The Interview Process For CTOs

Prepare for the CTO interviews

Inkmi is a website for CTOs, VPs of Engineering, senior engineering leaders, and senior developers to find their CTO dream jobs. I am giving tips on salary, promotions and your CTO career on the Inkmi Blog.

Disclaimer: Every company has their own interview process. Every interview process is different. Though there are similarities and general themes we look into, because in the end every company wants to do the same here: Hire a CTO

Interviews for CTOs are different than those for ICs or leads, I had lunches for interviews for engineering leadership and especially CTO roles. Other interviews were walking around and mainly talking to developers. So they are different than what you might have experienced in the past.

What is your USP? Why are you the best match for the job? What makes you unique? How can you solve their problems?

Interviewing is a Sales process Many things in life and your career are a sales pitch. You wanting a promotion or a pay raise, or working on that interesting project, all is a sales process. When you want something and the other party doesn’t want to give it to you by themselves, but you need to make your point, that’s sales. You want that job? A sales pitch where you are the product.

CTOs don’t feel good about selling themselves. They might have that insurance sales person in mind, whose pressure sales tactics they despise. They might be introverts or they have an aversion against sales. With your engineering background you might think the best facts win - and should win. This is not how sales works - there is no way around selling yourself to get that dream job. Why should they hire you and not someone else? The customer (your future employer!) doesn’t automatically see you as a solution to their problems. Selling means: paint the customer (future employer) a beautiful picture of their future with you in the middle. Don’t let them connect the dots, connect the dots for them. Don’t talk about your skills, talk about their problems and how hiring you solves them. An easy book I recommend, selling not with shady sales tactics but with what I wrote is “How I Raised Myself From Failure to Success in Selling”.

Interview with the CTO

Before you go into an interview, research the company. This is not some easy developer interview you aced in the past. Understand what the company is doing, in which phase they are, if they have money or need money, what their challenges may be (look at developer ads for the tech they use). Ask some questions before the interview if possible - number of employees, number of developers and prepare yourself.

Often there are no technical questions, but questions on how you manage people. Have you fired someone already? How did you support business strategy as a technology leader? How did you drive innovation for the business? What is your management style? How do you handle underperformers? How do you make sure the company gets most out of their development investment? There might be technical questions if the founders and CEOs are techies themselves. Just to check your credentials.

Technical assessments will primarily be done by senior engineers. You should be more senior than them and this shouldn’t be a challenge. Remember you’re going to be their boss - so they might not be as hardball as when they interview other engineers as peers. One of them might want to test you, don’t fall for it.

Questions during interviews involve business and strategic thinking. If these are areas you lack, do some reading on business basics for engineering managers and a strategy book. Read on engineering managers from Will Larson like “An Elegant Puzzle” (on my Must-read-books list for Engineering Managers) or “The Engineering Executive’s Primer”. Perhaps read my book, it’s short and highly condensed.

Come up with a list of questions interviewers might have, write them down, then write an answer to them down. Ask a spouse or friends for role-playing the interview with the questions. When you have heard and answered them once, they will not come as a surprise. Have a role play with a friendly CEO or a friend from HR. Practice answering common executive interview questions in role play to become more confident. Train with interviewing for CTO roles that you might not want to gain experience.

Executive Search Companies for CTOs

You might have an interview before with an executive search/placement company. Depending on the client, they will be either on your side or on the clients side. If the client is rather small, they just want the money and are on your side. They might subtle brief you on how to get the job. If the client is larger, and their reputation is on the line, they are selective and on the clients side, wanting to sort you out (but remember, they get paid when they place someone).

I’ll provide a comprehensive overview of the typical executive/CTO interview process stages. This will help you prepare effectively.

1. Initial Contact & Screening

• Usually through executive recruiters/headhunters
• Initial phone screening with recruiter or internal HR
• Basic alignment check on compensation, location, and timing
• Brief overview of your background and achievements

2. Preliminary Leadership Interviews

• First conversations with CEO and/or board members
• Focus on high-level fit and leadership philosophy
• Discussion of company vision and your potential role

3. Deep Dive Technical & Strategic Assessment

• Often by senior technology staff
• Detailed technical vision presentation (often requested in advance)
• Scaling discussions
• Technology strategy alignment
• Usually includes meetings with other C-level executives

4. Team Interviews

• Meeting with direct reports and key stakeholders
• Sessions with engineering leaders and senior engineers
• Cross-functional meetings (Product, Finance, Sales leaders)
• Assessment of leadership style and team dynamics

5. Business Case or Challenge Presentation

• Often asked to prepare:
  • 30/60/90 day plan
  • Technical vision and strategy presentation
  • Analysis of current challenges and proposed solutions
  • Long-term technology roadmap

6. Due Diligence & Final Rounds

• Reference checks (both provided and back-channel)
• Background verification
• Final meetings with board members
• Compensation negotiation
• Discussion of equity and benefits package

And then you’re through and hopefully have your dream job. Don’t forget to ask questions yourself. You might be so focused on getting the job that when you get it you wonder why you wanted it. We all want to win. Getting the job is winning. Right? No, getting a job that makes you happy, advances your skills and knowledge and where you have a positive impact to people, the company and society is the win. You can read more in “How to Assess Company Culture for a CTO Role”.

About Inkmi

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