The Simple Question

The Courage to Ask

Throughout Don Quixote, Sancho Panza asks questions that nobody else dares to ask.

“Master, are you sure those are giants? They look like windmills to me.”

“Sir, are you certain that’s a magical helmet? It looks like a barber’s basin.”

“My lord, do you really think that flock of sheep is an army?”

Every time, Quixote dismisses him. Every time, Sancho is right.

Sancho didn’t have education or eloquence. But he had something more valuable: the honesty to say what he saw, and the courage to ask what seemed obvious.

In Product Teams

The most expensive mistakes in product start with a question nobody asked:

Scene one. The VP walks the room through the new strategy. Jargon-filled slides, half the room squinting. In the room: silence. After the room, in the hallway: “Did any of that make sense to you?” “Not a word.” “Me neither.” Everyone saw the windmill. Nobody called it a windmill.

Scene two. The quarterly review. Usage is flat. Users are confused. Everyone knows the feature isn’t working—but the executive who championed it is sitting at the head of the table. Someone almost asks “should we kill this?” and then doesn’t. The slide advances. The feature lives another quarter.

Scene three. End of the planning meeting. “We’re all aligned, right?” Silence. Nods. Three teams leave and start building three different things. Two weeks later: “I thought we agreed on X.” “No, we said Y.” “Wait—I heard Z.” Nobody asked the one question that would have prevented all of it: “Can someone summarize what we actually just decided?”

The question was always there. Someone just needed to ask it.

The Sancho Approach

Sancho’s questions worked because they were simple, honest, and asked without ego:

1. Ask the Obvious Question

Sancho’s questions were never clever. “Are those giants?” wasn’t sophisticated. It was the question a child would ask. And it was exactly right. In your next meeting, notice the question forming in the back of your mind—the one that feels too simple to ask. Ask it. It’s probably the most important question in the room.

2. Ask “Why” Before “How”

Quixote always jumped to “how do I defeat these giants?” Sancho started with “why do you think those are giants?” Before diving into implementation, ask: “Why are we building this?” If the room can’t answer clearly, you’re about to build something nobody needs.

3. Ask What Was Actually Decided—and Admit What You Don’t Know

Sancho had a habit of seeking clarity: “So what are we actually doing, master?” He also freely admitted ignorance: “I don’t understand these knightly things.” Both impulses come from the same place—honesty over performance. End every meeting with: “What did we decide, and who’s doing what by when?” If nobody can answer, the meeting achieved nothing. And when was the last time you said “I don’t understand” in a meeting? If it’s been a while, you’re either a genius or you’re pretending.

Signs Your Team Has Stopped Asking

These are the warning signs:

• Meetings end without decisions—everyone talked, nobody concluded
• Post-meeting confusion—“wait, what did we agree on?”
• Recurring surprises—“I thought we were doing X” / “No, we said Y”
• Nobody challenges—ideas go from proposal to execution without scrutiny

Each is a room where the windmill question isn’t being asked.

Five Questions to Ask This Week

Keep these in your back pocket for your next meeting:

• “Can someone summarize what we just decided?”
• “What would make us stop or change direction on this?”
• “Sorry—I don’t follow. Can you explain that differently?”
• “Who is the user asking for this, and what’s their actual problem?”
• “What are we choosing not to do by doing this?”

You won’t need all five. But one honest question, asked at the right moment, can save weeks of misaligned work.

Be the Sancho

There’s a reason Sancho Panza has endured for 400 years in literature. It’s not because he was the smartest person in the story. It’s because he had the courage to see clearly and speak honestly.

Every PM needs a Sancho—someone who asks the uncomfortable questions, who points at the windmill and calls it a windmill.

Better yet: be the Sancho.

The right question, asked at the right time, is worth more than any framework, any dashboard, any roadmap.

Make space for honest questions

The Retro Template builds a structured safe space where your team can ask the questions that actually matter—without fear of looking foolish.

Get the Template →