Digital technology as well as technical competence in IT teams has matured to such an extent these days that most technical issues are resolvable.
Unfortunately most companies don't understand what a Digital Transformation is nor the effort it takes for a successful implementation. The tendency is to treat it as merely a digital upgrade or technical improvement, instead of a business transformation enabled by digital technology.
Thus companies never even consider defining a business wide Digital Transformation strategy nor what a successful transformation looks like.
And because transformations are limited to merely technical implementations, the major issues and problems on the business side are never properly addressed, resulting in failure.
Success starts first at the business end and having a post-transformation vision of what a successful transformation will look like. Which parts of the organization will need to be changed? Which functions will be impacted? Which stakeholders and decision makers need to be involved? Does the necessary competence exist within the company? If yes, do they have the capacity? How will day-to-day operations be impacted? Will external expertise be needed? And so on and so on.....
A transformation isn't for the the feint of heart, there will be trade-offs and it won't be without pain. Planning one will be weeks to months of hard work, answering critical questions and making tough decisions. Choosing the digital technology to enable the transformation will be the EASIEST part.