When I was in my early twenties there was a group of us who used to get together to play a board game. It was called "Scruples". In this game of moral dilemmas you were given a scenario and a yes, no or depends card. The dilemma in the scenario card needed to be matched with another of the game's players who would ideally answer yes, no or depends to the situation given. As for strategy, you could be honest in your reply, or alternatively you could play Devil's Advocate to stop someone else from winning. If you chose the latter option, you had to have a good reason for choosing the way you did and your rationale would be open to inspection/ridicule from the other players. A straight, or poker face was also a useful weapon, the first sign of a smile and people would know you were lying.
There are times in life when full fledged honesty is a choice that has to be made. The whole concept of white lies, or lies that don't hurt, came about from the desire to protect someone from a harsh truth. It has also been utilised to avoid saying what is truly on your mind. The downside is that sometimes by shielding someone from a truth makes that same truth doubly hard when it is eventually heard.
The rights and wrongs of absolute honesty is a conundrum for the ages. Biblical stories suggest that Peter denying knowing Jesus Christ was an act of self preservation in the face of betraying beliefs and principles. Such extremes show people to be shallow and untrustworthy. Yet in answer to a wife's question "Does my bum look big in this?", what should the husband say?
Sycophants, blithely agreeing with a boss to allow themselves the favour that may or may not come from that, are possibly self delusional but it's hard to deny them their choice when you look at the potential rewards that come from that sort of behaviour. Alas, if the superior is at fault, the wave of support can blind one to the reality and prudence of the situation. Nazi Germany, anyone?
So who amongst us hasn't wanted to tell a superior when they're doing something wrong? Sometimes blunt facts are the perfect broadside when leaving a job as you have no immediate reason to be wary of the words you chosse. But what if you're not leaving and still need to get your point across? A superior who doesn't want to hear the truth because they may not like it needs to look inwardly at themselves. I have seen 360 degree feedback used as an effective tool in this kind of situation. But it still comes down to the choice of words that one uses. A person who chooses to deliver information without considering the impact of what they're saying, shouldn't be surprised at the outcome, especially if in future they need something like a reference etc.
This is where diplomacy and tact join the party. These two guys allow us to pick and choose not only the words we use, but also the time and place in which we use them. Therefore it is possible to still tell the truth but also fall short of being considered impertinent. Alternatively, a good leader would encourage honesty, yet still to be delivered in a thought out manner.
As I said earlier, I guess it boils down to personal choice...