Most employees and freelancers tend to be one of two extremes:
- The enthusiastic type that runs at doing whatever they’re told. (Note that I love working with people like that—among my favorite types!)
- The stonewalling type, who is the precise opposite, where nothing seems to happen with him. Note that the stonewalling personality has many forms, from the well-intentioned but easily overwhelmed, to the lazy guy down the hall who does nothing.
It’s an art to find the right balance between the two because each has its downside. The downside of the latter type is self-evident. But the downside of the first type is that it’s fundamentally low value: it not only makes you less valuable, but it’s also more work for your boss or client to do what you’re not doing. (Of course, the first is still far preferable to the second; the second type gets fired eventually; the first type never gets fired but never gets promoted.)
Here’s the balance I like to strike between the two extremes: always asking my client or boss “Are you sure?” and they’ll usually respond with a yes but showing a small amount of doubt, “I think so” or “it’s my best guess.” And then just thinking it through with them for a bit. Doing that usually uncovers bigger issues. But then, once thought through, and agreed to, you’d be fully running with it, intensely and enthusiastically. I try to be careful where I jump, but when I jump, I jump.
An easy example is if your client asks you to create a logo and that that logo should include X, Y, or Z, or maybe the logo should adhere to technical specifications Q, R, and S. By asking, “Are you sure?” he’ll often give other key details that he just hadn’t thought to say before. “Well, I think so. I asked for this size because we’re going to use these images in AdWords, and I think that’s the size needed?” You see how the natural response to that question adds more color that helps you make a better design? Or, “Well, I asked that the logo has sunglasses just because I think it would look good” which gives you the key requirement that he doesn’t actually really truly want sunglasses per se, but he just doesn’t think it looks good enough.
Sometimes, it’s just the simple and small questions that give you the key information. Knowing the “bang for your buck” questions are key for great work. Some of these are general and discussed in this series, but many are very contextual depending on your role, your type of work, and your personality—and only you can figure out what those questions are.
