3️⃣ Dilemmas That Reveal Your Real Culture

November 4, 2025

Hi Reader

Part 2: Why One Operating System Isn't Enough

TL/DR: Your culture gets tested in three distinct ways: Standards vs. People dilemmas, Speed vs. Quality dilemmas, and Transparency vs. Protection dilemmas. Each requires a different decision framework. Without clarity on all three, your people are guessing..and getting it wrong.

(3-minute read)

A performance analyst made a mistake. A big one.

Because of it the wrong data went to the board. Decisions were made. Money was committed.

Now you know the truth.

Your values say "Accountability." But they also say "Psychological Safety."

Do you sack the analyst to show standards matter?

Or protect them to show learning matters?

Both feel right. Both align with your stated culture.

Welcome to the moment where decoration becomes decision.......

3 Dilemmas every team/company faces

In last week’s ‘Fine Lines’ Part 1of this culture-focused series showed why abstract values fail: They can't solve dilemmas where two right answers exist.

Today we go deeper. Because not all dilemmas are the same.

And treating them like they are destroys culture faster than having no values at all.

Kim Scott (author of "Radical Candor") spent years studying how great organisations handle competing values. She found something crucial: Most leaders try to apply one cultural rule to every situation.

That's the mistake.

High performing cultures don't have one operating system; they have three and each is designed for a different class of dilemma.

Dilemma 1: Standards vs. People

Context: Performance falls short. Someone needs to be held accountable. But that same person might be going through something difficult.

Why It's Hard: "Excellence" and "Care" both matter. But in this moment, which one leads?

Real Example: General Stanley McChrystal wrote in "Team of Teams" about dismissing a Special Forces operator who made a tactical error during a high-stress mission. The operator was exhausted, overwhelmed, and hadn't asked for help.

McChrystal's decision: Remove the operator from combat duty but keep them in the organisation with a development path.

The cultural rule? "Standards never drop. Support never stops. But role fit must be honest."

Not "we value excellence" or "we care about people." A specific instruction for when these values collide.

Dilemma 2: Speed vs. Quality

Context: Market conditions demand fast decisions. But rushing risks mistakes.

Why It's Hard: Both "Agility" and "Excellence" live in your values, but neither tells you when to prioritise which one.

Real Example: Amazon's Jeff Bezos created a framework for this. Type 1 decisions (irreversible, high-stakes) require slow, careful analysis. Type 2 decisions (reversible, lower stakes) require fast action.

The cultural rule isn't "move fast" or "get it right." It's "match decision speed to decision weight."

So, to give a common example from the world of sports, when your academy coach needs to decide whether to play an injured player, they need to know which type of decision that is and what your culture directs them to do.

Dilemma 3: Transparency vs. Protection

Context: Bad news exists. Sharing it might damage morale. Hiding it might damage trust.

Why It's Hard: "Honesty" and "Team Welfare" both matter but your values offer no tiebreaker.

Real Example: Brené Brown documents in "Dare to Lead" how Pixar handles this through their "Notes Day" system. When projects struggle, they share the problems widely but frame them as solvable challenges, not catastrophes.

The cultural rule? "We share problems early. We frame them constructively. We never let people get blindsided by information others already know."

A great example of a decision protocol for when transparency conflicts with protection.

Top performers behave differently

Most teams/companies have one answer to complex dilemmas: "It depends."

But is that culture? Or chaos about to sprout from a mission statement?

Top performing teams/companies have three distinct operating systems:

🚦For Standards vs. People dilemmas: Clear protocols about when standards override empathy (safety, ethics, core competencies) and when empathy overrides rigid adherence (development zones, personal circumstances, learning contexts).

🚦For Speed vs. Quality dilemmas: Decision classifications that tell people when to move fast (reversible, low-stakes, time-sensitive) and when to slow down (irreversible, high-stakes, permanent).

🚦For Transparency vs. Protection dilemmas: Communication frameworks that define what gets shared (problems, context, decisions) and how it gets framed (constructively, early, with solutions).

How does your team or company measure up to this? It’s a tough one to answer off the bat so here's how to test if your culture has operating systems or just decoration.

🔍Pick your three most recent tough decisions.

🔍 Ask: "Could someone else in the team/company have made the same decision using our stated values and culture guidance?"

🔍 If the answer is "maybe" or "probably not," you have personal preferences that change based on who's deciding. That’s not culture.

The Consequences

Without a north-star to guide them….

☢️ Junior leaders guess what you'd want and they optimise for not getting blamed instead of doing what's right.

☢️ Different teams develop different norms so your organisation becomes ten cultures, not one and confusion compounds.

☢️ Good people leave because they can't succeed when the rules keep changing based on who's making the call.

The Work Ahead

“Better” values won’t solve this. You need better instructions.

Next week in Part 3 we’ll look at how to build decision protocols that turn your values into actions people can actually follow.

I'll share how you can map your recurring dilemmas, create operating rules for each type, and build a system that guides behaviour(s) without micromanaging decisions.

But before that….

Gather your leadership team. Ask everyone to write down the hardest dilemma they faced over the past few months.

Then ask them: "What did our culture tell you to do?"

If they can't answer specifically, you know where the work begins.

Culture isn't only what you believe and value. Culture is what you do when beliefs collide.

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by Simo Schiassi

I help senior leaders influence without relying on authority. One free email per day. Each email will help you build your Executive Influence to become the leader that people choose to follow, even when they don't have to, in less than 2 minutes.