How to find the perfect thing to say in every situation

Your colleague had a baby, and congratulations are in order! But wait – the delivery was very difficult, and there were complications. Now what do you say? Or maybe your boss is leaving your company and you want to strike the right balance of thoughtfulness, professionalism and humour in your farewell message. It’s hard enough to know what to say in happy situations, let alone tricky ones. In almost any situation, a basic “Congrats!” or “I’m so sorry” follows etiquette rules and can suffice when the other person is just an acquaintance, but it often doesn’t feel like enough – especially if you are close to the person or want to build a closer relationship with them.

Rule No 1 of knowing what to say for every occasion: say something. The top etiquette mistake people make when trying to find the right thing to say is getting so hung up on finding the ‘perfect’ response that they end up saying nothing, says etiquette expert Valerie Sokolosky. “We’ve all been there! I can’t tell you how many times I’ve stumbled over words, trying to find just the right combination of witty, intelligent and original – and I’ve written whole books about this. It’s not easy, even for the pros,” she says. “But people don’t need a perfect Hallmark quote. They need to know you care – and there are lots of ways to communicate that.”

In both happy and sad situations, your perfectly imperfect ‘wish’ needs just three things, according to psychotherapist, Dr Fran Walfish. It should:

Be appropriate to the situation

Reflect your relationship with the other person

Share a heartfelt, funny or sincere sentiment

No novels or dissertations required!

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We often don’t know what to say when the situation is out of our experience or comfort zone, but that is exactly when we do need to say something. “Silence leaves the other person feeling isolated,” says Walfish. “You can simply offer to listen and let them know you’re thinking about them.” Sokolosky adds that it’s OK to admit you don’t know what to say: “Just be honest and then focus on your love and/or concern for them.”

Rule No 2 of knowing what to say in every situation isn’t actually about speaking – it’s about hearing. Have you ever been thinking so hard about what you’ll say next that you realise the other person has stopped speaking and you have no idea what they just said? This fixation on speaking over listening is one of the most common communication mistakes that people make, says Walfish, and it’s a recipe for saying the wrong thing.

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“Knowing the right thing to say has everything to do with being a good listener and very little to do with being a good speaker,” says Walfish. “Take your cues from them. Ask questions, preferably open-ended, about the situation. Once you know how they’re feeling, it becomes much easier to know what to say.”

People like to know they’re not alone, in the good and bad times, says Sokolosky. Share their feelings with them, like “I’m so happy that you’re so happy!” or “My heart breaks with yours.”

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Sincerity always trumps flowery words, says Walfish. Being overly syrupy or effusive comes across as inauthentic or, worse, like you’re making fun of them. That said, something as simple as “I’ve always admired your work ethic,” “I can see your happiness shining through your smile” or “You’re smart and strong” can take a basic message to the next level, says Sokolosky.

Avoid saying things like: “I know everything is going to be just fine,” “Time heals all wounds” or “Everything always works out great for you!” First of all, those things are often not true (and how would you know anyway?), and they invalidate the other person’s feelings or experiences, says Walfish.

Not excited for their promotion and not jazzed about working with them more closely? Don’t say it! Offering fake sympathy or false congratulations hurts you and risks hurting them as well. And you can forget brutal honesty – that’s usually just an excuse to be rude. “There is usually a way to say something both kind and authentic,” Walfish says. In the aforementioned scenario, for instance, you can say something like: “Congratulations on your job promotion – you worked really hard for it.”

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One way to show a feeling you don’t know how to speak is through a thoughtful gift. It doesn’t have to be anything big; it just needs to be appropriate to the situation and bring a smile to their face. When in doubt, food and flowers generally work.