Essential Questions to Ask When Hiring a CTO

A CTO shapes the future of your company's technology - here is what they should know

Sep 14, 2023

Fractional CTO skills
Fractional CTO skills

Hiring a Chief Technology Officer (CTO), even fractionally, is a key decision given the outsize impact of technology on business results today. The right CTO needs to have hands-on technology experience, but also needs to be able to put themselves in the shoes of the customer, intuiting their needs and how that impacts software requirements. This article is divided into two sections - a list of Do's and Don'ts for the tldr; crowd, and a longer list of capabilities to look for when searching for a CTO. We adhere to both lists when sourcing candidates for the Fraction CTO pool!

Essential Questions, AKA Do's and Don'ts in CTO Hiring:


  • Do they plan to write code as part of this job? From pre-product through growth stage ($5M revenue) this is mandatory. If they don't write code or won't write code anymore, they're not ready to be a leader at a startup. I've had so much failure hiring leaders that aren't willing to be ICs in the trenches with their team. Real leaders are willing to pick up a shovel and dig (or in this case a keyboard and code) with their team!

  • Do they believe in shipping the product fast, and iterating rapidly? I prefer tech leaders that value shipping product over refining the architecture or fixing every bug - a CTO just has to be willing to ship weekly in the early days. If your CTO wants to build perfection, they will still be building it on the day you file for bankruptcy. Even at scale, individual projects within the larger organization should retain a culture of shipping on a high-frequency basis.

  • Does the CTO communicate early and often? Nothing is more important than being proactive and over-communicating in my book. Over-communicating usually means firing away on Slack/Teams, and feeling very comfortable with public conversations + chats on issues. In the remote/hybrid world that exists at most software companies, the company chat becomes the source of truth. So it's essential that the whole team can see (read) what's going on as issues arise and are solved within a project.


  • Don't let your CTO drag you into a conflict of interest. On numerous occasions recently I've seen situations where the CTOs at a company also owns (or has a stake in) the outsourced software development shop providing software development services. This is ok if the CTO is themselves an outside consultant from the outsourced provider, with no stake in your business. But the moment they have a stake in your company, and control a vendor, they are essentially self-dealing - it becomes very difficult for a CTO in that situation to make rational decisions about how to outsource (or insource) work!

  • Don't hire a CTO focused on Engineering for Engineering's sake: The technology team exists to provide value for the business, and not to build engineering masterpieces. CTOs that fixate on technology architecture and engineering for its own sake either neglect a focus on customer value, or end up missing deadlines and shipping a product too complex for the scale of the problem. This disease runs rampant in the technology world. How do you find a CTO who focuses on the RIGHT problems? Find a CTO that cares as much about your business as you do - and doesn't focus solely on technology.

  • Don't work with a CTO who lacks flexibility and agility. Fast moving businesses require technology solutions that can evolve with business needs. A CTO who is unfamiliar with building a feature, and then trashing it a month later - is sadly unfamiliar with the business reality that most businesses face today. When ChatGPT exploded onto the market in early 2023, it up-ended hundreds of startups and established technology players. CEOs have to react to this business and technology reality - and so do CTOs. Successful CTOs immediately began to reexamine their strategy to incorporate LLMs and the new capabilities they provided. When the world changes, you need a CTO who is a partner in embracing that change, and who is not wedded to any particular technology architecture or solution.

Top Ten Capabilities to Look For in a CTO:

The CTO plays a crucial role in shaping the technological direction of the organization, driving innovation, and ensuring technical excellence. To find the right candidate for this pivotal role, here's a top ten list of the most important skills, expertise, and experience to look for when hiring a fractional CTO:

  1. Strategic Technology Vision, Coupled with Business Acumen
    A successful CTO has to simultaneously live in the business and technology worlds. They should possess a strategic vision for technology initiatives, and this must be aligned with business goals, guiding their team to deliver high business ROI (return on investment) from technology projects. A CTO will get requirements from the CEO, the CEO, the CMO, and perhaps other functions - so their technology strategic planning must balance different goals and align them with the company's overall targets.

  2. Technical Expertise
    A deep and up-to-date understanding of current and emerging technologies is a must. The CTO should have hands-on experience with relevant programming languages, software development methodologies, and architecture design. They should be well-versed in areas like cloud computing, cybersecurity, data analytics, and AI.

  3. Innovation and Creativity
    Innovation drives technological advancement. A great CTO fosters a culture of innovation within the company. Look for candidates who have a track record of introducing new ideas, technologies, and processes that positively impact the organization's growth and competitiveness.

  4. Problem-Solving Skills
    Complex technical challenges are inevitable in any tech company. A skilled CTO is a problem solver who can navigate through these challenges, finding practical and efficient solutions that keep the company moving forward.

  5. Communication and Leadership
    Effective communication is vital, as the CTO will collaborate with various teams, including non-technical departments. They should be able to translate technical jargon into understandable terms for stakeholders at all levels. Effective communication and leadership also enable team building - your team's performance will suffer without it. A CTO should have experience recruiting and nurturing growth in top talent, and should be able to use their communication skills to foster collaboration within the team.

  6. Adaptability and Learning Agility
    The tech landscape evolves rapidly. A CTO must be adaptable, and willing to learn and relearn to stay current with the latest trends and technologies.

  7. Risk Management
    The ability to assess and manage risks related to technology initiatives is crucial. A CTO should make informed decisions that mitigate potential security breaches, technical failures, and other risks.

  8. Industry Experience
    Look for a CTO who has a good amount of experience within your industry. They will be able to bring insights and expertise specific to your company's challenges and opportunities, along with knowing more about the technology, platforms, and tools used by your business vertical.

  9. Strategic Partnerships
    A CTO who has existing relationships or can easily cultivate relationships with technology partners, vendors, and industry leaders can open doors to collaborations that drive innovation and growth. This can be a boon if paired with the above Industry Experience.

  10. Track Record of Success
    Past achievements matter. Seek candidates with a proven record of successfully leading and implementing complex technology projects that have had a positive impact on the organization. Particularly with a fractional CTO, you want someone with a great deal of successful experience who can work efficiently and effectively in order to be productive in the allotted time.

Hiring a CTO is a significant investment that can shape the future of your company's technology endeavors. By focusing on qualities like strategic vision, technical expertise, innovation, and leadership, you can identify a candidate who will lead your organization into a successful technological future. The right CTO is not just a technology expert; they're a visionary leader who can harness technology to drive growth and innovation across the entire organization.

Need help finding the right fractional CTO for your company? Fraction vets only the best US-based CTOs from top-tier tech companies.

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Fraction helps companies tap into the best software talent - employees at top tech firms. Fraction taps into their spare capacity, providing you with access to top developers, designers, product managers, and software architects.

See more tech stacks

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