My boss is an introvert and has a slightly unusual character. It looks like he can't disagree or say no to people when they bring an issue to him.

I overheard him a couple of times agreeing with one side of a conflict when they complained, but then also agree with the other side if they approach him. Basically, if you bring him an issue, he will agree with you, and only after some time will he finally tell one of the sides to do something differently or settle out, etc.

As for me, it is fine if he acts like this, but as my career is growing I understand that it is important to make sure I'm watching what I'm saying. For example, when my boss agreed with one of the parties, I knew that when he quickly agreed, it was wrong and not professional, and I don't want to act like this in the future.

Basically, if I talk to people who bring me issues, I don't want to upset them much, I want to resolve a conflict and I don't want to support their view if it is wrong. How do I handle these three? Also, how do I develop a skill to make sure I'm watching what I'm saying and not gossip about other people?

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    You're saying that he's ultimately settling the issue but simply agreeing with everyone at first? That sounds pretty good to me. He's accepting everyone's opinion, thinking about it, then notifying the parties of his decision. What is wrong with that? – Dan Aug 2 '18 at 14:08

A few points.

If this question gets closed as being off-topic for the Workplace stack, you could try again over at Interpersonal.

It sounds like it's more your manager that needs to learn a new skill, namely to not just bend and agree with whoever is in front of him, but to take a moment to create their own opinion and stand by it.

Having a manager who bends as easily as this seems to me a recipe for Bad Stuff happening. Either, at one point he's going to "automatically" (and possibly baselessly or incorrectly) agree with somebody to your detriment. Or, his inability to take a stand will be detrimental to the department or company. When that happens, how will he react, and how will this affect you and your career?

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  • Thanks, as for now when it happrns it only upsets me, b.c. I have feeling he is taking sides and need to grow a lot – Mark Aug 2 '18 at 14:32

To monitor yourself, just monitor yourself. Keep notes. Say a coworker approaches you and asks you whether you think it's a good idea to X or not. In a paper notebook or (better) something digital and searchable, write today's date and:

A asked me if I thought it was good to X. Based on their use of C and D, and the planned move to T, I thought it was too much effort for the limited payoff.

Then put it out of your mind.

This will have several advantages. If you find yourself in a meeting where an angry person is yelling at A "why on earth didn't you X?" and A is all "Dan said not to!" you can say "yes, I did, [open notes and find it] on August 3rd, because you said you were using C and D and moving to T soon." And then if any of that is not right, the situation should resolve more quickly.

Also, from time to time you can look through it to see if you sometimes appear to take contradictory positions by agreeing with whoever is talking to you. You are literally "watching what you say" because you are looking at several days or weeks worth of saying all at once to look for patterns.

I find this kind of note-taking both personally enlightening and professionally useful. I tend to be the one who knows how long something has been under discussion, or what we did about this last time, or who objected and more importantly why. Detailed quick note-taking (usually, but not always, afterwards when others aren't around) is the key to that.

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How do I handle these three? Also, how do I develop a skill to make sure I'm watching what I'm saying and not gossip about other people?

I find that the best approach to deal with what your describing is the 10 second rule. By that I mean, wait to respond to any non basic/lame question 10 seconds before responding. This way instead of some knee jerk potentially harmful response, you allow your brain time to process the input/question, and to articulate a helpful response.

Also remember, sometimes its perfectly acceptable to say "I don't know" or "I am not sure". Both of these are better than an harmful or incorrect response.

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