Make Conversations People Love

There is no secret sauce to reaching people with the things we say. There is only authenticity and awareness.

Think about the best piece of advice you ever got. More than likely you still remember it because of its simplicity and sincerity. Chances are, unless you were talking to my inebriated Uncle Shorty, it also actually made sense for your life.*

When you think about it, great conversations are a lot like great advice. We feel most helped when our viewpoint is understood and valued. Great communication just boils down to one person showing another person that they matter. And regardless of the language you’re speaking in, you at any time and at every moment of connecting with other humans can make conversation great. “But how TIM, how?!!!” , you ask.

Well, first of all let’s chill on all those exclamation points. The succinct and yet witty numbered section is coming up!

  1. Clarify it please

Misunderstanding what someone says can feel uncomfortable. Sometimes we have the tendency to feign understanding in an effort to be nice. But if you don’t understand what Billy is saying, you put yourself in the corner of responding with “Hmm. Okay. Un-huh. Mad dope. Yup. I got you. Agreed.” When in reality you’re thinking “Did he just say illiteracy was funny? He’s evil.” If you’re not following, just stop the train by saying something like

“Oh wait so are you saying that…”


“Hold on, I want to be sure I understand what you’re saying. So you think that…”

You can interrupt people when you don’t understand. Just be sweet about it and let them know you’re only interrupting because you really care about what they have to say.

2. Keep the questions a-coming

I’ll take questions I should be asking for 300 Alex! I often think about how cool it would be to win Jeopardy. I’d be all like “Who is Kanye West?” and Alex would be all like “Yup! You got it! You win a million dollars and a recording session with Yeezy.” And I’d be all like “Yes. I deserve this.” That has little to do with this next point, but I’m sharing it anyway because I have dreams.

So you know how silence can feel bizarre at times? I’ve seen plenty of adult humans run for dear life from the silence in a conversation. Well TLDR: you don’t have to run. You can maintain the flow of conversation and show a person you care about their viewpoint by asking questions that dive into why they think or feel the way they do.

Some of my favorites include:

“Where did this idea come from?”

“What inspired you to go in this direction?”

“Which character of Fox’s hit show ‘Empire’ do you relate to the most?”

The truth is that we are quick to ask surface questions that feel as least invasive as possible, which is fine when you’re in an elevator with someone you don’t want to be in an elevator with. But when it comes to engaging with a human you actually like, you can go there.**

Going deeper into someone’s reasoning is a great way to find common ground, and it really goes a long way in letting people know that it’s okay to feel welcomed and accepted around you.

Also, just as long as you’re not asking about what’s in their bank account/love life/medical chart then you’re probably good on the nosey front.

3. Fake is a four letter word

I’m probably dating myself but remember that cute little 10 year old robot Vicki from “Small Wonder”? Remember her? Yeah, I despised that robot. She always creeped me out. So devoid of emotion. So robotic. Bleh. Scary.

From time to time we all have that little feeling in our gut that tells us not to be too real, or too vulnerable. But human connection is about vulnerability. That doesn’t mean that you have to tell your Barista Tameka about that time you had that mad case of hemorrhoids. (She’s being nice for the tips playa.). But what it does mean is that you have to have a certain level of openness, of vulnerability to reach people in a meaningful way. When was the last time you talked about something you feared? When was the last time you told someone about a crazy project you’re investing tons of time into that you’re not sure will even end up being a thing? Talk about those things once and awhile. And as equally as important, offer a space where other people can talk about those things too with you.

“What’s something you’re really looking forward to this month?”

“You know there is one thing I’m really looking forward to this month. And you know what that is? Falafels.”

“I put a lot into this presentation. I really hope our team will get it.”

“I know you put a lot into that presentation. How are you feeling about it?”

And there you have it folks-the TIM guide for making conversations people love. You now owe me $19.99. Ha, just kidding. I don’t want any money yet, but when I’m officially launched, I’ll definitely take all your coins, hontea.

Check back soon for more articles about awkwardness, human connection, and mad communication.

TIM out.

*This man told me I could save my money on stamps by putting the intended recipient as a return address. Bless his heart.*

** I only like about 7 out off 600 humans maself.”

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