How asking questions makes you a better leader


I’ve been fortunate enough to work with a few brilliant leaders so far in my career. And one common thread between them is that they ask questions. They don’t shy away from seemingly obvious questions. They aren’t afraid to be considered the dumb one in the room. Sometimes the simplest questions can uncover much more than the “smart-sounding” ones.

At the creative agency where I currently work, Ueno, we like to say to our clients “you know some things, we know some things, and together we know a lot.” Basically what we’re saying is that we’re no experts in the industry of every company we work with. But we are experts in digital design, marketing, and user experience. Our clients typically know much more about their business than we ever will. That’s where the together piece comes in to make real magic.

It all sounds great, but in reality it can be difficult to convince clients that the discovery phase, where we get to know our clients and their business, is absolutely necessary before we can begin working on a project. They wonder why they hired us to sit around and ask questions all day. Well, that’s the best thing we can do to get to the real problems that need to be solved. And someone who isn’t an expert in the business can uncover things that need to be clarified for customers and users, who probably aren’t experts either.

For example, if a client comes to us asking for an amazing website to sell their product — great! But if they have no idea who the product is for, well, that’s a problem. Our work together, no matter how beautiful it may be, will never be truly successful unless we are solving the right problems. That’s where the questions come in.

Early in my career I was afraid to ask any questions. I was certain that I’d be asking something people already knew by default, or something that would reflect my lack of experience or understanding. But by watching some brilliant people at work, I’ve realized that you shouldn’t assume everyone already knows the answers to what you’re wondering (chances are, they probably don’t). I was amazed at my CEO’s unabashed ability to ask the simplest yet most crucial questions, and to say “I don’t get it” whether he’s talking to a fellow CEO or a janitor. Now, I believe that if I don’t understand it, there is likely someone else in the room who doesn’t either. Even if there isn’t, I won’t be able to contribute effectively to the team unless I get what’s going on.

It’s amazing how simple questions can throw people off. It sometimes reveals the fact that even the founder or CEO really doesn’t know what he or she is talking about, and they are using some fancy words and run-on sentences to cover it up. Sometimes it just means the company needs our help clarifying these answers for their users or customers.

By now, you get the point. Ask more questions and don’t apologize. Even if they seem simple or unintelligent. You will be a much more valued person in the room when you uncover the problems, and get answers to the questions we were all wondering about. And by providing clarity to others, you will emerge as a leader in the room.

Oh, but here’s the kicker. You have to be a good listener, too. And that is a whole different blog post.

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