10 Tough Questions for your Chief Technology Officer

Alexandre Toulemonde
Decathlon Digital
Published in
4 min readApr 15, 2019


You probably came across a few articles like this one or this one mentioning thing like:

A majority of companies say lack of access to software developers is a bigger threat to success than lack of access to capital.

In other words, in today’s age, naming your technology leader(s) will be one of the most important decision of your company’s life.

But let’s start with one for you, the decision maker,

What do you expect from your CTO?

A great project manager, business manager or a great technology leader?

Software architecture, ops, mathematics, cybersecurity, stability, artificial intelligence but also… Negotiation, vision, project management, leadership, etc. There are so many skills to choose from.

Which ones would you value the most?

Our first suggestion is to give great importance technological expertise. After interviewing our IT Team members what makes a great CTO, this noticeable answer came up:

Someone who can listen to my technical concerns, understand them, but also turn them into concrete insights and actions. Not just someone “taking decisions” or “being responsible for me”.

So let’s get into it! Here are a few tough questions you could ask during your interviews. Disclosure: we attempted to answer them as best we could but feel free to complement or argue with them in the comments!

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

Build agnostic micro-services as opposed to monoliths. Hire, invest and trust talent as much as possible. Force yourself to tech your architecture against very weird and diverse user stories.

Follow-up question: “What are the key problems you envision with the micro-services approach?”

Software entropy, replicated data, cascading API failures, uneven API Quality. All in all a heck of a job for your SRE leaders. If you have one.

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

Who hasn’t been taken by surprise by the outdated monoliths approach?

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

Strong data capitalization habits. Put a price on data. Centralized datalake. Strong A/B testing culture. Research in mathematics. Ability to inject AI assistance in many software and jobs. Desire to explore.

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

Ability to reward talents. Great work environment. Being able to intellectually challenge your technical talents regularly. Sponsor tech conferences. Embrace inner source, open source, open data and knowledge sharing.

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

Most talents have very conscious blind spots: blockchain, AI, security, stability, ethics, etc. Your candidate should be able to know his weakness and surround herself/himself accordingly.

6) How do you decide to internalize vs externalize?

Usually externalizing something we don’t understand or has a chance to become a very strategic piece of technology isn’t a good idea.

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

CTO should have a very strong technical past experience and be able to have in-depth opinions about small corners of what technology has to offer.

Variation: “What’s the most impressive piece of software you’ve worked with? Kubernetes? Wow nice! What’s so cool about it?”

8) What do you think makes an excellent API Documentation?

Developers autonomous experience. Time to first API Calls. Clear value proposition. Great API Evolution principles. Culture of capitalization. Inspiring documentation on top of technical documentation.

9) Do you know about software extensibility?

Your piece of software can plug itself to many other softwares and enable great customer experience. Embrace event-driven technology. The wikipedia definition is great and we have an article on our blog just about that here.

Extensibility is a software engineering and systems design principle where the implementation takes future growth into consideration. Wikipedia

10) How do you keep yourself up-to-date with the latest technology?

Coursera fan? Tech conference addict? Influential friends? Book readers? Surrounded by talent in your previous company?

It was hard to stop at 10 questions! Let us know in the comments if you have good one or other insights.

To finish, it’s a bit more related content.

The great CTO of our times

Werner Vogels, 14-year Amazon CTO

Brett Taylor, Salesforce Inc. President, first Facebook CTO and Twitter board member.

Oskar Stål, Spotify’s CTO

I started out writing software at the age of 12 and then gradually moved into working on larger and larger projects becoming more of a leader than an individual contributor.

Interesting note: They all tend to have graduated in computer sciences and be genuinely great leaders.

Great other related articles

Special thanks to Arnaud Esteve, tech lead at Decathlon, for his in-depth feedback. As well as Alexandre Faria, Antoine Dubus and Sebastien McMurrich for your help.

If you are looking for a tech job and an opportunity to make sports more accessible, check out our careers section on https://developers.decathlon.com/careers



Alexandre Toulemonde
Decathlon Digital

Founder in stealth mode. Climate change enthusiast & tech advisor. Formerly Decathlon Canada CTO & Hockey Community founder.