CTO Interviews: A Perspective from a Hiring CTO

A field notebook sketch of programmer interviewing themselves in the mirror.

The current job market for technology executives and engineering leaders is not the easiest. The VC market has cooled, and big tech has reversed its course on Covid hiring sprees. Layoffs have also led to reduced team sizes, putting financial pressure on middle management. As a result, senior candidates are navigating the most challenging environment since the 2008 financial crisis.

Earlier this year, I decided to move on from my role and found myself in the unique position of interviewing my replacement. As a CTO interviewing other CTOs for my own job, I noticed simple mistakes that candidates repeatedly made. I began reflecting on these patterns to prepare myself for my own career move. In such a competitive job market, these mistakes became more pronounced as we saw a number of highly compelling candidates. This advice won't guarantee you a job if you don't have the necessary skills, but it will certainly enhance your interview performance.

Have Interesting Thoughts on Industry Standards

Tell me about the project management practices you’ve put in place.” “Scrum, Jira, Story Points, 2 Week Sprints, Retro.

Our industry has settled on standard responses for some topics. We all want high-performing yet humble engineering teams. We all want our teams to conduct code reviews (but not just for syntax!). We all use "some kind of agile."

My role in the interview process was to conduct an extended screening. The purpose was to ensure applicants had a baseline compatibility for the rest of the interview panel. Many of the questions could be answered with solid, industry-standard practices. After conducting over a dozen interviews, I began to view these stock replies not as wrong, but as dull and uninspired.

Use discussions on standardized industry topics as opportunities to showcase your unique insights. When I hear standard answers, I'm torn as an interviewer between asking leading questions to steer the conversation into a more revealing space and holding back to see if the candidate can direct the conversation themselves. Candidates who shared their insights on these cookie-cutter topics were much more compelling.

The best candidate (who ultimately received and accepted the offer) went one step further: he identified the standard response and deconstructed it, explaining what he agreed with and how he had adapted it in his own career.

Identify Your CTO Archetype

I consider myself the prototypical thought leader, budget master, mentor, and 10x programmer type…

The CTO position is renowned for its flexibility, encompassing a variety of responsibilities such as infrastructure building and operation, technology vision, customer advocacy, communication, and people leadership. In a competitive market, you may be open to a wider variety of roles, so be prepared to adapt your experiences to align with what a company is looking for.

A corollary to understanding the type of CTO you are is understanding the type of CTO the company envisions for the position. Is the organization seeking someone to manage remote teams and integrate third parties, or are they running major engineering and infrastructure projects in-house? Talking up a year-long software project done by three groups of contractors may impress, or it may signal that you’re not the ideal match.

To be prepared, make sure you push the recruiter for the ecosystem the role exists in:

  • Team Size. How many people are in the organization? How many are managers versus individual contributors?
  • Outsourcing Strategy. Does the company currently outsource? If so, what is the nature of those jobs and how are they integrated into the rest of the technical team?
  • Product Ownership. Does product management report to the CTO? If not, who is the CTO’s counterpart in the product space?
  • Core Technology. What technologies does the technical product rely on? Is the company built on top of third-party platforms, or is it predominantly custom built?

Understanding the kind of CTO you are, and what they want, will provide solid ground to either accentuate your role fit or pivot your experience into sounding like a fit. You want to be honest with your experience and how well you align to the company’s needs, but you’re also selling yourself. Understanding how you’ll adapt your pitch in advance is important. It sticks out when an applicant tries to refactor their CV on the fly to fit in with a very different role.

Understand What You Love about the Role

My passions include building great teams, shipping products users love, and watching paint dry.

Just as it's important to identify your CTO archetype, it's equally critical to understand what aspects of the role you are passionate about. Is it developing managers? Shipping a great product? Crushing KPIs and uptime targets? Every job has its fair share of vegetables to eat, and you can be a great leader without loving every part of the job. But know what really drives you in the role. As an interviewer, it’s exciting when a candidate is excited and brings that passion and expertise into our conversation. Know what you love about the job and let it shine when the time comes!

Companies have a rough idea of the archetype of CTO they’re looking for; it’s less obvious what passions they need from a new leader. Remember, in the words of John Mayer, “Love is a Verb”. Saying you’re passionate about building great teams is reading a resumé. Revealing your love in companies you’ve built and the careers you’ve nurtured is communicating your passion.

Realize Aesthetics Matter


Humans have evolved over tens of thousands of years to understand the nuances of in-person communication, but have had only about three years to adapt to communicating via screens. Our brains need to work overtime on remote calls to remember we’re talking to another human, not a screen. Video and audio quality are not subjective "nice-to-haves"; they are the foundation of communication. Improving the aesthetics of the call reduces the cognitive load required by your interviewer. Reducing the attention required to 'translate' your face, voice, and body language into human connection allows the rest of your interview to shine.

Before setting yourself up for a remote interview, consider the following aesthetic pain points your interviewer might encounter.

  • Camera Quality. Most people are fine on higher-end MacBooks, but not all webcams are created equal.
  • Lighting. Even more than the camera, lighting is crucial. Ensure your face is well lit and pay attention to backlights as well!
  • Connection Quality. Compression artifacts can worsen any visual issues in the feed.
  • Microphone Quality. Microphones on products like AirPods often produce a tinny and distant sound due to their positioning.
  • Framing. Position your camera to focus directly on your face, maintaining a head-on angle. Being too close or too far can create awkward framing, while angling the camera up or down may appear unnatural.
  • Virtual Backgrounds. Ironically, virtual backgrounds are effective only with proper control over lighting, the real background, and camera placement.
  • Holding Your Phone. Absolutely not.

Not everyone can control their remote work environment, but optimizing your setup within your means can elevate your conversations.

Remember It’s an Interview

Where to begin? I was born on a cold and bright December morning. My mother, a seamstress by trade…

As a candidate, an interview might have been the biggest event of your month. For your interviewer, it was Tuesday. And while you are a unique and precious snowflake, the interview you are going on is not. Your interviewer has goals for your time together; understand what those are and ensure they are met.

For the interviews I’ve conducted, once we’re through some pleasantries, I lay out the interview plan quite plainly. Intros, a review of our organization and stack, a discussion of engineering culture, and finally questions for the candidate. Despite this, the interviewee still hijacked the interview process. Examples of hijacking include:

  • One Person Show Biographies. Everyone has LinkedIn and knows where you’ve worked. When discussing your work history, craft a tight narrative of your career that culminates in your fitness for the role being discussed today. An hour interview is painfully short for a role as broad as CTO; I don’t need 5 minutes on every company you’ve worked at for the last 2 decades.
  • Going Down Rabbit Holes. We’re engineers; we can't help but poke at how things work. Ensure you’re communicating at the right level of detail for the topic. If you’re interested in a technical aspect of the company, take notes of questions to follow up with. Don't turn your interview into a developer conference for one.
  • Last Things First. Compensation, equity, time off, remote policies and the like are important, but not at the start of the interview. Generally, the person asking about Jira tickets and caching strategies isn’t the first person to ask about these things.

In Closing

I haven’t brought up technical excellence or languages or any of the other “CTO Interview SEO Farm Questions”. Certainly, these areas are important and merit thorough preparation. In competitive markets, with plenty of highly qualified prospects, the more human concerns I’ve mentioned above took on additional importance as myself and our hiring team tried to wring every drop of context from our interactions with candidates. If you’re not good enough for the job, focusing on these topics won’t get you to that level. If you do have the skills, then being mindful of the above might just nudge you across the finish line!

Good luck!

* John Mayer has the voice of an angel and the heart of a poet. What am I supposed to do, not have 2 ears and a soul?