How To Evaluate Technical Skills In The CTO Hiring Process

The CTO role is a significant one, and the right person can make or break a company. Having worked with hundreds of enterprise clients, we have seen it all:

A startup we would refer to as “examplestartup” had come to us trembling like a leaf. Their once-promising project had hit a wall of technical issues, and deadlines were being missed left and right. The realization was setting in that they had paid the price for cutting corners and placing their faith in a glittering façade of a CV and glowing reviews.

Unfortunately, the above scenario is as common as it is disastrous:

Treating technical assessment as an afterthought is a surefire recipe for disaster. Whether it’s a critical system failure, a security breach, or an inability to innovate in a rapidly evolving industry, the costs of not testing a CTO’s technical skills can be felt on an epic scale.

The solution? Find out below…

Understand Technical Skills For A Cto Role

The CTO role requires a range of technical skills, including knowledge of programming languages, database management, and system architecture. The CTO should also possess knowledge of emerging technologies and industry trends. The technical skills required for the role may vary depending on the company’s industry, size, and specific technology needs.

Examples of technical skills that a CTO may need include expertise in cloud computing, cybersecurity, and data analysis. They should also possess knowledge of programming languages such as Python, Java, and SQL.

Essential Best Practices In Assessing The Technical Expertise Of A CTO Candidate

It’s a simple truth: fairness breeds excellence.

By creating a standardized evaluation process, you’re not only ensuring that every candidate has a fair shot, but you’re also laying the groundwork for a process that will stand strong against the test of time. With this approach, the most qualified CTO candidate will rise to the top, shining like a star in a sea of mediocrity.

Here’s what to do:

Create A Scoring System For Each Skill

It bears repeating: clarity about your goals is a prerequisite for getting what you want.

So, when it comes to the technical evaluation process this should be step one.

The goal is to create a quantitative evaluation process that will allow you to objectively compare candidates and identify the most qualified individuals for the job.

For example:

You could use a scoring system based on a scale of 1-5, with 1 being the lowest score and 5 being the highest. Each skill would be scored based on the candidate’s proficiency in that particular area.

Here’s what a hypothetical scoring system could look like:

Skill A: Understanding of programming languages (Python, Java, etc.)

1: No experience

2: Limited experience

3: Moderate experience

4: Strong experience

5: Expert level

Skill B: Knowledge of cloud computing platforms (AWS, Azure, etc.)

1: No experience

2: Limited experience

3: Moderate experience

4: Strong experience

5: Expert level

Skill C: Project management skills (Agile, Waterfall, etc.)

1: No experience

2: Limited experience

3: Moderate experience

4: Strong experience

5: Expert level

Each candidate would be given a score for each skill based on their level of experience and proficiency, and these scores would be used to evaluate their overall technical expertise.

Use Best-in-class CTO Technical Evaluation Approaches

Once you’ve created a scoring system, it’s time to roll up your sleeves and dive into the evaluation process. To make sure you’re conducting a thorough and effective evaluation, consider implementing one or more of the following best-in-class technical evaluation approaches:

Administer A Technical Skills Test

This approach involves creating a standardized test that evaluates a candidate’s technical skills and knowledge. You can achieve this in a variety of ways, such as through online assessments, a take-home test, hands-on coding challenges, or whiteboard exercises.

Keep this in mind:

Irrespective of the method you adopt, ensure that the test is designed to assess specific technical skills required for the CTO position, such as software development, cloud infrastructure, and data management.

Secondly, when administering the test, it’s important to provide clear instructions and guidelines, as well as a realistic timeframe for completion.

Finally, you may also want to consider having an experienced technical evaluator review the test results to provide an objective assessment or leverage any of the third-party technical skill testing platforms available online.

Overall, administering a technical skills test is a great way to get a clear picture of a candidate’s technical abilities and determine whether they have the skills and expertise required for the role.

Conduct A Test Project

Another widely used approach to assess the technical expertise of a CTO candidate is to conduct a test project.

Here’s the long and short of it:

Assign the candidate a real-world scenario that they’re likely to encounter in their role as CTO. Additionally, the project should also require the use of the specific technical skills that the candidate will need to possess to excel in the position. Then give them a set amount of time to complete it, and then evaluate their performance based on the results.

But wait, there’s more:

A test project doesn’t just show off a candidate’s technical prowess. It also gives you insight into their project management skills, ability to meet deadlines, and attention to detail. And that’s worth its weight in gold.

Of course, communication is key. Be crystal clear about the scope of the project, the deadline, and the evaluation criteria. And make sure the candidate has all the resources and support they need to knock it out of the park.

Ask Technical Questions During Interviews

You might not extract rich qualitative insights from this method like the previous two. However, let’s still give it a nod.

Prepare a list of technical questions that are specific to your project needs and scope. These questions should be designed to test the candidate’s knowledge of programming languages, database management, network architecture, and cybersecurity, among other things.

Be sure to ask follow-up questions to dive deeper into the candidate’s thought process and ensure they have a thorough understanding of the subject matter. Additionally, ask the candidate to provide examples of past projects they have worked on and the technical challenges they faced, and how they overcame them.

Asking technical questions during the interview process is an essential component of a comprehensive technical evaluation process. But here’s the catch:

It should be used together with any or both of the two evaluation methods discussed earlier.

By doing so, you can ensure that the CTO candidate you choose has the necessary technical expertise to lead your business to success.

3 Pro Tips For Hiring A Top-notch CTO

Conduct Reference Checks

You might think you’ve got all your ducks in a row, every box ticked. But hold up. What if there’s an unforeseen flaw hiding just below the surface? This is why it’s critical to include reference checks as a part of your evaluation process.

But don’t just phone it in with some perfunctory questioning. If you want valuable insights into your candidate’s technical expertise, work ethic, communication skills, and team collaboration abilities, you need to ask open-ended questions that dig deep.

And while you’re at it, be sure to follow up with a varied list of references to ensure you get a well-rounded opinion of the candidate. Our advice: You can’t be too careful these days.

Don’t Neglect Cultural Fit

While technical skills and experience are certainly important for a CTO, cultural fit is equally essential. Your CTO will be working closely with your team and other executives, so it’s crucial to find someone who shares your startup’s values and vision.

Before you hire a Chief Technology Officer, be sure to evaluate candidates’ cultural fit by asking  interview questions that probe their communication style, problem-solving approach and leadership style.

Outsource The Risk

When it comes to hiring a CTO, know this:

With great potential comes great risk, especially if you don’t have experience hiring for this position. That’s why outsourcing the risk can be a smart move.


This not only reduces the risk of hiring the wrong person, but it also provides you access to a pool of highly skilled and experienced CTOs without the hassle of searching for one yourself.

One approach that is increasingly being leveraged by enterprises worldwide is the use of online IT talent marketplaces that specializes in providing CTOs and other top IT professionals with a wide and eclectic range of experiences and backgrounds.

Note: There are plenty of mediums out there that have already done the heavy lifting for you. They’ve got processes and frameworks in place for conducting background checks, verifying claims of qualifications, and testing the skills of candidates. So why not lean on their expertise?

By tapping into these resources, you can rest assured that you’re getting a CTO who has been thoroughly vetted and has the exact expertise you need to succeed. And for all you non-technical founders out there who may be feeling a little lost in the hiring process, this is especially beneficial. You don’t have to be an expert in all things tech to make the right choice.

In the end, outsourcing the risk of evaluating the skills of a potential CTO to a trusted provider can save you time, money, and the headache of making a bad hire.

Final Words

A strong CTO can help drive innovation, build competitive advantage, and accelerate growth, so it’s worth investing the time and effort to get this critical hire right. With the tips and strategies outlined in this post, we hope you feel equipped to navigate the CTO hiring process with confidence and success. We’re rooting for you!