CIO Leadership

When CIOs Have CEOs With Expectation Issues (aka Fantasies)

You will run into CEOs who do not have right expectations. They will run over you if you don’t know how to manage their expectations. How do you lead CEOs who have unrealistic expectations of IT while remaining an integral team player?

Scott Smeester


February 1, 2024

I have a friend with one of those - the first time aggressive CEO who measures everything by how it serves his objectives - and wants answers he wants to hear rather than ask questions whose answers he should hear.

Judging by the length of that first sentence, you can tell there is a lot involved here.

How do you work with CEOs who have unrealistic expectations about IT?

The stakes are high. Unless resolved, your team will be distracted by unwarranted demands, you will be measured by unmerited standards, and your company will be at risk because of unfounded executive decisions.

I’ve been there. I have tried to infuse progress; I have tried to slow reactionary pursuits. It’s exhausting. And educational.

I have worked with CEOs of all types, and I have realized that success with them is based on the same dynamics as success within IT: focus on people, process and technology. Specifically, working with the CEO as a person, as a process leader, and as a technology user.

The CEO Is Human (even if they want you to think otherwise).

We could certainly deep dive into many areas of psychology, but for now, let’s consider two aspects of your CEO as human, personality and preferences.

Personalities vary, of course, but you’ve met some typical ones. Sometimes a CEO is more steamroller than diplomat, operates with “or” perspectives (good or bad, right or wrong), and has difficulty following or trusting.

Some are overachievers, value what others define as success, and find failure unacceptable. They truly love work, and choose work for fun.

The list goes on, and there are plenty of personality studies available that you can read up on, identify which is most reflective of your CEO, and learn what you can about best dynamics of working with them (I like the Enneagram as an easy reference).

I’ve learned a shortcut. Humans assume that the way they do things is the best way to do something. It’s why couples early in a relationship fight over how something should be done. It’s why dictators dictate. CEOs are not exempt from the assumption (or becoming the occasional dictator). They have preferences.

Watch them. Does the long-winded person frustrate them? Do they start and end meetings on time? Do they admire a good challenge or are they threatened by intelligence? Is loyalty a high value? Is pragmatism their god?

We don’t try to change their personality and preferences.. We treat each as guides for productive interaction.

I don’t rush when they prefer to be deliberate; I don’t drag when they value movement; I don’t withhold updates when they like to be informed; I don’t give them information they don’t value.

Strength adapts. When you are dealing with a CEO with faulty expectations, you take the strong position and meet them where they are at. 

The CEO As A Leader Who Shoulders Responsibilities

CEOs are held responsible and report to boards (or to Congress, as we saw this week). I have yet to meet a CEO who enjoys looking bad. Where do you, me and CEOs look bad the most? When we are accountable for what we don’t quite understand. When we answer for what we don’t really know.

In dealing with CEOs with faulty expectations, two critical strategies rise to the top. First, it’s not that you have tied IT initiatives to the business (I trust that you have), it’s demonstrating and communicating that alignment.

How does the CEO know that what you are doing is a business strategy, a revenue generator, and a security essential? 

You are used to communicating what IT is doing; CEOs need to know why you are doing it, especially if you are framing it in a way that they can communicate it to others.

Integral to alignment with business is establishing an alliance with business. CIOs work with other business leaders to utilize “we” language. As one mentor said, “You want as many fingerprints on the smoking gun as possible.

Your C-Suite can’t do what they need to do without them; you refuse to do what you do unless it’s tied to them. They are dealing with the same CEO you are. Establish a united front. 

The CEO As A User

Your role as a CIO is to help your CEO with their understanding and utilization of technology. 

They are no different than anyone else when it comes to tech: If they understand what it can do for them, and then if they actually utilize it, they become users.

Questions precede experience. 

I have friends who asked about generative AI. I helped them understand how to use it, and then I taught them how to utilize it. Now they are hooked.

Expectations follow understanding and are shaped by usage.

In the end, right expectations are set because CIOs have done the hard work of leadership: being strong by adapting to preferences, being stronger by building alliances with one voice, and strengthening the CEO in areas they feel weak in.

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