CJ Mahaney, from his book Humility: True Greatness:
Paul teaches us that encouragement is the effect of appropriate words — “as fits the occasion” (Eph 4:29) — appropriate to the person I’m seeking to serve.
To effectively encourage or edify a person I must know something about that individual, which comes through studying the person, asking questions, and carefully listening.
That’s what we’ll do if we’re trying to truly serve others with our words and not simply impress them. From what we learn about others, we’re able to answer this question: What do they need now? Is it counsel? Exhortation? Warning? Comfort? Forgiveness? All of the above?
And here’s a helpful expansion on what that looks like:
In 1 Thessalonians 5:14, Paul urges us, “Admonish the idle, encourage the fainthearted, help the weak, be patient with them all.”
So we have to walk carefully here. Are they weak? Because it would be unwise for us to admonish the weak, and just as unwise to help those who are idle.
So what is their present circumstance? Are they experiencing a test of adversity or a test of prosperity? What season of life are they in? No matter what their situation, there’s something we can say to bring them encouragement.