For example, too often we treat IT training as a after-thought, communications with our users as a sidetrack from the "cool technology" itself, and the rollout and adoption of technology in our organizations as "you'll take what we give you, when we give it to you, and you'll like it!"
Certainly, generational differences have long been acknowledged in terms of IT awareness, understanding, desire, usage, and expectation. Those generations who grew up with the computer, PDAs, internet, social media and so on and so forth are not only versatile in them, but expect basically the "latest and greatest" to be available to them at work. While prior generations who did not grow up with these modern technologies, although fully capable of learning and using them, may not intuitively understand them or feel the same level of desire to adopt them.
As IT leaders, we need to work with people from many generations and walks of life--with various levels of breadth and depth of technical prowess, desire, and expectation, and we need to serve them all by understanding their particular IT requirements, service levels, and training needs, and tailoring our approach to servicing them to help each group--based on user segmentation--to be as productive, engaged, and comfortable as possible.
Of course, we can't make everyone happy all the time, but perhaps, we can work ever harder to be more understanding, empathetic, and helpful to our variety of users--"challenged" or otherwise.