Each year, I sit through dozens of hours of research sessions with consumers. If there is one theme I hear consistently it’s that consumers expect the brands they engage with to provide a flawless digital experience in their interactions.  And though that’s a notion that is consistent across all age groups, it’s a theme we hear unanimously from millennials.  It only takes a quick look around various industries to see that the companies that are delivering a strong, digitally-centric value proposition make up a substantial portion of the growth.

Meanwhile we’ve recently witnessed that many legacy brands are shrinking (i.e. The Limited) or going out of business entirely (i.e. Sports Authority). The bottom line is that companies born before the digital age must substantially transform in order to remain relevant. As Jack Welch said in the year 2000 “If the rate of change on the outside exceeds the rate of change on the inside, the end is near.”  Many great brands today are in just this situation.

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It takes five miles for an aircraft carrier to turn itself around 180 degrees. If you are on that aircraft carrier while it’s engaging in that ‘quick turn’, you better hold on to something solid because you’ll soon be tilting at a 30-degree angle.  Many large companies are not comfortable with making the difficult and rapid hard left required to align themselves with how the world has changed.

Being in the business of helping companies through their digital transformations, I have observed that many of the companies that struggle digitally do employ super-sharp and visionary executives who see what needs to be done. However, those executives face massive challenges when it comes to enacting the kinds of changes that are necessary in order to make that digital leap. Most of the work I do involves partnering with heroic innovators trying to change large enterprises from within. As a result, I have an insider’s perspective on the biggest challenges these companies face when taking on transformation projects and, in fact, spend most of my time working to try to overcome them.

Based on first-hand experience, here are the top five challenges to digital transformation. If you are facing any of these challenges, the list below may, if nothing else, give you comfort that you are not alone.