CIO Leadership

The Art of Overcoming Rollout Resistance

Resistance to rollouts are common, and failure to overcome them is an agony of defeat in a class all by itself. The art of overcoming is anchored in three essentials often unknown or overlooked by CIOs and technology leaders.

Joe Woodruff


January 18, 2024

A CIO had told me of a rollout failure he and his team had suffered. At the time, I recalled two famous business stories.

The first occurred in 1876 when William Orten, the President of Western Union, rejected the offer of a patent on a new invention called the telephone. In his words, “While it is a very interesting novelty, we have come to the conclusion that it has no commercial possibilities.”

The second happened in the office of Decca Records when the Beatles auditioned in 1962. The executive in charge of talent rejected them, citing that four-piece groups with guitars were finished.

Resistance can be catastrophic.

And you don’t want your company to live with the regret that follows.

When was the last time you faced resistance to your idea, project or product?

How do you overcome rollout resistance so that people enthusiastically embrace what you bring?

I had the pleasure of working with my friend and his team as they prepared for Rollout 2.0. I am grateful to report that they experienced a positive difference - an enthusiastic embrace - even to the point that users advocated for the change when executive leadership followed up on their implementation and satisfaction. 

Here is some of what I shared with them.

The Three Most Common Mistakes In Roll-Outs

Failure to connect with the users.

Overlooking the power of triggers for buy-in.

Not staging efforts that promote momentum.

The Art Behind The Display

Connect on one key benefit. 

It’s not enough for you to talk about the features and benefits of your idea, project or product. 

Anyone you are trying to serve or lead engages at their particular point of need. How do you help them attain a future state or avoid a current pain.What is their hell or heaven? What is their preferred reality as opposed to their current reality?

You have to think in terms of what is the shared need between you and them, the common enemy and the mutual benefit. 

Connection is based on relatability more than likability. And relatability is rooted in shared experiences. You want them to see you as on their side of the table.

I once worked with a group that created an app for chiropractors. It was beautiful in features and benefits - but it failed because little effort went into talking with actual chiropractors and what they wanted that the competition didn’t already offer.

The number one question a CEO will ask you is “What does this do that we don’t already have?” The CEO doesn’t want to hear a list - they want you to solve for a pain or a gain. So do the users who end up with what you provide.

Be attentive to buy-in moments

People sit in pain and do nothing to alleviate it; people hold to a dream and do little to move toward it.

People will buy, or buy-in, when the right situation presents itself. That is called a trigger.

Imagine that I have a great idea for how you can convert your extra room that is collecting junk into a beautiful, usable space. You tell me that someday that would be a great idea. I come over for months, even years, and the room collects more junk.

One day, you tell me that you need me to convert that extra room, and as soon as possible. I ask, “Why now?” You tell me that you are expecting a baby or that your mother-in-law is moving in or any number of reasons that demand action.


Your idea, project or product has an ideal buy-in time - an event or situation that changes and causes demand for what you have. 

What is the “why now” for what you want to roll-out?

Who is in the window of “now?”

Build bridges and avoid trenches

You have an easier time walking with people over a bridge than you do trying to pull them out of trenches.

Trenches are occupied by people who are comfortable with the way they do things, even if it means a slower slog to progress, productivity and profitability. I don’t pull people out of trenches.

I do build bridges, and I do so first with two groups in mind. Successful rollouts are focused best, initially, on who is new and who needs it most. They are usually the first to come alongside you.

Let’s say you have developed an app for moms. The app gauges children’s moods utilizing various measurements. The benefit is to be responsive with greater understanding to what your child is going through.

Experienced moms are going to be a harder sell, because they have “tried that stuff” or “I know my kids and I don’t need an app to tell me what they need.”

But new moms, or moms who are exasperated because they can’t figure out “what is going on with them” - an easier sell. 

We want all moms to benefit from the app; we are also aware of who might benefit more at the first. 

Those who are new don’t know better to resist; those who need it have little reason to resist. Just do your thing with them.

The trenches often represent those who require you to give greater efforts at connection or greater awareness of their triggers. But they are there to leverage. 

The Checklist

  • Have you or your team relied too heavily on features and benefits?
  • Have you tried to persuade others when the time wasn’t right?
  • Have you attempted a mass adoption and missed the mark?
  • Do you take the time to understand the shared need, the common enemy and the mutual benefit between you (and your idea, project, product) and the users?
  • Are you aware of buy-in moments and do you act on them?
  • Do you put your first focus on who is new and who needs something now?

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