Day 2: Connection Is the Leadership Skill of the Age of AI

The other day, a client asked me:

“How do I navigate networking conversations without feeling awkward?”

We usually start with tactics. Ask about something immediately relevant. The food. The space. The weather.

Then we move to strategy. Ask, “What got you interested in attending this conference?” Have a short story ready for when they ask you back.

Clients love tips, tricks, and traps. They feel actionable.

But they are never the thing that actually determines whether connection happens.

Because what actually determines connection isn’t the tactic.

It’s your relationship to networking itself.

• What makes you nervous?

• What do you believe networking says about you?

• What assumptions are you carrying into the room?

That is where connection actually lives.

Why This Matters More in the Age of AI

When I started diving into AI in 2024, I pressure-tested it emotionally.

I told it things I usually reserve for my therapist or a trusted friend. Anger. Fear. Frustration. Long, unfiltered thought spirals. (Turns out that I wasn’t the only one doing this). My partner of fourteen years could hear me talking out loud in my office for hours.

Over dinner one evening, when the conversation between the two of us felt strained and lulled, I said something that stopped me cold:

“Sometimes I think I want to talk with the AI more than you. I don’t have to make space for you. I can just be selfish.”

That sentence made a future visible. We have seen this pattern before.

• Walkmans allowed us to move through the world signaling “do not disturb.”

• Google Maps removed the need to ask for directions.

• Dating apps reduced the vulnerability of approaching someone face-to-face.

AI removes the friction of staying with another human in discomfort.

But friction is where meaning, trust, and connection are formed.

The Three Levels of Conversation

If you want to understand why connection is becoming a leadership skill, it helps to name what kind of conversations we’re actually having.

Level 1: Small Talk

This is the exchange of banal topics. Food. Weather. Sports. The thing you both can see.

A lot of people find it annoying. But Level 1 is doing a job. It’s a low-stakes way to sense who the other person is, whether they’re open, and whether they have time for a deeper conversation. You’re putting out feelers to see if there’s an invitation to move into something more real.

Level 2: Information Exchange

Now we’re swapping facts, data, and context. We’re telling stories. We’re getting specific.

This is where most work conversations live. And it’s useful. You learn what happened. You learn what someone thinks happened. You start to see whether you’re operating in a shared reality.

Level 3: Relational Meaning

This is where you start talking about your relationship to your beliefs, assumptions, and feelings that drove actions. Not just the story, but what the story represents. Not just the information, but how you’re exchanging it.

You can track tone. Timing. Body language. Turn-taking. The medium itself. You can “go meta.”

Level 3 is where people feel seen. Most workplaces spend nearly all their time in Level 1 and Level 2, then wonder why people feel disconnected.

A Quiet Parallel with AI

Interestingly, large language models are built in layered ways, too. Tokens. Context. Patterns. Meaning.

AI is made by humans. It is designed to mimic human connection.

By interacting with AI, we can actually learn something about how humans connect, if we pay attention not just to outputs, but to relational thinking. How context shapes meaning. How tone changes interpretation. How assumptions drive responses.

Leaders who understand this mirror effect can design conversations more intentionally, not just tools.

The difference is that AI is designed to be endlessly available, agreeable, and frictionless.

Humans are not.

Leadership in the age of AI is about protecting and modeling the parts of connection that cannot be automated.

Why Leaders Matter Here

If leaders do not model Level 3 conversations, the human need for deeper connection will be outsourced elsewhere.

Leaders may be one of the last places where this kind of connection is modeled.

Because how teams relate to each other shapes how they relate to ideas.

And how they relate to ideas shapes the products, services, and systems they build.

Connection is no longer a soft skill.

It is a strategic one.

What Comes Next

This is Day 2 of 10 on how to grow as a leader in the age of AI.

We are in the Connect phase of the framework:

Connect. Disconnect. Interconnect.

Day 3 will close out Connection by exploring what leaders actually say and do to help people connect more deeply at work.