The Squire's Dilemma

The Impossible Job

Sancho Panza had the hardest job in literature.

His boss was delusional, charging at windmills and picking fights with strangers. But his boss was also generous, well-intentioned, and genuinely believed he was making the world better.

Sancho couldn’t just say “you’re wrong”—Quixote would fire him (and did, temporarily). He couldn’t blindly follow every order—they’d both end up dead. He had to find the space between honesty and loyalty. Between reality and respect.

Every PM who’s managed up knows this dilemma.

In Every Product Org

Your boss isn’t delusional (probably). But the dynamics are familiar.

The CEO declares you’re going to disrupt the entire industry by Q3. The team quietly calculates that they can maybe ship one feature by Q3. But the vision has been declared, and now you have to make it real—or at least manage the gap.

Your VP wants a specific feature built. The data doesn’t support it. Users didn’t ask for it. But the VP “has a feeling.” And the VP controls your resources.

New strategy drops on Monday. The team has been working on the previous strategy for three months. Do you push back? Pivot immediately? Try to find a middle ground?

Your boss commits to a client in a meeting: “We’ll have that by June.” Nobody consulted engineering. June is impossible. But the promise was made.

And then there’s the subtlest version—the boss who’s so enthusiastic about every new idea that nothing ever gets finished. Each conversation brings a new priority, a new must-have, a new “what if we also…” that resets the team’s focus. No single idea is bad. The accumulated churn is devastating.

You didn’t create any of these gaps. But you own the consequences.

What Actually Works

Sancho developed a set of techniques over 1,000+ pages. The best ones translate directly to conversations you’ll have this week.

Redirect, Don’t Reject

When Quixote wanted to charge windmills, Sancho rarely said “that’s stupid.” He’d say: “Perhaps, master, we should eat first, to have strength for the battle?” Often, after eating, Quixote forgot about the windmills.

When your boss proposes something misguided, the instinct is to explain why it won’t work. Resist that. Instead, try something like:

“I love the intent behind this. What if we tested a smaller version first—say, with just the enterprise tier—so we can validate the assumption before we commit the full team?”

You’re not saying no. You’re redirecting toward a version that’s achievable and still honors the goal. If the small test works, great—you were wrong, and now you have data. If it doesn’t, you saved everyone a quarter of wasted effort without making your boss feel overruled.

Use Data as a Shield, Not a Sword

Sancho never attacked Quixote’s vision directly. He introduced inconvenient facts sideways: “Master, that army appears to be sheep.”

The PM version of this is never saying “your idea is wrong.” Instead, bring the evidence and let it speak. When your VP insists on a feature because of a gut feeling, the response isn’t a debate—it’s a dashboard. “Here’s what users are actually doing in that flow. Want me to set up three customer calls this week so we can hear it directly?” It’s much harder to argue with user behavior than with a PM’s opinion.

Pick Your Battles

Sancho didn’t challenge every delusion. Some were harmless—let the knight call the inn a castle, who cares? He saved his pushback for the moments that mattered—the ones that would get them hurt.

Not every bad idea needs a fight. Before you push back, ask yourself: “If this goes wrong, how bad is it?” If the answer is “slightly suboptimal,” let it go and preserve your credibility for the conversation that matters. If the answer is “we lose a quarter of our users,” that’s worth the uncomfortable moment. The PMs who fight everything get tuned out. The PMs who fight selectively get listened to.

Build the Track Record

Over time, Quixote started listening to Sancho more. Not because Sancho argued better, but because Sancho was right enough times that his judgment earned weight.

This is a long game. Every time you flag a risk that materializes, every time you redirect a plan and it lands better, you’re depositing credibility. You won’t win every argument—and you shouldn’t try. The goal isn’t to be right today. It’s to be trusted next quarter, so that when something truly matters, your voice carries.

Signs You Need to Manage Up

Watch for these situations:

• Strategy changes feel arbitrary—new directions without explaining what changed
• Commitments made without consultation—promises you’ll have to deliver
• Intuition overrides evidence—“I just feel like this is the right move”
• The gap between vision and capacity—ambition that exceeds resources
• Selective information flow—only hearing good news because the team is afraid to share bad news

None of these mean your boss is bad. They mean your boss needs a Sancho.

Next Time Your Boss Has an Idea

You’re in the 1:1. Your boss is excited about something that worries you. Here’s a script:

Don’t say: “That’s going to be really hard to build.” Say instead: “I want to make sure we set this up to succeed. Can I spend a day scoping what it would actually take, so we go in with clear eyes?”

Don’t say: “The data doesn’t support that.” Say instead: “I pulled some numbers on this—want me to walk you through what I’m seeing? I want to make sure we’re reading the same signals.”

Don’t say: “We can’t commit to that timeline.” Say instead: “I want to protect your credibility on this. Here’s what I think we can confidently promise, and here’s what would need to change to hit the bigger number.”

Notice the pattern: you’re not opposing—you’re protecting. You’re framing honesty as loyalty. That’s the Sancho move.

Honesty in Service of the Quest

Sancho never abandoned Quixote. He didn’t agree with everything, but he never stopped trying to make the quest succeed.

That’s the real skill in managing up: not choosing between loyalty and honesty, but learning to deliver both. Challenging the idea while supporting the person. Grounding the vision without killing it.

Your boss doesn’t need a yes-man. They need a Sancho.

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