Considering adding a CTO (Chief Technical Officer) to the management team? That need often signals that your company bottom line may be impacted due to a limited control of strategic technical decisions. This is especially true for smaller or growth-stage companies. When interviewing someone for this position, there are five focus areas that you should make sure to take into account: Technology, Execution, Leadership, Security, and History. Here’s more detail on these five critical skills and what you can hope to learn by asking these questions.

Technology

No surprise here. What you are really interested in is whether the candidate understands how to take business objectives and turn those into a technology roadmap. This would include an understanding of adjacent technologies that may ultimately replace existing technologies. Often, one of the critical decisions for some components include a “make versus buy” decision. How does the candidate make those decisions? They should be able to give one or two examples.

Execution

How does the candidate balance resources (time and money) to deliver a product on time? What has been their track record? It is a balancing act to be able to execute on a product delivery plan quicky and still maintain safety, reliability, and quality. How does the candidate manage those variables and still deliver on time?

Leadership

Ask the question, “ What does a high-performing engineering team look like to you?” and explore the candidate’s answers. Also, probe how does the candidate manage and develop talent. Have they ever built up a team from scratch? How is that different than scaling up an existing team? What is the role of culture in building teams?

Security

How do you approach cybersecurity? How is the incident response process incorporated in daily processes? Where do you see technical and cybersecurity risks? What steps do you take to minimize those risks? How do you instill a security mindset?

History

Ask the candidate for an example or two of when they made a technology decision that had the biggest business impact. Also ask for the opposite: a failure and what were the lessons learned as a result. Also did it result in changes to business practices?

The Part-Time Option

With modern systems and communication it is a viable alternative to have a part-time (or fractional) CTO position for your business. Properly structured, not only would you see overall cost gains, it can be a better match between your organization’s needs and the amount of “hands-on” direction available.

Here are some situations where you might consider a fractional CTO.

• You don’t have the time or skill to build a strategic direction, or technology roadmap.
• Staff positions are limited and you need someone to organize the existing workload.
• Someone is needed who can direct the scaling of your operation.

These situations are most likely to arise during these changes in operation:

• Early to mid-stage growth
• Legacy tech cleanup
• Security posture improvement
• Building first real product roadmap

For many small and mid-size businesses, starting with a fractional CTO first yields the highest ROI. It gives you a chance to build architecture, roadmap clarity, and risk management without executive overhead. As complexity grows, you can transition to a full-time CTO.

Small Business Resources welcomes questions from inquiring minds looking to improve their business outcomes using best business practices combined with available technologies. Submit any questions you would like us to explore on your behalf to contact@sbresources.com.