Surf Roots, Software Thoughts

I’ve always been the type of person that asks a lot of questions. I used to be very weary of asking questions in the work place, though, because I was scared of annoying my coworkers/superiors. A lot of times I would hold back if I was worried a certain question would be better unsaid. I was especially careful when I worked in e-marketing at KB Home the summer after my sophomore year, because the office politics there were strange. The Art of Project Management, a book Matt recommended to me, has really given me a new perspective on asking questions and the benefits of doing so.

Another motivation behind this post came from my family’s Hanukkah party last night, where I spoke with lots of family and friends about what to do next year. I’m trying to decide between an engineering internship with Google in Shanghai and a full-time PM position with Redfin. I think there are a few different scenarios where the usefulness of questions really shines:

Your boss tells you to do something
It’s usually the case that your boss is busier than you, especially when you’re interning. It’s also usually the case that when your boss assigns something to you, he (or she) will accidentally leave out details because he is in a rush or he has his mind elsewhere. Naturally, you should ask questions to get that missing detail out of your boss to avoid not fully meeting his requirements. It usually comes down to one choice: either ask questions to clarify the problem or risk misunderstanding some portion of the problem. Depending on the context, you might be able to refine the problem without nagging your boss, but I think asking questions and potentially being annoying is much more important than working towards the wrong goals. I know if I were a boss, I would rather have the people I manage take up a little more of my time to understand the problem in its full than have them spend weeks or even months with the wrong goals in mind. (Hopefully I’ll never be a boss that just tells people what to do — I’d rather work alongside those whom I manage.)

You and your colleagues are brainstorming
Whether it be brainstorming the solution to a technical problem, the solution to a dilemma (such as where to work), or the way in which a certain product should function, it’s often the case that the people around you have opinions. Asking questions in these cases does a number of things:

First, questions get people talking. In my experience, more people are introverted than extroverted, and questions will get the introverts to voice their opinions. With more spoken opinions comes more likeliness that synthesis of those opinions will lead to a positive conclusion.

Second, answers to questions provide a new perspective for everyone listening. It’s often the case that the people you associate yourself with are as smart or smarter than you, and it’s often the case that they see things slightly differently than you do. Answers to questions can solidify your opinions if your colleagues’ perspectives are in line with your thinking. Answers can also make you realize that you’re thinking about things incorrectly if your colleagues’ perspectives don’t line up with your thinking. I believe it’s important to realize that these new perspectives can often times be insanely valuable.

A friend of mine once said that the job of a CEO is to synthesize, decide, and delegate. I wanted to capture this process in a little diagram to show how questions fit in:

Perhaps the most important thing to realize here is that the more synthesized information you have, the more concrete your decision will be. That’s not to say that synthesizing information is easy — I think that the process of synthesizing information deserves a lot of explanation that should perhaps be discussed in a later post. I would also argue that questions are one of the most important aspect of synthesized information, because answers to questions open up the opportunity to have lots of different experiences, readings, and other things coming from different people. Also, synthesizing and deciding are common tasks in challenging jobs, so the above diagram doesn’t necessarily only apply to CEOs.

So, don’t let yourself get intimidated about asking questions in the office. If someone gets annoyed, then tell them that you’re just trying to make sure you have a grasp on the situation. Also tell them that they’re not helping you synthesize. It’ll be awkward and funny at the same time. With all jokes aside, though, questions are super important and should be taken seriously. Try to ask good, concise questions, and the answers will only help. In fact, they’ll probably help a lot.

Update: Bo Bennett agrees.