Most people have had a boss they didn't fully appreciate while they were there. The one who said the thing everyone else was too careful to say. Jeff Miller has spent a career trying to understand why that kind of feedback is so rare, and what it costs people when they never get it.

Jeff is a partner at Door2 and a longtime coach to leaders navigating the gap between how work looks and how it actually feels. This is Part 2 of our conversation. Part 1 is worth going back for, but this one stands on its own.

We talk about how to ask for feedback without sounding like you want reassurance, why "soft skills" is a name that undersells the hardest work in most organizations, and what it means to define success when the marker keeps moving and you're a few years from 60.

Near the end, Jeff got a Facebook message from a sixth-grade student he taught in 1995. Thirty years later. What that person said is worth staying for.

Three things from this conversation:

• Asking "how am I doing?" is too big a question for someone with 80,000 things going on. Asking for feedback on three specific things changes the whole transaction.
• "Soft" doesn't mean weak. It means the skill changes depending on who's in front of you. That's what makes it hard.
• The best boss most people ever had was someone they didn't fully appreciate at the time, because that person said the thing everyone else was too careful to say.