--- title: "Planning that stays honest · DeliverySheet" description: "Separating fact from assumption, modelling cross-cutting work as what it is, and knowing exactly where AI belongs." canonical_url: "https://www.deliverysheet.com/topics/planning" last_updated: 2026-10-10 meta: author: "Tan Gravam" "og:description": "Separating fact from assumption, modelling cross-cutting work as what it is, and knowing exactly where AI belongs." "og:image": "https://www.deliverysheet.com/_og/s/o_1cb2fd31e1cf5ea8.png" "og:image:alt": "Planning that stays honest — DeliverySheet topic card" "og:image:height": "600" "og:image:type": image/png "og:image:width": "1200" "og:title": "Planning that stays honest — DeliverySheet" "twitter:description": "Separating fact from assumption, modelling cross-cutting work as what it is, and knowing exactly where AI belongs." "twitter:image": "https://www.deliverysheet.com/_og/s/o_1cb2fd31e1cf5ea8.png" "twitter:image:alt": "Planning that stays honest — DeliverySheet topic card" "twitter:title": "Planning that stays honest — DeliverySheet" --- > Index of every page on this site: [llms.txt](https://www.deliverysheet.com/llms.txt) [← All writing](https://www.deliverysheet.com/blog) **Topic ** # **Planning that stays honest** ## **What makes a delivery plan honest?** **The short answer ** An honest plan does three things. It separates known facts from assumptions from open questions, because a request written in one confident voice makes an assumption indistinguishable from a fact and every downstream estimate then inherits it. It models vertical delivery streams and horizontal cross-cutting concerns differently, because verticals consume capacity continuously while horizontals consume it in bursts and gate other teams' progress. And it lets assessed-and-nothing-found be a first-class answer, distinct from not-assessed, because otherwise people invent dependencies and risks to look diligent, and invented entries are worse than blanks. A plan is a set of claims about a future nobody has seen. It stays useful for exactly as long as it keeps being honest about which of those claims are established, which are believed, and which are guesses wearing the same typeface. ## Separate what is known from what is assumed Requests arrive as [a blend of fact, assumption and open question](https://www.deliverysheet.com/blog/known-facts-assumptions-unknowns), written in one confident voice. The damage is done by the formatting: an assumption written in the same tone as a fact is treated as a fact by every subsequent reader, and the estimate, the commitment and the quarter plan all inherit it without anyone consciously deciding to accept it. Split the three, name the evidence behind anything you called a fact, and the list of assumptions turns out to be a better risk register than the one you would have written from a blank field. ## Model cross-cutting work as what it is Vertical work is a delivery stream owned by one team, consuming capacity continuously in its own lane. Horizontal work — security, legal, compliance, design, accessibility, privacy — pulses into several verticals at gates, is driven by other people's schedules, and gates their progress. Planning both with the same object, usually called an epic, is why the most predictable bottleneck in delivery keeps arriving as a surprise: four lanes reach the same gate in the same fortnight, and the two-person group behind it had no way to see it coming. ## Let "nothing found" be an answer A planning dimension needs three states, not two: not assessed, assessed and nothing found, assessed with items. Collapse the middle one into "empty" and an honest blank becomes indistinguishable from a skipped step — so people invent dependencies and risks to look diligent. Invented entries are worse than blanks: they consume the scarcest resource in the process, which is review attention, and they make the register look trustworthy when it is not. ## And keep AI on the reversible side The dividing line is not model capability, it is accountability. Use AI where the output is verifiable in seconds and a wrong answer costs one edit — turning prose into a structured draft, listing what a plan has not answered, challenging a too-clean "no known risks". Keep it away from anything carrying an organisational commitment: what gets committed, who owns it, how much capacity it takes, whether something is ready. ## **The full argument ** Separating fact from assumption, modelling cross-cutting work, and knowing where AI belongs. - [**A risk register that gets read: mitigate it, accept it, or it blocks**](https://www.deliverysheet.com/blog/risk-register-that-gets-read) A project risk register in five columns, the three ways a risk can leave it, and the rule that makes people read it: a serious open risk blocks the commitment. - [**How to run a pre-mortem: forty-five minutes before you commit**](https://www.deliverysheet.com/blog/how-to-run-a-pre-mortem) A project pre-mortem in 45 minutes: imagine the failure, write reasons alone, pick the fatal ones, and turn each into a risk, a dependency or a cut. - [**Delivery roadmap: how to build one that survives the quarter**](https://www.deliverysheet.com/blog/how-to-build-a-delivery-roadmap) How to build a delivery roadmap from commitments: the five columns, a worked example, the update rhythm, and the three ways a roadmap rots. - [**The RAID log, minus the theatre**](https://www.deliverysheet.com/blog/raid-log-without-the-theatre) Risks, assumptions, issues, dependencies — the RAID log is the right instinct wrapped in the wrong ritual. What to keep, and what a log can't hold. - [**A discovery is a decision with a deadline**](https://www.deliverysheet.com/blog/discovery-is-a-decision-with-a-deadline) A spike that never ends is a parking lot. What separates discovery from research is a time-box, a target date, and a conclusion someone must record. - [**AI should draft and challenge. It should not decide.**](https://www.deliverysheet.com/blog/ai-should-suggest-not-decide) Where an LLM genuinely helps in delivery planning, where it must not be trusted, and the design rule that keeps the two apart. - [**The dependency you don't own**](https://www.deliverysheet.com/blog/the-dependency-you-dont-own) Most delivery risk sits in work another team has to do for you — and the usual tracking treats it exactly like work you control. - [**A decision without a record is a decision you will make again**](https://www.deliverysheet.com/blog/decisions-need-a-record) Teams re-litigate the same architectural and scoping calls every few months, because what was recorded was the outcome and never the reasoning behind it. - [**Scope is mostly what you're not doing**](https://www.deliverysheet.com/blog/scope-is-what-youre-not-doing) An in-scope list describes an intention. The out-of-scope list is what actually holds when someone asks for one more thing in week six. - [**"No known risks" has to be a valid answer**](https://www.deliverysheet.com/blog/no-known-risks-is-an-answer) Planning templates that only accept filled-in fields get filled in. The result is a risk register full of fiction, which is worse than an empty one. - [**Vertical and horizontal work: the distinction planning tools miss**](https://www.deliverysheet.com/blog/vertical-and-horizontal-work) Delivery streams and cross-cutting concerns behave differently, need different capacity models, and fail differently. Most tools call both an "epic". Defined in the glossary: [Vertical work](https://www.deliverysheet.com/glossary/vertical-work), [Horizontal work](https://www.deliverysheet.com/glossary/horizontal-work), [Readiness (three-state)](https://www.deliverysheet.com/glossary/readiness-three-state), [Time-boxed discovery](https://www.deliverysheet.com/glossary/time-boxed-discovery), [RAID log](https://www.deliverysheet.com/glossary/raid-log), [RACI matrix](https://www.deliverysheet.com/glossary/raci-matrix) I'm Tan Gravam. I build **DeliverySheet** — it takes a vague work request to a clear delivery decision, so the shape, owner, capacity, dependencies and open questions are on the table before anyone commits people or a date. $189/month per workspace, unlimited members. 7-day free trial — card required, cancel before it ends and you're not charged. I answer the support email myself. [**Start 7-day trial **](https://www.deliverysheet.com/login?next=/app) [**See pricing **](https://www.deliverysheet.com/pricing) [**Glossary **](https://www.deliverysheet.com/glossary) ```json {"@context":"https://schema.org","@graph":[{"@id":"https://www.deliverysheet.com/#website","@type":"WebSite","description":"Turn raw work requests into structured, decision-ready demands before you commit people, budget, or a date. 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