THE BRAZEN CAREERIST- Question your questions: Your career depends on asking them

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. And maybe all my writing is actually about my obsession with a good question. 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. 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. 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 with unintended consequences

Melissa Mansfield asked me to write about 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.


Penelope Trunk has started several companies and worked for many more.