Q: I’ve had a new boss for about six months who means well but is the epitome of “this meeting could have been an email.”

He goes over the same things multiple times, tells me his vacation schedule when I have access to his calendar and messages me asking things he should be able to figure out himself. Yesterday, I asked him for something from a system I don’t have access to. He called me over to his desk to explain his thought process and showed me some unnecessary stuff before finally sending me what I asked for.

Basically he likes to hear himself talk, needs his hand held and thinks I need mine held as well, and it’s become overwhelming. I like to keep to myself. I feel like he doesn’t respect my time. I’m having a hard time finding a balance between respecting my boss and setting boundaries. Any advice?

A: What you’re dealing with is at the heart of every return-to-office versus remote-work power struggle right now. On the one hand, you’ve got the process-focused, let’s-talk-this-out collaborator; on the other, a leave-it-to-me-I’ve-got this problem solver. Both have their place and purpose, both are valuable, and both will inevitably be paired up and drive each other bonkers.

Your power dynamic makes things tricky. When the person you report to is the person impeding your progress, you have to tread carefully. Failing to mask your impatience, or rationing your responses to his half-considered queries in the hope he’ll find his own answers, could be perceived as disrespectful and uncooperative.

Some reasons your boss may feel the need to confabulate everything to death:


– He may still be learning his way in your work environment.

– He may have a neurological processing difference/insecurity/anxiety/compulsion that requires him to verify in person that he’s gotten his message across.

– His repetition may be as much about reminding himself as informing you.

And finally:

– Maybe you’re just a smarter, faster thinker than he is.

I realize that I’m doing the same thing as your boss, rattling on about clock design when you just want to know the time. But if one of the above explanations clicks with your sympathies, it may help defuse your annoyance.

Replacing “he doesn’t respect my time” with “he can’t help himself” can put you in a better frame of mind when you try to gently rein him in, as follows: After he cycles through an explanation, repeat it in a condensed form, and then say, “I think I have the gist. How about if I start on it and get back to you at [future time] with a status update and any questions I have?” Translation: I hear you, I understand what you want, and I’m eager to get started on it.

After you’ve repeated this process a few times and delivered your usual great results, your boss should, ideally, start to trust that you know the work and are best left to do it. Eventually, you may get to the point of being able to head off his filibusters with a bright “Yep, got it.”


That is, of course, assuming he’s capable of change and can pick up on feedback without taking offense. If he truly does value the sound of his own voice over results, there may not be much you can do to make working with him tolerable.

As for his habit of asking needless questions, think of the following scenario as an example of how not to handle it.

Q: I was on a contract with a team of 60 or 70 people in a client’s large facility, including “Rachel” (also a contractor) and “Lisa” (an employee of the client, same rank as Rachel and me).

One day I needed to discuss something with Rachel. The only other person in the room was Lisa. I said, “Lisa, do you know where Rachel is?”

Lisa said, “She’s there.”

“Where is ‘there?'”

“Where would she be?”

Finally, after I’d asked eight or nine times, Lisa vaguely motioned toward an office off the room we were in and said, “She’s in that office.”

Lisa had clearly known where Rachel was all along and held out on me for no apparent reason. Even if she had a valid reason for not telling me where Rachel was, the appropriate response would have been, “She’s unavailable,” not a bunch of evasions. After the incident, I made a mental note that if I ever needed to find someone who was out of the room, I wouldn’t ask Lisa. Do you have any insights on this exasperating situation?

A: I can imagine any number of motives behind Lisa’s uncooperative response: She didn’t like you; she was distracted; she had been asked all day where other people were and was tired of being used as a personal tracking service. Whatever her reasons, the power dynamic leaned in her favor as a full-time employee, so there wasn’t much you could do about it.

In any case, you learned that Lisa is not a helpful resource, and you’re better off relying on yourself. Mind you, if conveying that lesson was her goal, she could have saved you both a lot of frustration by pleading total ignorance.