It started over lunch with my son. He asked me a question I wasn’t prepared for:
“Dad, how do you define masculinity?”
I hesitated. Tried to find the right words. Then realized there wasn’t a simple answer. The question itself forced me to think more deeply than I had in a long time. It made me examine not just what I believed, but why I believed it.
That process, the wrestling, the digging, the uncovering, was what reminded me of a lesson I remembered from Socrates.
Socrates didn’t hand people answers. Instead, he asked the other party questions that stripped away everything false until only what was real remained. He called it the pursuit of truth through inquiry. And it made me think: What if Socrates sat down with a small business owner today, he’d do the same thing. He’d ask questions that challenge the very way we understand entrepreneurship.
So, imagine you’re sitting across from him. No spreadsheets, no buzzwords, just you, your business, and a philosopher who won’t let you off easy.
Here’s what that conversation might sound like.
1. What Is the Goal of Your Business?
“What is it that you seek to achieve and why that, and not something else?”
Socrates would start by questioning your assumptions about purpose. He’d ask: What is your business for?
Is it to make money or to make or provide something meaningful?
If the goal of your business is growth, what’s the purpose of growth itself?
At what point does “more” stop being progress and start being a distraction?
He’d keep asking until you confronted the difference between making a living and living with purpose.
2. What Does It Mean to Be Excellent at What You Do?
“Is excellence a product of luck, or of habit?”
Socrates didn’t believe success came from talent alone. He believed it came from cultivating virtue like habits of excellence.
So, he’d challenge you to think:
Where in your business are you operating on autopilot instead of intention?
What daily habits separate your best work from your average work?
How often do you define excellence by comparison rather than by craft?
Do you reward busywork or progress?
He might even ask, “If your competitors all disappeared tomorrow, would you still strive to improve?”
3. What Truths About Business Have You Never Questioned?
“Do you believe what you believe because it is true or because it is just familiar?”
Most entrepreneurs build on a pile of untested assumptions: How customers behave, how teams should be managed, what “growth” should look like.
Socrates would press on that.
Why do you price your products or services the way you do?
Why do you measure success the way you do?
When did you last test whether your “best practices” still serve you or just feel safe?
He’d say, “The danger isn’t ignorance; it’s thinking you already know.
4. What Do You Mean When You Say ‘Value’?
“Do you sell what people need or what you wish they valued?”
Socrates loved to redefine words. He’d take something simple like “justice” or “virtue” and make people realize they’d never truly defined it. Like me, when my son asked me to define masculinity. In business, value is one of those words we rarely truly try to define.
He’d ask:
What does your customer actually value and how do you know?
Is the value you provide measured by features, outcomes, or trust?
If your customers stopped buying from you, would you know why?
Is your business designed around your customer’s needs or your own ego?
5. What Is the Cost of Growth?
“At what point does expansion become excess?”
Growth is a sacred word in entrepreneurship, but Socrates would make you examine it.
He’d ask:
Why do you want to grow?
What part of your business breaks when you push too far, too fast?
If you could only grow one thing: profit, reputation, or freedom, which would you choose?
He’d remind you that more isn’t always better, and that wisdom often hides in restraint.
“When you choose, are you guided by reason, by habit, or by fear?”
Socrates believed the examined life was built on conscious reasoning.
He’d ask:
How do you decide which clients to take and which to walk away from?
Do you rely on data, intuition, or the crowd?
Whose voice carries the most weight when you’re uncertain and why?
Are you acting from principle or reaction?
He’d push you to uncover the framework behind your choices, because unexamined decisions compound into chaos.
7. What Kind of System Are You Building?
“Can a business be healthy if its parts are in conflict?”
Socrates saw harmony as the mark of wisdom.
He’d ask:
How do the parts of your business support one another or work against each other?
Are your team, customers, and finances aligned toward the same goal?
Where are you fixing symptoms instead of causes?
If your business were a body, which organ is overworked and which is starved?
He’d challenge you to think like a systems architect, not a firefighter.
8. What Does Success Look Like When No One’s Watching?
“Who are you when applause fades?”
Finally, he’d take you beyond the metrics.
He’d ask:
What kind of person is your business turning you into?
Would you still run it this way if no one ever knew your name?
Is your business serving your life or consuming it?
Socrates believed the measure of a life wasn’t external achievement but internal coherence.
He’d remind you that the greatest failure isn’t going broke, it’s losing yourself in the process.
Thinking Like Socrates
To think like Socrates is to slow down and ask the questions most people avoid because they make you feel uncomfortable. It’s to challenge not just your plan, but the beliefs that built it. It’s to see business not as a race to win, but as an inquiry into what matters.
So, before you optimize, scale, or automate, ask yourself:
What do I really know?
What am I assuming?
What am I afraid to question?
Because the wisdom that shapes great businesses doesn’t come from certainty, it comes from curiosity that refuses to quit.
How would you answer all of those questions about your business?
