This article dives deep into the CTO interview questions. It is a summary of a live session with Richard Weaver, an expert recruiter who started his HR career in the late 1980s, placing over 1000 candidates into roles in organisations of all shapes and sizes.
The purpose of this guide is to show both perspectives: the interviewer’s and the interviewee’s to better understand how to interview for a CTO role on one hand and how to prepare as a candidate on the other.
Matching the right talent with the right opportunity is crucial for any business leader. — Jim Collins, Good to Great
One of the first things we must understand is why we interview in the first place.
To better grasp the subject, we will go through some common interview formats to show you how to best prepare for the interview; again, on both sides of the table.
Some questions we are going to answer are:
The main purpose is to predict the candidate’s future performance; in other words, trying to assess if a candidate is a good match through several methods.
One of the methods is assessing interpersonal skills or the so-called soft skills (eg, leadership style, communication, critical thinking…). Hence, it is about examining a behavioural skill set. For example, how do people behave in certain situations? Are those behaviours desirable in the context of our company? It’s basically an attempt to assess whether or not a candidate is a good fit from a cultural or behavioural perspective.
The other is assessing hard skills. Can they read and write code? Can they deal with difficult personal situations? Do they know how to give feedback?
Another important thing an interviewer likes to assess is the candidate’s long-term thinking capabilities. That is, they want to see if the candidate is going to be successful 2, 3, 4 or 5 years from now. Is the candidate able to look further and think long-term? Can the candidate apply what he or she has learned so far?
SELF QUESTION: You possess a lot of experience, but can you leverage that experience in the context of the company you are applying to?
The last thing on the list is what motivates the candidate. The organisation is eager to learn answers to the following questions:
Today’s interviews delve into the candidate’s strategic thinking, leadership style and adaptability. They are more about understanding how they navigate challenges and integrate within the company’s ethos.
Functional interviews enable organisations to assess the functional skills (hard skills) for a particular role. But before drafting the questions, the company must define four things:
The questions are based on these criteria and corresponding data points that are, effectively, success or failure indicators. Furthermore, they must be relevant to the context of the role.
Questions are then broken down into categories. An engineering role, for example, could have questions relative to the architecture and coding skills. A leadership role, on the other hand, could look into organisational and problem-solving skills.
But since these are all hard skills, the most optimal approach is to challenge a candidate with a concrete problem and ask the candidate to solve it. That’s also the signal that you are in a functional interview setting.
TIP: Listen carefully to the questions to grasp the context. You don’t want to answer a technical question with an organisational answer and vice versa.
As a candidate, the one thing you can expect during functional interviewing questions is problems designed to scale. This method allows probing of different characteristics of a candidate. For example, the initial question on cybersecurity in a start-up can scale to how would you handle that same problem with 1,000 engineers.
Behavioural interviews determine and analyse the behavioural tendencies of a candidate.
If you think about your job and an average day at work, it’s more important to think about how we do things rather than what we do. It sounds philosophical, but it hides the reason why an otherwise skilful employee just doesn’t function inside the collective and that reason is: opposing behavioural tendencies.
The common approach is to discuss experiences and then understand the context while keeping in mind that those tendencies can be extrapolated in the future. In simple words, if a person tends to behave a certain way, that person will most likely exhibit similar behaviour in the future.
TIP FOR INTERVIEWERS:
STEP 1: Define the problems your engineers face daily.
STEP 2: Now design your questions around those problems.
STEP 3: Design the answers as well to predefine specific points you want your candidates to bring up.
Combine open-ended questions and use probing. That way, you can quickly assess that something doesn’t really add up either because they are serving you fiction or not telling the complete truth.
Additionally, don’t be afraid to inform candidates about the types of questions you will ask to give them time to prepare. Remember, the interview is not about tricking or surprising people but about generating data points that can help you make an informed decision about the candidate’s fitness.
TIP: Adopt a structured approach that goes beyond your technical expertise and start by actively listening to the question and understanding its core components.
Let’s take, for example, a query about implementing a new cybersecurity framework within a company.
In summary, addressing a functional question involves:
It’s about showcasing not just technical proficiency, but also your ability to apply that knowledge to solve real-world challenges and drive positive outcomes for the organisation.
Behavioural interviews focus on your experiences and actions to predict how you might behave in the future. For example, the question that begins with ‘Tell me about the time when you…’ indicates a behavioural interview question.
A company has determined that successful employees when feeling stuck, reach out to people around them to solve the problem rather than just banging their heads through the wall. This has been identified as a behaviour.
In such a scenario, you can expect a query to describe a situation where you got stuck on a project and explain how you dealt with it. During your presentation, expect additional open-ended questions because they are trying to establish the context and thought process.
One of the criteria here can be whether candidates have carefully considered if it’s something they can solve by themselves or if they need help with it. This is the moment where data points come into play:
(The last bullet point may be a criterium on its own.)
Use the STAR method to structure your answers (Situation-Task-Action-Result).
TIP: If you can draw a clear line between the task and the action, that always helps.
Remember, the end state here does not always have to be a success. More often than not, we find ourselves in situations where the context has changed and our actions did not yield the desired results. So make sure you point that out if that’s the case with your example.
Q: What kind of functional skills can one showcase if the intent is to transition from individual contributor to leadership roles?
A: Organisational skills. That is, demonstrate situations where you’ve brought a group of people together, managed a project by breaking it into chunks and assigned each chunk while being on top of everything.
Q: How do you show that you will fit without previous experience in a managerial role?
A: Point to concrete situations where somebody had a problem and came to you. You took them under your wing and you helped them grow. In other words, you coached more junior employees.
The CTO interview process is a complex dance between assessing technical prowess and understanding the individual behind the skills. It’s about finding someone who not only possesses the necessary hard skills to navigate the technical landscape but also exhibits the soft skills and leadership qualities to inspire a team and align with the company’s vision.
Both interviewers and interviewees must approach the process with careful preparation and a genuine desire to understand the other’s perspective. By embracing transparency and focusing on open communication, both parties can ensure a successful outcome – a match that fosters innovation, growth and a shared vision for the future.
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