For a word of encouragement to be valid and helpful, it has to be honest. The word encourage can be broken down to mean: put courage into. That’s the essence of what encouragement is. Good encouragement builds a person up, giving him a new sense of boldness and confidence.
However, there’s a vast difference between building someone up with true encouragement and propping them up with patronizing fluff.
Recently I was the guest speaker at an event, and before I got up to preach, a band played several worship songs. As I took the stage, I said what any good guest speaker would say: “Thanks band, that was wonderful.”
Only it wasn’t wonderful. It was mediocre at best. By saying that it was wonderful I wasn’t encouraging anyone. I was just being political and slightly dishonest.
I immediately wished I hadn’t said it.

It’s not that I think I should have taken it to the other extreme by being tactless:
“Guys, you need to practice more. That was a poor rendition of those songs, and it was a little painful to have to sit through. We’re all breathing a sigh of relief that it’s over. Amen, church?”
And I know I’m not going to hell for saying it was good when it wasn’t, so don’t think I’m trying to be melodramatic here.
It’s just that several of my staff members were there with me, supporting me, and they heard me say “that was wonderful” when it was nowhere near wonderful… and we all knew it.
Next time I tell them they did something wonderfully will they believe me? Or will I have slightly devalued the weight of my words, causing them to wonder:
Did he really think that was good or is he just saying it?”
I don’t ever want to just say it, I want to mean it. If I can’t mean it, I’d rather search until I find something I can say that I really mean.

It is right to offer encouragement and praise liberally. I don’t believe you should withhold encouragement from people so that it will “really mean something” when you do tell them they did a good job.
But encouragement that isn’t rooted in truth at the core isn’t encouragement at all.