One of the things you likely dread (loathe, hate) about the holidays is not so much seeing the family, but fielding any number of triggering questions that set you on your heels, flare your defenses, and bring your blood to the boiling point.

And that’s because sitting down across from relatives who haven’t seen you in a while means facing up to their often innocent (though sometimes not) questions, but also, to who you are, where you are, and whether you’ve progressed from, well, the last time you sat down from them.

Questions like,

So, are you still with what’s-his-name?”  (Read: Have you dumped him yet?)

Aw, where’s what’s-his-name?” (Read: We liked him more than the others.)

That’s too bad it didn’t work out. Seemed you two got along.” (Read: I know nothing about your relationship but it seemed good to me.)

“You still at that job?”

“Have you found a job yet?”

“You still single?”

“Have you set a date yet?

“When are you going to have kids?”

“When are you having another kid?”

I won’t even get INTO any of the ribbing, barbs, or flat-out aggression that revolves around sports, religion, or politics.

Here’s the point: Every great conversation begins with a good question. The problem is, we so often lead with lousy ones.

Sometimes it’s because people wield questions with an agenda (to incite, to offend, to ruffle). But, to be fair, often that’s not their intention—or yours! Because sometimes it’s you asking the same-old questions, not because you’re a jerk, but because the questions themselves are knee-jerk; you ask them because you always have.

It’s time to change it up.

Let’s stop poking at the same old sore topics, triggering each other’s defenses or boring each other to death.

Newer, better, more complex questions can bring out the best, most interesting stuff in the people you already know. Most of our questions are about status updates, and to some extent that’s fine. But when’s the last time you learned something totally and utterly NEW about the people you’ve known for decades, maybe your whole life?

I believe good questions aren’t just key to better dinners, or dates, (which they are, by the way), but the only way to get at the best, most interesting part of you, no matter what you’re trying to do.

Whether that’s “get along with my mother-in-law”—or give a talk, or explain to someone why they should work with you. Literally, any of those things.

And so to that end, I want to give you some good questions to use during this very social season, and you should feel free to use them liberally—at cocktail parties, at dinners, on first dates, in prepping for client meetings, the talk you’re giving at that upcoming event or conference.

I curated 25 good questions (get that collection here) but for now, let’s start with three good ones:

  • What common bit of wisdom do you hear a lot but that you completely disagree with?
  • When in the past year have you done a total 180 on a thing, and why?
  • What’s one thing you always thought you hated or would hate, and you now love?

Like these? Get the curated collection I created, 25 Questions to your TED-worthy idea, right here.

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