Mfcttrf

My company has a tool that they use for requesting & providing feedback from others in a respectful & productive way (for both positive & negative feedback). It has a list of standard questions, like "What am I best at?" and "What can I improve at?".

Using this tool is highly encouraged, and my impression is that senior management are pushed even more to use it.

One of the senior people in the company recently requested my feedback. This coworker is 3 levels higher than me and manages the relationship with our company's biggest client. Since I'm one of the people tasked to work on that client initiative, I've had a very nice amount of interaction with him & exposure to how he operates.

My feedback for him is mainly positive - He's excellent at his job & a good communicator usually. However, I'm aware of a big flaw (which I don't think he fully realizes). This feedback request is the only potential opportunity to make him aware of his issue, but feedback is not anonymous and I don't want to strain our great relationship.

The problem is that he tends to say jokes (usually an attempt at lighthearted teasing) which often get taken the wrong way by people. I've worked with him enough that these are rarely misunderstood by me, but I've seen him say things to people I work with, and some of them have confided in me that they thought he was putting them down or making them look bad in public.

For example, one junior employee (I'll call him Bob) has a neutral expression that looks like a slightly frowning face, unless you work with him alot, in which case you know its just neutral. (Whether Bob should work on that facial expression or not is separate from this question). Since Bob is junior, he doesn't always have anything to add to meetings (very normal & expected in the context of those meetings).
During one of those meetings with 9+ people of all levels, this senior person threw out a comment saying: "Hey Bob, why don't you speak up ever? You seem way too excited about what's going on!"

Based on my experience with this senior coworker, I believe he was simply trying to make a light comment to help Bob feel relaxed & willing to participate if he disagreed with anything. Although the comment itself isn't so bad, the delivery of the line was said in a way that made myself (and others in the meeting) fall uncomfortably quiet for a minute, with forced awkward smiles.

Bob told me afterwards that he felt majorly put on the spot, highly uncomfortable, and wondering if he was doing something wrong (which he wasn't). Having been in the meeting, I wasn't surprised to hear that he felt that way.

Should I mention this in the feedback note (even though it's not an issue for me?)

If yes, what's a respectful, kind, & clear way to phrase this (while making it clear that I personally don't misunderstand his comments usually)?