Konamoxt, Inc.

As I mentioned in my last post, one of the many things I do as an entrepreneur is to advise other start up companies. One of the common requests I get as an adviser is the help interview and vet potential CTO candidates. Unfortunately in many cases, the choice to hire a CTO is the worst choice a CEO or management team could make.

But don’t misunderstand me, every technology startup needs the skills embodied by a great CTO, you can’t afford to NOT have a CTO.

So what do I mean, but the skills embodied by a great CTO? Understanding these skills is critical to understanding how to hire the right people to flesh out your technology team.

I recommend that management teams think about the roles of engineering management in three parts:

• Leading, inspiring, and managing the engineering team - Some people think of this as primarily a “people management” skill. We often give the title of “Development Manager” or “Technical Lead” to this role. These are very much “soft skills”, related to making other people successful, happy, and motivated.
• Leading the architecture and technical direction of the product - This is closely related to leading the development team, but it is really a different skill set. These responsibilities are much more focused on hard skills, related to deep technical knowledge. We often call this role “Architect” or “Chief Scientist”.
• Executive technology representation and leadership - Representing the technology team to the rest of the executive team, Board of Directors, company, key outside customers, government or legal parties. This is high end stuff, requiring a level of maturity and preparedness. It’s a combination of soft and hard skills, mostly soft skills. But it should be noted that the more sophisticated versions of these skills are only rarely needed in most start ups.

In very large organizations you will often see these roles divided into different jobs: “Development Manager”, “Architect”, and “Chief Technology Officer”. But in a start up, you can’t realistically afford to pay three six figure salaries to fill these skills.  So what are you to do?

Can you live without these skills? NO! You need to find these skills for your start up!

You need these, and hopefully, you can find them in a single person on your team. My recommendation is to start as close to your engineering team as possible and find the person who is closest to embodying these skills. Once you find that person on your team, then cultivate them to fill out their talents to include the rest of these important skills.

I’ll explain how to do this briefly, but before I do that let me quickly address the most common retort I hear to this advice. Often CEOs and BoDs will insist that executive technology representation is the most important skill they need filled. From there, they usually assume they already have a good enough architect but what they really want is “someone to manage those engineers”. This reaction is understandable, most of us feel more comfortable with “people like us”, so executives want to find other executives to hang out with, and they are afraid of those “engineers” and they want someone like them to “take care of it”.

The problem with this view, is that engineers are usually only inspired by other engineers. Yep, that’s the hard truth of it.

If your “engineering leadership” lacks street cred, then you can be certain that they won’t get far with your team.

Air-lifting in an “expert people manager” is one of the most dangerous things you can do. But finding that inspiring engineer on your existing team, and making sure they have or are learning good soft skills, is a sure way to take your engineering team’s productivity to the next level. If you have five engineers on your team, and they’re being productive and getting stuff done, then you can be certain you already have that leader on your team.

If you don’t have that person on your team, then you need to be very careful in how you add that leadership to your team. Look for someone who could slot into your team and sit side by side with your engineers and write the same code that your existing engineers are writing.

Don’t confuse years of leading large teams, with street cred. In fact, the longer that manager has lead large teams, the higher the probability that they’ve lost their street cred.

This is critical! If your “hired gun” hasn’t fired his weapon in years… he won’t make it on your team. Your engineers will eat them alive. Instead, look for an engineering manager that is still comfortable writing code. Maybe you won’t have them writing code in your organization, maybe you will. But if they can still write code, then they will do a great job leading your engineers that must write code.

Another common mistake that executive teams make is to assume that your architect and your engineering manager can’t be the same person.

It’s certainly possible for these roles to be seperate, but it’s much more efficient and cost effective to have a single person who fills both these skills. And I’d argue that a great engineering manager has many of the same qualities of a great architect. In particular, as your team and your mission grows, more and more delegation to talented engineers are required. This means that your CTO will need to be able to unselfishly delegate to the rest of the team, and truly inspire those engineers to run with the vision of the company and build a great product to meet the business needs.

Finding all of these skills in a single person may seem like a daugnting task, especially when you consider that I’ve said that person also needs to be able to code. But these people are out there, and if your company has a great idea, with an exciting market and the opportunity to work on great technology, then you’ll have no problem attracting them to work for you.

Filed by Brad Hefta-Gaub at 9:00 am under Entrepreneurship, Hiring, Leadership
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Before Founding Konamoxt, my last gig was the Chief Technology Officer for a local Seattle Startup. I have the classic resume for a CTO of a Startup company… if you’re trying to hire a CTO, I’m sure your recruiter has called me… I get those calls all the time. Mr. Startup CEO, I’m here to tell you, you can’t afford to hire a CTO.

[Note to tech managers and wannabe CTOs out there: Oh, don't worry guys my next post will be why you can't afford to not hire a CTO.]

Today, one of the many things I do as an entrepreneur is help advise other Startup companies. I’m on the Board of Advisers of several other startup companies in the Seattle area. One of the common requests I get as an adviser is the help interview and vet potential development leadership candidates.

Inevitably someone on the management team will say “What we need is a CTO! Can you help us make sure this candidate would make a good CTO?”

Whenever I hear this, my alarm bells go off. Do they really need a CTO? What is happening in the organization that causes them to think they need a CTO? And maybe more importantly what do you think you get when you hire a CTO?

Most of the time, a startup CEO (or more likely the Board of Directors) will decide he or she needs a CTO because the organization is feeling pressure about the product. Maybe the schedule has slipped, maybe the product is buggy, maybe they just have this feeling that something isn’t working right. This usually happens in the case where the CEO is not technical themselves. That CEO/Founder was very likely the product visionary, but they don’t know how to build a product, write code, or lead an engineering organization to build the product.

Another very common situation is when outsiders, often the Board, is frustrated with the overall performance of the business, and they begin looking for “problems”. Unless one of the founders has a past track record of being a CTO or VP Engineering in a larger organizations, this lack of experience will often be blamed for the frustration without much analysis at all of the actual facts on the ground.

Sometimes, this “gut reaction” is correct. Sometimes the engineering organization is indeed rudderless, and the right solution is a new technology leader joining the team. But more often then not, I’ve seen the non-technical leadership jump to the conclusion that new “experienced” blood is what’s needed. When in many cases, that move can actually be counter productive.

The common euphemism seems to be “We need some adult supervision in here!”

But if you’re looking to hire a CTO, you probably already have your engineering team in place, you may already have a team of engineers that are building and have built something. How have they gotten as far as they have without this “technical leadership” you’re so convinced is missing? Nine times out of ten, the CEO has become convinced that the existing team is just lacking that leadership.

That search inevitably begins like this… “Let’s find someone with years of experience. And since this company is gonna be huge, we need someone who’s managed big teams, someone who can take us all the way to going public! We’re going to be a $100m/year business with hundreds of developers in different divisions. We need the kind of leader who’s been there and done that.” Sounds like a job for a CTO, right?

Hiring that CTO, will be the biggest mistake you make. You’ll alienate your engineering team, you’ll waste your money, you won’t be satisfied with the results, and in all likelihood that CTO won’t last in your organization anyway.

Here’s the problem… 99% of the time “that guy” you think matches your wish list, hasn’t written code in years. He might have managed a 1,000 developer organization, but he hasn’t directly managed engineers in years. She looks great on paper, managed a 10,000 cpu data center processing billions of transactions a day… but she hasn’t ever done anything with cloud computing.

When ever I’m confronted with this dilemma as an adviser I’m reminded of a great quote I once heard about NASCAR, I believe it was the late great Dale Earnhardt that said…

“If you see a wreck in front of you, drive toward it, because by the time you get there, it won’t be there!”

This philosophy can apply to a lot of things about startups. The key to applying this quote is to recognize that things are always changing… and if you continue to move forward, then in the future you’re guaranteed to be someplace other than where you are right now. What looks like a disaster in front of you if you stay on course, may in fact be the best, safest, fastest, game winning decision by the time you actually get there.

How does this apply to searching for a CTO? Well, it may be the case that you already have your CTO on your team. You don’t recoginze them yet, because they haven’t yet managed that 100 person development team. That doesn’t mean they won’t be ready when the time comes. You probably only have 3 to 6 developers right now. And even though you don’t think you have a development manager, doesn’t mean that team doesn’t have a leader.

Sure, it’s possible your team has gotten as far as they have with no leadership… maybe as the CEO you’ve been guiding that product vision and you’ve been managing those developers. But unless you speak their language, because you’ve sat in their chair before… then I’d be willing to bet you that one of your developers is actually leading the team while you’re not there. Maybe it’s the most senior developer, or maybe its just the most passionate and sharpest developer.

Instead of hiring an outside CTO, you probably need to take a close look at your team and try to determine if you already have a CTO working for you… but under a different title.

Next post… Why Your Startup Can’t Afford To NOT Hire a CTO

Filed by Brad Hefta-Gaub at 8:20 pm under Entrepreneurship, Hiring, Leadership, Technology
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