How to strengthen your relationships by asking good questions

Hey there,

I’ve been trying to reach you about your car’s extended warranty.

No, I’m just kidding.

I’m here to help you improve yourself! In my opinion, that's cooler than a car warranty.

Anyway, we have a great message today that has been key to my growth in relationships. I’ve gotten closer with friends and family because of this…

And I’m confident you can too.

I don’t know about you, but I hate small talk.

The classic “What do you do for work” or “Where are you from” or even “What is the meaning of life?”

Maybe not the last one, but you get the point.

You see, I’ve never been great at small talk… My talents lay elsewhere.

Not to toot my own horn, but I think I’m pretty good at big talk.

Actually, that's probably not the right word for it.

Let's use “deep talks.”

If you read the newsletter I sent out two weeks ago, you already know this. If you haven’t, I’m only slightly devastated.

Either way, the question we’re answering is this:

How do we build strong relationships through deep talks?

The answer?

Asking good questions.

Let me show you how:

Open-Ended Questions: Think of these as your magic carpet to a whole new world of conversation. They're the questions that can't be answered with a simple "yes" or "no", but instead, invite people to share their thoughts, feelings, and life stories.

Do ✅: "What's the craziest adventure you've ever been on?"

Don't ❌: "You didn't get arrested on that adventure, did you?"

Active Listening: This is not your regular "in one ear, out the other" listening. It's about absorbing their words, understanding them, and bouncing back a response that shows you're not just physically present, but mentally and emotionally invested too.

Do ✅: "It sounds like you have a real passion for vintage cars. What got you started on this?"

Don't ❌: "Sure, you love vintage cars. Did you start when dinosaurs roamed the earth?"

Empathy: This is like putting yourself in their shoes, except you don't actually have to wear their probably-not-your-size-and-maybe-not-even-your-style shoes. Just try to see things from their perspective when you ask your questions.

Do ✅: "That sounds really tough. How did you handle that situation?"

Don't ❌: "So, you got fired. Ever thought about not messing up?"

Non-Judgmental: Leave your judge's gavel at home. Your questions should create a zone of acceptance, not an interrogation room. Their answers should be met with understanding, not a scorecard.

Do ✅: "You mentioned you enjoy reading graphic novels. Which one is your favorite?"

Don't ❌: "Graphic novels, really? Isn't that just comic books for grown-ups?"

Relevance: Make sure your questions are in sync with the conversation's rhythm. They should dance along with the topic, not step on its toes.

Do ✅: "You mentioned spending a year in Spain. What was your most memorable moment there?"

Don't ❌: "You lived in Spain? Cool. So, do you believe in Bigfoot?"

Patience: We all need time to process, like a good cheese or a fine wine. Give them the space to think and respond.

Do ✅: Wait for them to fully answer before moving on to the next question.

Don't ❌: "So, your favorite color is...? Never mind, do you like dogs?"

Follow-Up Questions: These are the breadcrumbs that lead you deeper into the conversation.

Do ✅: "You lived in Italy? What was the most unforgettable experience you had there?"

Don't ❌: "You lived in Italy? Ever run into the Pope at the supermarket?"

Personal but Respectful: It's great to get personal, just make sure you're not trespassing on their private property. If they start pulling up the drawbridge, change your line of inquiry.

Do ✅: "What's a life lesson you've learned that you hold dear?"

Don't ❌: "So, when was the last time you cried?"

Positive Language: Keep your questions sunny-side up. A positive spin can turn any conversation into a joyride.

Do ✅: "What's something you absolutely love about your job?"

Don't ❌: "How often does your job make you want to pull your hair out?"

Honesty: Be real with your questions. Genuine curiosity is like a boomerang – it always comes back to you in the form of engaging responses.

Do ✅: "I've always been fascinated by astronomy. Can you tell me more about your research?"

Don't ❌: "Space stuff, huh? You believe in aliens?"

Woah.

That’s a lot of information.

I hope you’re still with me. If not, give me 30 seconds to go over the most important points…

Here is what you need to know:

1. Be genuinely interested in whoever you're talking to, whether it’s a friend, family, or colleague.

2. Listen to understand, don’t listen to respond. Stop thinking about what you’re going to say next when the other person is talking.

3. Ask relevant follow-up questions. Keep the conversation flowing and don’t let it turn into an interrogation.

4. Answer questions yourself or share personal stories that relate to what they’re talking about. This makes others feel understood.

These are my four pillars of asking good questions.

You may ask, why is number one highlighted?

That's because it’s the most important. If you get absolutely nothing out of this newsletter, at least try to understand number one.

An important note before we sign off for today:

There is still a place for small talk. We don’t just go up to people and ask them to share their deepest darkest secrets.

If you do that…I’m a little scared of you, to be honest.

Let deeper topics come up naturally and ask questions that prompt deeper responses (without being pushy).

That’s all for this week’s post.

I truly believe that asking good questions is one of the most important skills you can learn.

Yes, it’s a skill. And yes, you can learn it with practice.

My weekly challenge for you is this:

Ask a friend or family a deep question.

It doesn't have to be crazy, just slightly more in-depth or personal than usual.

If you don’t do the weekly challenge, then your lame.

Don’t be lame.

Keep making progress. Change for the better. Live the Heming-way.

See you next Monday,

Trevor