What Interview Questions Should You Ask A Potential CTO?


The easy part about hiring a VP Engineering/CTO is finding a great technologist.  Yes, that's the easy part.

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However, you stand a really good chance of hiring the wrong person if you just look for a technologist.  It turns out there are two key parts to hiring a VP Engineering/CTO to your executive team:


Part One: Does your VP Engineering/CTO Candidate meet your hiring criteria?

You want to make sure, as you get to know your potential VP Engineering/CTO, that this person meets your overall criteria for what you want out of all your executives:


A. Make sure your potential VP Engineering/CTO is hungry.


A definition of insanity is doing the same thing again and again and expecting different results.

I recruited two people that were wealthy to be co-founders and both failed.

Wealth is not enough to disqualify someone from being a co-founder, but sometimes you lose your edge when you’ve already made it financially. That’s what happened in the case of our VP Sales, Ken.

Ken was living the life. I hoped for the best, but I knew there was likely going to be a problem with Ken’s motivation when he choose to live in a fancy building in San Francisco instead of buying a home in the Silicon Valley where the company was located.

I wondered, “Would Ken really be willing to spend all that time on the road away from his family?” I wondered, and I did nothing.

I didn’t have one conversation with Ken about my concerns until the day before he quit (read What's Your EQ And Why It Matters). Instead I just hoped things would work out.

Things didn’t work out.


B. Make sure your vision for the company matches.


This one I got right. I had a very clear vision of how I wanted the company to evolve, and what I wanted the company to do.

I recruited like-minded people that shared the same vision. This is crucial to success because there are enough other problems that can derail a company.

You need everyone in the company marching in the same direction. Imagine the chaos if you and your fellow co-founders can’t agree on what direction to take and what to do?

The odds of your success go way up when you and your co-founders are on the same page.


C. Make sure your potential VP Engineering/CTO has integrity.


Maybe I should have listed this one at the top because integrity in business is everything.

To me, integrity means that you are going to be honest. It means that you are morally sound. It means I can implicitly trust you with my life (which I am if I am asking you to be a co-founder).

Becoming a co-founder is a huge responsibility. Sadly, many people don’t take the responsibility that comes with being a co-founder seriously enough.

Many potential co-founders just don’t understand the commitment required. You can vet these people out by just spending enough time with them. I would say a minimum of three months, but sometimes you need nine months or more.

The ones you have to worry about are the ones with bad intentions. I had this happen to me (Read What Are The Eleven Steps You Can Take When A Co Founder Quits?) And bad intentions can destroy even the best plan.


D. Make sure your potential VP Engineering/CTO has the energy to stay the course.


Ask yourself the following question about your co-founders:

“Do my co-founders have the perseverance to stick with the company when times are tough because there are going to be tough times?”

You’ll see the signs of trouble early on. Get worried if your co-founder is asking you to radically change the direction of the company at the first sign of resistance.

I’m not saying you shouldn’t listen to valuable feedback. I am saying that you can’t be changing direction every time an investor rejects you because you’ll be changing direction a lot.

This is when you need to have a steady hand at the wheel. Nothing is easy at the start because you are simultaneously building a brand, growing your team, and growing your business.

It’s supposed to be hard. Your co-founders need to understand this.


E. Make sure your potential VP Engineering/CTO is great.


Always hire the best. Always work with the best. You want superstar co-founders, and you only want superstar co-founders.

It’s very difficult to start a company with B-level talent and then transition to A-level talent. Start with superstars instead.

Superstar co-founders attract other superstars to work with them. In turn, these new superstar recruits attract other superstars. This is the best way to recruit your initial team.


F. Make sure your potential VP Engineering/CTO is a cultural fit.


The importance of a great company culture is often overlooked. Don’t make this crucial mistake when it comes to your company and co-founders.

Remember that you can’t decree your culture. Your culture is going to evolve based on the employees you hire. And the first employees are your co-founders.

So stay away from bringing on a brilliant jerk as a co-founder unless you want a team of brilliant jerks. Hire smart, passionate people that share your vision for the company.

I’m not saying your team shouldn’t be diverse. Diversity is good. But there needs to be agreement on the basic direction of the company and the core values of the company. (Read Why Your Startup Culture Is The Key To Your Company's Success.)

You can take all these six steps and there may still be a co-founder that doesn’t work out, That’s okay. Just learn from what happened. The next person you hire will be a better fit.


Part Two: Can the candidate do the job?


Let’s say the candidate meets your overall hiring criteria. How do you know the candidate is a good VP Engineering/CTO?

I’m sure you’ve noticed by now that I’ve been using VP Engineering/CTO, not CTO to describe what you should look for. The reason for that is all technology companies need a VP Engineering, but not all technology companies need a CTO.

Here’s what you want to ask?


A. How do you intend to build your team?


In other words, how is your VP Engineering going to recruit? You want to hear that the VP Engineering:

  • Has a following. In other words, there are people the candidate already knows that are going to join the company.
  • The qualifications of the people the VP Engineering will recruit. How many years of experience will these people have? Where will these people have worked prior? What type of skills will these people have? What universities will these people come from?


B. How do intend to manage your team?


You want to understand the management style of the candidate. Is the person hands on or hands off? Does the candidate have a way of managing projects? Does the candidate have experience releasing new products? If so, what is it? What is the candidates criteria for new product releases?


C. Are you planning on doing technical work or just managing the team?


You want a VP Engineering that is going to be hands-on; especially early on. Later, it will be okay for the VP Engineering not to design or code, but now, early on, your VP Engineering has to be an active designer.

For more read: How Do You Evaluate A Potential Technical Co-Founder?

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