When the Boss Questions Your Every Move

How to Manage a Micromanaging Boss

Posted Aug 18, 2013

“Is that really going to work?” “Are you sure of your numbers? Is this really what the client wants?” “When does the printer repairman arrive? Are you sure it’s broken? It would be nice if you could do your job without a barrage of questions, driving you to fantasize about hiding under your desk. But take heart, you can mitigate endless boss questioning.

Why do some bosses have more inquiries per minute than a curious toddler? Does your manager feel you’re not competent or seem like a control freak? There comes a time when your micromanager must be managed – by you.

Here are some Do’s and Don’ts for dealing with bosses who have more questions …than answers.

Dealing with the Endlessly Questioning Boss


Hold Back. Guard Information Closely. When your boss asks questions, respond, “That’s on a need-to-know basis.” Suggest that a vast trove of data exists in your office, but that you are unwilling to share it. Tell your curious manager that for proprietary and career indispensability reasons, you keep a small circle of “insiders.”

Do This . . .

Over-Inform. Make it a habit to routinely send updates to your boss, such as weekly e-mails. Anticipate questions she might ask. Organize regular meetings designed to keep your questioning boss in the loop. Where insecurity lives, micromanagement thrives. If things get out of control, sit down and ask how you can engender a greater comfort level with your work product.


Research Everything Asked. Work incessantly to answer every one of your manager’s questions, especially rhetorical ones. If your boss says, “I wonder if sending the proposal by Pony Express would have been more personal than an e-mail,” immediately conduct a Web search to determine the actual cost of that shipping method.

Do This . . .

Keep Your Focus. Remain fixed on overall business goals. Your toddler-like boss may ask questions that inadvertently distract you. Although you’ll need to acknowledge his inquiries, redirect his focus toward the pressing business tasks at hand. When he ponders, “What would it be like for productivity if we painted the office in a dark teal?” consider: “That’d be interesting. Speaking of interesting, what’d you think of the client proposal I sent you this morning?”


Fight back. Respond to irrelevant questions in a loud, aggressive way. Begin shouting: “That is one lame question!” Then turn the tides. Ask: “Why don’t you Google the answer to that?,” “Were you a curious child as you grew up?,” “Why is the sky blue, and really what is the meaning of life?” There are a number of responses you can get—some shorter than others.

Do This . . .

Force a “Mind Chuckle.” It’s okay to laugh off endless questions (as long as you do it in your head!) A little humor can reduce some of the stress of the questioning barrage. Keep a mental tally for a day of the number of legitimate questions your boss asks you - versus the number of unanswerable questions. You may find internal humor in your boss’s endless ruminations. When appropriate, however, try some external, polite levity—you’d be surprised how it can shift the dynamics.


Freak Out. There's nothing more fun than dusting off your drama skills and making a scene. If you’re surrounded by a pack of senior managers in the break room, create a crisis. As questions torpedo toward you, just fall on the floor, flail around and speak in loud, unintelligible phrases.

Do This . . .

Stay Calm. Not every inquiry requires an answer. Sometimes, a question just needs an active listener because the boss wishes to vent or think things through. If your supervisor’s questions are designed to play devil’s advocate, for example, listen politely and engage in some non-committal small talk. In other words, you can sometimes enable your boss to answer his own questions.

Points to Remember

• Preemptive answers are the best way to curtail endless questioning. Take the initiative; the more your boss knows in advance, the less he will pester you with questions—and the more he will trust you.

• Constant questioning can often be held off by regularly scheduled briefings. You’ll also have your ducks in a row.

• Give some thought to what’s behind all the questioning. Not every question requires an answer.

• Use an internal “Levity Lens” to see the TOT/toddler parallels, and remember, a light-hearted comment can often disarm rapid-fire questioning.

With some strategic efforts on your part, your micromanaging boss’s persona will likely shift from untrusting, to: “Well it seems you have things under control. Do you have any questions for me?”