The problem
The Jobs to Be Done framework forces product teams to ask a harder question than 'what features do customers want?' It asks: what job is the customer hiring your product to do, and what are they firing when they hire you? The answers are almost always surprising. The functional job (transfer files quickly) is rarely the real driver. The emotional job (avoid looking disorganized to my manager) or the social job (signal that I'm a sophisticated professional who uses the right tools) often explains the actual purchase decision.
Capturing a JTBD session is difficult because the insights are non-obvious. A customer doesn't say 'I hired your app to make me look competent.' They say 'I needed a faster way to send large files.' Getting from the stated need to the real job requires facilitation, probing, and synthesis — all of which happen in a workshop that's usually held around a whiteboard.
The workshop output is the hardest thing to document. Job statements need to be written in a specific format: 'When [context], I want to [motivation], so I can [outcome].' Getting that format right from memory, after the session, is nearly impossible. Getting it right in real time, on the board, with the group watching, is very possible.