Lots of people—me being first in line—have the instinct to always ask the question that’s on their mind. Including asking it to clients and bosses. Asking questions, overall, is a serious sign of competence, shows the fact that you’re thinking through issues, and overall is a key marker that separates the highly competent from the less competent.
But there is a particular case in which you need to be careful before you ask a question, when you’re not sure you want to know the answer to it.
This leads to obvious questions: “Why wouldn’t you want an answer? What are some cases in which you wouldn’t want an answer?”
There are a bunch of situations where this might arise. An important one is in a common and important case and involves asking for permission.
Let’s think through this situation. You truly believe that it’s in the best interest of the company to do a mockup of a new landing page. But you suspect that your boss or client won’t see or understand the value. As a result, if you ask him for permission, “Hey, can I do a mockup of up a new landing page?” if you suspect that he’s the type of guy that would not see the value in you spending 2 hours on it, only ask for permission if you’re prepared for a “no.”
But if you suspect that he’ll say “no” but he would actually appreciate the final product and/or the final product would be an improvement over the current landing page—then it doesn’t make sense to ask him the question. Just do it and show him the final result!
Look at it as a cost benefit analysis; in the best case he says, “this is great. I didn’t think it would be this helpful, but it is. You’re awesome.” And in the worst case, he hates that you spent time on that and he says, “next time, ask me for permission first.” In that case, you’ve learned a lesson, and you’ll need to ask yourself how come you predicted his response badly. Maybe in that case you’ll need to improve your modeling of his mind.
There’s a broader version of this insight, that—for me, at least—applies to life. Your great-grandfather made tons of money so you can be financially comfortable, so are you sure you want to investigate how he actually made it? There’s an old Latin observation, caveat emptor, “let the buyer beware” but perhaps we should have our own modification of it let the inquirer beware.
