The CIO Career Path Paradox (Chapter 11)

CIOs are uniquely positioned to move into different chairs around the executive table, but only if they seize on the opportunities.

From CIO to COO

Raise your hand for enterprise initiatives

  • To transition from CIO to COO you either look for a new CIO role where you can onboard differently, or look for a COO position at another company.
  • You may also look around your current company and see where you can expand your reach.
  • Remember that people are defined by the problems they are asked to solve, reaching beyond IT is a critical step in securing a COO role.
  • Demonstrate enterprise leadership in your day job and you’re on the road to your next position,



Go for continuous improvement

  • If you’re good at project management & at driving structured change, you will be a good continuous improvement champion.
  • Continuous improvement is a natural extension of your CIO role. It makes you a better leader & will give you more than technology problems to solve.



Don’t be shy

  • It’s always a good idea to tell people what you want, let it be known that you are interested in taking on the larger, more interesting problems.
  • As COO, you have to be the business. It is tempting to continue to solve technology problems, but if you do, you will never be embraced as the COO & your new CIO will never grow into the role.
  • As COO, you must engender change at a very different level. Now, the meat of your job is to come up with the business strategies that other people enable & support.



Be prepared to diversify your management style

  • As COO, your teams include a much more diverse group, which may well require you to change your management style.

From CIO to CEO

As CIO, you need to be great at strategic planning, finance, HR, sales, and marketing, with businesses using more data & becoming much more scientific in the way they run, someone with a technology background could be a great candidate for the CEO role.

CIOs must be experts at solving complex problems.

They must be precise and experienced planners, they have to spring into operational mode, and they have to be more global than their peers.


Learn to balance internal and external demands

  • The CEO has a much larger group of external constituencies than the CIO, including the board, investors, partners, and customers, & must know when to prioritize the internal versus the external.


Change up your management style

  • When you take on teams outside of IT, you should think hard about your management style and make some adjustments.
  • As CEO, you have far more diverse group of people to manage—HR, finance, product development, sales—learn to relate to them in different ways.


Run IT like a business

  • Think of yourself as the CEO of your own business where demand for your services will always be higher than your ability to supply them.
  • Everybody is an expert in your consumer business, but nobody understands your enterprise business.



Develop your “minors”

  • CEOs have a major in something, and they’ve had to build their knowledge of other functions off of that core.



Scale your conception of systems relationships

  • CIOs live in a systems world, they understand the interdependencies among the elements of the systems, scale this notion of interdependencies to a broader level that includes boards & governance, product management, people, services, & sales.



Embrace variety

  • While consistency, focus, depth, and loyalty are important, it is also true that the greater diversity of roles you have had in your career, the more career options you will have open to you.
  • Balance tenure with variety, you will have a much better shot at new executive roles, including CEO.


Know what you are good at

  • There is a difference between universal capabilities—like leadership and communication—and business specialist skills.
  • Know what you’re good at and be good at it. It’s a learned instinct thing.

Use the two-way mirror approach

  • Use the “two-way mirror” model: while evaluating technology for your own business, you ask the right questions to gain insights about how your competitors are using that technology.
  • Every time you look at a technology, consider not just what it does for you, but what it does for your competitors.

Running a Technology Company

Polish your leadership skills

  • When you are focused on project delivery, it is critical that everyone follow a road map with strict attention to roles, budgets, and timelines.
  • If you are providing real leadership, you want teams that are not necessarily following your direction.
  • You need a team that will challenge you, but who will provide the innovation

Make sure you love to sell

  • CEOs sell and that can be a real transition from being a CIO.



Fill in your skills gaps

  • Become a student of the skill sets required to run a business.
  • As CIO, you have access to a wide variety of leaders both inside your company and out.
  • Interact with those people and start to understand where the gaps are in your own skills.



  • Recognize your strengths and be careful what you wish for.
  • The DNA necessary for thinking through the details of a complex technical problem may be different from the DNA necessary to get a market excited about a new company or product.
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