What does it mean to make your boss look smart? At a basic level do a good job. Beyond that you want to make things on your boss’s wishlist happen. Fix a bug that is low priority but your boss wishes he could get it done now. Refactor a class that your boss or the lead engineer has mentioned being frustrated with. Don’t make the mistake of fixing something that you think is broken. Focus on things that you know your boss is frustrated with not things that you are frustrated with. This is not to say that you shouldn’t fix the things that you are frustrated with, but do not expect to be rewarded for fixing your frustrations instead of other people’s frustrations. The reward for fixing your own frustrations is that you are not frustrated anymore.
At the Vice President and director level bosses want to see proposals that align with their strategy. If machine learning is a market area of interest to the VP, make a proposal that uses machine learning to fulfill a business goal that either makes or saves money.
Learn when to shut up. If you disagree with the strategy find a new job. You are an employee you don’t get to have public opinions on strategy. If people want your opinions you will be promoted to VP or get a fat consulting contract.
Make proposals that align with the strategy or wishlist. Don’t worry about stuff that doesn’t fall in those categories because it’s probably not important to the business. And if you see an iceberg you should be looking for a new job not wasting time sounding the alarm. Tell your direct boss about the problem and wipe your hands of it. Unless you have a substantial equity position in the company it’s not your problem.
If you don’t know what is on your boss’s wishlist, you don’t know your boss well enough. Start getting to know your boss better this week.