the customers? Who is paying you?
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?

TECHNOLOGY

1. Is there a working minimal viable product(MVP)?
2. What's on the roadmap? Features or scale?
3. What is the tech stack, and why was it chosen?
4. How hard is it to make improvements to the codebase/product?

ENGINERING PROCESS

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?

CASH AND FINANCES

1. Who are the investors?
2. How much runway is available?
3. Is there another round of funding expected? If so, 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?

LEADERSHIP

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?

ORGANIZATION

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. Are there candidates for career growth?

MY ROLE

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?

EQUITY AND LIQUIDITY

1. How many shares are outstanding?
2. How is equity currently offered to employees? Stock options or restricted stock units?
3. Does the company offer opportunities to liquidate vested shares prior to IPO?
4. What is the vesting period?