There are many ways that digital transformation fail; when it's treated like an IT project.  "We are going Cloud" we often hear.  Cloud is just a mechanism, a tool.  And we all know, a fool with a tool is still a fool.

Or the shiny new object syndrome.  IOT, Cloud, Big Data, AI, again all just tools, that may or may not be applicable for your business.  The most important aspect of any Digital Transformation is the people and the process.  Are you taking the people along with you?  Do you have the right skills?  Can you train the people you have?  Do you have the right talent?

I used to work for a company where they were convinced that no digital talent resided in the company and it all had to be recruited in and I was told by a VP "the only place where you will find Digital talent is in the US".  There was Digital talent in the company, they just hadn't looked and to say the only place in the world where there is digital talent was the US which just incompetence. 

With any digital transformation, you must start with a strategy.  This isn't about teaching the CEO Twitter, it's have a common aim and purpose, that can then drop down to the department level.  What are the blockers?  What is the mission?  Can that be articulated by the whole Board?

And the biggest mistake, one company said to me "we as senior management don't need to understand digital, we have interns to do that".  I'm sure it's just a couple of bad quarters, (since that quote that company has posted 2 bad quarters) and the share price had dropped, the share is now a hold, rather than a buy.  Coincidence I'm sure.