fmilne
The reason it clicked was because at the time, a colleague offered to mentor me. This helped since he would assign me cases related to my skill level, show me how to ask better questions, and explain how things worked in context to our tech stack.
Other useful resources
http://robertlenne.com/requiredreading/
Universal Design Princples http://www.amazon.ca/Universal-Principles-Design-William-Lid...
Inspired: How to Create Products Customers Love (great for teams) http://www.amazon.ca/Inspired-Create-Products-Customers-Love...
On one end of the spectrum of human behaviour, you have people who skip the manual entirely and go straight to trying to figure it out themselves. They will be pissed if you don't have a tutorial when they get stuck.
On the other end, you have the type of people who will carefully follow every instruction you provide them, and will be upset if you don't provide a guide or instructions upfront.
Regarding interactive messages, I recently used this plugin on a recent project. If a new user opted to take the tour, they could follow along down a series of options, interact with the form fields or UI that was being highlighted and close the tour at anytime. They could also opt out and start the tour later if they got stuck. One week in and we are already seeing an impact on the KPI for the project. http://usablica.github.io/intro.js/
A tea timer by your desk is a great way to approach this at work, personally I find 15 - 20 minutes of work 5 minutes of procrastinating is good balance.
That being said, if you need to keep the roof over your head, let a few people try the product for a short amount of time, and ask them how much they would be willing to pay. You can fine tune the amount as you add more customers and get more feedback.