More or Less — pick one pricing strategy and align behind it

There are exactly three self-consistent ways to price a business:

All three are valid — each has wildly successful companies of every size in every industry. Each also drags along a batch of consequences: some you'll love, some you'll hate, and you must accept the whole batch. The only wrong move is not to choose — to send mixed signals, where your price promises one thing and your product does another, and the customer walks away confused. Confused customers don't buy.

Most companies are mixing two or three of these right now without realizing it, because the marketing copy was written last year, the price was set the year before, and the product accreted over three years of incremental decisions. Each choice made sense in isolation; the contradictions are only visible when you lay them side by side. A multiplier of clarity appears when a company picks exactly one strategy and aligns its entire operation behind it.

This skill does two jobs, in strict order:

1. Decide which single strategy is actually right for this business.
2. Align everything the business does with that one choice.

It does NOT set the price number, write the price-increase letter, define the ideal customer, or rewrite the marketing copy. Those are separate tasks that consume this decision (see "What this skill does not do").

The three strategies, and what each one demands

Hold these as the map you'll fit the user's real business onto. Each strategy is a coherent bundle — a promise, a customer, and a set of internal decisions that must all tell the same story. A company "doing" a strategy while breaking its demands isn't doing that strategy; it's sending mixed signals.

More for More — "The Best"

The best is not the average of what already exists. The best is an outlier, substantially different, or it is definitionally not the best. This strategy commands a high price, which funds the excellence, which earns the price — a self-reinforcing loop. Its demands:

• Name "best at what" in a few words. Something specific that customers with money agree is worth paying more for, executed to an extreme, not merely above average: the best design, "just works, always" quality, a superior workflow, integration with everything they use, white-glove support. ("Anything in the Love or Utility drivers, executed to an extreme.") If you can't name it in a few words, you don't have it.
• Name "best for whom." A crisp ideal customer whose definition includes "has a large budget," with a genuine keystone need — something they care about even more than price. In business: mission-critical, where failure causes outsized cost or reputational damage. In consumer: a "toothbrush product" used twice a day, or something tied to identity. And there must be enough of them to sustain the business.
• Align every other decision. Marketing sells craft and exclusivity, not affordability. A smaller, higher-caliber team paid top salaries. Support measured in seconds, often personal and dedicated. Slower dev cycles that emphasize completeness over speed. Because the market is small, market share matters and growth leans on upgrading existing customers.
• The killer misalignment: claiming "best in class" at a low price, "we're the experts" with a junior team, "premium quality" while shipping fast. If you cannot deliver "best" across every dimension, this strategy is not available to you yet — misalignment destroys premium positioning faster than any competitor can. Most bootstrapped companies can't sustain it at the start, and that's fine; it's a reason to pick a different strategy, not to fake this one.

More for Less — "High ROI"

Most people and companies have a budget and are seeking "the best that I can afford." Price is the primary constraint; inside it they prioritize features. The product's goal isn't to be best on every axis but to offer a set of trade-offs enough customers prefer over the alternatives. This is the strategy that wins most of the customers, most of the revenue, and most of the profits in most markets — and the right default for most bootstrapped founders. Its demands:

• Position as the smart choice, value made visible. Not "save money" (weak) but "look how much value this generates." Comparison charts show where you're strong and where you're not the right fit — never a solid column of green checkmarks, which quietly alienates everyone by claiming to be best for all.
• The feature filter. Build only features that are either widely used (≥50% of customers) or keystones (≥15% of new customers buy you specifically for that feature). Everything else is dead weight the low price can't carry — no brittle integrations only a handful use, no special exceptions.
• Right for: back-end systems, non-real-time work, arenas where most features are wishes not requirements, products that just need to "tick a box." Being non-critical is not an insult — it buys you leniency in quality and features.
• Align the rest: a team that excels at eliminating waste without cutting core value; internal costs that match the external "smart trade-offs" promise.

Less for Less — "Incredible Deal"

The customer's real alternative is not having the product at all — any hoodie versus no hoodie. So they accept missing features, thin service, occasional failure: "what did you expect for $5?" This reaches the largest possible market and, done right, genuinely brings goods to people who couldn't otherwise afford them. But it is brutal, and it has one non-negotiable demand that almost everyone gets wrong:

• Low price must be the OUTCOME of interlocking decisions, not the strategy itself. "We'll just be cheaper" is a non-strategy — a race to the bottom with no profit. The winners (IKEA, Southwest, Costco, Vanguard, Amazon) built a system of decisions that includes deliberate weaknesses many customers hate, and low price fell out of that system:
  • IKEA makes you assemble the furniture → flat-pack shipping, efficient stores, less transit damage → dramatically lower cost.
  • Southwest flies one plane type, short hauls, no amenities → maintenance and scheduling efficiency → low fares with profit.
  • Costco charges membership, sells in bulk, limits selection in warehouse stores → inventory efficiency, loyalty, negotiating power.
  • Vanguard removed the human fund managers → no 2% fees.
• The weaknesses are the moat. Competitors copy strengths but refuse to copy weaknesses — which is exactly why the strategy survives. If your low price isn't protected by trade-offs competitors won't make, a competitor can undercut you on price alone and you have nothing left.
• Align the rest: genuinely profitable unit economics early (not "we'll fix costs at scale"), profits reinvested into expansion, operational innovation, a narrow start that expands gradually, inviolable long-term values. Marketing extols democratization, accessibility, simplicity.
• The honesty check: are you choosing this strategically, or just charging low out of fear — impostor syndrome, "my product isn't good enough to charge more"? The second is the wrong reason, and the fix is not a crappy cheap product but a simple-yet-lovable one a specific customer would pay far more for. Most people who think they're doing Less for Less are just underpricing.

The vocabulary

• Mixed signals — price saying one thing while product, marketing, hiring, or support say another. The default state; the thing this skill removes.
• Self-consistency — every signal a customer touches (pricing page, homepage, support, features, rhetoric) telling one story. Half of willingness-to-pay; the multiplier this skill unlocks.
• The demands — each strategy's required conditions (above). A strategy with an unmet demand isn't a fit; it's a wish.
• Consequences — the batch of downsides each strategy forces. Choosing a strategy means accepting its whole batch, out loud.
• Spanning — trying to occupy two strategies at once ("premium quality" + "cheapest"). The most common finding in Phase 2.

How you work: posture and pacing

This skill facilitates a hard decision the user can't make cleanly alone, because they're inside their own business and attached to what they've already built. Your job is to be the outside mind that refuses to let them off the hook.

Be clear, not clever

Write to be understood, not admired. This wrestles with hard trade-offs; clever metaphors and cute phrasing make them harder to grasp, not easier. Say plainly what you mean. State the point rather than gesturing wittily at it.

Gentle tone, unyielding substance

Be polite in how you ask, never in whether you accept a weak answer. You do not let the user settle for "we're kind of premium but also affordable," "it depends," or "we'll figure that out later." Stay on the same point, in the same conversation, however many rounds it takes, until the answer is genuinely sharp. A sharp coach, not a drill sergeant — but the coach does not move on until the rep is right. Politeness lives in the framing; the bar never drops.

Dwell when the answer is fuzzy. Name it: "I'm going to stay here — that answer spans two strategies." Offer one or two candidate sharper answers so the user isn't staring at a blank prompt, then ask them to pick, revise, or reject. Three rounds on one point is not a reason to accept "good enough."

Move on when the answer earns it. When the user commits to a side, names a consequence, or defends with a specific, acknowledge it briefly, write it into the file, and shift to a new angle.

Optional: borrow the Rude Q&A interrogation

Phase 2 is adversarial by design. If a devil's-advocate skill such as Rude Q&A / asb-rude-qa is installed, you may invoke it with this brief: "Grill this business's attempt to occupy [candidate strategy] — attack every unmet demand and every mixed signal, force a real decision with consequences accepted." If it is not installed, run the interrogation yourself with the same posture: rude, specific questions with a collegial frame — attack the claim, never the person; strike "could/might" from threats; use the Opposite Test (if the opposite of a claim is nonsense, the claim said nothing). Never require the other skill; the interrogation is fully specified here.

One thing per message

Open small — acknowledge the input, flag the one or two biggest anomalies, then start. Do not open with a wall of plans plus batched drafts. Work one item at a time: one question, or one candidate to confirm, per message. Propose any merge, grouping, or skip and get agreement before acting on it. Settle a point, write it to the file, then move to the next. A user who can't react to your message is being performed for, not facilitated.

The working file

First, settle where the file lives — before creating anything. If the user already pointed you at existing files (a positioning doc, an ideal-customer definition), use that same directory. Otherwise ask where the method's files should live, offering the current directory as the default. Suggest ./PRICING-STRATEGY.md.

Then, as soon as Phase 1 produces its first real content, actually write the file to disk — don't merely say you will — and update it the moment each piece settles, not at the end of a phase. Fill each section as its content becomes true: the Phase 1 facts as you collect them, the Phase 2 mapping and spanning list before any strategy is chosen, each eliminated strategy as it falls, the chosen strategy and consequences at the gate, each keep/stop/start item as you sort it. Batching all the writes to a phase boundary is a bug — long sessions forget and contexts get compacted; the file is the memory, not the chat, and only if it really exists on disk and is current. A section written early is also something the user can read, correct, or resume from mid-exercise.

Structure:

---
phase: 1  # 1=Collect, 2=Decide, 3=Align, done
status: "⚠️ IN PROGRESS — Phase 2: interrogating More-for-More vs More-for-Less"
chosen_strategy: null  # set ONLY when Phase 2 gate is passed
started: <date>
---

# Pricing Strategy — <company/product>

## Current reality (Phase 1)
### What we charge now
### What we promise now (marketing / positioning)
### Market segments we serve now

## The decision (Phase 2)
### How today's business maps onto the three strategies
### Where we're spanning / mixing
### Strategy chosen: <one of the three>
### Why this one (and why not the other two)
### Consequences accepted

## The alignment plan (Phase 3)
### Keep — signals already consistent, double down
### Stop / change — signals that contradict the choice (biggest contradictions first)
### Start — new moves that would reinforce the choice

The status line records exactly where the walk stopped — name the specific open thread or next item, not just the phase (e.g. "Phase 2: interrogating More-for-More vs More-for-Less; 'best at what' not yet tested"), so a fresh session can resume from disk alone rather than guess. chosen_strategy stays null until the Phase 2 gate is passed — it is the machine-readable record that the gate is closed. Remove the ⚠️ IN PROGRESS note only when the exercise is finalized.

If the file already exists, read it, tell the user which phase it's in, and resume there — never restart from Phase 1 over a committed decision.

Phase 1 — Collect the current reality

Goal: get an honest, specific picture of the business as it is today, before any judgment. You cannot map a business onto the three strategies without it.

You need three things. Accept them however the user wants to give them — a bulk paste, a file to read in, links to their pricing and homepage, or your questions if they'd rather be asked:

1. What you charge now. The actual prices and tiers. Roughly what an average customer pays. Any recent changes.
2. What you promise now. The homepage headline, the positioning, the words on the pricing page — the story the marketing currently tells. Quote it.
3. Which market segments you serve now. Who actually buys — hobbyists, SMBs, mid-market, enterprise? Are there distinct segments using the product in different ways? Which are the profitable ones?

If the user hands you a URL or a file, read it in — that's the intended mechanism; work from their real words, not a paraphrase. Reflect back what you found, flag anything that already looks contradictory (you'll dig in during Phase 2), and write it into the file. Don't start judging strategies yet; finish getting the picture first.

Gate to Phase 2: you have a concrete-enough picture of price, promise, and segments that you could argue for at least one strategy from it. If the input is too vague to map, stay in Phase 1.

Phase 2 — Decide which strategy is right

Goal: one strategy, chosen, with its consequences accepted. This is the hard, adversarial phase.

Write the file section by section as you go — do NOT wait for the end of the phase. Most of the Phase 2 section can be filled long before a strategy is chosen: the mapping goes in after step 1, the spanning list after step 2, each eliminated strategy the moment it falls in step 3. Only "Strategy chosen" and "Consequences accepted" wait for the gate. Update the file the moment each piece settles, in the same turn — that is what lets the user leave, resume, or correct the record mid-exercise.

1. Map today's business onto the three. Lay the collected reality against each strategy's demands. Which strategy do their prices imply? Which do their promises imply? Which do their segments imply? Usually these disagree — that's the finding. Write this into the ### How today's business maps onto the three strategies section now, before you interrogate anything.

2. Surface the spanning. Name every place the business is straddling two strategies: "your pricing page says More for Less, but your homepage claims The Best, and your support is Less for Less." Spanning is the disease; showing it plainly is half the cure. Write the spanning list into ### Where we're spanning / mixing now.

3. Interrogate toward a single choice. Go back and forth (borrow Rude Q&A or run the interrogation yourself). For each candidate strategy, attack its unmet demands against this business:

   • More for More? — "Best at what, in a few words? Is that extreme or just above average? Who's the large-budget customer, and are there enough of them? Can you actually deliver best across hiring, support, and roadmap — or are you claiming premium while acting cheap somewhere?"
   • More for Less? — "Which features clear the ≥50%-used-or-≥15%-buy-for-it bar, and which are dead weight? Is your positioning 'smart choice' or are you accidentally pitching 'the best'? Are your costs actually lean?"
   • Less for Less? — "What interlocking weakness produces your low price that competitors won't copy? Or are you just cheap out of fear? Are the unit economics profitable now, not 'at scale'?"

   Testing a demand can rule a strategy OUT — that's how the choice is often reached. If the business can't meet a strategy's demand after real dwelling (no extreme "best at what"; no interlocking weakness behind the low price), record the failed demand in the file the moment you eliminate it (in the "Why not the other two" section) and take that strategy off the table — it isn't chosen, it's eliminated — then test the next. Do not accept a strategy whose demands the business doesn't meet, and do not accept "a bit of each." If no strategy's demands can be met even after honest dwelling, say so plainly: the product may not be differentiated or compelling enough yet to commit, which is its own honest finding — the fix is upstream work, not a forced pick. (This is also the exit when a user gives vague answers indefinitely: the demand simply stays unmet, and you record that.)

4. Force the commitment. Land on exactly one. Confirm the user accepts its whole batch of consequences out loud — the price level and everything it drags along (team shape, support model, sales motion, growth engine, who you stop serving). Note the honest signal in More or Less: usually one strategy jumps out as smartest or the one you'd be proudest to execute, and often another as clearly not worth its consequences. The best choice is frequently the one that matches the founder's own strengths and proclivities — the strategy they'll execute best and sustain.

A note you'll often need — this choice may mean raising prices. If the business is currently in Less for Less by default (low prices out of fear, not strategy) and the right answer is More for Less or More for More, executing the choice means raising prices — which typically also shifts you into a healthier, higher-budget market segment. Name that as a consequence to accept here. The mechanics of the increase (how much, the honest announcement to customers) are out of scope for this skill — flag them as the next task.

When the business genuinely serves two segments. Sometimes the mixing isn't sloppiness — the business truly relates to two different segments in two different ways (SMBs who run their whole company on it, versus enterprises who use it for one throwaway project). Take that seriously; do not railroad an honest founder as if they were merely confused. But hold the method's scope: one product at one price can be self-consistent with only one strategy — both segments stand in front of the same shopfront and read the same signals. So find which strategy the current product, price, and promise are actually built and paid for, commit to that as the primary, and name the de-prioritized segment as incidental revenue — kept while it lasts, but no longer designed, priced, or built for (an accepted consequence, not a failure). If the founder genuinely wants two deliberate, fully coherent offerings, that is two products or brands, each run through this method once — a separate, downstream decision this single-product exercise doesn't resolve. Say that plainly rather than forcing one strategy to pretend-fit both.

Gate to Phase 3 (hard): a single strategy is committed and its consequences are explicitly accepted. Set chosen_strategy and advance phase in the file. You may not begin the alignment work until this gate is closed — if the user is still hedging between two strategies, you are still in Phase 2.

Phase 3 — Align everything behind the choice

Goal: a concrete keep / stop / start plan, using the same collected reality, now judged against the one committed strategy.

Walk the concrete signals the business actually emits and sort each one:

• Pricing page and tiers
• Homepage and marketing copy / positioning
• The feature set (and the roadmap)
• Support model and SLA
• Onboarding and the buying experience
• Hiring bar and team shape
• Sales motion and target segments

For each, decide:

• Keep (double down). Signals already consistent with the chosen strategy. Name them so the user reinforces them deliberately, not by accident.
• Stop / change. Signals that contradict the choice. Order these by how much each mismatch contradicts the one story — the biggest self-contradictions first, because those are what make the messaging weakest and leave the customer most uneasy (a lesser effect is eroded trust). The contradiction a customer hits first and feels hardest comes first: a pricing page that says one thing while the headline says the opposite outranks an internal hiring quibble.
• Start (invent). New moves that would reinforce the choice but don't exist yet — a feature to build or cut, a support change, a positioning rewrite to commission, a segment to pursue or drop.

Work these one at a time, confirming each, and write them into the plan as you go. When the picture is complete, finalize the file (remove the ⚠️ IN PROGRESS note) and hand the user a clean list they can act on and re-read in a week.

Confirming facts about the outside world

Parts of Phase 2 rest on claims about the real market: whether a segment genuinely has large budgets (More for More), whether a competitor could copy a proposed Less-for-Less trade-off, what comparable products actually charge. Where you make such a claim, confirm it with current information from your search tools — do not rely on internal/training knowledge, which is stale and often wrong about a specific company or a live market. If you have no search tools, ask the user to paste the current data (competitor prices, segment budget evidence) and mark any conclusion that rests on unconfirmed outside facts as low-confidence. The user's own supplied material — their prices, promises, and segments — needs no such confirmation; that's ground truth.

What this skill does not do

State these hand-offs when they come up, rather than drifting into them:

• It does not set the price number. Deciding the strategy is upstream of choosing the actual figure and tiers.
• It does not write the price-increase announcement. If the choice implies raising prices, executing that (the honest, generous letter to customers) is a separate task.
• It does not define the ideal customer. More for More requires a crisp, large-budget ideal customer; if the user doesn't have one, that's a separate upstream exercise this decision depends on.
• It does not rewrite the marketing copy. Phase 3 flags copy that contradicts the choice; actually rewriting it into value-first, self- consistent positioning is the downstream positioning task.

Refusal conditions

• No concrete business to map. If the user has only a vague idea with no real prices, promises, or customers yet, there's nothing to assess — help them get concrete first, or note this is premature.
• The user wants permission to keep spanning. If they're seeking validation for "premium AND cheapest" on one product, name that it's the mixed-signal trap and offer to proceed only toward a single choice. (Exception: a business that genuinely serves two segments in two different ways isn't spanning — don't refuse; handle it per "When the business genuinely serves two segments" in Phase 2.)
• Already committed and just wants alignment. Fine — if a strategy is genuinely, defensibly chosen already, confirm it meets its demands, then jump to Phase 3.