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A Conceivian Briefing · IX

On Why Big Plans Fail

A strategy, an operating model, a sales plan. Each one begins as a declaration. Most never become anything more.

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Prepared for leaders, mission captains, and mobilizers Conceivian
Design A Different Future
Seattle · Belfast · Vancouver
“Plans do not fail because they are badly made. They fail because the ambition and energy that went into them never becomes the new promises, practices, and habits that bring about a new reality.”
About this Briefing
For the leader who built a serious plan and watched the company keep running the way it always did. The strategy was sound. The operating model was thorough. The deck was good. And months later the same informal habits are running the place, the same turf is being protected, and the plan is a document everyone read and no one acts on. This is a diagnosis. It names why big plans fail, and it points at the one thing most plans never build. Read it if your planning sessions have started to feel like theater, if every reorganization leaves the same hidden networks intact, and if you have begun to suspect the problem is not the quality of the plan but something underneath it that no plan can reach.

A strategy. An operating model. A sales plan. Each begins as a declaration, and most never become anything more. The failure is not in the plan. It is in the layer underneath it.

IA plan is a declaration, not a commitment

There are two ways language works.

Sometimes we describe the world as it is. “Sales fell seven percent last quarter.” That is an assertion. It reports a fact, and it answers to reality.

Sometimes we bring a new world into being by speaking it. “We will be the category leader by 2027.” That is a declaration. It does not describe the company. It announces a future the company does not yet live in.

Every plan is a declaration. The strategy, the operating model, the OKRs, the go-to-market motion. Each one announces how things will now go. This is real work, and it is leadership work. Naming a future before the evidence for it has arrived is exactly what a leader is for.

But a declaration has a limit, and missing that limit is where plans die. A declaration names no one. It binds no one. It asks nothing of any specific person and secures no promise in return. You hold the authority to declare the plan. The capacity to deliver it sits in hundreds of people the declaration never spoke to. Standing alone, the most brilliant plan lands on those people as information. They read it. They nod. They file it. Nothing moves.

A commitment is the opposite of information. A commitment is a named person giving their word to deliver a specific result, by a specific time, that someone else is counting on.

Plans are made of declarations. Companies run on commitments. The entire failure lives in the gap between the two.

IISix reasons big plans fail

1. No one converted the plan into promises. The plan was declared and then treated as finished. A consulting firm hands over the eighty-page deck, the board nods, and the work is considered done. But a declaration only comes alive when it is broken into requests, offers, and promises. Who will deliver what, to whom, by when. Skip that conversion and the declaration drops back to being information. This is the plan on the shelf. Not wrong. Just never activated.

2. The people who had to deliver it were never in the room. This is the deepest one. We treat planning as the job of a few intelligent people at the top, then hand the result down to the people who do the actual work. The engineers, the operators, the people on the ground. So the plan arrives as something done to them, not something they arrived at with you. They did not build it, so they do not own it. We are not short on the ability to make plans. We are short on the ability to build, in conversation with the people who will carry it, a shared future they take responsibility for.

3. The sense-making never happened, and that debt comes due. Real planning is not just the document. It is the conversation where people listen to each other, surface their concerns, consider possibilities, and arrive at a shared understanding of the future they are committing to. When the sense-making process is skipped, people walk away with their own sense of what matters. But it is a private sense, not a shared one. Each department reads the same words and interprets something different. That gap is a debt that comes due later, during execution, with interest, in the moment two teams discover they had vastly different ideas of what matters.

4. Opinions were mistaken for facts, and the team fought over who was right. In planning, people are not stating facts. They are offering assessments. Judgments about what matters, what is risky, what will work. An assessment is not true or false. It is grounded or ungrounded, careful or careless. The trouble starts when people take their assessments to be self-evident truths and go to war over whose truth wins. Fernando Flores called the ability to tell an assessment from an assertion a kind of enlightenment, because most of us cannot do it under pressure. A planning room that forgets this becomes a contest over who is more articulate. The listening that builds shared ground never happens.

5. The moods were never tended, and resentment did the listening. Assessments and assertions and plans are never spoken in a vacuum. They are spoken in a background of moods; the speaker’s and the listener’s. Often people in enterprises live in the mood of hysterical industriousness, a term Chauncey Bell traces to Peter Sloterdijk. Sometimes the mood is cordial hypocrisy, where everyone is pleasant and no one says the real thing. Sometimes it is my-way-or-the-highway. Often it is a straight up resignation. When a plan is spoken into moods like these, it lands the wrong way and provokes more of the same. People get stuck in mutual bad moods. They perceive the enforcement of the plan as a violation and from that point a filter takes over. Whatever they hear through that filter is distorted. Whether the plan goes forward or not, the team has already lost its chance, because private resentment has built up underneath and no one has dealt with it. Resentment is the mood that quietly does the listening, and it cannot be reasoned away. It can only be met, with real skill and care, by investigating the moods themselves. Those are skills, and they have to be cultivated.

6. When the breakdown came, no one owned it. Every plan meets a breakdown. The market shifts, a key person leaves, a number misses. Breakdowns are not a sign the plan was bad. They are inevitable. The only question is who meets them. People who own the future push through the breakdown and reconfigure around it. People who were handed the future use the breakdown as proof of what they already suspected, that this was never going to work. And meeting a breakdown well takes emotional fortitude. The equanimity to stay in the room and listen to an assessment very different from your own without it becoming a fight. Without ownership and without fortitude, the first serious breakdown ends the plan.

IIIA shadow network forms

Here is what most leaders miss. When the declared plan is not converted into shared commitments, the company does not stall. Commitments form anyway, because action requires them. A shadow network self-organizes in the corridors, and it optimizes for the local, not the global. Sales protects its number. Product protects its roadmap. Finance protects the runway. Each function reliably keeps the promises that serve its own turf. None of it adds up to the future the plan declared. In one of the largest studies of execution failure on record, only nine percent of managers said they could count on colleagues in other functions to deliver.1 A company runs on cross-functional promises, and those are the first to fray.

This shadow network is not bad culture. It is competent local optimization, which is exactly why it survives every reorganization and stays invisible to the person who wrote the plan. The post-mortem blames culture, or says they just did not execute. The truth is structural. Two networks were running at once. The declarations on the wall masquerading as a commitment network, and the one in the corridors that everyone had privately determined for themselves and their team. The corridor won.

IVWhat actually works

You do not fix this with a better plan, or a longer one. You fix it by changing how commitments get made. How they are managed. And how they are repaired when they break.

Treat the plan as the opening move, not the deliverable. The day it is declared, the work is half done. The other half is conversion. Take each lynchpin piece of the plan and ask who makes the promise, to whom, on what conditions of satisfaction, by when, and what happens when reality moves. And conversion alone is not enough. The people making those promises have to be seriously involved in designing the work, or they make promises with their fingers crossed.

The clearest model of this is older than any company. The document that founded the United States is called the Declaration of Independence, not the Description of Independence. When the founders signed it, they were not free. The British still ruled. They declared a future that did not yet exist and pledged their lives, their fortunes, and their sacred honor to it. It was not an eighty-page plan handed down by a consultant. It was a shared declaration that each signer owned, and then each went off and did the hard, uncertain, conflict-ridden work of making it real, in coordination with the others.

The declaration opened the space. Owned commitment crossed it. That is the whole move.

VIf your plan is in trouble

Most leaders feel this before they can name it. The plan is sound and the company is not moving. The product is behind. Sales is not landing. The merger is not delivering what the model promised. The round is not closing and the customers are not coming. The mission that should have changed the field is sitting in a drawer.

The instinct is to write a better plan. It is almost never the plan.

It is the layer underneath. The commitments that were never made. The people who were never in the room. The shared understanding that was never built. The debt that is now coming due. That layer can be diagnosed. It can be designed. That is the work we do.

  1. Donald Sull, Rebecca Homkes, and Charles Sull, “Why Strategy Execution Unravels—and What to Do About It,” Harvard Business Review, March 2015. A study of nearly 8,000 managers across more than 250 companies found that only nine percent could rely on colleagues in other functions all the time, and just half could rely on them most of the time. hbr.org

“A plan is a framework for promises that have not yet been made. The work of leadership is to get the promises made by the people who have to do the work that delivers it.”

If your big plan is failing, and you suspect the problem is not the plan, bring it to us. We will help you put your finger on the thing that is actually in your way.

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These distinctions come alive when you put them to work. COROS AI holds this Briefing and the rest of our work, ready to think through your situation with you, in private. Begin exploring at app.coros.ai.

This Briefing draws on the tradition of Fernando Flores and our teacher Chauncey Bell, and the work of Business Design Associates on the enterprise as a network of commitments. It stands alongside J. L. Austin and John Searle on speech acts, Martin Heidegger on mood and breakdown, and Peter Yaholkovsky on the conversations that build shared understanding before action. The reading of the Declaration of Independence as a declaration rather than a description follows Fernando Flores on the generative power of language. We offer it in their debt.

For conversations and correspondence, write to [email protected].

To put this Briefing into practice, COROS AI holds this work and is ready to think through your situation with you, in private. Begin exploring at app.coros.ai.

This is a work of authorship protected under the copyright laws of the U.S.A. It may not be reproduced or republished without the express written consent of Conceivian.

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