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Insights | By Howard Tiersky

How to Sabotage a Digital Transformation

Digital transformation is essential to the future success of your company but, there are many people who actively resist it. They rationalize that it isn’t needed and try to focus everyone on its dangers. And if a change still gets adopted, they can attempt to sabotage it.

If you’re one of those people who have strong reasons for wanting to see digital transformation fail, this article will show you some tips and pointers on how to effectively block change at your company.

And if you’re the one who’s trying to lead digital transformation, this article is an invaluable look at the techniques being used by the opposition. If you know how your enemies are likely  to try to undermine your efforts to drive transformation, you can counter their moves and put yourself in a better position to influence them to change their minds.

Here are the most effective tactics when trying to sabotage a transformation.


Don't be the one that thinks the company should not try to get better because you will sound unreasonable and then people will discount everything else you say.  

If you oppose change just for the sake of it, Instead, make sure that you’re still cheerleading for the general ideal of trying to improve things.


When someone presents a transformation opportunity, point out the hard dollar costs as well as the “opportunity costs”. What is this transformation going to take the focus OFF of? What won't you get if you spend money, time and energy on this digital transformation?

In fact, try to find some pet project of the CEO that might need to have its funds and efforts diverted in order to support the transformation. That will land hard.


Remind everyone that you’ve been doing things the same way for a long time and have been successful for many years. This gives you the opening to argue that transformational change isn’t really necessary. Small improvements are welcome but why make drastic changes if the business is doing fine?

This risk is this argument can be overcome by those driving transformation by simply pointing out how rapidly the world is changing. In the last year, it's changed probably more than it's changed in the prior nine years because of the continued acceleration of digital technology.

But you can still try to find reasons why your company is an exception. Yes, the world is changing but somehow the demands of your customers are more static. 

You can probably also find an example of a prior initiative that tried to drive radical change and failed. Remind decision makers of that and then try to generalize it to prove that radical change is a mistake because it’s failed in the past.


Question whether it is absolutely certain that this investment is going to yield the promised results.

Of course, there is no way for the other side to be a hundred percent sure of that. They can show you trends and forecasts drawn from their market research, but even those things can only project outcomes, not predict them.

Take advantage of the fact that it can't actually be proven beyond a shadow of a doubt that the company would not be successful without this transformation.


If you find yourself losing the argument that transformation is needed, then disagree with the specifics—the vision.  Raise the possibility that you could actually transform into something worse without the right vision.  

If they do market research to prove that their vision will work, question the methodology of the research. Or the validity of market research in general (remember New Coke?).

If you are outvoted regarding the vision, then argue that they don’t have the right plan to accomplish that vision. Great ideas can fail if they are approached in the wrong way.


Sometimes there's just too much excitement around a transformation and you lose on all of the above points. The transformation gets the green light.  Don’t worry, you haven't lost yet. That transformation is going to take time. And a big transformation is inevitably going to hit problems. Those problems can cause the people who initially were excited to approve the transformation to start to lose faith. Capitalize on that.

Just keep on top of it. Wait for the problems to start rolling in and try to just make your case that problems prove the transformation was the wrong idea to begin with—that it's off the rails and needs to be put out of its misery.

For example: if the project is behind schedule, point out how the costs will pile up if the project keeps slipping. If the early tests of the new experience are disappointing, use these as evidence that the team will never get it right. If the beta version of the product has some bugs, point out that this level of low quality is not consistent with the company’s brand. If there are any customer complaints about changes resulting from the early part of the transformation, collect them, curate them and use them to prove that this is annoying your customers and risks the destruction of your entire business. It doesn’t matter how many happy customers there are, just collect the negative reactions.

There are many great projects that were successfully killed 20% or even  60% of the way in because people who had that initial enthusiasm for pursuing those initiatives just lost faith. Magnify the slightest reason for doubt and there are going to be people who will get buyer's remorse and decide that it’s better to cut their losses.

Sometimes trying to sabotage digital transformation efforts can feel quite daunting. Don’t be disheartened. There are many talented and intelligent executives who have been able to block change at their companies very successfully.

It can be done, especially when the people who fund and support transformations don’t know what they're getting into and fail to make sure that everyone understands the risks and has realistic expectations about what's going to happen next.

My Wall Street Journal bestselling book, Winning Digital Customers: The Antidote to Irrelevance, talks extensively about the mindset of people who resist change, the arguments and tactics they use, and what transformation proponents can do to counter them. Get access to the first chapter for free at https://WinningDigitalCustomers.com.
Get FREE access to the first chapter of FROM`s
Wall Street Journal Best Selling Book


  • Learn the three patterns of all successful digital brands (including companies like Apple, Netflix and Uber).
  • Understand why many great new products fail, and the formula for building products that won’t.
  • Discover the key reasons companies resist change and how to overcome them.
Get FREE access to the first chapter of FROM's
Wall Street Journal Best Selling Book


  • Learn the three patterns of all successful digital brands (including companies like Apple, Netflix and Uber).
  • Understand why many great new products fail, and the formula for building products that won’t.
  • Discover the key reasons companies resist change and how to overcome them.