CEO Best Practices

The Overlooked Trait Every CEO Needs In The CIO

The CEO needs a CIO who knows how to read context. It improves their effectiveness as a team leader, as a decision-maker, and as a communicator. To help them do so, make sure that they have a coach, a learning community and more context-conversations than content-conversations.

Joe Woodruff


January 19, 2021

“Taken out of context I must seem so strange.”

— Ani DiFranco

The one thing the CEO needs in the CIO is the ability of the CIO to read context. Though a technology leader may be well-versed in a discipline, (s)he brings very little strategic value to the table without the ability to see, understand and interpret larger elements outside of their discipline.

Meaning is derived from context. Words, actions, and data depend on context. So do roles, responsibilities, and decisions. Skilled positions still need knowledge of the game. Adjustments are based on context.

Context is the ability to measure. It gathers insight from outside to in, from larger to specific. A CIO cannot measure effect or difference or cost or gain without knowledge outside of their own purview. When the CIO fails to get context, decisions are ill-informed, progress lags behind, and shifts in strategy are missed.

Of course, the CEO needs this in the CIO. As the CIO is brought more into business strategy and closer work with stakeholders, they need to be able to gather and interpret not just relay information or convince. Content may be king, but context is wisdom. Pity the kingdom of a foolish king.

Communication studies recognize that a conflict often arises out of three fields. Parties in conflict either have different information, different interpretation of the same information, or different implications related to the information. In other words, I may not know what you know, I may see something differently, or I may care more or care less about the information at hand. These are all issues of context. Leaders think the answer to a problem is more information; usually, it’s about greater context.

If a CIO is a master of context, it improves their effectiveness as a team leader, as a decision-maker, as a communicator, and as a person the CEO enjoys working with. No one likes a long-winded or out of touch bore.

How does the CEO help the CIO master context?

Ensure that three things are true:

  1. They have a Coach.
    My coach, Joe Woodruff says, “A coach draws out; a mentor pours in.” Both are needed, and both are distinct. A coach who draws out is helping a person master context, perspective and decision making. You don’t want to give your CIO a coach who tells them what to do; you want them to have a coach who helps them think, and helps them master the art of helping others to think. Imagine the day your CIO leaves a critical meeting and the impression from others is that (s)he not only fully understands the scope of the business strategy, but left people thinking at a better level than when they arrived. That’s what you want. That’s what a good coach will produce.
  2. They have a Learning Community.
    Your CIO doesn’t need another seminar or even another consultation. They do need a group of peers willing to tackle their real-time issue and to offer unbiased, outside-eye insights. It’s what I have gained from my CIO Mastermind group, and it’s what the CEO wants for the CIO. A learning community dials in and pours in. The CIO needs a group in which they can bring issues related to them (leadership skill) and for their team and stakeholders (leadership strategies). Effective learning communities are about context: taking the CIO’s immediate context into account, and helping resolve issues by drawing from larger contexts and insights. We certainly don’t need your CIO wasting time at another course on Issue X that has nothing to do with the real context of their work.
  3. The CEO and CIO have Context-communication more than content-communication.
    If your meetings with the CIO are about exchange of information, you are missing out on what you and (s)he need. Context beats content. Information is important, but it only becomes insight when drawn from a larger perspective. As CEO, you seek to understand a larger technology picture so that you have a frame for the information and questions that do come your way; the CIO needs the larger business picture. Together, you are able to have a “so what” conversation. That’s context, that’s anticipation, that’s working on the business not just in; that’s wisdom.

As a CEO, you value a CIO who can answer questions. To really step up the contribution of a CIO, you want one who knows how to ask questions. You will be far more impressed by the leader who drew out of you all that they needed to know than one who simply, or at least apparently, took in all you had to give. They sought out your context to better shape their context. It doesn’t get any better than that.

If you need help finding a coach or community for your CIO, CTO, CISO or Director, let me know.


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