When Your Boss Won’t Stop Questioning Your Every Move

Some bosses can’t stop asking questions. “Why are you doing that? Will this really work? Are you sure? Why do you think so?” A barrage of this type of questioning makes many people feel that their bosses do not trust them. It’s like taking care of a curious toddler, but it’s not cute when it’s your boss. Here’s how to handle the situation.


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A healthy work environment is one in which people may ask each other questions and learn from each other. This is a two-way street: workers and managers may ask each other questions and keep lines of communication open. However, it is dispiriting and distressing when bosses question you on every little thing.

Constant questioning is an especially toxic form of micromanagement. It sends the message that you are incompetent. My personal least favorite is, “Are you sure?” If I wasn’t sure, I wouldn’t have suggested it/done it.

To survive in your job, remember these three techniques:

1. Communicate

When somebody is upsetting us, it’s easy to clam up and wait for them to go away. This is the worst thing to do with your question-happy boss. Better to overcommunicate.

Answer every question as it is asked, even if it seems as obvious as, “Yes, 2 + 2 = 4.”

Be willing to let your boss know what you are doing and why at every move. This strategy may make the boss feel more secure and he may stop barraging you with questions.

2. Stay Focused

Lynn Taylor at Psychology Today agrees that this type of boss should be communicated with at length, but warns workers not to go the extra mile of researching the boss’s endless questions. Better to keep your focus.

Remember what your business goals are, and don’t let your boss’s questioning throw you off-track. For example, you schedule a meeting right after lunch with a client. Your boss says, “After lunch? Gee, I wonder if it would have been better to schedule it right before lunch.”

Bring the focus to the reason for meeting: “We need to talk about X for Y reasons at the meeting.”

3. Use Humor

Use humor to maintain your own sanity. In your own mind, keep a tally of legitimate and unanswerable questions. Or picture him as an actual toddler.

Just keep your coping mechanisms to yourself. Even friends who don’t work directly with you could turn out to be networking connections some day. You don’t want them to think that you generally make fun of the boss.

Finally, keep in mind that it’s not personal, but most likely just a quirk of personality that has nothing to do with you. Best practice is to do your job well, don’t let his seeming lack of faith in you get you down.

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