The worst career advice I ever gave was to my brother’s college roommate, Robert Buckley. He was one year out of college when he asked me if he should quit healthcare consulting to become an actor.

I said, No, that’s the dumbest idea I ever heard.

He told me he thought he had talent, and then (like I wasn’t against the idea enough) he told me he was dating some girl he met in Vegas, and she is going to be an actress, and she said that he had talent.

I actually questioned how my brother could be such good friends with someone who was so stupid. I tried to be patient, but mostly I told Rob that everyone in LA has a girlfriend who thinks he has acting talent. I thought maybe his best career move might be to find a girlfriend who was impressed with his healthcare consulting talent.

But really, he did not think he had any future in healthcare consulting. So I became a largely useless advisor to him. And then my brother forwarded me a trailer to Lipstick Jungle and there was Rob: naked, with Kim Raver. And he looked so good. Who knew? And more importantly, who knew I could give such poor career advice?

I think the reason that I gave such poor advice is that I had such strong preconceived notions about the acting career. But I actually don’t know anything about making it big as an actor. I only know that when I played professional beach volleyball in LA we were constantly surrounded by casting agents and entertainment industry types. And I learned that the competition to get anywhere in acting is so tough that you should buy lottery tickets instead.

It’s ironic, though, because I’m a writer, where the odds are not much better. And both actors and writers generally ply their trade because they love it, not because they think the odds are great. If someone asks me if they should become a writer, I repeat the advice I received in graduate school: No. Try anything else first. Writing is too hard.

And I was thinking the same thing with acting: No. Big no. But I needed to adjust my advice. I needed to be able to see when I was looking at someone who could not feel fulfilled if they did not do this type of work.

So every week I watched Lipstick Jungle (I loved it, by the way—for the writing, of course) and I thought about how I could have given such misguided career advice. And I figured out that the hallmark of a bad advisor is to not understand where she is coming from, what preconceived notions she brings to the table.

I didn’t think much more about this until I was in Menlo Park last week for the roundtable organized by Ben Casnocha and Chris Yeh. They posed questions to the group of entrepreneurial types: What makes good advice? What makes bad advice?

The answers were interesting, and each shed more light on why I gave Rob such bad advice. Here are some ideas that came from the group:

1. A good advisor asks good questions. Mostly in order to understand the goals of the advisee. No advice is given in a vacuum. Understand that an advisor can probably give you great tips on how to get to your goals, but really, the hardest part of making any decision in life is understanding your goals in the first place.

So your advisor needs to be very attuned to your goals and where you are in your life. This is why the best advisors ask questions rather than make proclamations. Often a good advisor is more sounding board and less Magic-8 ball.

2. A good advisor is a good listener. Advice is so much about understanding the particular situation that if she is not listening most of the time, then you are probably receiving advice based on incorrect assumptions that actually apply to a different circumstance. But it’s hard to listen when you are a subject matter expert.

In general, all situations sound the same when you give advice to the same types of people all the time. The trick for the advisor is to stop focusing on the similarities, which make her job easier, but to focus instead on the differences, which is more challenging—but makes for better advice.

3. Good advice is not fly-by-night. Advisors are best when they really know you, and they really know the arena where the issues live. So cultivate a relationship with someone who is a subject matter expert, and then he can give you ongoing advice that is relevant to your particular circumstances based on both what you are telling him, and on the relationship that provides a context for your questions.

Wondering how you are going to attract this kind of advisor? Be one yourself. Giving good advice is the same thing as giving a good kiss. You attract what you deserve. Not in a Secret sort of way, but in a way where if you are practicing good behavior then you will attract good behavior.

And, while I hesitate to give advice at the end of the piece about how advice should not be in a vacuum: You usually get in life what you expect to get. So expect good advice. And good kisses. And they will come.