06 Apr 2026 4 min read agile-is-anarchy

The Conversation That Doesn't Exist

Do you know your place in the big charade?

Are you more than they?

— Bad Religion, "Leaders and Followers"

Mark,

There's a conversation that doesn't exist between me and every boss I've ever had. I'm trying to have it with my team, but I'm not sure how.

We're working on OKRs right now.

I'm not against OKRs. I'm not against KPIs. I'm not against goals. The SMART framework — Specific, Measurable, Achievable, Relevant, Timely — makes sense. But there's a gap between the goals and the work. There always is — it's structural. That gap is usually filled with silence. We need conversation instead.

The Map

OKRs are maps. We call them "roadmaps" — they show us where we want to navigate as a company, a department, a team, an employee over the next year.

Here's how it works at most companies. The company sets OKRs. The department aligns theirs to the company's. The team aligns theirs to the department's. The employee aligns theirs to the team's — if we're lucky. At each level they ask for feedback. This sounds collaborative but it isn't — the goals are written top down. The feedback loop exists but in practice it's: here are the goals, any questions? Good.

Then they ask for team allocations. Not alignment — allocations. Bodies to tasks. How many people are working on what. The language tells you everything. They're not asking how our work connects to the vision. They're asking how many heads they can count against each line item.

Nobody asks whether the OKRs make sense to us given the other work we've been asked to do. Nobody asks how our goals align with our own career growth. Nobody discusses whether "team allocations" and "meaningful work" have anything to do with each other.

Everyone assumes that's fine. Maybe it is?

It's Structural

Alfred Korzybski said "the map is not the territory." OKRs are useful maps. But maps are always wrong — they're simplifications by design. The question is whether anyone acknowledges where they're wrong.

Let's try to write a SMART goal for what I actually do. Not to complain about the framework — to show you where the map and the territory don't match.

Specific. What's a specific unit of measurement for trust? Comfort? Confidence? Psychological Safety? The most important part of my job is ensuring my team can work through a fundamentally creative process, every day, on demand, on a deadline. I can't measure those things — I'm not sure anyone can. We can measure the second-order effects though: DORA, CALM, SPACE, etc.

Measurable. Trust and performance aren't independent variables — they're conjugate properties, like position and momentum in physics. The more precisely you measure performance, the less you can see the trust that makes it possible. The more you try to pin down trust, the less you can see what the team is delivering. And the act of measuring either one changes how both behave. You're working with linked properties that shift when you look at them.

Achievable. Here's the trap. You can only measure what matters through second-order proxies. Measuring those proxies changes them. So achieving progress on the measurable goal might mean working against the actual outcome you want. You hit the DORA metrics and miss the team health. Many frameworks build in contradictory metrics on purpose — metrics that fight each other so you can't game one without tanking another. The system guarantees that achieving one goal damages another. The A in SMART is fighting itself by design.

Relevant. How relevant can the measurement of a derivative of a derivative be?

Timely. You can't put a due date on "create an environment where people feel safe enough to say what they actually think."

Goodhart's Law closes the last door: "When a measure becomes a target, it ceases to be a good measure." Even if you could get the map closer to the territory — even if you found the right metric — the moment it becomes the metric, people start building the territory to match the map. The OKR stops describing reality and starts replacing it.

Korzybski, Heisenberg, Goodhart. Three independent reasons you can't solve this with better measurements.

The Missing Conversation

The few who ride peripheral maintain subtle advantage

Fighting hard to abstain and redress

The map is not the territory. My job is helping people navigate the gaps between. And I don't know how to do that for myself, let alone my team.

Nobody has this conversation. Nobody says: "The SMART framework is going to feel like writing fiction. Here's how to think about it instead." Nobody says: "Your OKRs might look different, and that's fine."

So everyone sits down alone, stares at the OKR template, and writes something that sounds plausible. Something specific enough to pass review but vague enough to be true. Something they can achieve by the end of Q4. Paper towns on the roadmap — places that don't exist, put there because someone above you expects to see them.

Everyone knows that's what happens. Nobody wants to say the quiet part out loud.

Having It Anyway

I said there's a conversation that doesn't exist between me and every boss I've ever had. The one about the gap — what I'm doing, why it matters, and how we'd know if it stopped. Not in SMART format. Just in words.

I don't know how to have that conversation yet. But I know it starts with admitting I'm standing in the same gap as my team. I can't hand them a framework for navigating the distance between OKRs and reality when I haven't navigated it myself. The honest thing is to say that out loud and figure it out together.

Which is what this letter is.