Jeffro, thank you for posting this. We need to talk about this far more than we do!

Your timing is awesome because I'm actually presenting on the same topic this weekend at (shameless plug)WCTO. Come join us!

@Bob, I disagree that WordPress that it's "too much maintenance". I think it's all relative and if you have a well built site then WordPress is exactly the right amount of maintenance. The answers are all out there and they are mostly in an understandable format.

@Carl, you hit the nail on the head. I used to try and explain a CRM and now I just say "think of it as your website's operating system". If you don't mind, I am going to adopt the "If you can use iOS then you can use WordPress" mantra and see if it fits.

My thinking is this. Non-technical people see most new software as big and scary. The problem with WordPress is that all they hear from their friends, colleagues and the internet is how easy it is which leads them to believe there's some magic button that will do it for you. (Sidekick for WP comes close but it's not perfect)

A new user needs to be on-boarded properly and it's our job as well versed members of the WP community to make sure that happens. To me that means doing things like holding meetups geared towards beginners, being patient with newbie questions, providing training and not just "help" and making sure we keep hammering Automattic when things start getting too complicated.

Of course I realize this all sounds nice and the reality is that we don't all have the time but if we're really invested in WP being a great platform for DIY all the way up to Enterprise, then the time has come to start considering how we train the users and as trainers maybe we need some training too.

Thanks again, great article!