You've observed that she has the need for certain security blankets when she strays outside her comfort zone of schmoozing clients in person. For example, since the last computer upgrade two months ago, your TOT has been calling on you (and not her admin) to help her send out e-mail blasts. At first, she said she was too busy, and you agreed to help. After the third blast, you realized you had moved from simply sending her e-mails to editing them first—and now, you have ended up writing, editing, and sending them.
You notice other tell-tale signs. She asks you to take all notes during client conference calls, and after each major point, she asks you if you got that down. Later on, she can't find the "most salient" point made in the notes you e-mailed her, and calls you in a panic to ask for a quick recap.
The way she fumbled for that simple information made you wonder if she wasn't able to open her e-mail or the file at all. Come to think of it, she always carries a huge stack of paper around and has never responded to a text message. "Yikes," you think, "my boss borders on tech illiteracy."
Something about the word "new" virtually morphs her into a three-year-old on her first day at preschool. When the teacher says, "We're playing a game. Come join us," your toddler hides behind you and says, "I don't know how." If you arm some TOTs with the ...