Things you don’t learn from a book

I’ve read a bunch of books and articles on managing. Some are good, others less so and generally they cover typical scenarios in an office environment—providing feedback in a way that fosters change, modeling good communication skills, time management skills, things like that. A few of those resources have touched on the trickier topics—letting someone know that their attitude is holding them back, stuff like that. But there are others that defy easy categorization or are inherently not a lot of fun but must be done regardless. For examples, over the course of my career as a manager, I’ve had to do the following:

• Tell someone with combat-related PTSD that he couldn’t work for me anymore because of the breakdown he’d had with our clients. I feared he might commit suicide or go on a rampage—thankfully he didn’t, but it could have gone that way pretty easily.
• Tell someone else that I didn’t have full time work for him, only part-time and not much at that. I knew he was living paycheck to paycheck augmented by credit cards. While not my fault or responsibility, I knew that was a hard place to be. 
• Tell another employee that in order for her to go in front of our clients, her skirts needed to be longer and her necklines higher. Yeah, that was an awkward conversation.
• Tell yet another employee that when the dress code said dress pants and dress shoes (no athletic shoes), that’s what it meant and no, he wasn’t exempt.
• Counsel another person that while we absolutely would make accommodation for her disability of narcolepsy, I needed her to take her naps some place a little less public (she’d been tossing her sweater over her head while sitting at a conference room table with the rest of us and then going to sleep).
• Attend the memorial service for the father of one of my direct reports. He died very suddenly and she hadn’t known that he was that ill. 
• Tell employees on my team who’d applied for a promotion that they didn’t get it—and hopefully in such a way that they weren’t demotivated or wanted to quit. 

How do you prefer to get feedback? What’s been most helpful to you when you’ve needed to change what you do at work?