How do I work with a boss who’s always testing me? Elaine Varelas offers advice

Working with a boss who seems like they're testing you can be frustrating. Why are they doing this? And if you want to try to talk with them about it, how do you approach it? Elaine Varelas offers advice on how to communicate and find a process that works.

Ask the Job Doc.
Ask the Job Doc. –

Q: I work in desktop support and my boss is always testing me. She waits for me to begin researching solutions before telling me she knew the answer in the first place. I’m not sure if she’s trying to figure out how good I am at my job, or if she wants to flex her experience over me. How do I help her understand that offering development prior to resolution could improve the way we work with our clients and teach me things more quickly?

A: How frustrating for you to be working hard and then having your boss tell you that she could make your work easier but chose not to. Why your manager is choosing this behavior is a mystery. Is she insecure, and trying to remind you and others she knows more than you do? This manager may feel threatened by you and the experience that you have. She’s not doing a great job developing her team. A manager should not stand by until her team solves everything themselves; they should, instead, add value by giving them a clue or some direction, which could in turn enhance their ability to learn, save time, and make you and your clients more productive.


If in fact she thinks doing the research and learning to solve the problem on your own is the best form of development for her team, then someone needs to remind her that she doesn’t then need to tell you that she knew the answer all along.

Maybe your boss is waiting for you to ask a question even as you take the assignment. She may want to know you have the ability to think critically about your job, the task in front of you, or that you understand the assignment. Try asking something like, “It sounds like it’s this, this, and this could be causing the problem, do you have any experience in those areas?” or “I’m going to research the following three areas before I go, am I missing anything?” You don’t want to necessarily ask her to solve your problem, but double-checking to see if there’s some quick direction that she can provide can reaffirm your abilities and give her a chance to offer support. You may not want to do this every time you get an assignment from her, but asking clarifying questions is smart before you take on any work.


You might want to have an entirely separate conversation on what she thinks the process would be if it ran perfectly and smoothly. This gives you the opportunity to find out if she expects you to ask the clarifying questions, to do the research on your own, and what kind of information she wants back from you at the end of the assignment. You could then come up with a process the two of you can agree works well for both of you.