4. ASK FOR A GUARANTEE OF SUCCESS.
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.
6. WAIT FOR A SLIP UP—AND THEN POUNCE.
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.