So, you’ve built your company, and things are rolling along nicely. But now you’re at that stage where the tech side needs to level up. You are now facing the fortunate challenge of having to hire a Chief Technology Officer (CTO) who can connect your business goals with the technology that can bring them to life. CTOs are the ones who can take your vision and make sure your tech not only works but also scales as you grow.
Bringing the right CTO is a crucial step in your company’s next phase. They’ll help steer product development, manage your development team, and make sure the technical side of things is in sync with your overall strategy. Your CTO needs to be a better manager than they are a coder, and they need to be a better communicator than they are a leader. It’s not just about tech know-how; you need someone who can lead, communicate, and keep everything running smoothly—especially when you’re not the tech expert yourself.
Before you dive into hiring a CTO, it’s worth asking yourself a big question: Do you actually need a full-time CTO right now, or would a technical lead be enough? A lot of non-technical founders jump straight to looking for a CTO without fully understanding what that role really involves. In some cases, especially if you’re still early in your growth, what you might need is someone who can steer the technical ship but without all the high-level, long-term responsibilities of a CTO.
It’s an important distinction. A CTO typically handles the big-picture stuff—long-term tech strategy, scaling, and aligning with business goals. On the other hand, a technical lead is more hands-on, focusing on the day-to-day challenges and keeping things running smoothly. Now that we clear that out, let us share with you a couple of insights and questions to ask a CTO in an interview.
Identifying the Key Skills of a CTO
When it comes to hiring a CTO, you need more than just someone good at writing code. Sure, coding is important, but a successful CTO needs to know how to juggle both the tech and business sides of things. They’ve got to help develop your product while also making sure everything lines up with your business goals. Just because someone has mastery in a particular programming language doesn’t mean they understand the business use case.
The ideal CTO isn’t just a coding genius—they’ve got to think big picture too. They need to understand the market you’re in, anticipate challenges, and create solutions that can grow with your company. It’s all about finding that balance between making smart short-term technical decisions and keeping your long-term business strategy in mind.
Questions to consider asking are:
- Can you describe a time when you made a critical technical decision that had long-term effects on the product? How did you approach it?
- How do you stay updated on emerging technologies, and how would you determine whether they are worth pursuing?
- What technology stack would you recommend for a SaaS platform like ours, and why?
The Communication Factor
As a non-technical founder, staying updated on the technical aspects of your business without a CTO and sometimes even with one. It can be a huge amount of information to process without the proper communication. As we stated at the beginning, A CTO must be a better communicator than they are a leader. We want to make that very clear. A great CTO needs to have a knack for breaking down technical challenges, progress, and decisions in a way that makes sense to you.
When communication is on point, you’re kept in the loop and can wrap your head around the technology strategy, which helps you make smarter business decisions. Your CTO should be able to take all that complex tech jargon and turn it into clear explanations about where the product is at, what challenges are coming up, and how they plan to tackle them. It’s all about making sure you’re not just informed but also empowered to move your business forward.
Questions to consider asking are:
- How do you handle situations where you disagree with the CEO or the business side about technical matters?
- Can you give an example of how you’ve fostered communication and collaboration between engineering teams and other departments?
- How do you ensure that complex technical concepts are communicated clearly to non-technical stakeholders?
Cultural Fit
Your CTO will be a key partner in shaping the future of your company, so you want someone who truly aligns with your values, work style, and vision. It comes down to shared perspectives. You and your CTO need to agree on the direction you are going.
But cultural fit dives deeper. Meaning communication styles, how they tackle problems, and how well they work with your existing team. You want a CTO who can lead the tech team but also foster a positive company culture, creating an environment where everyone is pulling in the same direction.
They will help you build a cohesive team where collaboration is key, ensuring everyone is aligned on goals and feels valued and heard. This is especially important as your company grows. If everyone shares the same vision and values, you’ll find it much easier to navigate challenges together.
Questions to consider asking are:
- What steps do you take to foster a positive company culture, particularly within the tech team, and ensure everyone feels aligned and valued?
- How do you adjust it when working with different types of personalities and departments?
- How do you build a team where collaboration is at the forefront, especially as the company scales?
The Importance of Failures and Lessons Learned
One of the big things to consider when hiring a future employee is how they handle failure. During a CTO interview, you are going to want to hear about failures. What could you have done differently in a situation where things went south? Those failures can be goldmines of insight into how a candidate thinks critically, learn from their mistakes, and adapt to challenges.
If someone says they have never faced failure, it is a huge red flag. They could lack the real-world experience needed to tackle the bumps in the road that come with scaling a tech company.
Their response will give you a good feel of their resilience and problem-solving skills. Startups are inherently uncertain, and you need a CTO who can steer the ship through those stormy waters. After all, it’s not just about getting things right—it’s about how well they bounce back and keep moving forward when things get tough.
Questions to consider asking are:
- Can you share a significant setback you’ve experienced in your career? What went wrong, and how did you handle the situation?
- In hindsight, what would you have done differently in a situation where a project didn’t go as planned?
- How do you communicate failures to stakeholders and the team while maintaining trust and morale?
The Role of CTO as a Manager
Your CTO shouldn’t be doing the bulk of the coding unless they’re just an expert at it. Their main job is to oversee the technical team and make sure everything aligns with the company’s vision. A fantastic CTO knows how to delegate technical tasks and focus on managing and scaling the team instead of getting lost in the code.
As your company expands, the ability of your CTO to lead and manage will become even more critical than their coding skills. They should be good at hiring the right talent, keeping the development process on track, and making smart technical decisions that help your business keep moving forward. In a nutshell, you want a CTO who can inspire and guide the team while ensuring that the software development side of things is running smoothly.
Questions to consider asking are:
- What qualities do you look for when hiring developers or technical leads?
- Can you describe your management style and how you adapt it when leading a technical team versus interacting with non-technical executives?
- How do you inspire and guide your team through challenging technical decisions or complex development processes?
Fractional CTO vs. Full-time CTO
Try before you buy is a great way of getting started. Hiring a CTO full-time right away might not make sense for where you are right now. In the early days, you might not need (or be able to afford) someone full-time. That’s where a fractional CTO could be the perfect fit. These folks work part-time or on a contract basis, stepping in to help solve specific tech issues or lay down a solid technical foundation without the long-term commitment.
Considering that a decision like this has a stage of trial and error, hiring a fractional CTO could be a good start. If things go well and everyone is on the same page, short-term engagements can lead to longer-term engagements. It’s a smart way to figure out if you need someone on a full-time basis or if a fractional CTO can do the job for now. Think of a fractional CTO as someone who can get you off the ground, especially if you’re aiming for a Minimum Viable Product (MVP), without needing them around 24/7.
But as your company grows and things get more complex, you might start feeling like a full-time CTO is a must. That’s when you need someone who can not only manage your team but also take charge of the bigger tech strategy. A fractional CTO can be great for getting things started, but when it comes to scaling, expanding, and dealing with all those “big picture” decisions, a full-time CTO will be your go-to.
Where to Find a CTO
Many successful founders swear by personal referrals or their existing networks. Your personal network is a great way to start, especially when you’re looking for someone trustworthy and proven. So, don’t hesitate to tap into your own circle! Reach out to industry contacts, attend founder meetups, and hit up startup events where you can connect with experts who share your vision.
That said, relying solely on your network might put some blinders on you. Don’t shy away from exploring other avenues! Online platforms like LinkedIn, specialized job boards, and tech communities can be fantastic resources. Plus, when you start talking about your challenges and vision, you might just attract the right talent who’s as passionate about solving problems as you are. By broadening your search, you might just find that perfect fit!
Other Questions To Ask a CTO
When you are thinking of questions to ask a CTO during an interview, focusing on their technical experience doesn’t seem like the most important aspect. As a non-technical founder, there is a limit to the knowledge we have on the subject, so you will probably want to get a feel for how they think and operate.
Questions like “What’s your 30 60 90?” or “What kind of KPIs are you looking at?” are great starting points. They help you understand the candidate’s approach to leadership, how they tackle technical challenges, and their overall problem-solving mindset.
Don’t forget to dig into their experience leading teams, scaling technology, and learning from failures. The stories that come from these questions for CTOs can be incredibly revealing and often provide the best insight into their real-world experience.
You may also want to ask them to talk about how they’re going to run the first meeting. This question can give you a sneak peek into how they plan to lead, manage, and fit in with your team from the get-go. After all, you want a CTO who can not only talk tech but also make sure you’re on the same page right from day one!
How CodingIT Can Help You Find the Right CTO
Some of the best CTOs we’ve worked with have been the ones we met through trade organizations, a friend of a friend, or word of mouth. We understand that without the right network, there are unique challenges that come with the decision to hire a CTO. That’s why at CodingIT we are here to lend you a hand and match your company with candidates who fit your vision and culture.
Whether it’s a full-time CTO, a fractional CTO, a technical lead, or even the right software development team, CodingIT can help you find the right person for the job. We emphasize cultural fit, clear communication, and solid technical expertise, so you can be confident that the talent you hire will be a valuable asset to your business for years to come. Get in touch with us today and let’s make sure that your success keeps on going.