Tell Me More: The Small Invitation That Changes Conversations

As soon as Halloween ends, the clocks fall back, and the calendar flips to November, there’s an unmistakable energy to this time of year. I feel it every season.

The air gets cooler, and I get to break out my sweaters, hot chocolate, and marshmallows. Every family has its traditions, and ours is no different. We plan quality time together, look forward to meals shared and memories made, and fill the calendar with friends and family, commitments and chaos, obligations and over scheduling too. At times it feels rushed and relentless, as the sudden flood of festivities surrounds us. It is the unmistakable energy of this time of year.

I guess now that my kids have grown, I’ve realized that the secret to enjoying this time of year is to make more meaning out of less time.

I know what you’re thinking: Michelle loves a paradox! 

Think of my Big Ideas, Small Words series. https://www.nextchaptercoaching.org/post/big-ideas-small-words-vol-iv

Well, it’s true. I won’t deny it. I love the idea that more can come from less.

And here’s the kicker: connection is built into the season.

Whether we like it or not, everywhere from Starbucks to Target reminds us - ’tis the season to celebrate something. Sure, there are trees, lights, and candles. But there are also candid conversations, genuine connection, and moments to cherish together.

The simple things are often the most extraordinary.

So, what if this season we focused a little less on doing more and a little more on connecting? What if we made the conversations we’re already having more meaningful?

The Season of Catching Up

November brings familiar questions.

“How are you?” “How have you been?” “What’s new?”

We ask these questions as we reconnect with friends, gather around the dinner table, see extended family, or catch up with someone we haven’t seen in months.

And often, before the other person has finished answering, we’re already preparing our response. We’re thinking about what we want to share, a similar story we can tell, or the next thing we need to do.

We mean well. We’re busy, we’re excited to see one another, and there’s a lot to catch up on. But sometimes, in our eagerness to participate in a conversation, we miss the opportunity to really connect. We can be in the same room, sharing the same meal, and still miss what matters most to the person sitting across from us.

What if we slowed down just enough to hear what someone is really saying?

What if, instead of rushing to respond, we offered two simple words:

TELL ME MORE

Attention Is a Form of Generosity

I’ve spent more than twenty years working as a casting director, watching people reveal themselves through stories, choices, and the way they show up in a room. Now, as a coach, I’m still interested in the same thing: what makes people who they are, what matters to them, and what helps them feel seen. One thing I’ve learned is that people don’t always need us to have the right answer. Often, they need us to be genuinely interested in their answer. That’s where attention comes in.

Organizational psychologist Adam Grant explores the science of connection in his book Vibe: The Secrets of Strong Connections in a Lonely World. One of the ideas that stands out is that meaningful connection doesn’t require us to have everything in common. It grows when we become curious about another person’s world and move beyond surface-level small talk. In other words, we don’t have to be alike to connect. We have to be willing to learn about one another.

That may sound simple, but it asks something of us. It asks us to pause our own stories long enough to make room for someone else’s. To listen without immediately comparing. To be curious without trying to fix. To ask a question without needing to steer the answer.

Attention is a form of generosity because, for a moment, we give someone the gift of our presence. And in a season when everyone seems to be rushing somewhere, that gift can mean a great deal.

Three Levels of Listening

I often think about listening in three simple ways:

1. Listening to hear.

We hear the words. We follow the conversation. We know the general outline of what someone is telling us.

2. Listening to understand.

We become curious about what the person means. We ask questions. We listen for what matters to them, not just the facts of the story.

3. Listening to connect.

We pay attention to the person behind the words. We make space for their feelings, their experiences, and their perspective—even when it’s different from our own.

All three have a place. But the third invites us to do something more than exchange information. It invites us to build a relationship.

Think about the difference between asking your adult child, “How’s work?” and asking, “What’s been the most interesting part of work lately?”

Or asking a friend, “How was your trip?” and following up with, “What was the moment you’ll remember most?”

The first question invites an update. The second invites a story.

And stories help us understand one another.

The Small Invitation: “Tell Me More”

“Tell me more” is one of my favorite invitations because it doesn’t assume we already know the whole story. It says: I’m interested. I’m listening. There may be more here than I can see right now.

Imagine a friend tells you she’s thinking about making a change at work.

You could immediately offer advice, share what you would do, or tell her about someone who made a similar move. Or you could pause and ask, “Tell me more. What’s making you think about a change?” Maybe she’s frustrated. Maybe she’s excited. Maybe she’s afraid to leave something familiar. Maybe she’s been thinking about it for years and is finally ready to say it out loud. You can’t know until you ask.

And the same is true at home.

When a family member shares something that surprises or concerns you, it’s easy to jump into problem-solving mode. We want to help. We want to protect the people we love. Sometimes we want to make the uncomfortable part of the conversation go away.

But advice offered too soon can close a conversation before it has really begun.

Try asking:

• “What was that like for you?”

• “What feels most important about this?”

• “How are you thinking about it?”

• “What do you wish people understood?”

• “Tell me more.”

You don’t need a perfect question. You need genuine curiosity.

And remember, “Tell me more” is an invitation, not an obligation. Connection also means respecting when someone isn’t ready to share.

A Little More Curiosity. A Little Less Assumption.

We think we know the people we love because we know their history. But people change, and their perspectives change, too. What if we asked, “Can you tell me a little more about that?” instead of assuming we already understand? We don’t have to agree with someone to be curious, solve their problem to support them, or have an opinion about everything.

Sometimes, the most meaningful thing we can do is stay present.

It’s not about standing out with our insight or advice. It’s about standing with another person.

Making More Meaning Out of Less Time

As the season gets busier, I’m reminding myself that meaningful connection doesn’t require a perfect holiday, a beautifully set table, or an entire afternoon free of distractions.

Sometimes it happens in the kitchen while the coffee brews.

Sometimes it’s a conversation in the car.

Sometimes it’s a phone call that lasts five minutes longer than planned because neither person is ready to hang up.

And sometimes it’s sitting across from someone you’ve known your whole life and discovering something new.

We can’t always add more time to our days. But we can be more intentional about how we spend the time we have.

This November, try a small experiment. In one conversation each day, resist the urge to jump in with your own story, advice, or solution. Ask one more question. Leave a little more space. Be willing to discover something you didn’t already know.

You might be surprised by what opens up.

Because the goal isn’t to have more conversations.

It’s to make more of the conversations we already have.

And perhaps that’s one of the simplest ways to celebrate this season: less rushing to respond, more willingness to understand; less assumption, more curiosity; less time spent trying to say the right thing, more time spent really hearing one another.

So, as you gather with friends and family this season, consider this your invitation:

Tell me more.

Then listen.

You may find that the smallest invitation creates room for something extraordinary.

As we head into the holiday season, I hope you find moments to slow down, connect, and make meaningful memories with the people who matter most.

I hope we can stay connected, too. And I’ll leave you with one of my favorite sayings:

How do you spell love? T-I-M-E.

My wish for you this holiday season is simple: more time to connect, more moments to cherish, and more opportunities to remind the people you love that they matter.

Wishing you a meaningful November and a holiday season filled with connection, curiosity, and a little more room for what matters most.