Speed Dating Interview Questions can be effective to ensure you cover the necessary ground. I’ve been surprised how often interviews for VP and C-levels roles are unstructured. This exasperates the issue of not covering necessary ground in key hires. Very often in exec interviews, including interview CTOs, VPEs or other engineering leaders, you can go down rabbit holes or off on tangents and never quite get through understanding if the candidate is a qualified match for what you seek. Before you know it, time is up and you don’t have a full picture.

I recall in my interview for the VP, Engineering role at Twitch, the head of HR, John Sutton, told me they been looking for 18 months, but they realized the head of engineering role in a disruptive tech company is likely the most critical role to fill. When I looked back, I saw that the interview process took 5 months from beginning to end. They had lots of challenges they wanted to address. The CEO, Emmett Shear, would ask me how I would handle a particular challenge, and then he’d disappear for a week or two. He’d come back and say, “Well, that worked really well. What would you do if …” Obviously he couldn’t do that with all candidates. A key question is how do you wittle down the field.

As such, I devised Speed Dating Interview Questions. These change over time and with the role in question. The ones below are an example I’ve used for a specific role. I inform the candidate up front that they’ll have two minutes to give a concise answer to each questions before moving on to the next. The questions are designed to assess their perspectives and approach rather than specific technical knowledge. Each is targeted to see how they think in a certain area that will shed light on their approach to building and running a tech organization. Several CTO candidates have told me that the below process resulted in the most comprehensive, thorough and mutually informative interview experience they’ve had.

Speed Dating Interview Questions

Speed-Dating Interview Questions

If you consider a presentation of two minutes per slide, consider two minutes per question.
When two minutes are up, I’ll move to the next question.

  1. In your experience, what’s the one thing to be religious about when it comes to Agile and why?
  2. What are the two most important characteristics in an employee who would flourish under your leadership vs one you’ll likely let go?

  3. Describe how to find out (e.g. in an interview) if the prospective employee possesses what you’re looking for/is someone that would flourish under you.

  4. Describe a failure or mistake you made, how you discovered it, learned from it and what changed afterwards.

  5. If you’re faced with an antiquated code stack
    • When and why does that matter?
    • What would you do about it and how?

  6. What makes a quality product a quality product?

  7. How do you know what your customers want?

  8. How do you discover you’ve made a bad hire?

  9. How do you decide if you rebuild/rewrite or refactor.

  10. How do you decide build vs buy?

  11. What are the most important things about postmortems?

  12. What are three advantages of using micro-services?

  13. Briefly describe what good requirements to build a bridge would look like coming from a good product manager build a bridge.

  14. Name 3 pros and 3 cons of cloud vs on-prem.

  15. Describe why this company and role is a fit for you and how it might not be.

Four follow-up questions:

These may take a little longer. However, it helps if you mention that quickly getting to the point is a plus for their communication skills. If you include these in the first interview, you will want a well-structured hour.

    1. “What questions did I not ask that I should have asked a CTO candidate?”
    2. “Of the areas probed today, which do you feel strongest in and which least strong?
    3. How does our Mission and Vision line up with your values, objectives and journey?
      (You want a truly passionate, inspired and engaged leader for many obvious reasons.)
    4. Tell me about a time where the company you were at was at the brink of going out of business and needing to let people go. What did you do to turn it around and why did that work?
      (For most companies, it’s not a question if they will hit such crisis mode but when. See also Ben Horowitz: The Hard Thing About Hard Things, and Ed Catmull: Creativity, Inc. You want a leader that will be strong and effective in good times and bad. Product Market Fit Hypothesis can turn out to be off, a key investment can fall through, there can be a paradigm shift in the market or economy. You want a leader that will not only help the company survive but see this as an opportunity to focus and leap ahead.)
    5. What have you done to groom the replacement for yourself in the company you are leaving?
      (I’ll always remember when Bill Campbell stepped down as CEO of Intuit. He told us one of the most important roles in a leader is to choose and groom their replacement. Then they set them up for success. This is how I always felt coding since my first job. Someone who does this has the mindset of a multiplier rather than a micromanager.)

    Bonus question:

    Interview Candidate

    Each of the 15 questions goes well beyond the specific question. They are designed to reveal how a candidate thinks about things where there is no completely wrong or right answer and the answer. The short response time how conscious they are of the complexity and how succinctly and convincingly they can speak to it.

    If you’ve established a human connection, which is doable in 30 minutes, this answer to the bonus question may tell you the most about the human you are considering for the role. I have people tell me of amazing transformative moments that they often say they’ve never told anyone of, including their spouse.

    1. “Think of and describe one experience, event or incident that changed who you are and how you see the world.”

    The Close – Reviewing the Speed Dating Interview Questions

    Part of interviewing is also the sell. Helping the candidate appreciate how and where you’re aligned can give them a level of comfort on whether this is a good place for them. To that end, I like to close by providing how I would answer each of the above and why. This also tells us more about the candidate as their answer will have differed in at least some aspects.

    • Are they open to other perspectives and can see the merits, or do they get defensive and hold their ground stubbornly?
    • Are they able to find a balance between appreciating the value of another perspective without blindly caving to appease the interviewer?

    I believe you will learn little to nothing from a candidate that either agrees or disagrees with everything. I further suggest that such a candidate will add little effective value to your organization. The learning and value comes from navigating different perspectives. They will see some merits in your views while also being able to make a case for the merit of their view.

    Understanding what makes a 10x Engineering leader is similar to understanding what makes a 10x engineer.

    10x Companies and 10x Leaders

    10x Leaders at 10x Companies

    In his book, Great by Choice, Jim Collins also refers to 10x companies and 10x leaders:

    • We labeled our high-performing study cases with the moniker “10X” because they didn’t merely get by or just become successful. They truly thrived. Every 10X case beat its industry index by at least 10 times.”

    • We labeled our high-performing study cases with the moniker “10X” because they didn’t merely get by or just become successful. They truly thrived. Every 10X case beat its industry index by at least 10 times.” …

    • On the one hand, 10X-ers understand that they face continuous uncertainty and that they cannot control, and cannot accurately predict, significant aspects of the world around them. On the other hand, they reject the idea that forces outside their control or chance events will determine their results; they accept full responsibility for their own fate.

    In his case studies, it is clear that 10x leaders are not only very conscious of how they choose their teams, but it also became how they role model for and inspire they teams to greatness to outperform other teams by 10x or more.

    See Also

    Other references for interviewing engineering executives

    After writing the above, I found some related articles that offer some more color on how and why an approach like “15 Speed Dating Interview Questions” can be very effective. I thought I’d come up with a great metaphor with speed-dating, but clearly, others have seen that analogy before. I do think the closing conversation pulls it all together to provide the deeper insight.

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