Chief Technology Officer (CTO) Interview - Toughest Questions and Answers
Published on: July 03, 2024
Last updated: July 03, 2024 Read in fullscreen view
Last updated: July 03, 2024 Read in fullscreen view



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CTO is a top senior role in technology, often available in larger companies or smaller startups. This executive function requires knowledge of all aspects of the company, including financials, to plan for technological needs.
I was recently asked to help a partner of our company to interview a prospective CTO. Here are some of the questions I used during the interview process, and I hope they help you in your CTO hiring process. I’ve ordered these by topic so that you can jump to the ones that best suit your startup’s needs.
Technical Questions
Describe a time you joined an existing code base that was in a bad shape? What did you do and how did you improve? |
Example: When I joined my previous company, the existing code base was riddled with technical debt and lacked documentation. My first step was to understand the architecture and identify bottlenecks by talking to team members and reviewing the code. I then prioritized issues based on their impact on performance and maintainability. To get acclimated I started by fixing smaller bugs to familiarize myself with the code and the development environment. |
How do you describe the technical aspects of a project to stakeholders who don’t have a technical background? |
Example: I try to give examples of the design and engineering elements in a software project in terms that are easy to relate to. For instance, if I'm speaking with a client who requests an e-commerce application, I try to describe the development process in terms of a sales funnel or a transaction to help them understand the complex aspects that go into a feature of the application. |
Explain an Agile development workflow that you've used in the past? |
the specific roles you've played in the process to demonstrate your hands-on experience |
Example: In my previous role we used the Scrum framework as part of our Agile development workflow. We started with a Product Backlog which was a prioritized list of features, bug fixes and Technical tasks. Every two weeks, we held a Sprint Planning meeting where the team would select DoD items from the Product Backlog, move them into Sprint Backlog and then work on DoR items during the next Sprint.
Daily stand-up meetings helped us stay aligned. Each team member would share what they've worked on on the previous day, what they plan to work on that day and any blockers they faced. We use JIRA to track our progress and maintain transparency. |
Budget Management Questions
Explain your process of preparing an IT development budget where do you tend to cut costs and how do you review expense requests? |
Example: Preparing an I.T Department budget is a comprehensive and strategic process. The first step is to align the IT objectives with the organization's overall strategic goals. I work closely with Business Leaders, Project Managers, and Technical Leads to identify key initiatives and their estimated costs for the upcoming physical year. This involves gathering data from past budgets, current expenditures and future projections to form a baseline.
Once we have a clear understanding of our objectives each team within the department submits their expense requests. These requests cover everything from hardware and software to personal and operational costs. I take the time to review these requests meticulously evaluating the necessity and potential return on investment (ROI). I also consult with team leads to validate assumptions and explore cost-effective alternatives. |
How do you deal with budgetary constraints in the face of technological requirements? |
Example: I can explore cost-effective solutions like open-source tools or Software as a Service (SaaS) models. Incremental implementation can be a cost-effective approach. Strategic partnerships and collaborations can reduce costs, while optimizing existing technologies can free up resources for more critical investments. Effective cost management is crucial throughout the process. |
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