Interviewing with the CTO? 3 Strategies to Help Prepare

If you’re headed for an interview with a CTO, congrats on making it this far in the hiring process—but don’t breathe easy just yet. A senior management interview can often make or break a hiring decision, regardless of what the rest of the team thinks, so be sure to do some extra due diligence before this specific conversation.

Interview basics

Before diving into the specifics of CTO interviews, be sure to have your basics down pat, which can also help you perform better in interviews with other team members.

To begin with, practice telling your career story and be sure the narrative reflects the journey you want to portray. Even for the most technical roles, great communication skills will reflect positively on your candidacy, and being able to clearly walk an interviewer through your past experiences is a great way to demonstrate this. As CTOs don't generally manage the day-to-day work of their subordinates and are more concerned with the cohesiveness and effectiveness of the technical team, demonstrating effective soft skills is even more important.

In addition, remember that practice makes perfect—and this certainly applies to technical interview prep. While the more technical questions will likely be asked in your other interviews, it doesn’t hurt to be prepared for whatever the CTO throws your way. If you’re interviewing for a smaller company, chances are the interview process will be less structured, so there’s a higher chance that your interviews with the management team could include more technical questions as well.

Know your interviewer

Some background research can be of huge assistance before your interview. Start with basic internet research on the CTO in question. Check his or her LinkedIn, GitHub, and other online profiles—particularly those associated with the more technical side of things. If they have a personal blog, be sure to read at least a few of the articles. This can give you an idea of not only the industries and types of companies they have worked for in the past, but also their technical competencies, experience and thoughts on managing teams, and potentially insights into how they might approach leading engineering at your target employer.

It can also be particularly helpful to do some backchanneling via your network to hear about their working style and temperament. While online research will give you a good sense of the CTO’s path and experiences, getting personality-level data is much easier from an insider. Further, going in for an interview with a senior management team member can be stressful, but hearing a first-hand account from someone you trust can disarm you a bit—and being more relaxed helps many candidates perform better during interviews.

Even if you don’t have connections who know the CTO, don’t be afraid to ask the recruiter or hiring manager for their thoughts. Particularly if the team wants to hire you, it’s in their best interest to help you do well when you speak to the CTO—and the worst they can tell you is ‘no’ if they’re unwilling or unable to offer any insights.

Know the broader context

As mentioned before, it’s unlikely that the CTO will be drilling you on technical trivia (unless you’re one of their first engineering hires). Once you’ve nailed your tech basics, put yourself in the shoes of the CTO and make an educated estimation about what he or she might have on the mind when going into your interview. Senior management typically thinks less about the details and more about overarching company strategies, synergies, and risks—so be prepared to talk through your thoughts on and questions about these topics. If you’re interviewing with the CTO, chances are you’re a highly-valued candidate, and one that the team will expect to be able to think at a higher level.

When it comes time to ask questions of the CTO, have some prepared that show you’ve done your homework and can think critically about not only your day-to-day, but also the company as a whole. This is a good time to ask about longer-term company goals and how you might evolve with the organization, as well as about growth projections and how your role might fit into a changing team over time. If you can, mention an insight you gained from other interviewers—something you wouldn’t have learned elsewhere—and tie it back to a question on your mind to demonstrate that you not only listen intently, but can also incorporate various data sources to form deeper insights.

Lastly, try to come to the CTO interview prepared with a suggestion or two. What would you do differently if you were in his or her shoes? While you’ll certainly need discretion to know whether it’s appropriate to mention, this can be a powerful way to show the CTO you’re an independent thinker, and that you already care about the organization’s success.


About the Author

Napala Pratini

Napala is a consultant to early-stage technology companies. Prior to going independent, Napala led marketing initiatives across both consumer and B2B fintech for employers including NerdWallet and Earnest. In past lives she was a ballet dancer and a cancer researcher.