Some time ago, I had the privilege to moderate a conversation between CTOs - while I was still fresh into the scene. Interesting those questions are now relevant to me as I look back at my journey thus far.

In this article, I will share with you some reflective questions you can consider as a CTO yourself:

1) Origins & mindset

1. How did you end up becoming a CTO? What drew you to the technical leadership track, as opposed to other paths?
2. What’s something people assume about CTOs that’s completely wrong?
   1. What’s something about the CTO role people often misunderstand or overlook — especially compared to the CEO?
3. How do you personally define success in your role, especially in a startup environment?

2) Building for change

4. How do you design a technology architecture that survives — and thrives — in fast-changing conditions?
5. What’s your philosophy on internal vs. external development? When do you choose to build, buy, or partner?
6. Can you walk us through one early architectural decision you made — and how it paid off (or backfired) six months later?
   1. What’s one “invisible” technical decision you made that turned out to be critical to the company’s success?

3) When things break

7. What did the failure feel like in the moment? How did your team react?
   1. Tell us about the highest-stakes technical project you’ve seen fail. What happened — and what did you learn?
8. Was there ever a time when your team pushed back hard against your idea — and they were right?

4) People, Culture & Team

9. What does it really take to attract and retain strong tech talent in a startup?→ Include your answer about small, experienced teams with a mix of rising stars. Expand on mentorship vs. management.
   1. “What’s the best hire you’ve ever made — and what did you learn from it?”
   2. “How do you spot someone who might become a 10x engineer or leader?”
10. How do you structure a culture of ownership, but not burnout?
11. What cultural shifts do you think companies need to embrace to unlock the full potential of AI — not just adopt it as a buzzword?

5) The CTO’s Toolbox

12. What’s one technical tool, pattern, or quirk you love — but most people don’t appreciate?
    1. What’s your favourite algorithm or language feature — and why does it excite you? Can you give an example?
13. What do you think makes excellent API documentation? How do you ensure developers want to use your platform?
14. Do you think your tech stack and platform are truly extensible? How do you test or design for that?
15. How would you rate your current scalability strategy? What’s your plan for hitting the next big growth milestone (e.g., million users, 10x traffic)?

6) Vision & Exploration

16. What’s a tech frontier you’re personally watching — but wouldn’t bet the company on yet?

7) Reflection

17. What advice do you think is commonly given to future CTOs — that you think is actually wrong?

Even more questions coming from the article of reference below

1. How do you build an IT architecture that can adapt to a fast-moving environment ?

2. Tell us about the highest technical project failure you experienced?

3. What culture change you suggest for companies that want to embrace the full power of AI?

4. What does it take to attract and retain tech talents?

Some answers are:

I tend toward smaller, experienced teams rather than armies of recent grads, but like a mix of both. I typically reply that I position our best and brightest for positions of leadership (not necessarily management, depending on their career goals), but like to give opportunities to newer staff because every once in awhile, they will surprise the hell out of you.

5. What are the technology transformations you haven’t explored yet?

6. What’s your favorite algorithm? What’s your favorite programming-language feature? Why? Can you show me?

7. Does it scale? How do you plan to scale to meet XYZ target (million users, revenue, orders, etc)?

8. Do you know about software extensibility?

9. How easy would it be for competitor ABC, Inc to replicate your technology?

10. What do you think makes an excellent API Documentation?
11. How do you keep yourself up-to-date with the latest technology?

Reference

Tough questions to ask your CTO