Step One: Hire Me. Obviously, I would prefer you take this route, but I understand that some of you want to at least try to do it yourself first. If that's the case, I still think you should tell your folks about my articles where I address some of the questions I have received most often.
Step Two: Reserve Some Time. Most likely, it'll be an hour. Most beginners get the most out of a 30 minute session, regardless of the discipline they are studying, because these new skills take a lot of focus. As they develop their skills and confidence, expanding to 45 minutes or an hour makes a lot of sense. An hour is a great because it's long enough for most tasks to be explained, demonstrated, and practiced with good focus. Two hours can be useful if it's a more advanced user, and if that person has a lot of energy or a lot of specifics they need to work on. After that point, though, you tend to see diminishing returns. One reason workshops tend to be longer is that there is less individual focus, and there is usually an opportunity for a break.
Now, WHEN should you reserve time? The best time is when the student has the energy to focus. The second best is whatever is convenient for both of your schedules. Most people are most awake from 9:00am-11:00am, but do what you can when you can.
Step Three: Decide What They Need To Learn. True story: computers became much easier for my mom when she discovered Amazon.com. That gave her some transferable skills for Facebook. These are both important her life, because she likes shopping for specific things, and she enjoys her friends and wants to stay connected with them. She does not, however, need to create an audience on Instagram by utilizing the algorithm and choosing the most effective hashtags. Your parents, grandparents, and even your children are pretty much the same: pick one or two things they look forward to doing, and use those one or two things to cultivate their interest.
Step Four: Reminders. First, remind them that they are only going to get better if they practice. Remind them that there are opportunities online that may not exist in the real world, like buying tickets to shows. Remind them that you don't know where every little thing is–you just know where to look. Remind them that it's a muscle that develops over time. Remind them that they don't even really need a Twitter account, but if they at least know what Twitter is, they can make a conscious decision to enjoy it or avoid it, instead of being forced to stay off due to their lack of ability. Remind them that like many other skills, it comes down to making time and doing a lot of repetition.
Step Five: Empathy. Remember that if this is a new skill, there's no reason for them to be good yet. You didn't come out of the womb knowing how to read; you went to school for 12+ years. It's the same thing, so be patient. If they are tired, just finish up whatever you can, and give them a break, even if you still have 20 minutes of the hour you reserved for them. When they are frustrated that a site changed their layout yet again, validate that opinion. Basically, just show them you're on their side.
Step Six: Encouragement. A lot of your folks are already beating themselves up for not getting it, for not starting 10 years ago, etc. You don't have to add on to that. Second: if they only see using the computer as an opportunity for failure, and if there is no reward, they are just going to avoid it. Be encouraging, even if you're saying things like, "It's not much, but you didn't know how to do that an hour ago!" The more you do to make it pleasant, the more they'll want to do it.
Step Seven: Hire Me. Just thought I'd give that another shot.
Thanks for reading, and I'll see you on the internet!