Detecting bad strategy skill

Detecting Bad Strategy

Table of Contents

• Bad Strategy Is Its Own Species
• Hallmark 1: Fluff
• Hallmark 2: Failure to Face the Challenge
• Hallmark 3: Mistaking Goals for Strategy
• Hallmark 4: Bad Strategic Objectives
• Why Bad Strategy Proliferates
• Auditing a Strategy Deck Section by Section
• The Audit Report Format

Bad Strategy Is Its Own Species

Bad strategy is not the absence of strategy, and it is not a good strategy that failed. It is a recognizable construction with its own logic: it skips the hard work of diagnosis and choice, and fills the space with substitutes — buzzwords, ambitions, templates, and positive thinking. Because it has structure, it can be detected systematically. Hunt for the four hallmarks below; finding any one is a finding, finding three is a verdict.

Hallmark 1: Fluff

Fluff is gibberish masquerading as strategic concepts: inflated language, restated obviousness, and abstraction stacked on abstraction to create the illusion of high-level thinking.

Detection checklist:

• Plain-language restatement. Translate the sentence into ordinary words. If it collapses into the obvious ("our strategy is customer-centric intermediation" → "we are a bank"), it is fluff.
• The negation test. Negate the claim. If the negation is absurd — "we will not pursue excellence," "we will not put customers first" — the original carries zero information.
• Buzzword density. Count occurrences of leverage, synergy, world-class, best-in-class, ecosystem, holistic, next-generation, win-win, empower per page. More than two per page in load-bearing sentences is a red flag.
• Abstraction stack. If defining one term requires three more undefined terms ("a platform-led ecosystem strategy enabling scalable value creation"), the stack is hiding an empty center.
• The Monday test. Ask: what would someone do differently on Monday because of this sentence? No answer, no content.

Before: "Our strategy is to leverage best-in-class AI capabilities and a customer-obsessed culture to deliver differentiated, scalable value across the full customer lifecycle."

After (plain restatement): "We use AI and try to be good to customers" — which every competitor would also claim. A real replacement: "We will win mid-market support teams by being the only vendor whose agent resolves tickets end-to-end inside Zendesk — accepting that enterprises with custom stacks are not our market."

Hallmark 2: Failure to Face the Challenge

If a strategy document does not name and analyze the obstacle, there is no way to evaluate the strategy or improve it. International Harvester's 1979 plan was full of projections and initiatives — and never mentioned its famously toxic labor relations, the actual problem that sank it. The omission is rarely accidental: naming the challenge embarrasses someone or implies a painful choice.

Detection checklist:

• Search the document for an obstacle. Is there a section that says what stands in the way? (Not "risks" boilerplate — the actual difficulty.)
• Does it explain why performance is what it is — why deals are lost, why churn rose, why the last plan missed?
• Would a smart new executive, reading only this document, learn what is hard about this business right now?
• Are competitors named, with the specific reason they win when they win?
• Is anything in the document unflattering to the team that wrote it? A document with no self-implicating facts has been sanitized.

Before: "Building on our momentum, we will accelerate growth through product-led expansion, strategic partnerships, and operational excellence."

After: "Inbound demand fell 40% in two quarters because AI answers absorbed the search traffic our content funnel depended on. Our growth model — SEO → trial → sales-assist — is structurally broken at the top. The challenge is rebuilding demand generation around channels we can defend." Now a strategy can exist, because there is something for it to overcome.

Hallmark 3: Mistaking Goals for Strategy

Goals are ambitions: revenue targets, market-share numbers, "20% growth." Strategy is the lever — the diagnosis and approach that make the ambition achievable. A CEO whose plan is "20/20: twenty percent growth, twenty percent margin" plus exhortation to push harder has a desire and a pep talk, not a strategy.

Detection checklist:

• Verb audit. Circle the verbs in the "strategy" section. Achieve, grow, increase, deliver, drive, accelerate, maximize are ambition verbs. Concentrate, exit, rebuild, target, replace, consolidate are choice verbs. A section with only ambition verbs is a goals list.
• Mechanism check. For each number, is there an answer to "what changes in the world or in our conduct that produces this?"
• Effort substitution. Phrases like "relentless execution," "raising the bar," "one team, one dream" used as the how signal motivation standing in for method.
• Source of the number. Was the target derived from a diagnosis ("fixing activation should lift conversion from 9% to 15%") or from desire ("the board wants 2x")?

Before: "Our strategy for FY26: grow ARR 25%, raise NRR to 115%, launch 12 features, expand to two new regions."

After: "Diagnosis: expansion revenue stalled because our pricing caps usage growth. Guiding policy: re-price around the metric that scales with customer value (documents processed), concentrating sales on the 200 accounts hitting plan ceilings. Actions: usage-based tier (Q1), migration playbook for the 200 accounts (Q1-Q2), retire per-seat plans for new sales (Q2). The 25% ARR target is the forecast of this working — not the strategy."

Hallmark 4: Bad Strategic Objectives

Even when leaders move past fluff and goals, they can produce objectives that no one can act on. Two failure shapes:

The dog's dinner — a long list of "strategic priorities" that is really a union of every department's wish list. One city's strategic plan contained 47 "strategies" and 178 action items; item 122 was "create a strategic plan." Tests:

• Count the "priorities." More than five means none are priorities.
• Check for resourcing. If the list exceeds what the org can staff, it is a wish list, not a plan.
• Check for conflict. Real choices conflict with something; a list where nothing conflicts with anything was assembled, not chosen.

The blue sky — an objective that simply restates the desired end state, skipping over the gap between here and there: "become the #1 platform," "be the most trusted brand in the category." Tests:

• Can the team see how? If the objective is as hard to act on as the original challenge, it has added nothing.
• Is it a re-description of winning? "Win the market" is not an objective; "win 10 of the 30 design-partner candidates in fintech by June" is.
• Does it resolve ambiguity, or just relocate it?

Before: "Strategic priorities: 1) Delight customers 2) Win the enterprise 3) Build a world-class team 4) Operational excellence 5) Innovate boldly 6) Expand internationally 7) Strengthen the brand..." (and 16 more).

After: "Objective for the next two quarters: make the EU instance fully self-serve — signup to production without a sales call — because the diagnosis shows sales-assisted onboarding caps us at 40 deals/quarter. Everything on the old list that does not serve this is parked."

Why Bad Strategy Proliferates

Detection improves when you know why bad strategy gets written despite everyone preferring good strategy.

1. Choice is painful. A real guiding policy rules things out, and every ruled-out option has a sponsor. Faced with that conflict, leaders produce "strategies" that fund everything a little — universal buy-in, zero concentration. Digital Equipment Corporation's leadership, unable to choose among three rival futures, blended them into "DEC is committed to providing high-quality products and services and being a leader in data processing" — mush that chose nothing while the company sank. When you see mush, look for the unresolved fight underneath it.

2. Template-style planning. A whole industry sells the fill-in-the-blanks format: Vision → Mission → Values → Strategies. The template manufactures documents that look complete while containing no diagnosis and no choice — the "strategies" slot gets filled with goals because nothing upstream forced an analysis of the obstacle. The template is how organizations produce bad strategy in good faith.

3. New Thought culture. A nineteenth-century idea — that visualizing success produces success — survives in business as the cult of vision: believe, project confidence, never entertain doubt. It makes diagnosis feel disloyal ("too negative") and substitutes shared belief for analysis. The tell: a document whose emotional register is inspiration throughout, with no section that could disappoint anyone.

Auditing a Strategy Deck Section by Section

A practical procedure for auditing a strategy document, deck, or annual plan:

1. Inventory. List every section/slide. Classify each as: diagnosis, guiding policy, action, goal, evidence, fluff, other. Most decks classify as 60% goals + fluff, 0% diagnosis.
2. Hunt the diagnosis. Is there one falsifiable paragraph naming the critical challenge? If absent, the audit's top finding is already written.
3. Test the policy. Apply the negation test and the competitor-paste test (would this read as false in the rival's deck?). List what the policy rules out; if nothing, flag it.
4. Test the actions. Coherence (do they reinforce each other?), resourcing (owners, budgets, dates?), and traceability (does each serve the policy?). Orphan actions reveal the real, unstated strategy: momentum.
5. Apply the hallmark checklists above to the remaining sections; log each hit with a quote.
6. Score it on the skill's 0-10 scale and write the rewrite path: which sections to delete, which single paragraph to write first (always the diagnosis), which list to cut to three.

Deck section	What to look for	Typical red flag
"Vision / Mission"	Anything load-bearing	Strategy expected to live here — it can't
"Market"	Facts that imply the obstacle	TAM slides with no implication for conduct
"Strategy"	A guiding policy	Goals with ambition verbs; platitudes
"Strategic priorities"	1-3 choices that conflict with something	10+ items; every department represented
"Roadmap / Initiatives"	Coherence and resourcing	Independent projects; nothing stopped
"Financials"	Forecast linked to mechanism	Hockey stick justified by "momentum"

The Audit Report Format

Deliver findings in this shape:

STRATEGY AUDIT: [document name]
Score: X/10 (skill scoring bands)

THE CHALLENGE THE DOCUMENT FACES (or fails to):
[your one-paragraph statement of what the real challenge appears to be]

HALLMARK FINDINGS:
- Fluff: [quote] → [plain restatement] → [verdict]
- Challenge: [named? where? what's missing]
- Goals-as-strategy: [quote] → [the missing mechanism]
- Bad objectives: [dog's dinner / blue sky, with counts]

WHAT SURVIVES: [sections worth keeping, evidence worth reusing]

REWRITE PATH:
1. Write the diagnosis paragraph (draft provided below)
2. [specific next steps — policy candidates, list cuts, no-list]

Lead with the diagnosis you believe the document avoided — an audit that only criticizes is itself a dog's dinner. The goal is not to shame the deck but to leave its owners one page away from a real kernel.