We often see in the life cycle of startups that the organization starts with a couple of engineers who handle all aspects of technology and as the team grows specialization starts to be required. At some point, QA engineers are hired, sys admins take over deploying and maintaining hardware, and DBA’s are brought on board to tune databases. This is a very natural evolutionary process but does require some adjustment by the individuals as they are forced to give up responsibility and become more specialized. One of the toughest hurdles to overcome is getting engineers to relinquish their access to the production environment. Taking control or responsibility away from someone is very hard on people’s egos.

Another often seen necessity in hyper growth startups is to upgrade leaders. A leader who was capable of leading and managing five engineers isn’t necessarily capable of running a 50 person tech organization. Often people in particular leadership roles don’t scale with the fast pace growth rate of the organization. In these cases the individuals either need to relinquish their roles or be replaced in order to continue to scale the company. This doesn’t mean pushing them out but more likely it means finding a more suitable role for them. A great role for many CTO’s who need to step aside is to remain in a leadership and technical role as chief architect.

The key to being successful in this evolution is to be open and address people’s fears and concerns. It is much better to speak openly during reviews about an individual’s capabilities rather than have that person worry about their future. The same goes for engineers being asked to relinquish control of the production environment. Be open, talk to them, and listen to their concerns. An open dialogue about why the organization needs to change at this particular time in order to continue to grow and scale is usually accepted very well.

One of our earliest post was the Path To CTO/CIO, where we focused on not only the “path” but the path that would make you successful once you arrived in that position. One of the necessary skills that we mentioned you must gather along the way is “great technical experience”. We promised to revisit this topic in a later post so I thought I’d come back to this question of how technical does the CTO/CIO need to be? This is especially relevant for those individuals coming from a non-technical background but I think it is a question often asked by technologist as well. Do you need to have engineering and operations experience? Can you come from QA and become a CTO? Do you have to know how to code?

CTO and CIO jobs come in all shapes and sizes. In some businesses the CTO is the chief architect and not a manager, in others it is the VP or SVP of all technology teams. For the purpose of this discussion I’ll define the CTO/CIO as the role that has the technology organizations (such as engineering, quality assurance, operations, etc) reporting to them.

To be upfront about answering the question in the title of this post, I think a CTO should be very technical. I don’t think there is a prescribed path to the top technology job in a company and you don’t necessarily have to come up the technology ranks. I do, however, believe that possessing certain technical skills and experiences are far more likely to land you in that role than if you do not have them. More importantly, while these skills and experiences won’t guarantee your success in that role, they lack of them almost ensure problems or even failure. The skills and experiences that I mentioned fall into two categories, broad and deep.

Deep experiences and skills are ones that are most likely gained early in your career and should bring you proficiency in a subject area. For some this might be programming in a specific language, automating testing on a specific tool, or administering an operating system. If you believe Malcolm Gladwell in Outliers this process takes about 10,000 hours. Thinking of this in terms of travel or language, these deep experiences and skills are the kind you gain by living in a foreign country and becoming immersed in the culture and able to speak the language fluently. Deep experiences and skills are important because they develop in you a strong knowledge foundation that can be built upon when broadening your experiences. This deep foundation allows you to learn other technologies easier, similar to how proficiency in one foreign language makes the next one easier to learn. These deep experiences also give you a base of confidence that when peered with other experts provides credibility and when faced with uncertainty provides a history of solutions.

Broad experiences and skills are ones that are somewhat superficial but serve to give you a general understanding. Continuing our travel and language analogy, broad experiences and skills are the ones you acquire by spending a few weeks in another country and being able to get by asking for directions and food. The broad experiences that a CTO/CIO should have are working with multiple technology disciplines (engineering, quality assurance, architecture, operations, etc.) as well as business disciplines (marketing, finance, legal, etc). These experiences should serve to give you an understanding of their responsibilities, their day-to-day jobs, and most importantly their perspectives on technology and product development. You don’t have to have a job in each of these departments to gain this experience. Other ways to gain these include, acting as a liaison, serving on joint boards, working together on special projects, or volunteering to stay late to help the other teams accomplish their work.

Perhaps not prerequisites but rather as identifiers that will set you apart and prepare you well for the top technology role, look for establishing first deep skills and experiences. Once that foundation is firmly built then begin to broaden those through interdisciplinary work. Don’t forget that this is focusing of the technical skills and experiences. There are still other skills such as leadership, management, communication, and business that must be developed as well if you not only want the top technology job but want to keep it and do a great job while you are there. It’s not unusual for the most technical CTO’s to be the ones who need the most management and business coaching.

Having thrown down the gauntlet that a CTO must be technical it is only fair to address those who didn’t rise up through technology roles and are currently CTO’s or desire to be CTO’s.  We’ll save this for a future post but in the mean time break out a coding book.