In this article, I will show you a skilful way to conduct technical interviews for CTO / VP of Engineering / program manager / project manager role. It is a technique designed to screen for such role, taking into consideration its unique requirements.
Special care must be taken when screening a candidate for such key opening, because after all, these are important management roles that are pivotal to the team or the company.
A different approach is needed
You may have been looking for good interview questions to screen CTO candidates. You probably have learned how to screen software engineer candidates, and wonder if you should follow the same approach for a CTO opening. Unfortunately, that is not a good idea.
I have seen a non-tech CEO delegated to his engineers to conduct the technical assessment for their future CTO. The interview was off the mark, because the guys were looking for someone in their likeness. What they liked was an experienced software architect, but the company needed a CTO!
A CTO role often deals with high-level concerns in his/her work, such as technological vision, product/growth strategies and people management. These are not same as programming.
The purpose of a CTO interview is therefore different from that of a software engineer interview. You are trying to see if the candidate can coach, lead and inspire.
That begs a different approach.
Depending on the stage the company is in, they have different requirements for the CTO. This should be reflected in the J.D.
If the company is an early-stage startup, the CTO will most likely also wears the hat of the lead developer, in which case, some technical interview questions for software engineers may be applicable. If the company is at later-stage, a CTO will take on more managerial and advisorial responsibilities, providing insights to the company to help sustain growth.
A blunt technical question will tell you nothing about how this individual can contribute to your company as a manager. Yes it checks what he/she knows. But unless the candidate initiates the question him/herself and the context of the discussion is about the company’s operation, it is difficult to see if he/she will effectively use the knowledge in setting your company in the right technological direction.
So turn the table around and allow the candidate to interview you instead!
When you are interviewing a candidate for CTO position, he/she should be the one who asks you the technical questions. The more relevant the questions are, the better fit the candidate is to your organization.
Starting a conversation
It is not very often you will get to conduct an interview for CTO role. If you do, here is what I suggest:
- Start the interview by doing a product demo to the candidate.
- Tell the candidate about your business.
- Show the candidate the technological stack.
- Introduce your tech team members to the candidate.
Depending on how the conversation goes, you can probe him with further questions about his past experience or about a specific skill listed on his CV:
- Could you give us an overview of the technological operation of your company?
- Name a new technology that you have tried and applied successfully to your job? How did you do so?
Or you can take an interesting turn by asking some hypothetical questions:
- If an engineer in your team often comes to work late (say 10:30 a.m.), and leaves early (say 5:45 p.m.), what would you do?
- If the product owner always prioritizes new features over chores, what would you do?
Reflect on the conversation and try to see if the candidate has the following qualities:
- communicates well, has good coaching skill, is empathic, believes in empowerment.
- has clear vision and strategy, is results-oriented.
- has key technical skills.
Listen carefully to the questions he may ask during the interview. Here are a few possibilities on what may transpire:
- Your candidate asks considerably more questions about the development process and the team dynamics, such as what agile methodology has your team adopted? How does a typical sprint look like? What project management tool do they use? Are they facing any obstacles?
- He/she is either not a technically strong person, or not familiar with the tech your company use. OR
- He/she has a natural inclination to managing people than managing the technology.
- Your candidate asks considerably more questions about the technology and codes, such as how do you plan to scale out? why did you choose/not choose a particular technology/tool? how does a key algorithm work?
- He/she prefers to solve technical problems than dealing with people, and is likely not a people manager.
- Your candidate asks less questions than you, and speaks more.
- He/she is likely not an experienced technical leader.
- You candidate remains relevant in the questions he asks, however the discussion is heading nowhere, as if he is only extracting information from you, or the solution or vision he presents seems way off the ground.
- He/she is likely from a research / academic / consultancy background, and lacks industrial experience. OR
- He/she worked in a company with hierarchy, and had a team of executives to support him/her, did not manage the engineers directly.
- Your tech team members express no confidence in the candidate.
- Your tech team has a unique culture, and they are judging the candidate in their likeness. OR
- Your candidate may not have the necessary leadership skill.
None of the above could necessarily mean a bad thing. It really depends on what you need, and whether his/her skills can complement the current management team. I have seen cases where the role where the management kept delay hiring for was actually the role they needed most.
Pay attention to details, I am sure you will be able to decide if he has the temperament to be the CTO you want.