Dead On Arrival: Today’s CTO & CIO

Image By: Ethan Sykes

March 3, 2018: Question Series #4

Written By: Marc Moskowitz

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It’s becoming harder and harder to be a CTO or CIO in today’s fast-paced, extremely-complex, technology world. This much I know for certain. However, today’s technology leaders, and those executives responsible for appointing these roles, aren’t doing themselves any favors either. It has been my experience over the last 15+ years meeting CTOs and CIOs via consulting work, conferences, vendors, and at every place I’ve worked, that most of them would grade out at a C- level or below. Further, the average tenure of these roles is less than four years and declining (in-line with other studies as well: Korn Ferry). There are exceptions of course. I’ve met a couple of amazing CTOs and CIOs, but those are as rare as finding an endangered frog species in a remote, tropical rain-forest. This executive role struggles more than any other.

The purpose of this #QuestionSeries article is to ask why companies and CTOs collectively struggle to achieve success. What I mean by this is, companies picking the right leader and the CTOs/CIOs in executing the role at a high level. That is what we’ll explore below. As always, I’m interested to hear about your experiences in this area, and what can we do as technology leaders to give ourselves a brighter future.

Picking the Right Technology Leader: Why do so many companies do a poor job with picking their technology leaders, especially those companies that can afford to pay them at the top of the market? There are a few factors contributing to many of these less than excellent decisions. They include:

  • Picking the best technologist instead of picking the best leader (who also happens to know technology well). This is by far the most common mistake made in all types of organizations. In every executive role in the C-Suite, you need the best leaders. It’s the CTO and CIO roles that most often have this key characteristic overlooked, and it’s the driving reason why the failure rates are so high. Technology workers want to be led, inspired, and communicated to clearly. When the CTO or CIO is missing these capabilities, attrition rates will be high, stakeholders and customers will be unhappy, and projects/products will fail.
  • Being too cost conscious. Yes, technology leaders are expensive. Every organization must decide what value technology brings to the equation for them and determine what level of leader they want to hire. It’s possible to not only under-hire, but over-hire, as well. Neither situation is ideal, and both will lead to shorter tenure and bad results. An under-hire will lead to someone being overwhelmed and unable to execute appropriately. An over-hire will likely lead to boredom for the CTO or CIO and likely over-spending on projects/people that the organization may not be ready for.
  • Having a poor search committee. More times than not, there may not be a technology person on the committee that is hiring the technology leader. Companies and executives would benefit from having internal and external technology experts of varying levels as part of the hiring team. It can only help the quality of the hire and increase the chances for long term success. Including lower level technology employees in the process as well, can help build early relationships and trust.

Poor alignment of expectations of the role to the person that is hired. One of the keys to any good hire, for any role, is ensuring you align the expectations of the role to the person you are going to hire. This holds true from a career perspective and a skill set perspective. Organizations tend to do this well at the lower levels, yet miss the mark at the higher levels. From my experience, the mark is missed in the form of having too many unrealistic expectations for the CTO or CIO role. Further, the candidates typically just nod yes and accept this fact, without doing the proper push-back. A high-quality CTO or CIO candidate will ask good questions and temper unrealistic expectations before accepting anything. It may cost them the job, but they would have failed in the role anyway, as they wouldn’t have been able to meet the expectations of the organization.

CTOs and CIOs executing at a high level and having success: Why do so many CTOs and CIOs fail? What qualities do the most successful technology leaders have? Let’s first look at why so many fail:

  • Lack of true leadership skills. This can often be traced back to companies promoting the best technologist instead of the best leader (with technology skills), but more and more often, it’s increasingly difficult to find great technology leaders with the skills to lead large teams and deal with groups such as stakeholders, other executives, and customers.
  • Too much micromanagement. Technologists are used to writing code with a lot of details and controlling machines/processes. That can translate into how they might manage a team if they are put in a position of leadership. It’s one of the key traits I’ve noticed in CTOs and CIOs that haven’t done as well as expected. They start to lose their ability to be strategic and drive away their employees. No one with any type of skills likes to be micromanaged.
  • Not enough communication. This is a big one. It can affect all aspects of their role and the people who work for them. There is a reason why the stereotypical technology geek is placed in a corner by himself. Conversely, to be a CTO or CIO, you must have top-notch communication skills to share your overall vision, work with stakeholders, and deliver the complicated nuances that are technology projects. I can’t say enough about this one. If a CTO or CIO doesn’t communicate well, it’s all over before it even started.
  • Not balancing the newest trends with business as usual (BAU) platforms. It’s fun to have all the gadgets, newest cloud architectures, and the highest end infrastructure (whether on prem or off) right? Well, yes, but a good CTO or CIO will understand that this is a balance between want, need, and cost (both dollars and opportunity). How many times have you seen CTOs and CIOs rush out to purchase the newest gadget/software, only to reverse that decision fairly quickly? Recent examples have a lot of large companies rushing to the cloud and then pulling things back when they realize: 1) The cloud isn’t necessarily cheaper, and 2) it’s all operational cost (Opex) instead of capital cost (Capex). I’ve seen, and heard this example numerous times in the last two years alone. CTOs and CIOs must always keep in mind their core businesses and what is needed to run them, even if it means living with older technology longer.
  • Focusing too much on cost, rather than value. Technology and technologists are expensive, like I mentioned previously. However, the big mistake that a lot of CTOs and CIOs make is focusing on pure cost, rather than focusing on value. If something or someone is expensive but adds a lot of value to the organization or a program, the value proposition may be aligned and the spend well worth it. The best leaders understand this and ensure that they are not after the least common denominator. We see clear examples of this failure when focusing on local or off-shore contracting spend. Lower rates aren’t necessarily better. Contract firms will keep their margins no matter what, so it’s just a matter of finding the right balance/structure of rates to ensure the type of resources you need are high-quality and bring value to the table.

There are certainly more areas that cause CTOs and CIOs to fail, but I’ve highlighted the ones that are common and key. Further, the inverse of the above examples would be a good place to start in terms of what makes someone successful in these roles.

  • Excellent Leadership Abilities (People want to follow and are motivated.)
  • No micromanagement; let people showcase their skills and let your next level managers take care of things, while you focus on the overall vision and strategy.
  • Communicate clearly and often. There is no such thing as over-communication. Hire an admin or chief of staff, if necessary and make this happen!
  • Focus on today’s business needs and what’s generating revenue, while stepping out on the bleeding edge to find what new technologies will be of benefit, in a targeted fashion.
  • Focus on value and not on cost. This is what separates the winners from the losers these days. This goes not only for technologies but more importantly people, too.

On top of these, let’s look at what I believe are the other keys to a successful run as CTO or CIO:

  • Hire the right #2s and put them in the right roles. The next level down from a CTO or CIO is crucial to get right. Having the best people to run the day-to-day shop is key to being able to spend the right amount of time on strategy, with stakeholders, and with customers. Coincidentally, these are very tough positions to fill and keeping all of them happy and working together is even tougher. All the CTOs and CIOs I’ve met that are successful have the right #2s in place and working together.
  • Trust. Related to the point above, trusting your people (up and down the organization) will make you a winner. Let your people shine and let them bring you ideas, innovations, and corrections as often as possible. Your job as CTO or CIO should be picking between them, not dictating your solutions.
  • Say Thank You and really mean it. Technology is a thankless job more often than not. Long hours, always getting blamed for problems, and always the group that gets crunched for time, even when other parts of the organization have been slow in launching a project, defining requirements, or getting funding. Saying Thank You, and meaning it, is key to keeping a team happy. Make it personal and make sure your lieutenants are doing the same thing.

The best Thank You I’ve ever received was extremely personal…It was related to my baseball passion and my beloved St. Louis Cardinals. I still smile about it today…

  • Let technology bring value to the organization; they shouldn’t be order takers. Technology workers have a brain and can understand the business as well as product managers and other business leaders. CTOs and CIOs should encourage their people to speak up and contribute to business discussions. Often, they understand the data and processes even better than the product management folks. Most technology organizations turn their technology workers into order takers. They just take the requirements, code, and don’t ask questions or contribute new ideas. Sad.
  • Understand how to showcase the value of your technology organization to other executives. This happens out of sight a lot of times, but the most successful CTOs and CIOs are good at presenting their KPIs, value propositions, and what they bring to the organization. Technology executives have access to all sorts of data that can be of help to them. Most of us just need to figure out how to mine it and use it properly. This one ability alone can extend the tenure of the role by years.

It’s not all gloom and doom for CTOs and CIOs. There are good ones out there and organizations can get better at hiring the right ones. It just takes some effort and a little bit of time. To recap, organizations can be more successful in hiring the right CTO or CIO by:

  • Hiring the best leader
  • Having the right people involved in the hiring process
  • Aligning expectations to the right candidate

CTOs and CIOs can be better at their jobs by:

  • Being a leader and communicating often
  • Hiring well at the next level down
  • Trusting their staff
  • Focusing on value rather than cost
  • Saying Thank You
  • Not forgetting about their organization’s BAU
  • Doing an excellent job showcasing the value of their organization to other executives

What do you think? I’m certain there are more driving factors for CTO and CIO success. What would you add to the list?

Thanks for reading!

Be on the lookout for more upcoming #QuestionSeries articles on the topics of Program Management, Leadership, Technology, and Careers.

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