What details/tools have you found help people transition to similar, open software from closed software, or think could help?

You would be surprised with how common it is for the lay person to have problems on their computer. I like to start from there, and suggest a free as in freedom software solution. Then, once their issue has been solved, I will talk about the free software movement, explaning that these are the reasons that have motivated the authors of the software solution I promoted. Hopefully this leads on to a discussion about freedom in the digital world.