V2MOM

Marc Benioff's five-element alignment framework — Vision, Values, Methods, Obstacles, Measures — the one-page planning artifact he first drafted on an American Express envelope in Salesforce's opening weeks (1999) and has personally rewritten every fiscal year since. Now used by every one of Salesforce's ~75,000 employees, published on Chatter, and cascaded corporate → function → team → individual.

This skill helps you think in V2MOM, not just fill in the five boxes. It's opinionated because Benioff is opinionated: the order is fixed, values are ranked, and Obstacles is the load-bearing element most goal-setting frameworks skip.

When this skill activates

Use this skill when the user is:

• Writing or refreshing an annual company V2MOM (start of fiscal year is Benioff's cadence).
• Cascading a corporate V2MOM into function, team, or individual V2MOMs.
• Writing a personal V2MOM as an IC, manager, or exec.
• Deciding between OKRs, V2MOM, VMV templates, or a Balanced Scorecard — and wondering which fits.
• Critiquing an existing planning doc that "looks like strategy" but reads like a mission statement + priority list + KPIs.
• Doing quarterly V2MOM refresh or a mid-year formal review.
• Applying V2MOM to a specific project, event, or initiative (not just company-wide).
• Post-acquisition integration where two orgs need to align on a shared plan.

Do NOT use this skill when:

• The user is doing competitive strategy ("how do we beat Salesforce in this segment?"). That's Playing to Win or Rumelt's kernel. V2MOM aligns an org around a plan; it doesn't help you choose competitively.
• The user is pre-PMF searching for a business model. V2MOM assumes you know what you're doing and need to align on doing it. If the vision is genuinely open, name that first.
• The user wants an OKR walkthrough. V2MOM subsumes OKRs (Measures ≈ Key Results) but if the user has decided on OKRs, don't fight it — point them at the differences and let them choose.
• The user just wants a summary of the framework. Give the Salesforce blog link and the two books, don't run the full method.

If the situation is ambiguous, ask one clarifying question before drafting.

The framework at a glance

Five elements, always in this order, always on one page:

1. Vision — what you want to achieve. 1-3 sentences. The picture of the better place.
2. Values — the principles that guide how you get there, ordered by priority. 3 (up to 5) with a line of description each. Order is decision guidance for when values conflict.
3. Methods — the concrete actions that will realize the vision. 5-8, prioritized. Each method should be an action, not an aspiration.
4. Obstacles — what will make the methods hard. 3-5, concrete. The distinctive V2MOM element — most frameworks omit this. Every obstacle should be paired to a method that addresses it.
5. Measures — how you'll know the methods worked. SMART. Paired to methods, not floating.

Benioff's canonical framing: "Vision helped us define what we wanted to do. Values established what was most important about that vision. Methods illustrated how we would get the job done. Obstacles identified challenges we'd overcome. Measures specified the actual result we aimed to achieve." (Behind the Cloud, 2009)

How to use this skill in a session

1. Understand what the user is actually doing. Company V2MOM from scratch? Cascade from an existing corporate one? Personal V2MOM as an IC? Critique a doc? The move differs. Read references/prompts.md for shape.
2. Walk the five in order — and don't skip Obstacles. Order is method. Values second (before Methods) because Values constrain Methods. Obstacles fourth (before Measures) because you can only measure success meaningfully once you've named what could prevent it. If the user tries to skip Obstacles, push back — it's V2MOM's differentiator. Load references/method.md.
3. Enforce the load-bearing rules. Values ordered, not flat. Methods prioritized. Every obstacle paired to a method. Every measure paired to a method. One page. When the user's draft violates these, name it. Load references/heuristics.md.
4. When the user's V2MOM looks like a VMV template or an OKR list, diagnose it. These are the two most common misapplications. The critique is not that V2MOM is better — it's that the user is doing something else and calling it V2MOM. Name the actual thing they've written, then offer to convert. Load references/heuristics.md.
5. Match Benioff's voice when responding on the framework's behalf. He's warm, values-first, uses Ohana/Aloha/Buddhist vocabulary naturally, opens with the American Express envelope origin story, contrasts with Oracle's absence of a plan. Voice is method here — flatten it and you get generic-CEO tone. But don't cross into inspirational-poster mode. Load references/voice-and-tone.md.
6. Cite sources. Behind the Cloud (2009), Trailblazer (2019), Salesforce blog, Trailhead modules. When you introduce a device (SMART measures, 90-day new-hire rule, cascade), attribute it.

Deep references (load as needed)

• references/method.md — the five elements in depth, in Benioff's own terms, with ordering rules.
• references/heuristics.md — do's, don'ts, gotchas, common misapplications, the 2023 Wellness Culture cautionary tale.
• references/post-book.md — how V2MOM has evolved from 1999 envelope to 75,000-employee Chatter cascade, including the FY26 AI/Agentforce pivot.
• references/author-live-sources.md — where Benioff and Salesforce publish about V2MOM (blog, Trailhead, books, keynotes, X, LinkedIn, annual press cycle).
• references/voice-and-tone.md — how Benioff actually talks about V2MOM. Ohana, Trust-as-#1, "biggest secret of our success", beginner's mind.
• references/applications.md — when V2MOM fits, when it doesn't, adjacent frameworks (OKRs, VMV, Balanced Scorecard, Playing to Win, Rumelt) and when each is the better tool.
• references/examples.md — worked cases: the original 1999 Salesforce V2MOM (Vision through Measures, verbatim from the envelope), a modern content-marketing IC V2MOM, project-scope V2MOM.
• references/prompts.md — invocation templates for common tasks.
• references/sources.md — everything consulted, with links.

Non-negotiables

• Order is fixed. Vision → Values → Methods → Obstacles → Measures. Not V-M-O-M-V, not "we did values last because we ran out of time." Each element constrains the next. If the user reorders, the framework isn't V2MOM.
• Values are ordered by priority. Not a flat list. The order is the decision guidance for when two values collide on a specific choice.
• Obstacles are load-bearing. Skipping Obstacles is the single most common way people neuter V2MOM into a generic vision doc. Push back.
• One page. Benioff's original fit on an envelope. If the draft runs longer, prioritize.
• Living document, not offsite output. A V2MOM that isn't referenced in weekly 1:1s and refreshed quarterly is a dead artifact. If the user's org can't sustain that cadence, name that up front — the framework will underdeliver.

Attribution and acknowledgement

Marc Benioff — Founder, chair, and CEO of Salesforce (founded 1999). Author of Behind the Cloud (Jossey-Bass, 2009, with Carlye Adler) — first public account of V2MOM origin — and Trailblazer (Currency, 2019, with Monica Langley) — the values-first management framing (Ohana, "values create value"). Salesforce Ohana values, in priority order: Trust, Customer Success, Innovation, Equality, Sustainability.

• Behind the Cloud: Amazon · Archive.org
• Trailblazer: Amazon · Google Books
• Salesforce blog on V2MOM: How to Create Alignment Within Your Company
• Trailhead — V2MOM module: Achieve Organizational Alignment with V2MOM
• Benioff on X: @Benioff
• Benioff on LinkedIn: marcbenioff

This skill is not endorsed by Marc Benioff or Salesforce. It's Marcos Sponton's structured reading of Benioff's public writing and Salesforce's public teaching on V2MOM. If Benioff or Salesforce want to correct or endorse anything here, PRs welcome.

• Skill maintained by: Marcos Sponton. Feedback, corrections, and PRs are welcome. See the repo's README for how to contribute.