Right speech in social situations

Find out what is really bothering the other person and give them an opportunity to be heard about that. We have two ears and one mouth, so Right Listening is more important than planning a response.

If you redirect the conversation away from external things and back to how the person is feeling and what they want, then you will be assisting them to re-see, which is the most important thing.

When I was a programmer, lots of people used to "chat me up" because I would listen with empathy. Usually I could offer some kind of suggestion that they tried which helped. After the conversation they would be more focused and productive. (I usually had to go to the "thinking room" and splash water on my face or go outside for a non-smoking break. Being the "Ship's Counsellor" is not easy work.)

Someone said, "90% of life is just showing up." If you work with others, then showing up for them in a clear and unconditional way, with attunement and congruence, will solve most problems to a large degree. Please seek out the book Becoming a Technical Leader by Gerald M. Weinberg and read the part called "The Payoff For Being Congruent" on pages 169-171. It could very well change your life, as it did mine. (But then, I am a Hetaira Archetype person, so I look for this sort of thing in striving to improve relationships.)

Antagonising a boss may bring difficulties, but this is exactly why it is very hard to break away from samsara, it is often too easy to fold, and compromise just this one time.

Dharma is not a magic formula that fixes all the problems of samsara, it merely teaches us to be okay with a hard landing if one's only choices are between soft quicksand, a rock and a hard place.

Perhaps there is a right time and way to tell him that you don't enjoy his gossip or a way to remain silent without giving offense, but it is also wise to consider that you may fail at this.

There's a Zen saying that the tiger needs to live in the forest to be safe, a tiger out and about in the town is quickly dead.

Merely awakening to one's true self may even seem easier in comparison to mixing nirvana with samsara.

There are several contemporary world leaders like the Dalai Lama, or Barack Obama who are in my opinion very skilled in saying the right thing to people at the right time, but they always have detractors. The Dalai Lama gets a number of negative comments on his social media posts, even if he is only saying something harmless and wise.

The Buddha too didn't attempt to make everyone happy.

It is naive to assume that merely because one is pure hearted, soft spoken and gentle one won't have detractors. Following right speech or right action is not automatically easy, there are tough choices to be made all through life.

The Buddha knew of several people who were angry with him, including his father at one time, and some of them regularly tried to harm or kill him, but this didn't stop him from doing what was correct.

People are quite attached to their world view and will not agree to change their views no matter what is said. In these cases silence maybe the best among available choices even if they all appear unsatisfactory.

When King Ajatasattu, newly coronated, meets the Buddha after killing his father King Bimbisara at the urging of Devadatta, the Buddha never brings up the topic of patricide; though it must have hung heavily in the air. Instead he speaks to him as if nothing had happened, telling him about the benefits of being a monastic.

See: Samaññaphala Sutta: The Fruits of the Contemplative Life

What if you replied, something like, "I'm sorry you feel that way"? If so then your talk with your boss would be about the boss' feelings, instead of gossip about the client.

Or ask, "Is he really so bad?" That would give the boss feedback that he is speaking negatively, and an opportunity to come up with a more balanced view.

Or turn the conversation to the boss' opinion about the business relationship, rather than the boss' opinion about the person.

If you know the client can you contradict the boss: "Oh I don't think he's so bad. He's always polite when I talk with him. He's a good customer. He pays his bills on time." or whatever?

If I read through the right speech guidelines a lot of them are about being timely (not an issue in this case sine it's the boss that decided when to bring up the subject), gentle, and not malicious.