As if I just go around analyzing the outfits of everyone I pass on the street! Certainly not. I never say anything unless I’m asked, and then if I’m asked, I consider the matter carefully and offer an honest opinion.

I try to phrase criticism in the nicest possible way, but I also never lie. If people ask, I assume it’s because they want to know. People are not dumb about these things; they can tell when a compliment isn’t sincere.

My grandmother had the most backhanded way of delivering compliments. She was always saying things like, “You look so much better than you did the last time I saw you.”

What in the world does she mean?we were always wondering. What did I look like the last time?Her compliments always left us confused rather than proud.

WHEN YOU PUT YOURSELF out there, whether it’s by delivering a speech, acting in a play, or putting out a collection, you want feedback that’s positive, or at the very least helpful for the next time.

If you want to stay friends with people who put themselves out in this way, it’s often necessary to deliver vague praise that doesn’t actually address the specifics of the production. Examples include: “Congratulations!” or “That was quite a performance!” or “I’ll never forget that!” or the classic: “Oh, you!”

I find myself in the position of delivering a lot of these euphemisms. My favorite is “That was unforgettable!” For the right reasons? (Pause.) Repeat: “That was unforgettable!”

IT’S VERY IMPORTANT TO be totally honest when it comes to things that can be changed and that must be changed. As you know, I am passionate about education. When you expect a lot out of children, they will rise to the occasion. Education is so important, and I love when I see children at a school that’s right for them. Having a great teacher can change a child’s life. And while I know how busy parents are today, I love seeing families doing their best to support their schools and work as partners with their children’s teachers.

“Make it work” applies to all areas of life. If there’s something you hate about your school, or your neighborhood, or your child’s sports team, make it work! Get involved in the PTA, contact your representatives in the government, or offer to assistant coach.

Too many of the parents I dealt with in higher education seemed to feel that they had to start a fight to get what they wanted. As the chair of the Fashion Design Department, I was the enemy. If the students didn’t have top-of-the-line resources or materials, it had to be my fault. Well, I was working incredibly hard to improve those things and was making great strides, but with no help, things take a while. What I always loved to hear was, “We need to get the students X, Y, and Z. What help do you need to make that happen?”

It wasn’t like I didn’t know. Frequently, I would disarm students and parents by saying, “You’re right. There is a problem there.” There is no reason to try to hide things; it doesn’t work! I could tell the complainers, “We need this amount of money added to our budget in this area,” or “We need a contact at this organization to get this grant.” If others besides me were advocating for something, it tended to happen much faster than it otherwise would have.

They would expect me to be defensive, but I would say, “You’re right. We need to fix that. Here’s why we haven’t fixed it so far, and here’s our plan to get it done.”

It gets a little trickier when you start talking about faculty. I couldn’t really say, “You’re right. She’s a lousy teacher.” It used to be that you could say, “This isn’t working out,” and let someone go. But when a faculty union arrived at Parsons, I couldn’t even use those sobering words, because I was “threatening” them. I asked, “Who are we serving? Answer: the students. If they’re being disadvantaged by a teacher’s failings, we’re at fault.”

Furthermore, under the new union guidelines, once a teacher had been there for a while, it was all but impossible to dismiss her.

I had one teacher who was a real problem and who was approaching the deadline after which we couldn’t let him go without a great deal of work. So I spoke to the Legal Department and I spoke with HR, and we were all in agreement that I could do the deed after the semester’s grades were posted. We had meetings. We were all set to go. And then both departments backed down. I said, “This appointment shouldn’t have been made to begin with, and I made it. I regret my mistake. Now we have an opportunity to get out of it, and you won’t stand by me?” I had a responsibility to the students. Ironically but thankfully, I left a month later to join Liz Claiborne Inc.

When I used to give tours of Parsons, it was a real dump. I would proudly talk about all the positive aspects of the school and would avoid mentioning the poor facilities. With some frequency, parents would say, “This places looks … crummy.”

Antagonistic tour takers would make me crazy. Sometimes they’d be especially rude, and I always thought, What if your kid winds up going to this school? He’s going to be the Son of That Jerk from the Tour.

But the ones who asked why the building looked so bad had a point. For a long time, I would try to ignore it, like that W. C. Fields line, “Get away from me, kid, you’re bothering me.”

Finally, I realized I had to address it, so I turned it into a joke. I would say, “I’m sure you’ve noticed the state of our building. Well, this didn’t happen overnight. It took years and years—and years—for us to get it to look this way. Ha-ha.”

It didn’t lessen the amount of peeling paint, but at least people would laugh. And it gets directly to my point about the monkey house. If you’re going to live in one, you at least have to keep reminding yourself that it still does stink!

Know What to Get Off Your Chest and What to Take to the Grave

“GET IT OFF YOUR chest” is one of the all-time worst clichés. If you have done something shameful, the logic goes, you should confess and be forgiven.

Hold it right there. Think about it. Would revealing your mistake hurt others? If so, then hold your tongue. It may make you feel better to tell someone you’ve cheated on him, for example, but it makes the other person feel miserable. That’s not fair. He did nothing wrong, and yet he has to suffer while you get to feel cleansed.

I know a woman who said of her husband: “If he cheated on me, I would hope he had the maturity to keep it to himself. Let him suffer with the secret. It’s his penance for doing what he did.”

I’m with her. You hear people say, “I’ll feel better if I tell my spouse I was unfaithful.” Of course youwill. But maybe you’re not supposed to feel better.

On one Project Runwayhome visit, I was struck by how the designer’s parents’ divorce was still weighing on her. Her mother and father had been separated for years and years and came together for the occasion of this home visit to celebrate their daughter’s success.

I thought that was lovely, but I also felt so sorry for the designer’s mother. She was reminding her daughter of what her father had done, and you could tell she was still suffering years after the fact. Then the father walked in, happy-go-lucky and carefree. Clearly, when he revealed to his wife that he was a cad, he felt purged and had his catharsis. Meanwhile, his wife was destroyed by it.

That’s why “getting it off your chest” isn’t necessarily a good idea.

As you probably know, if you are familiar with any recovering addicts, those in twelve-step programs like Alcoholics Anonymous typically try to make amends to those whom they have hurt. But in my experience some people don’t pay attention to the second part of the step: “Make direct amends to such people wherever possible, except when to do so would injure them or others.”