The Principle of Charity: Interpreting Others at Their Best

The Core Idea

The Principle of Charity, rooted in philosophy and rhetoric, states: When interpreting someone’s argument or behavior, choose the most rational, reasonable interpretation possible.

Rather than assuming ignorance, malice, or incompetence, charity asks us to:

Assume good faith and positive intent
Interpret ambiguous statements in the most sensible way
Fill gaps in reasoning with the strongest possible argument
Consider context and constraints the person might face

This isn’t naive optimism or avoiding hard truths. It’s a disciplined cognitive practice that leads to better thinking, relationships, and outcomes.

Historical Context

Philosophical Origins

The principle emerged in philosophical debate as a method for engaging with ideas honestly. If you want to truly understand or refute a position, you must first understand it at its strongest, not its weakest.

Ancient roots:

Aristotle taught students to understand opposing views thoroughly before critique
Medieval scholars defended heretical positions to strengthen orthodox arguments
John Stuart Mill argued that truth emerges from engaging the strongest counterarguments

Modern formulation: Philosophers Neil Wilson and Donald Davidson formalized the principle: interpret speakers as rational and coherent unless proven otherwise.

Why It Matters for Technical Leaders

In engineering, the principle of charity transforms:

Code reviews:
❌ “This code is terrible. Did you even think?”
✅ “Interesting approach. What constraints led to this design?”

Architecture disagreements:
❌ “They clearly don’t understand distributed systems.”
✅ “They’re optimizing for different trade-offs. What am I missing?”

Stakeholder requests:
❌ “Another stupid business requirement that makes no technical sense.”
✅ “What problem are they trying to solve? How can we meet the need?”

The Practice: How to Apply Charity

1. Pause and Reframe

When you encounter something that seems wrong, stupid, or frustrating:

Instead of: “This is obviously wrong.”
Ask: “What would make this reasonable?”

Instead of: “They’re not thinking clearly.”
Ask: “What constraints or information might they have that I don’t?”

Instead of: “This person is incompetent.”
Ask: “What skills or experience gap might explain this?”

2. Steelman, Don’t Strawman

Strawman: Misrepresenting an argument to make it easier to defeat.
Steelman: Strengthening an argument before engaging it.

Example in technical debate:

Strawman approach:
Engineer A: “We should use microservices for this system.”
Engineer B: “Oh, so you want to add complexity, increase operational overhead, and make debugging impossible? Terrible idea.”

Steelman approach:
Engineer A: “We should use microservices for this system.”
Engineer B: “Interesting. You’re probably seeing benefits in: independent scaling, team autonomy, technology diversity, and failure isolation. Let me think about the strongest version of this argument… Given our team size and deployment complexity tolerance, would the benefits outweigh the distributed systems challenges?”

The steelman approach:

Surfaces the real reasoning
Enables productive debate
Shows respect for the other person’s thinking
Leads to better decisions

3. Assume Context You Don’t Have

Every person operates with information, constraints, and history you may not see.

The junior engineer who writes “bad” code:

Maybe they inherited a tight deadline you don’t know about
Perhaps they’re optimizing for something you don’t value (speed to ship vs. elegance)
Could be working around a system limitation you’ve forgotten

The product manager with “unreasonable” requests:

Might be responding to customer pain you haven’t seen
Could have revenue pressures from leadership
May be constrained by legal or compliance requirements

The colleague who seems checked out:

Might be dealing with personal crisis
Could be burned out from months of crunch
Perhaps got negative feedback and is demotivated

Practice: Before judging, ask yourself: “What context might make this reasonable?”

Benefits for Technical Leaders

1. Better Decision-Making

When you engage the strongest version of opposing views, you:

Identify real weaknesses in your own thinking
Discover solutions you wouldn’t have found alone
Make more robust decisions that consider multiple perspectives

Example: You want to rewrite a legacy system. A teammate argues against it.

Uncharitable interpretation: “They’re just resistant to change and want to protect their old code.”
Result: You push through, miss real risks, rewrite fails.

Charitable interpretation: “They’ve seen rewrites fail before. What risks are they anticipating?”
Result: You discover deployment complexity, data migration risks, and customer impact issues. You design a safer incremental migration strategy.

2. Stronger Relationships

People sense whether you’re interpreting them charitably. It affects everything:

In 1-on-1s:
Uncharitable: “You’re not putting in enough effort.”
Charitable: “You seem less engaged lately. What’s going on? How can I help?”

In conflict:
Uncharitable: “You’re being difficult and blocking progress.”
Charitable: “We have different perspectives. Help me understand your concerns.”

In feedback:
Uncharitable: “Your design is wrong.”
Charitable: “I see a different approach. Let’s compare trade-offs.”

People are more honest, collaborative, and loyal with leaders who interpret them charitably.

3. Organizational Learning

Teams that practice charity create psychological safety - the #1 predictor of high-performing teams (Google’s Project Aristotle).

When people know their ideas will be interpreted charitably:

They share controversial opinions
They admit mistakes earlier
They ask “dumb” questions that reveal systemic issues
They take intelligent risks

Contrast:

Uncharitable culture:
“If I propose this and it’s not perfect, I’ll look stupid.”
Result: Silence, conformity, missed opportunities.

Charitable culture:
“Even if my idea is half-baked, the team will help strengthen it.”
Result: Innovation, learning, rapid iteration.

When Charity Is Hard

The Bad Code Review

You’re reviewing code that seems objectively poor - inefficient algorithms, unclear naming, missing tests.

Uncharitable response: “This is unacceptable. Didn’t you learn basic algorithms?”

Charitable process:

Assume context: “What deadline or constraint led to this approach?”
Ask questions: “Help me understand the reasoning behind this design?”
Offer learning: “Have you seen the X pattern? It might help with Y.”
Set expectations: “For production code, we need tests. How can I help you add them?”

Outcome: Learning happens, relationship strengthens, code improves.

The “Stupid” Business Request

Product wants a feature that seems to violate technical best practices.

Uncharitable: “This is technically impossible / stupid / shows they don’t understand systems.”

Charitable:

Find the need: “What problem are customers facing?”
Explore alternatives: “Could we solve it differently that’s technically simpler?”
Explain trade-offs: “Here’s what this would cost in maintenance/complexity.”
Collaborate: “Let’s find a solution that meets your need within our constraints.”

Outcome: Trust builds, better solutions emerge, you influence product direction.

The Persistent Disagreement

Someone keeps pushing back on your direction despite explanations.

Uncharitable: “They’re being obstinate or don’t understand.”

Charitable:

Acknowledge uncertainty: “I might be missing something. What concerns you most?”
Find the crux: “What would change your mind? What would change mine?”
Test assumptions: “Let’s prototype both approaches and measure.”
Respect autonomy: “I hear your concerns. Here’s my decision and why. I’m accountable for the outcome.”

Outcome: Even in disagreement, respect remains. Learning happens.

Limits of Charity

The principle isn’t infinite. Some situations require different responses:

When to Reduce Charity

Repeated bad faith:
If someone consistently misrepresents you, ignores evidence, or argues dishonestly, charity becomes enabling.
Response: Set boundaries, disengage from unproductive debate.

Harmful behavior:
Harassment, discrimination, or abuse aren’t “different perspectives.”
Response: Protect people, enforce consequences.

Urgent safety issues:
When systems are down or security is breached, there’s no time for extended charitable interpretation.
Response: Act decisively, debrief with charity later.

Charity Isn’t Agreement

You can interpret someone charitably and still disagree:

“I understand you’re optimizing for speed to market, which makes sense given our competitive pressure. I still think the technical debt will cost us more in 6 months. Here’s my reasoning…”

Charity means understanding the strongest version of their position, not surrendering your own judgment.

Building the Habit

Daily Practice

In meetings: When someone says something that seems wrong, pause and ask a clarifying question before responding.
In Slack/email: Before sending a frustrated message, rewrite it assuming positive intent.
In code review: For every critical comment, find one thing to praise or learn from.

Weekly Reflection

Ask yourself:

When did I interpret someone uncharitably this week?
What context might I have been missing?
How could I have responded differently?
When did someone extend charity to me? How did it feel?

Team Culture

As a leader, model charity explicitly:

“Let me steelman that position…”
“What am I missing in your reasoning?”
“That’s an interesting constraint I hadn’t considered.”
“Help me understand your perspective.”

Others will mirror your approach.

The Deeper Wisdom

The principle of charity is ultimately about epistemic humility - recognizing the limits of your own perspective.

You don’t know:

What information others have that you don’t
What constraints they’re operating under
What experiences shaped their reasoning
What you’re misunderstanding about their position

Charity is the rational response to uncertainty.

It’s also about respect - treating others as intelligent agents worthy of understanding, not obstacles to overcome.

And finally, it’s about effectiveness - charitable interpretation leads to better decisions, stronger relationships, and higher-performing teams.

Closing Reflection

Think of a recent frustration with a colleague, stakeholder, or report.

What was your initial interpretation?
What’s the most charitable interpretation possible?
What context might you be missing?
How would you approach it differently with charity?

The gap between those answers is where growth happens - yours and theirs.

The principle of charity isn’t about being nice. It’s about being wise.

When you interpret others at their best, you bring out their best. Including your own.

2025-10-19

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