Introduction  

Reaching the top in the world of technology is no mean feat, and technologically speaking, there aren’t many spots higher than that of Chief Technology Officer within an organization. Larger companies normally have this role open for senior executives that have the skills, knowledge and foresight to help them take the company to the next level on the technological front. Some smaller startups with a technological focus also have the role of CTO available, although this is likely to be more of a hands-on role with programming and coding duties.

The role of CTO is an executive function, which means that it is a top senior role with lots of pressure and responsibility placed on the individual. While it is a technical role, it is not always a hands-on position — especially if the company is large and well-established. Smaller companies with smaller budgets may require their staff to perform many different roles, so be aware of the requirements of the CTO post that you are applying for ahead of time.

The CTO also needs to be aware of all aspects of the company, including its financials. This is so that the forward planning for the organization’s technological needs can be catered for in all time horizons (Short, Medium and Long-Term).

The following sample questions are the kind you might find if you were to sit in on a CTO interview and listen to it play out. It has been divided into three different sections: Opening Questions, Technical Questions and Final Questions. They start off with personal- and individual-styled questions and then move on to technical background and understanding. Finally the closing questions focus more on the running and planning of the technical side of a company and how the methodologies and techniques that the candidate has learned could be harnessed by the company if they were to be hired.

Opening Questions

Most interviews will start off with a series of standard personal questions that aren’t necessarily technical in and of themselves, but they do help the interviewers to assess your technical background. You can expect the standard interview questions that look at your background, hobbies and interests as well. This all helps the panel of interviewers to build up a personality profile of how you operate and how suitable you would be for the position.

With most interviews it is important to understand who the company is, what it does and what its main line of business is. If you are interviewing for such a high-ranking position within a company, then you will no doubt have some familiarity with it.

It is important that you do as much research about the company as you can before the interview. You need to show that you understand the company’s technological requirements as they relate to business operations, financial requirements and possible future planning. You could even have some suggestions ready for the panel if a question comes up in the interview that warrants any. It all depends on how well the interview unfolds.

1. Tell us about our company. What do we do here?

This is quite curveball for a first question, but it does happen from time to time. If you have been considered for such a high-ranking position in the company, then you might have had some preliminary discussions with a company contact ahead of time, or with a recruiter if you have gone through an agency. Either way, they could help you with some key points that you should definitely have prepared for the interview.

The interviewer generally wants to gauge how well you know the business, as it shows that you have taken a key interest in how the organization operates, and what they need in terms of technological oversight from you. You must always do your homework about the company before the interview, so definitely be prepared for this kind of question. In your answers you can suggest that a company such as theirs that works in such a sector can benefit from A, B and C suggestions. This shows that you not only understand the technology that is required for the company to succeed, but that you also understand the context in which the technology applies to them as well.

2. Tell us about your professional journey. What led you to this point?

These kinds of questions are a great way to lay out your career. It’s always a good idea to clarify how long they would like the story to be, as at this point in your career you probably have quite a long history. Try to keep the story as relevant as possible for what has been asked of you while still doing justice to the story itself. You don’t want to compress your work history into a version that leaves out all the important parts, so work on encapsulating your experience into a coherent storyline that the interviewers will remember.

You don’t have to retell every single job that you have ever worked in your life, but if an interesting anecdote or a conclusion that helps to make a point comes out of it, then mention it.  These could even be non-tech related jobs like waiting tables or working part-time while you were studying. This shows that you have a strong work ethic and helps to contextualize your current success.

3. What makes you successful?

If you are not normally a person that likes to list their achievements or speak about why you are so good at what you do, then you might struggle with this type of question. Being in the executive suite of a company requires confidence, so make sure that you have answers to these kinds of questions. It’s a good mental exercise to think about as well: What is it that has driven you to this point? What good habits do you have? Make a list of the best attributes that you possess and highlight them. If you aren’t sure, then ask friends or family for honest feedback and take notes. Remember the most relevant points for the interview.

4. Describe your current role for us

These types of questions are aimed at finding out what it is that you are doing presently and how you would explain it. This isn’t a good time to complain that you are doing everybody else’s work, or that your current team is lazy (even if it’s objectively true). Never speak poorly about your current company in an interview. Instead, highlight all of the current roles and responsibilities that you are undertaking, especially ones that relate to the role of CTO.

You are probably in a senior technical or managerial role with at this level of interview, so think about how your skills and experience would translate best into this role. If you already occupy a CTO role, then you will probably have less trouble explaining how your current skills would be a good fit for the role that you are applying for.

5. What value would you bring to our company?

This is another opportunity for you to shine a light on your past experiences and projects. Talk about the efficiencies that you were able to introduce to your current company by implementing a new IT solution or policy. Mention the frameworks that you developed with your dev teams, or anything else that brings cost savings and streamlining in the technology space.

6. How do you deal with the unexpected?

Being in senior-level management is not easy, and sometimes things don’t go according to plan. You will want to show the interviewers how your planning contains failsafes, backups and contingencies if the worst should happen, either operationally or during a project.

You want the panel to understand that you are dynamic and adaptive in your day-to-day work life, and that you are able to meet unexpected challenges.

7. How would you describe your management style?

You might not see yourself as a manager, especially if you have previously held senior technical roles that focus solely on dev and technical work. Some CTO roles don’t even have hands-on technical requirements. Instead, these roles may focus on policy, technological implementation and organizational culture relating to technology. But having said that, some smaller startup companies have multi-faceted roles that will require that the CTO still manages heads of departments and sometimes even key individual members on the team.

Think about how you work with people, how you lead and how you guide your teams. You might be surprised to find that you have a management style that fits in with the role that you are applying for. The key is to think about all of these elements before you sit down for your interview so that you are not caught off guard if this kind of question comes up mid-interview.

8. Do you have any favorite books or authors?

This is a good question to have an answer for, even if it is a generic one. You don’t want to come across as someone that doesn’t read, so maybe have one or two ready for the interview, just in case. Suggested reading lists are widely available, such as the examples here and here.

9. Why are you leaving your current employer?

We all have our reasons for wanting to leave a job at some point in our lives. You don’t need to go into specifics, but you can bring up the fact that you see this as a positive step up in your career. If you are coming from a senior-level position with a heavy technical background such as systems architect or head of systems development, then you can mention that you are looking to try something more challenging in the executive sphere.

CTO roles are great for candidates that have a technical background but feel like they would be better off in a more supervisory or planning role where the company’s policies and operating procedures are directly influenced by their input.

10. What are you passionate about?

If you get to this point in an interview, you can generally assume that the interviewer is looking to get a bit more of a personal insight into what interests you as a person, and how that fits in with what you have told them thus far. Most CTOs are extremely passionate about technology, from design to implementation and everything in between.

Don’t be shy about sharing some of your other passions as well, such as hobbies or worthy causes that you support outside of your professional life.

Technical Questions

There are no easy interview questions when applying for the role of CTO because the span of topics and skills that you need to possess differ from company to company. You need to be just the right fit for such a senior role, so don’t be surprised if some technical requirements come up that you hadn’t thought of as being necessary for the role. Not many CTOs actively code, but if you are applying for such a senior role in an organization that only creates software and is composed of developers, then having experience in that type of environment would put you ahead of someone that has never worked with internal dev teams before.

11. Do you still code?

It is unlikely that you have gotten to this point in your career without picking up at least some rudimentary coding skills, even if it has been some time since you’ve used them. If you haven’t got any skills in that department then it might not matter, depending on how the company sees your role. If you are there as a “big picture” visionary with ideas and plans for how the company is supposed to evolve over time on a macro scale, then coding skills probably won’t matter. But if you have coding experience, then your ability to understand the tech stack requirements and provide input about the direction of the system architecture of a product that is under development will be far easier for you.

Questions like this are there to assess your technical level in terms of software development. If you are working with a team of developers that need to answer to you, then you should be able to question them technically when required. If you don’t have the ability to fact-check a claim, then you run the risk of being taken advantage of by teams that are under pressure.

12. What programming languages and development methodologies are you familiar with, if any?

Questions like this seek to explore the level of competence you have with teams of developers that create software products. There are certain standards such as Agile, Scrum or traditional waterfall methods. Some CTOs take an active role with the managers and product owners of these teams, and some only rely on meetings and feedback to ascertain how well a project is doing.

This question will vary from company to company. Some organizations will have a heavy development requirement, while others will outsource this function. It all depends on the company.

13. We have an extensive internal dev team. How well do you work with developers?

If this line of questioning comes up, then it is safe to say that your experience and resume has brought you to the interview because you possess the qualities that the company is looking for. Dealing with a dev team is not always easy, especially if you have not been a part of the project from the beginning. Running a successful project requires tight deadline adherence and a lot of data for reports and meetings. Understanding how to get the maximum amount of progress from such structures could be important to landing the job, so be on the lookout for questions that want to know how you work with software developers and engineers.

If the team runs with Agile, then mention how important the daily standup meeting is, when to sprint and general best practice when working within the Agile framework. If they only work with traditional waterfall models, then ask why Agile is not an option. You might find that it hasn’t been tried or that the incumbent CTO is not familiar with the framework. Questions like this open up many possibilities for the rest of the interview, so be ready to go into detail when you need to.

14. What is your technical background?

They will have all of these details in front of them, so you don’t need to parrot back all of your experiences. Instead, try to distill groups of experience into a single skill that you developed over time. If you spent years as a systems engineer and then moved into software development, then speak about how the core knowledge that you picked up during your early years built a foundation for you to pursue more technical roles.

Remember that the interviewer wants to hear your take on what your experience is and how competent you are in a given domain. It doesn’t hurt to think about how you got to where you are, so summarize the experiences that you have into a coherent timeline that highlights your technical background and abilities.

15. What are some of the technical projects that you have overseen?

This is a fun question to answer, especially if you have some accomplishments that you are proud of. Frame your answer in relation to the problem that you had to solve and then outline the solution, how you found it and how you implemented it. Speak about the results, and how it added value to the business.

At this point of the interview you should probably have an idea of what technical abilities they interview panel are looking for in their potential CTO. Try to answer the questions in such a way that you show that you are aware of what they are looking for and can relate some of your skills to their current needs.

16. Do you get involved in technical projects? If so, what value can you provide your team with?

Questions like this will try to determine what your general attitude is towards managerial tasks, and the requirements will be different for each company. Some CTOs don’t get involved in the technical details of the way that projects are carried out, while others micromanage and ask for constant updates.

If your style of management is the former, then you can say that you bring value to the organization by giving your teams the freedom to explore possibilities and work without being interrupted. If your management style falls more in line with the latter, then you could say that your value lies in your ability to keep the executives constantly aware with updates and details so that there is no guesswork. Perhaps you are good at generating reports and dashboards that track projects as well as performance of your technical staff.

Or perhaps you have a mixed style, and that could also be a strength. Knowing when to get involved and when to leave your team to get on with the work is a valuable skill in itself. If the organization is new or just getting started, then you may have to get your hands dirty on the design and creation side of things. You will have to use your judgement depending on the interview, the company and the panel that is interviewing you. Just remember to be on the lookout for this kind of question, especially if it is a startup company.

17. Following up from the previous question: If you prefer to delegate tasks without getting involved, how do you measure performance and progress?

This is a great opportunity for you to mention some of the productivity tools that you use on a day-to-day basis for tracking and maintaining visibility with your technical divisions. This could be a simple spreadsheet, a SharePoint resource or a custom application. Mention your favorite performance metrics such as KPIs and SLAs and how they let you keep an eye on your projects.

This question might not apply to your CTO role if you are joining a well-established company that already has systems in place for tracking performance. You might even find that the CTO role that you are applying for doesn’t even interact with this side of the business, focusing instead on the long-term and intrinsic implementation of technology within the organization.

18. What informs your decisions when choosing a programming language and design framework for a product/project?

This question is aimed at finding out how you weigh up the pros and cons in the developmental,  early stages of a project or product development cycle. While a CTO doesn’t always have intimate programming and software application knowledge, it certainly helps if that is the industry space that you occupy.

If this question comes up in an interview, then you will no doubt be aware that your role as CTO at this company might involve some pretty fundamental development questions. If you have the experience that is required for this environment, then explain your methodology for choosing your preferences. You can mention the time taken to get a working prototype up and running, the ease at which teams can share their work between one another, or any other dev related preferences that you might have.

19. How do you translate your ideas and vision into terms that the technical teams can get behind?

Having a technical background is a huge advantage here. Skills that stem from systems architecture experience, design and development experience, and a general understanding of the technical requirements of the task at hand are all helpful tools at your disposal. You can apply all of this knowledge to help explain the details to your dev teams and technical staff right from the get-go. If you have a technical background, then it is far easier to explain your vision to those that need to make it a reality.

As CTO, it is your job to take the unimaginable and turn it into an actionable plan that is not only achievable but is also time-sensitive with a deadline. One of your abilities as CTO should be your ability to inspire your technical teams, making sure that your vision is carried out exactly as you imagine it. You have to learn how to deal with pushback from your teams when your expectations are challenged, especially when you are exploring new technologies and potentially difficult projects. You need to take on the role of facilitator and ensure that any roadblocks and impediments that are in the way of your teams are removed, giving them your full support and guidance during difficult times.

20. Do you have any examples of a technological change that you have implemented within an organization? What was the outcome?

This question requires that you dig into your past and relate how well you did with initiating a change within the company. You probably have many examples, so pick the best ones that you feel would resonate with the interviewers the most. Go through your process, what your expectations were and how well you handled the entire project. You can go into as much detail as they will allow, so be sure to brush up on a few of these examples prior to your interview.

Final Questions

Although these are structured as the final questions in this article, they could very well come up at any point in the interviewing process. You may even find that all of the different question types are randomly interspersed throughout the interview, so try not to get taken by surprise if things are not as straightforward as the question numbering may suggest.   

21. How important is the culture of technology to you?

This is an interesting question, especially if you haven’t sat around thinking about what culture has to do with technology in the first place. Well, if you think about an organization and the business culture that is fostered there, you can also draw conclusions about how technology is treated in the same way within that business.

Organizational culture encompasses things like open-door policies with management, the chain of command, security, transparency — basically, every aspect of the business. Think about how you prefer technology in the workplace, how it is implemented and how people engage with it. Do the technology capabilities match the work environment? Think about remote work and flexible working hours: How do you embrace this new way of working, and do you support the infrastructure that is required to make this work? How do you feel about the Bring-Your-Own-Device movement that many large companies favor, and how do you feel about the security issues that BYOD brings to the situation?

Also think about your own personal relationship with technology, and how it fits into your life. If you are going into the role of CTO, it wouldn’t make a lot of sense if you shunned technology outside of the workplace and took no interest in it. Think about how you would define yourself in terms of technology and culture, and how that would translate into your role as CTO.

22. What are you passionate about in the technology space?

This is a very general question, so we can assume that the answer is not as important as the way that you give the answer. If you give a general answer that doesn’t seem very specific, then you run the risk of sounding bored or disinterested.

Think about your interests and what keeps you excited about developments in technology. There are so many exciting emerging technologies out there, from artificial intelligence and machine learning, to blockchain and augmented reality. There hasn’t been a better time in the course of history to take an interest in technology, so you won’t have to look hard to find inspiration.

23. How do you lead an organization through technological changes?

Think about the question in its distinct parts. Any project that requires change, especially big technological ones will require planning, impact assessments, cost analysis, training, downtime — just about anything that you can think of. You will want the interviewer to know that you are aware of all of these elements and how they have the potential to negatively impact a business.

As the CTO, the rest of the organization looks to you for guidance and advice during times of change, so you will be the face of any type of action that requires people to do things differently than what they are used to. Lead by example and be accountable when things don’t go according to plan. If a new system is set to replace an old one, then be the first to start using it, get people excited and get them to adopt the change. Leadership means motivating people, especially when there is uncertainty in adopting a new standard or system.

24. How do you deal with resistance from other executives?

This question looks to understand how you deal with people that are your equal or superior and how good you are at finding solutions to conflict with them. Each organization has its own procedures in place for these situations, so be sure to mention that the way that you deal with a certain scenario will depend on the specifics of each incident.

Think about funding for a project that won’t get approved by the CFO, even though you have reworked it multiple times and changed the scope and timeframe. How you deal with such things will depend on both your personality and the mechanisms that are in place within the business for you to fall back on. Do you go through official channels or do you go to the CEO and ask for an intervention? Think about how the business would expect you to act and what course of action would be better for the overall health and wellbeing of the organization.

25. How do you feel about remote working? Have you dealt with remote technologies before?

Most companies have embraced the “Gig Economy” and they are more frequently taking on flex hours, part-time and freelance workers. The access that these workers need to connect to the network needs to be secure enough to prevent unauthorized access to other company resources and open enough so that the work can actually get done.

This question expects you to weigh in on how you see remote work, and if you think that there is a place for it in business. If you have had experience with things like Citrix and Terminal Server, then this is as good time to mention it, as well as what you like and don’t like about the tech. Most businesses have some kind of remote technologies available, and any CTOs are in favor of being able to provide a technological solution to the entire company, wherever they are.

Also mention solutions like MPLS if you have any experience there. You might find that smaller organizations haven’t thought much about consolidating their communications like this, which could show that you understand the requirements of the company right from the get-go.

26. How important is cybersecurity to your role?

Cybersecurity generally falls under the domain of the Chief Security Officer, but there is sometimes a bit of overlap — the CSO ultimately reports to you. You will need to work closely with the CSO and the security department to ensure that the technologies that you are proposing are actually viable and secure for your operating environment and that compliance is maintained throughout.

This question is looking to see if you understand your role as CTO, and how it doesn’t necessarily exclude you from thinking about the security impacts of your decisions. Now is a good time to find out what the company feels is the right level of engagement between the CTO and CSO, as each company is different. Generally speaking, the CSO will report to you and will let you know how compliance and security will be impacted by the decisions that you make. Again, this varies between companies, so find out what you can ahead of time; this gives you a chance to prepare for any follow-up interviews that might have the current CSO present, if they are not currently part of the panel already.

27. Do you keep up with the latest trends and movements in the (insert name) industry? What changes do you see relating to tech in this space?

Part of your interview preparation for such a senior position should involve as much research as possible about the business and how it operates within the sector that it has been established. If you are joining a logistics company then you might want to look at how autonomous vehicles, both on the road and in the warehouse installations, could benefit the company technologically. If you are joining a financial institution, then blockchain might be a technology worth pursuing, as security and speed of transactions becomes more important over time. The examples are endless, so research as much as you can.

The main thing to take away from this question is that you need to be prepared to answer questions not only about the company, but also about the industry that it serves in. There are many technology-based solutions that you can suggest, so be sure to read as much as you can about the company before you go into your interview. Subscribe to publications that are specific to the sector that you are looking to enter, read articles, watch business reports — anything that relates to the way that the business runs. This not only helps you to prepare for the interview, but for the role if you are successful.

28. How do you deal with budgetary constraints in the face of technological requirements?

This question looks at your problem-solving abilities within the executive suite, how you handle a suggestion being rejected and what you would do if your request should be denied. Sometimes it is not worth pursuing an expense if the company feels that it cannot absorb the cost at the present moment, so picking your battles is crucial. There will be times when you need to fight for your ideas to be implemented, especially when nobody else seems to understand how the changes that you are proposing would benefit the entire organization.

The second element to this question is how well you can come up with alternative solutions with a much lower cost implication for the company. Are you able to use the resources at your disposal to create an in-house equivalent of the technology that you are pushing for, or can you leverage an open-source version for a better cost outlay? Creativity is an important part of being CFO, so creative solutions are always welcome when they can achieve similar results for a lower cost.

29. If you could change one thing in your life up until this point, what would it be?

This is a question that comes up in all kinds of interviews, so try not to be too taken aback if it surfaces in your interview. Think about your professional progression and what you could have done a little better or avoided altogether. Some people regret not studying more, others regret moving to another area or company that didn’t quite pan out like they had hoped. Perhaps you don’t have any regrets; that’s OK too.

This is a question that normally materializes towards the end of the interview after all of the key mid-level questions have been answered, so you’re probably in good shape when this question comes up.

30. Do you have any questions for us?

You would be surprised how many times this question comes up in an interview, and even more surprised by how few people actually prepare for it. Of course you have questions, but which ones are relevant at the moment that they ask you?

Think about the things that weren’t made clear to you in previous jobs where you worked and how you wish you had known the answers to them before you started. Because this role is a senior position, you will probably have plenty of opportunities to ask further questions in additional interviews and sessions, so don’t worry if you don’t have any questions at this point. You can always prepare some questions for the next round of interviews, giving you more time to articulate what it is that you want to know.

Conclusion

For some people, interviews are terrible. They get nervous, anxious and stressed out even before they get started. It is important to remember that no matter what level you are at in your career, it is perfectly normal to be a bit apprehensive before a big interview. Prepare as much as you can and be ready to answer truthfully and honestly about your personal experiences. The more natural and composed you are in the interview, the better.

Remember that the more questions you practice with, the more chance you have of carrying yourself confidently in the interview. There are many more questions that you can practice with than these thirty examples! We recommend that you take a look at Skillset.com, which has more than a hundred thousand practice questions related to various certifications. The list of cert-related questions includes is vast, with PMP, CISSP, CEH, CHFI, Network+ and Security+ being just a few examples.

Stay focused, relax and good luck!

 

Sources

  1. What is a CTO?, Business News Daily
  2. Chief Technology Officer Job Description: What Does a CTO Do?, dev.to