The Cliques Never Really Went Away
I have been thinking a lot about the “cool kids table” from high school.
I did not sit there.
The cool kids knew me, but I was not invited to their parties. I was not picked on, and I was not some total outsider either. I lived in the middle. I knew people in a lot of different groups. My main circle was not even a defined clique. We were just a group.
I like to believe we were welcoming.
But if I am honest, we had our own walls too.
That may be why the metaphor still sticks with me all these years later. High school had obvious cliques, obvious insiders, and people who were clearly left out. But even the less formal groups had boundaries. Some were spoken. Others were silent. Either way, people usually knew where they stood.
We like to think we leave that behind when we grow up.
I am not sure we do.
In business and in communities, there are still cool kids tables. They just look more polished now. They show up as private dinners, curated events, invitation-only circles, job-title sorting, wealth sorting, political sorting, and social circles built around status and access.
And to be fair, not all curation is bad. Sometimes people gather around shared interests, similar responsibilities, or common experiences. That can be useful. It can even be necessary.
But when every room is curated, something important gets lost.
Serendipity disappears.
Collision disappears.
The kind of unexpected conversation that changes how we think, who we trust, and what we imagine becomes far less likely.
If CEOs only spend time with CEOs, if investors only break bread with investors, if sales professionals only talk to sales professionals, if founders only gather with founders, if lawyers only stay around lawyers, then we should not be surprised when perspectives get narrower and communities feel more fragmented.
A company does not reach its full potential when leaders are only listening sideways to their peers.
A community does not reach its full potential when influence is concentrated in rooms full of people who already know one another, agree with one another, and live at the same altitude.
And society certainly does not get stronger when the people with the most access slowly drift farther away from everyone else.
This is one reason I keep coming back to Human Interaction (H.I.) as the antidote to all problems. Community, collaboration, and conversations are more important in today’s tech driven world.
In a world moving faster and becoming more digital every day, we need more than efficient communication. We need more real contact across levels, industries, and lived experiences. We need leaders who are willing to walk around, not just sit at the head table.
Years ago, Tom Peters popularized the idea of “leadership by walking around”. It was smart advice then, and it still matters now. Good leaders do not lead only from conference rooms, board meetings, or private gatherings with designer bourbon. They lead by being present. They mingle. They ask questions. They listen to people who do not have the same title, background, income, or worldview.
That is true inside companies.
It is also true in communities.
The healthiest cultures are not built only through strategy. They are built through interaction. Through chance conversations. Through being accessible. Through showing up in rooms where not everyone is just like you.
Too many people today want every gathering to be optimized. They want to know exactly who will be there, what the ROI will be, and whether the room contains the “right” people.
But some of the best opportunities in life and business come from curiosity with no destination.
From talking to someone outside your lane.
From sitting with people who see the world differently.
From listening without an agenda.
From being willing to leave your usual table.
This is not an argument against ambition, success, or excellence. It is not a criticism of people in tech, or people with money, or people with influence. But it is fair to say that in our current culture, wealth and status often function like the cool kids table did back in school. People notice where power sits. People notice who gets invited in. And people notice when the same circles keep deciding who matters.
Leadership should be bigger than that.
Real leadership is not about protecting access. It is about expanding it.
Real leadership is not about curating every conversation. It is about creating conditions where unexpected conversations can happen.
Real leadership is not about staying comfortable with your peers. It is about staying connected to people.
Real leaders show up.
So maybe this is worth asking:
Who is at your table?
Who never gets invited?
Who have you stopped noticing because your world has become too curated?
And when was the last time you chose to be in a room where the value was not obvious in advance, but the human connection was real?
The cool kids table may never fully disappear. Human beings have always sorted themselves into groups.
But strong leaders can choose not to worship that model.
They can walk around.
They can intermingle.
They can create more room for collision, serendipity, and trust.
And they can remember that healthy communities and strong companies are not built by guarding the table.
They are built by making it bigger.
If you want a stronger culture, start by asking who is missing from your table.
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*** This article originally appeared on Thom Singer’s LinkedIn blog titled “Uncommon Connections” in March 2026.
Thom Singer is a keynote speaker on the topic of human interaction and the power of business relationships, trust, and engagement. He is also the CEO at the Austin Technology Council.