How far you get, in almost anything, is limited mainly by your ability to ask good questions.

The problem is that we are not taught to ask good questions. We’re trained to answer questions. But only answering questions doesn’t make an interesting life. After all, if you have all the answers, and you’re spewing them all the time, then you are not learning anything new.

Asking questions is how we get smarter. One of the earliest signs of a child with Asperger syndrome is that they fall behind in their learning because they do not understand how to ask a question. It doesn’t occur to them that someone would have information.

And maybe all my blog posts are actually about my obsession with a good question. For example, my recent rant about how blogs need topics is really about how a good blog is based on a good question. (My question is: how can we make the the intersection of work and life better?)

Today I’m going to focus on the kinds of questions that back us into a corner.

1) The question that asks: What is the meaning of life?

I think a lot about how people ask questions because I get them all the time. Often, the questions are so vague and poorly framed that I can’t believe the person actually sent an email. Here’s an example of one:

Hi Penelope,

I am from Bangalore India and an avid reader of your blog. I have recently quit my job at [big, international tech company] after working with them for many years. I would like to start something of my own but do not know how to go about it.

Can you guide me please?

Thanks for taking time out to read my mail. I will look forward to your response.

I sent a reprimanding email back to this person. In hindsight, I should have directed him to the post titled How to Write an Email that Generates a Good Response. Instead, I told him that there is no answer to this question. The question is so vague that it is not actually a question but a plea for respite from the inherent difficulties of adult life.

2. The question that reveals that you don’t care.

The questions that are most interesting are ones that create a conversation. My friend, Marci Alboher is great at these questions, because I love the conversations we have, even though she never likes my answers.

One of the most frequent mistakes people make in a job interview is when you switch to complete BS when the interviewer asks, at the end, “Do you have any questions for me?” Face it: the best way to ask questions in an interview is to ask them the whole time, not just at the end, so you can create the conversation that the interviewer needs so she can learn that yes, you are the right person with the right ideas for this position. If you wait until the end of the interview, it’s obvious that you don’t care—you have already had your conversation, based only on you answering the questions and having nothing to contribute on your own.

3. The question that generates an answer you can’t cope with.

I like to think that I’ve learned to be great at asking questions. I spend days dreaming up the perfect question for my mentor who I haven’t spoken to in a month. I want to make sure I ask a question that is interesting, and engaging to him and useful to me.

And I hear so many bad questions that I think I have become immune to asking them.

But it turns out that I’m not. Because I knew I was going to have a hard time getting myself to write a blog post today. Last year, I’d often go five days with no post. But that was when I was CEO of Brazen Careerist, and traveling every week, and also worrying that the company had no money.

Today I have a relatively calm life. The company is going great, and there is a new CEO, and my job is to write this blog, be a thought leader about the workplace, and talk to the press. So I need to be posting more regularly.

I know that having a trick works for me, from days when I can’t get myself to go to the gym. Like, I tell myself I will go to the gym and just sit in the locker room and listen to my ipod and then go home. Invariably, if I convince myself to do that, I don’t actually stay in the locker room. I end up doing some sort of exercise.

So I thought of a trick for blogging. I told myself that I’d make a game of it. I asked my Brazen Careerist chat group (sign-up required) for a topic. I told them I’d write about the first three topics people suggested.

But here’s what happened: I didn’t like the topics. Well, some of them I liked a lot. Like, Karen Gaustad and Mara Lunaria both asked why we link to Facebook profiles from Brazen Careerist. It’s a good question, because I talk all the time about how Facebook is a network for personal –and often unprofessional — aspects of your life, and Brazen Careerist is for building your professional network. So I actually don’t know why we link to Facebook. I keep asking Ryan and Ryan and they say something which I will summarize like this: Wait. Hold it. I can’t even summarize what they say, because I can’t remember exactly, but I think it’s something like “You’re too old to understand” but I don’t want to write that.

Okay. So I asked a good question that generated good questions in return. But I don’t like that question. I try to spend my life not hiding from hard questions. You’d think it’d be the abortion stuff that flummoxes me. But I’m pretty clear on how I feel about that. Why to link to Facebook, though? That’s a tough one.

4) The question that has unintended consequences.

Melissa Mansfield asked me to write about how companies that are highly ethical and also highly profitable. She will think I didn’t write about this topic. But I did. Because we can’t control companies. We can only control ourselves. So I’m always more focused on how I can change the world personally than how I can try to require institutions to change the world.

The thing is, though, that ethical workplace behavior is based on asking good questions. They lead to honest conversations and meaningful connections and the world of good behavior is build on relationships like these.

Not that every good question leads to a great relationship. The world is not perfect, of course. Because sometimes you ask a question that reveals only that the person you’re asking is useless.