Ask your boss the right questions

- One of the great underappreciated skills in the workplace is the ability to ask the right questions. When I was working as the New Hampshire Communications director on a presidential campaign, I had a staffer named Kumar who is a truly fantastic employee. Part of the reason was a question he asked. "What can I be doing that's most helpful to you right now?" Now, I had been an employee before and I'd never asked my boss that question. I had a clear idea in my head about what my job was and I was going to do that. But what I didn't realize and Kumar did was that you can make yourself uniquely valuable and appreciated if you show that you're not just willing to do the tasks you think you were hired to do but to go above and beyond in being helpful, knowing that your priority is taking things off your boss's plate and helping them, gives them existential peace and they'll be incredibly grateful to you. Another great question to ask is, "How should I prioritize that?" We talked a little bit about this in the video on managing expectations, but it bears repeating. If you don't know how your boss is ranking different projects, you're flying blind. You have no idea if you're working on the most important task or the 20th most important task. And even if you're working hard your effectiveness could be nil if you're not working on the right things. So be sure to ask upfront and often to see what your boss cares about. Then do that. Another great question to ask is, "Do you see anything I'm missing?" Here's why. Most bosses, except for the pathological micromanagers don't want you bothering them all the time asking them how to do something. They want you to figure it out. They want to give high level instructions and then you go develop a plan and execute it. They simply don't have time to plan it all out for you. So asking them to do so is counterproductive. However, it's always a good idea to get your boss's feedback and input before you're too far down the road. So a great compromise then is for you to come up with a written plan or a slide deck, if that's a relevant option, explaining how you plan to approach a given problem or project that you're working on. Then you can run it by your boss early on and ask, "Do you see anything I'm missing?" You're not making them do your job for you. You've come up with a plan, but you're also being inclusive and benefiting from their wisdom because they may indeed see some gaps that hadn't occurred to you. You get their buy-in and the idea improves too. Often in the workplace we think the key is having the right answers and looking smart, but the truth is we can often get further by asking the right questions in the first place.