How often do you find yourself in a situation when you have to say something to a person which might often him/her...or strain your personal relationship...yet you got to say it to accomplish a goal or motive...or to avoid or to rather prevent future conflicts.
I have found myself in such situations quite a few number of times..the latest one being very very recent..I wouldn't like to mention the incident at this point of time though. In such a situation where I cannot avoid not saying because it would complicate things and my thoughts/feelings regarding that further, I look for a suitable environment or time...before meal or after, morning/afternoon/evening/night..then comes suitable mode of communication...verbal/written, letter/mail....face to face/phone...and finally the exact words to be said...and the tone of course... In short, all rules of communication are applicable... Believe me it's a very tough job...
One more situation common with me is when I'm intolerably angry and pissed off with someone...have carried/subdued my anger for long enough and I'm at no peace! And I have to let out my anger and convey my feelings to that person...Normally I am patient and wait till the time I can bear no more. There also I need to plan my words to reflect my feelings!
Although such situations can be tricky especially when it is difficult to say how the other person will take it an d react..The closer the person is to you, more difficult it becomes... It is also awfully difficult with friends because high chances are there that he/she would be offended enough to draw swords with you. Yet I have realized that such times need to be faced if unpleasant consequences (in the long run) are to be avoided...Sometimes we just cannot afford to be all goody-goody and allow to be made a fool...