Years ago, I led a company with a large team in India.
Our conference calls included some exceptionally smart technologists and business leaders.
But most of them rarely spoke.
Usually, the most senior person on their side did the talking. Everyone else listened.
I’d stop and ask.
“What do you think?”
“Are we missing something?”
“Does anyone see this differently?”
Silence.
Then I got to know them.
I visited them in person. We spent time together outside the formal meetings.
They had strong opinions.
They saw risks we hadn’t discussed. They questioned decisions we’d made. Sometimes they were frustrated with the direction we’d chosen.
They just hadn’t said so when we were making the decisions.
I assumed some of this was cultural. Age, seniority, and respect for authority.
But I’ve seen the same pattern plenty of times in American organizations too. Smart people with something to say staying quiet for all kinds of reasons.
I eventually realized I had something to learn.
Telling people they’re free to speak isn’t the same as creating a setting where they will.
Consider the question, “Does anyone disagree?”
To answer yes, someone has to challenge the idea already sitting on the table. And depending on who put it there, they may feel like they’re challenging that person too.
Try another question.
What would make this fail?
Now disagreement is part of the assignment.
Find the weakness. Challenge an assumption. Spot the risk.
We aren’t deciding who’s right. We’re trying to make the plan better.
That’s a different conversation.
The next time I was on a call with that same team, I didn’t ask if they disagreed. I asked what would make the plan fail.
Someone I’d rarely heard speak chimed in.
Then someone else did.
A small shift in the question opened the conversation to ideas and perspectives we hadn’t heard before.
Leaders should design for agency.
Ask what would make the plan fail six months from now.
Ask for the strongest argument against your own idea.
Then listen, especially when the answers are uncomfortable.
People learn quickly if you really value their input.
The goal is better thinking and a stronger plan. That requires the leader to make disagreement part of the work.
Don’t just give people permission to think independently.
Jobs was speaking at Lund University in Sweden, long before smartphones, search engines, or the AI tools we use every day. His hope was that someday we might capture the underlying worldview of a great thinker like Aristotle within a computer, so a future student could ask him questions and get answers.
It sounded futuristic then, but that future is here today.
We can open an AI tool and ask it to explain Aristotle, compare him to another thinker, or respond in a way that tries to reflect his philosophy.
That doesn’t mean we’re talking to Aristotle. We’re talking to a machine-generated synthesis, built from writings, interpretations, and patterns available to the model. Worth remembering, especially in a minute.
Jobs saw computers becoming more than storage devices. He saw interactive learning companions that could move us from consuming information to questioning it, testing our understanding, and entering into a dialogue with the past.
So, I ran a little experiment. I asked an AI tool to respond as if it were Aristotle, drawing on his known writings and philosophy, then I asked three questions…two about leadership, one about relationships.
Here’s what I learned, before you even read the answers. The AI handed me answers that sounded wise. It couldn’t do anything with what the answers asked of me. That work stayed mine, every time. Keep that in mind as you read the three exchanges below. Each quote is the AI’s synthesis, in Aristotle’s voice, not a historical record of what he actually said:
Question 1: Aristotle, what makes someone a good leader?
A good leader must first be governed within himself. He cannot guide others well if his own desires, fears, and ambitions are disordered.
Leadership is not merely a matter of authority or skill. It is a matter of virtue. A leader needs practical wisdom to judge what should be done, courage to do it, justice to give others what they are due, and temperance to restrain his own appetite for power, praise, or comfort.
The good leader does not seek the good of himself alone. He seeks the good of the community entrusted to him.
That answer sounds about right. Confidence, drive, decisiveness, and the ability to win can carry a person a long way. But without character or virtue, those same strengths eventually start working against the people they’re supposed to serve.
Whether it’s true of me is a separate question.
Question 2: Aristotle, how should a leader make decisions when the right answer isn’t obvious?
In uncertain matters, the leader needs prudence. No rule can fully replace wise judgment, because human affairs are too varied and particular.
The prudent person considers the purpose of the decision, the facts of the situation, the people affected, and the likely consequences. He also considers his own motives. A decision can appear reasonable while still being driven by pride, fear, anger, or vanity.
Good judgment is formed over time. It comes through experience, reflection, correction, and the habit of choosing what is noble rather than merely what is easy.
Most leaders want clarity. We want the right answer to announce itself. The spreadsheet, the policy, the consultant, the precedent that makes the decision obvious.
Unfortunately, difficult decisions usually live where the information is incomplete, the tradeoffs are real, and the consequences land on people who are more than names on an org chart.
But, he asks an even harder question. What’s happening inside me as I make this call? Am I deciding from courage or fear? Justice or favoritism? Humility, or the need to be seen being right?
AI can organize the options. It can summarize the arguments. It can show me possibilities I might have missed.
But it won’t clean up my motives. That responsibility remains with me.
Question 3: Aristotle, what makes a friendship or relationship worthy of trust?
The highest friendship is rooted in virtue. Some relationships exist for usefulness. Others exist for pleasure. These are not necessarily bad, but they are fragile because they depend on what the other person provides.
A deeper friendship is different. It is based on willing the good of the other person. Such a relationship is steady because it rests on character, not convenience.
To be worthy of trust, a person must be truthful, faithful, and committed to the good of the other. A trustworthy relationship helps both people become better than they would be alone.
We understand relationships of usefulness. Work relationships, customer relationships, networking relationships, even friendships that lean heavily on shared convenience.
But, are we willing the good of the other person? Do we want what’s good for them, or only what’s useful to us? Do we want them to become better, or only to make our life easier?
Seeing this short exercise, I think Mr. Jobs would celebrate how close we’ve come to his 1985 vision. We have more access to information than any generation before us. We can retrieve facts instantly, summarize books in seconds, compare ideas across centuries before lunch.
That’s amazing!
Yet the more powerful the tool gets, the more responsibility shifts back to the person using it.
Ask Aristotle about leadership, and I have to ask whether I can govern myself.
Ask him about prudence, and I must examine my own motives before I decide.
Ask him about friendship, and the real question is whether I’m willing the good of the other person or just protecting what’s useful to me.
AI tools can generate answers. Wisdom starts when we let those answers question us back.
The machine can help us ask Aristotle a question.
It can’t make us become the kind of person who can live the answer.
Grandpa Bob Encouraging Leadership 
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