A Jeffersonian Dinner in Upstate NY Changed How I See Leadership

Hey there,

I want to walk you through something a little different: a recap of a dinner I hosted in Upstate New York and the raw, honest conversations that unfolded there. I've been mulling it over for days and had to share it with you.

Let’s dive in.

Jeffersonian Dinner: Deep Conversations with Growth-Minded Leaders

A few weeks ago, I drove from Philadelphia to Utica, NY to host a Jeffersonian dinner— 14 entrepreneurs, one table, and two powerful questions. It's a great way to structure a conversation and get to the deep sharing on which epic entrepreneurial relationships are built.

The rules are simple:

✔️ Everyone answers one at a time.

✔️ No yes/no questions.

✔️ Authenticity is the only requirement.

Question 1: “What do you want from your business?”

The answers were striking in their uniformity:

• “More growth, but less chaos.”
• “A culture that wins.”
• “Consistent profitability.”
• “Simplicity in scale.”

In essence, everyone at the table wanted the same thing: a stable, growing business that doesn’t consume their lives.

So, I followed with the second question.

Question 2: “What’s the #1 thing preventing you from getting that?”

Now this is where the night got real.

Themes That Emerged from Around the Table

1. A Culture of Kindness, Without Accountability

One leader described his team as fun-loving, value-aligned, and just plain nice. The problem?

“They aren’t accountable to results. They’re too nice to call each other out.”

This is what we call ruinous empathy, when culture becomes comforting and results fall behind. Great cultures aren’t just kind—they’re winning cultures. Otherwise, the smiles eventually fade under the weight of frustration.

2. Global Teams, Misaligned Communication

Another leader wrestled with the complexity of running global teams— South Korea, India, Singapore, the U.S., and Europe.

“We just can’t speak the same operational language.”

When cultures clash, clarity suffers. But when you align your Core Values, processes, and communication rhythms across all geographies, synergy is possible.

3. Product Obsolescence and the Fight for Relevance

One brewery owner shared the hard truth:

“People just aren’t drinking like they used to.”

He pioneered the seltzer category, but market dynamics have shifted. His challenge? Pivoting with purpose, creating new offerings, leveraging current assets, and aligning with what the market wants now.

4. A Vision That’s Too Big for the Room

One leader’s vision was powerful, but overwhelming:

“I think I’ve shut my team down. The goal feels impossible.”

This is a classic breakdown in The Vision Component. If your team can’t even see the next step, they won’t take it. The vision must feel possible, even if ambitious, what we call the adjacent possible.

5. Hiring for Heart, Not Just Hands

Another story hit home:

“We just can’t find people who care. They don’t share our Core Values.”

When you hire for technical skills and ignore values alignment, you’re building on quicksand. One leader realized their biggest limitation wasn’t demand, it was people who believe what they believe. EOS Worldwide has a great tool for this, the People Analyzer. It'll turn your recruiting strategy on its head.

Becoming a Level 5 Leader

And then, just when I thought the night was going to end, a powerful discussion emerged:

“How do I become a Level 5 Leader, like Jim Collins talks about?”

My answer? You can’t do it alone.

True humility + confidence comes from:

• Living in your Personal Core Values (Dan Sullivan with Strategic Coach calls it your Unique Ability®)
• Delegating and elevating what you’re not great at
• Building a team that will call you out when you’re off track

Humility isn’t weakness. It’s clarity. And confidence isn’t ego, it’s rooted in knowing your lane.

Clarity Only Comes With the Conversation

This dinner was a reminder of something every entrepreneurial leader needs to hear:

“You are not the only one facing these challenges.”

Every company hits the ceiling. Every Visionary needs a sounding board. And every team has blind spots they can’t see from the inside.

That’s why we do the work we do. That’s why EOS exists.

If you’re wrestling with some of these same issues, let’s get your team in the room for a 90 Minute Meeting. You’ll walk away with a deeper understanding of where you are, where you’re stuck, and how to get what you want from your business.

Let me know if you'd like an introduction to an EOS Implementer in your area.

Onward,

-MOD.