Published on February 28th, 2023 | by Bibhuranjan


Best Practices for Conducting Interviews with CTOs

Congrats, your startup has grown to the point that it has become necessary for you to begin your search for a chief technology officer (CTO). These executives tend to be some seriously heavy hitters when it comes to building and incorporating all things tech.

Once you have your candidates narrowed down enough to begin the interview process, there are certain things you should know about the person you hire to be your new CTO. This article will serve as a guide for how to conduct interviews with CTOs, so that you are prepared to make a good impression.

Hiring a CTO is no small or cheap venture. The average annual CTO salary is $130,000-$195,000, according to SearchCIO. According to a 2018 report from the InfoSec Institute, CTOs in the financial sector earn around $200,000, while e-commerce CTOs earn around $76,000.

So, you will want to make sure that your capital investment in the person that will be leading your company in technology is the right fit. You will also want to ensure that he or she is compatible with your current technology team.

Therefore, you will want to make sure that you properly vet your CTO candidates. Here, we will discuss the three main parts of a successful interview process with a CTO. Each part will serve as a means of vetting your candidates. You need to know whether or not they’ve done their homework on your company; if they have the necessary experience to lead in the right direction; and whether they are up-to-date in their knowledge of the tech industry as a whole. Understand that CTOs must make their own hiring decisions as your company continues to grow.

First Credibility Check: Make Sure They Did Their Homework

The first part of the vetting process for your CTO candidates is to make sure that they have successfully prepared for the interview with your company. This can be shown through probing into what they already know about what your company’s mission is, how you serve this mission and the tools that your company uses to achieve that mission.

After the pleasantries of introductions, handshakes, and small talk have been made, get right into it. Ask them point-blank: “What do you know about our company?”

See if they can provide specific details without much prompting. Make sure they know what your company does. If you are a digital marketing firm, see if they know who your customers are, in what industries they operate, and who your target audience is.

Get them to talk about the methods and means that your company uses to achieve the finished product. Ask them if they can tell you which programming languages you use to build your software or the websites you build for your clients. Ask them questions about the data science techniques your company deploys such as artificial intelligence (AI) and other automated tools that your company uses to help achieve your goals.

This information should be rather easy for a motivated CTO to find, assuming they have done their homework by researching the public information about your company. This should be readily available on your company’s website, social media, and depending on the size of your company, this information might even be available through channels such as public earning reports, or even an internal, or third party recruiter.

At the end of this first part of the interview, and the first credibility check, throw them a curveball. Ask them what suggestions they might have on how your company can improve your current processes.

The answers they provide will give you valuable insight into their experience, as well as how projects they have worked on, or processes they have implemented in their past roles can now serve your company. Their answers may also provide insight into their creative ability. This metric will be different for each company, but a CTO needs to have a certain level of creative problem-solving ability, as this will allow them to help your company make necessary pivots in terms of technology strategy.

Second Credibility Check: Their Professional Experience

After you ask them about the company, the next area you will want to focus on is their professional experience, and how what they have done previously in their career relates to leading the technology operations for your company.

Start with a fairly creative question to kick off this second part of the interview. Ask them a question like: “what has your professional journey looked like so far?” This is a relaxed and fairly open-ended question that will allow them to more freely answer how they started in the tech industry.

These are some good questions that you could ask next:

  • Did they take the traditional route of a computer science degree before beginning their climb through management and seniority positions?
  • Alternatively, did they get their start through a short term, intensive coding bootcamps?
  • What did their upward trajectory like?

After you have a good idea of the story of their career up to that point, ask them this: “What specific roles have you held in the past, and how will that experience benefit our company?”

As they answer, listen for specific titles, but keep in mind that titles carry a different weight depending on the company. A candidate that has already served as a CTO at a startup will most likely have a different experience in that role than a candidate that was the CTO at a small business not primarily in the tech field. Likewise, a candidate that has held a position such as “director of software development” at a large technology company may have the experience that could be more valuable for your company than someone who has been a CTO at a large retailer.

What you want to look for as your candidate tells the story of their career journey are the actual responsibilities they had in their previous roles.

After you have a good picture of their career up to this point, ask them to share two stories from their career. The first one should be a story of success about how they rose to a challenge or implemented a new technology policy at a previous company. Look for details as they tell this story. Do they largely credit themselves with success? Or do they give the credit to the team they led? This will show the leadership abilities of your candidate, as a good leader will speak of success as the result of a team effort.

Next, ask them to tell a story of failure. Understanding how a candidate has dealt with failure in the past is a great guide to how they could cope with future situations. If they can be honest and frank with you about a failure they experienced, this will further show their leadership abilities. Moreover, the ability to talk about what they learned from that failure, and how they took what they learned through that failure as they went forward, will also show great leadership ability.

On the topic of talking, according to Juozas Kaziukėnas, founder of Marketplace Pulse, communication is a critical skill for a CTO. Quoted in a Forbes article, he said:

“[Being a] CTO depends on communication. It involves understanding what other departments are doing and being able to communicate the role technology will play in this. This is not about explaining technical decisions to everyone, but more about explaining why certain things work the way they do, or why some features are not a good idea (security, privacy, scale implications), etc.”

Julia Austin, CTO at DigitalOcean, agrees: “It’s really important to understand what people need on the business side and then listening to developers and understanding their challenges, or even application providers and understanding what products did and didn’t do.”

Other important skills, according to industry experts, are technical know-how, love of learning, adaptability to different roles, and big-picture thinking. Make sure your questions address all these skills to get a complete picture of the candidate.

Third Credibility Check: Is Their Knowledge Up-to-Date? What is Their Perspective on the Industry?

Once you have a good feel for their previous experience, as well as their leadership abilities, the last thing you will want to vet them on is how they keep themselves relevant in the tech industry. Are they keeping their skills refreshed, and expanded through online courses? Are they up-to-date on the new programming and software trends, and the companies that are pushing the industry forward?

Camille Fournier, former CTO of Rent the Runway, says “Great CTOs are curious and eager to learn new things, and they aren’t afraid of change. Change is the name of the game in technology.”

Jon Walker, from AppFolio CTO concurs. “CTOs have to be life learners who are always constantly going deep in new areas. Technology has to be one of the areas where CTOs sponge up information, but the best CTOs also learn about finance, sales, marketing and other aspects of the businesses they are involved in.”

Have the candidate share an interesting fact about a new technology used in your industry to demonstrate that they are staying up-to-date with the times. Ask for their perspective on where the industry is heading.

Lastly, ask your candidate how they plan to keep their team engaged, and creative. Ask them which tech summits and conferences they have been to, or would like to go, that they believe might be vital learning experiences.

Toss them a curveball question to round out the interview—ask them how they keep themselves creative. At its very essence, the tech industry is about creativity. It is an entire industry devoted to helping the world solve problems by creating new and innovative technology. A top-notch CTO will understand this, and they will keep up their narrative methods and habits. Ask them what they do outside of work, as a means of destressing, and how they believe this helps keep them creative.

Ultimately, the decision on the CTO you will hire will be very much dependent on the needs of your company. We hope the interview practices we have discussed here will help you in the vetting process of whoever that may be.

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Editorial Officer, I'm an avid tech enthusiast at heart. I like to mug up on new and exciting developments on science and tech and have a deep love for PC gaming. Other hobbies include writing blog posts, music and DIY projects.

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