Maybe it was the greeting cards industry in America that watered down what “encouragement” means. Now, it means something between “comforted” and “cheered up.”
What it really means is the impartation of courage.
If you are trying to bless someone who actually needs a well-fluffed pillow and a nice nap, by all means offer to help them into that. If the person has been assaulted by something or abandoned by someone, has just been told they have cancer, been fired by their 30 year employer, or some similar promise of misery has been dealt to them, they probably need courage. So, give them some of that!
Remind them of their prophetic words. Remind them of Yahweh’s everlasting never failing unquenchable love. Pray for them, then and later. Check on them tomorrow.
Remind them that they are awesome, and that the real battle is what this lion or bear is preparing them for – something like Goliath.
Aim at their courage more than their comfort. If they get courage, they are likely to find comfort. If they only get comfort, but need courage, they won’t likely have either soon.