A reader writes:

I am a middle manager who works with an employee I’ll call “John.” John does not report to me, but there are scenarios in which I supervise aspects of John’s work and am in a position to give him feedback.

John has a lot of experience (he’s been doing his job about as long as I’ve been alive), but at times he doesn’t know what he doesn’t know. He reacts defensively to most disagreements/feedback and regularly gives staff feedback and suggestions that directly contradict what managers have told them to do. He also is willing to die on pretty much every hill (let’s say we were making teapots with flowers painted on them and each flower had six petals; John would loudly and publicly insist it is CRUCIAL that the flowers have seven petals, to the point of making a scene in front of his peers). There have been times when I have had to pull John aside to discuss this behavior.

One thing John does in those conversations drives me bonkers. He will insist I don’t understand his argument, and then say some variation of, “Repeat back to me the point I was just making.”

This feels so condescending and I hate it. I recognize I may be sensitive to this in part because of the gender dynamics (he is a man and I am a woman, and he has done this with other female managers). It feels like he is a professor who is scolding his student.

On the other hand, I don’t want to overlook something I could improve in our interactions simply because his behavior gives me the ick. I now try to summarize his points early on in the conversation (“what I’m hearing you say is…”), but somehow we still usually end up with him pushing me to repeat his argument back to him. It almost feels like an attitude of “Clearly you don’t understand my point, otherwise you would agree,” but of course I don’t know for sure that that is his intention.

What can I do to help improve the quality of our conversations without being a pushover?

Ugh, yes, he sounds condescending.

There are times when it can make sense to say something like, “Can you tell me your understanding of my concern, so we can spot if something is getting lost in translation?” And when I’m managing someone and assigning work, I’m a fan of, “To make sure we’re on the same page and I didn’t miss anything, can you do a quick summary of next steps?” (The latter can be really helpful because managers sometimes think they’ve been clear about their expectations and then are shocked to discover that the other person came away with a very different understanding.)

But the minute there’s any whiff of any condescension in your tone or manner, this will stop sounding collaborative and start sounding obnoxious. And it doesn’t sound like John is doing it in contexts where it would make sense; as you say, it sounds more like he implying, “Maybe you aren’t smart enough to understand what I’m saying.”

Since he clearly thinks this is an acceptable way to communicate, I’m curious what would happen if you start doing it back to him to  level the playing field. The next time he asks you to repeat back his point, do it — and then say, “And now I’d like to ask you to repeat back the point I was making too, so we can ensure we’re both understanding each other.” Do this a few times and he might dislike it enough that he’ll stop doing it to you. Or who knows, maybe it will result in improved communication on both sides, which would also be good!

There’s also the option of simply telling him how it’s coming across. For example: “I get the sense you’re asking me to repeat back your point because you assume I must be misunderstanding or I’d agree with you. That’s not the case.” And maybe: “You’re coming across as very adversarial right now. Is that what you intend?” (You need to say this calmly and in a tone of genuine curiosity — don’t sound agitated or it loses its power.)

But also, John sounds like a tool and, if you haven’t already, it might be useful to share some feedback about his approach with his manager.