Coaching has to start from the positive. There is something right going on here. What is it? In Bella's case, it was a skill set that nobody else in Minneapolis has. Specific knowledge and experience in a niche industry. "Bella," I said, "you've got all the right skills for the job you applied for."
But... "We need to pull your story together. You know you're good. I know you're good. How are we going to convince the manager that you know more than anyone about this job?" By framing the question in a positive light, Bella understands that we're on the same side and we are going to work together to bring the manager on board. In coaching, how you ask the question matters more than why you ask it.
Now, set some expectations. "This position requires strong attention to detail. It's going to be extremely important to demonstrate that throughout your application. Let's run a spell check on your resume and see what we need to do to perfect it." There. The typos are on the table. Let's let the computer call out the errors, keeping our own relationship neutral.
Finally, about that letter of recommendation. Bella was so proud to have worked for that company back then. But something that occurred 20+ years ago is only relevant insofar as it got you to where you are now. I was a pretty good athlete in 1993, but no one has offered to draft me for anything more than a slow pitch softball team in a long time. So what have you done lately, Bella? Let's look at getting letters about how great you are now.
Coaching. Criticizing. Tomayto. Tomaato. Focus on the results you want by keeping your buddy focused on those results. It isn't personal. It's critical.