Hiring a CTO for Your Startup

Several people have recently come to me to help them source and/or hire full-time CTOs for their startup having found me through my post that looks at: Startup CTO Salary and Equity Data. 

The first thing I do is suggest they explore if they really need to hire a full-time CTO for their startup and if so, what kind of CTO they need.  There's a lot on my blog already around this topic.  I'd suggest: Startup CTO or Developer, Startup Founder Developer Gap, Part-Time CTO, Technology Advisor, CTO Founder, Acting CTO.  In some cases, this changes the conversation from "I need help hiring a full-time CTO for my startup" to "I need help finding a part-time CTO who can direct a full-time developer."

But let's assume you really do need a full-time CTO for your startup and you've done the homework so that you know the specifics of what this CTO will be doing for you.  You now have two issues: sourcing and hiring.

I'm not going to spend time on sourcing because I'm really not in that business.  I have a great network of fellow CTOs, especially in the Los Angeles area.  I've organized the LA CTO Forum (a private group of 150+ CTOs in Los Angeles) for 10+ years.  I often will tap into that network to try to help find people for startups.  But that's a pretty small pool and it's really the top end of the spectrum.  There are also a few recruiters that I recommend.  But sourcing candidates is tough.

Interviewing them is also tough, especially if you are not yourself technical.  Get a Technology Advisor that can help.  Even with that help, there's a lot you are going to need to do.  And I've talked about lots of things you can listen for as a non-technical person to determine if this will be a good CTO candidate.  There are a bunch of questions in Startup Software Development – Do Your Homework Before You Develop Anything, Startup Founder Developer Gap,  and in Startup CTO or Developer.  You should be hearing many of these questions coming up from your CTO candidate.

Interviewing and Hiring Process

Get a resume and LinkedIn profile and review both closely:

• Do they know the world of startup technology?  It's very different than at large organizations.  This is a must.
• Do they have a solid development background?  A must if you are going to lead developers. 
• Do they have experience leading developers?  Several years, ideally in a couple organizations.
• Have they found and hired developers?  Have they worked with outside developers?
• Have they switched jobs too much?  Not enough?
• Be on the lookout for words that suggest they were there went it happened, but not really doing the work.  This happens A LOT among technical people.  Words and phrases like: led, directed, knowledge of, assisted with - all suggest that they didn't really do it.  Make sure you plan to drill down to what they really did.

The next step is a phone interview.  Often it's only about 20 minutes.  It will be spent:

• Finding out more about the reality of their background.  It's often hard to tell from a resume and LinkedIn profile.
• Finding out what skills they think they have and how they match with what you need.

If this will be a hands on role, then you need to conduct some kind of Technical Screening/test.  If you are a non-technical founder, you will definitely need help to do this.  If this is not a hands on role, then you might be able to get away without it.  But I'd recommend someone technical still interviews them.

Then comes the in-person interviews.  There are lots of good resources on this, especially for hiring technically-oriented people where intelligence and problem solving is a key ingredient:

• The Guerrilla Guide to Interviewing, Version 3.0
• The Microsoft Interview (Wikipedia)
• 80+ Microsoft Interview Questions
• Traditional Employment Interview Questions
• 10 Google Interview Questions
• 140 Google Interview Questions

Just be warned - asking these kinds of hard questions (and doing technical tests) can result in VERY uncomfortable situations.  The candidate clearly doesn't have a clue how to answer the questions.  You can nudge them along to help them get to the answer.  But it becomes pretty clear when things are not working out.  I've seen flop sweat, people who just want to run from the room, and other similar reactions.  You need to be ready to help the person out of an uncomfortable situation.

I do have a question though - how long should the interview continue once it's become clear on both sides that the candidate has completely bombed?  Is it fair to continue?  Should you look for an early exit?  I most often look for a graceful, early exit.  But it can feel like it drags on a bit even in that case.  Any suggestions on what to do?

Make sure you do all the normal things during an interview:

• Give them lots of opportunity to ask about the business and any other questions they have.  Listen for the right kinds of questions (see above).
• Make sure you take notes during and after the interview.  It sometimes is hard to remember the details otherwise.
• Cover all the different aspects of the job: technical, smart, analytical, able to inspire, lead, direct, manage, good communicator, good decision making, etc.

Now you have a couple of good candidates.  They are bright, eager, a good fit.  Make sure you do reference checks.  Most often I ignore the list of references they provide.  If this person is from Los Angeles, I know I can easily find a few people who have worked with them.  Even if they are from somewhere else, I likely can navigate LinkedIn to find people to talk to.  The references they provide are often a last resort.

Okay, they check out.  Act fast.  If they are good, the market right now is HOT for CTOs.  Have your offer together in a formal letter, but call and make the offer by phone.

Once you have an acceptance, please be nice to the other candidates and let them know that you've hired someone else.  Don't burn bridges.  You never know when you will run into those same folks again.  In Los Angeles, the answer is "often."  I personally do this via a quick call and follow-up with email/LinkedIn connection, etc.

I will close with one last thought.  Trust your gut.  Any time I've hired someone who somehow didn't quite feel right, I was sorry later.