• Digital transformations are typically complex, cross-functional projects with extended timeframes
  • This complexity makes determining the likelihood of success difficult
  • Understanding the most common signs of a failing digital transformation is critical to ensuring eventual success

I recently rediscovered an old PC game from my youth called Oregon Trail. In this game, you are responsible for getting a wagon train of settlers to the West. Despite its text-based interface and barely discernible graphics running on really limited code, the game is ludicrously difficult. I can’t count the number of times I started off with what I thought were all the supplies I needed and a very strong plan – and yet still ended up washed away in a river, dying of dysentery, or starving to death somewhere in the desert.

Digital transformation e-book

Digital transformations are like Oregon Trail (minus the dysentery and river crossings). They are complex journeys that often take companies well outside their comfort zone. As a company enters these unfamiliar territories, how can they gauge whether they are going in the right direction or veering into dangerous areas? The ability to confidently assess where you are and where you’re going is critical to the overall success of a digital transformation effort. Here are the top four signs that your digital transformation is not going where you intended:

  1. You can’t explain why you’re doing it. Digital transformation initiatives are the new must-have accessories for companies, and every company seems to think they must have their own. Unfortunately, in this rush to keep pace with their competitors or react to this widespread market trend, companies are launching digital transformation efforts without properly understanding why they’re doing it or what they’re hoping to achieve. If your organization can’t clearly state the reasoning behind your transformation efforts or what you expect to get from it in a clear concise paragraph, this is a sign that you’ve embarked on a journey with no clear endpoint. Slow down and make sure the organization knows where it’s going.
  2. You can’t point to an individual or a function that is in charge. Given the length and complexity of a digital transformation journey, it’s critical to make sure there is clear leadership to address any issues that may arise during the initiative. If there is no clear consensus about who is in charge of your digital transformation, it is likely to go off track and you’ll end up wandering aimlessly in the desert. Make sure that before you embark on this journey, there are clear lines of responsibility and authority and that someone is in charge of keeping the transformation headed in the right direction.
  3. You don’t know how you’ll get there. While defining the destination of digital transformation is often fairly straightforward, the route to get there is not. In most cases, getting to your destination will require the careful and coordinated efforts of multiple functions within your organization. A critical part of any digital transformation is knowing what the steps are and how they connect to each other. This should be established before you start your journey. If no plan of record is agreed upon by all parties, there’s a good chance that not all of those parties embarking on this journey will end up in the same place. Take the time to identify all the necessary steps, including who is responsible for each step, so you can eventually reach your destination.
  4. You don’t know when you’ve arrived. One obvious key to a successful journey is knowing when to stop. If you don’t know what you’re trying to achieve, can’t articulate what the transformed company will look like or are unclear on what metrics will be used to prove that the journey was successful, you won’t know when you’ve made it to your destination. Before starting a journey, make sure all parties understand where it ends by clearly outlining the changes you want to complete and the metrics for measuring success.

If you’re about to embark on, or are in the process of, a digital transformation journey, ask yourself these questions to remain on the right track and avoid all the pitfalls of the long, complicated journey to digital transformation.