3 Tricky Questions Your Boss Will Ask and How to Answer Them

Our relationships with our bosses are always difficult. Even if our boss is a great boss- the sort that you can talk to just about anything, there’s always that awkwardness in the relationship that stems from the fact that they are in a more authoritarian position than you are. And because of that most of us are happy to have a friendly relationship with our bosses but nothing more than that.

See Also: Are you a Good Boss?

Yet our bosses seem unable to understand this dynamic and they always try to trick us into conversations we do not want to have with them, from office gossip to asking you to take on a project you so do not want to take on. It’s not always easy to know how to answer to your boss’s tricky questions, but this is what we are here for, the list below features some of the trickiest questions your boss is bound to ask you at one point or another as well as the replies you should have handy.

1. What’s Up With Jane?

Office gossip is inevitably a part of every employee’s existence, whether you like it or not learning personal information about your colleagues comes with the job description. And although you probably couldn’t care less that Jane just broke up –you do have your own drama to deal with after all- there’s no way to get out of finding all the gory details of Jane’s break up.

But what happens when your boss chooses you as their confidant and asks to find out all the latest gossip about Jane’s breakup? You can’t exactly say “it’s none of your business” to your boss and even if you don’t want to betray the secret vow of fellowship between colleagues every office has, you have to give some kind of answer to your boss.

The best way to go is to show your boss that you’re above gossip. Express your surprise that there’s something going on with Jane, with something along the lines “Oh, there’s something wrong with her?” and then proceed to change the subject into more work related matters. Basically, you just have to show your boss that you’re not interested in gossip and they’ll leave you in peace.

2. Am I a Good Boss?

Big Short

Umm, this is an awkward one isn’t it? If you wanted to be honest with them you’d probably show them the list you secretly keep with all their disadvantages but alas you can’t do that.

Bosses always think they are the greatest boss that ever lived for reasons that are beyond my comprehension. They have a tendency to believe that just because they pay us, or because they don’t yell or because they crack a few jokes on a daily basis, they are God’s gift to employment.

But because I’m sure you have a different opinion from your boss, hold your tongue and keep the feedback positive. Tell them a couple of things you like about their managerial style –invent some if there’s nothing nice you can say- and then just to get them off their high horse throw in a comment about something you’d like them to do differently. Pick something that won’t get you into trouble, but make sure that you say something that gets them thinking that they might not be as great as they’d like to think they are.

3. Can You Take On This Project?

Of course you can’t because you are already swamped in work and this project will add to the list of things that hold you from having a personal life, but what can you do when your boss asks you to take on more work? Saying no thank you won’t be taken well, and you don’t want your boss to start thinking that you are slacker.

Your response to this question will have to depend on the kind of the project; if it’s something that will showcase a whole new set of skills to your boss then it’s going to win you points with them and you definitely want to win points with them so, consider the possibility of actually taking the project on.

If on the other hand, this is a project that will add no value whatsoever to your work or you then be discreetly reluctant to take it on. Ask your boss when it’s due and list everything else you are currently working on so that they take a hint.

Bosses are the bane of every employee’s existence, but we must all deal with them if we wish to continue paying our bills. Understand what your boss is like and find ways to deal with their brand of weirdness and you’ll do great in the workplace, no doubt.

Has your boss ever asked you a tricky question? How did you respond to that? Share your experiences with us in the comment section below.