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What questions to ask a CTO of a startup?

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Mid-Level Software Engineer at Taro Communitya month ago

I am at the final stage of a interview with the CTO of a startup.

All my interviews were scheduled via an automated system on their end and hence have no method to contact a recruiter or anyone from the said company. The interviews till now followed a “big tech” process with tech phone screens, system design, etc.

This final interview is for 30min and i am guessing its going to be behavioral and some “getting to know each other” type of thing.

What are some questions i can ask to show I'm interested in the company and the role. But, at the same time i want to understand their long term plan (think 6 months, 1 year and forward)?

A side question: Should i keep interviewing for public companies? Given I'm on a visa, but the tricky situation for me being that my current employer will be undergoing a layoff in the last week of April. If i do end up getting an offer from this startup should i still be looking out for jobs at more stable companies? (i do acknowledge that there isn't any such thing as “stability”)? Any pointers or guidance on this would really help me out in making a final decision 🙏

Note: they are willing to sponsor visa



  • 2
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    Team Lead (people manager) at Mistplay
    a month ago

    With 30 minutes to talk to the CTO at the end of the process, I would demonstrate that you are not yet sold on working at the company, ideally by genuinely having a bunch of questions they can answer about the future as you mentioned.

    Alex or Rahul said the best thing a hiring manager wants to see in a candidate is that they have done this exact thing very well before. So if you can ask questions like, "At my last company I built XYZ pipeline with the similar tech as you all and we had ABC results. What's the next big project in the pipeline here? What is the desired outcome for customers and the company if we hit that milestone? If we land our next 1 year of roadmap whats next after that? Tell me about the past year of projects that you all built? What was exciting about the last year, what were the challenges? What is our biggest challenge in the next year?"

    My answer for what to look for in scrappy startups is relevant here too:

    The most important thing at your small startup is who are the other people at the company esp engineers and would you like to work with them.

    • In the interview are they asking interesting questions and having good conversations?
    • Are they describing interesting projects they are working on?
    • Would you like to learn from them?
    • Would you like to have drinks with them?

    The company finances are also important so here are some questions for that:

    • How much runway do you have before you run out of money? (2 years would be great)
    • What are your plans for growth and hiring (lots of hiring is a good sign)
    • Where is the company in terms of product market fit?
    • How much revenue is there and where does it come from?
    • If venture backed, how big was the last round of fundraising and who invested? (A big round with well known backers is a great sign)
  • 3
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    Tech Lead @ Robinhood, Meta, Course Hero
    25 days ago

    Given that the round is just 30 minutes, that's probably not enough time to give system design and I doubt the CTO would give a LeetCode problem. So assuming the round will be behavioral is probably safe. However, I think it's more likely that the round will mostly be the CTO asking you questions instead of the other way around - 30 minutes isn't a ton of time.

    When it comes to asking the interviewer questions, here's my 2 go-to's:

    1. "What is the biggest challenge facing the company?" - This is an inversion of the lazy "What's your favorite thing about working here?". By asking about the tricky stuff, it shows that you care about the company and its future as you want to help it conquer its toughest problems.
    2. "What's the best thing that you have learned at this company?" - Again, this is a twist on the "favorite thing" question. This shows a growth mentality on your end: You want to keep getting better as an engineer, and you want to understand how the company can facilitate that.

    On top of these, Ryan is spot-on in that you want to show that you've done your homework. When you can reference specific XYZ feature of the company in your question, you are showing the interviewer that you care enough about the company to use its product, read through the recent launch announcements, etc.

    Here's more resources on behavioral interviews: [Taro Top 10] Behavioral Interviews

    I'll be wrapping the above playlist into a course soon-ish as well.

A startup or start-up is a company or project undertaken by an entrepreneur to seek, develop, and validate a scalable business model.
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