EOL Stakeholder Sequence

Purpose

Plan the order of EOL conversations, and what each one must cover. The output is a sequenced list of stops — each with what you need from them, what you owe to them, the red flags to listen for, and what the conversation must produce.

EOL is not a broadcast. It is a series of conversations where each one informs the next, and each one surfaces something the last one missed. Sequenced well, the awkward discoveries happen in a conference room. Sequenced badly, they happen in public, after the announcement, in front of customers.

Input

Works best with: The product being sunset and who already knows about it.

Also useful: Scale (customers, revenue, contracts), whether channel partners or regulators are involved, and any political sensitivities, strained relationships, or past surprises worth planning around.

Anything supplied with the invocation itself — text after the skill name, a pasted context dump, or an appended ARGUMENTS: line — counts as answers already given. Use it and skip whatever it covers; don't re-ask.

Arriving empty-handed? That works too. The skill asks up to three questions — what's being sunset and who knows, how big the blast radius is, and whether there's history to plan around — then builds the sequence. Political sensitivities are optional; the sequence works without them and sharpens with them.

Example invocations:

• Sequence the stakeholder conversations for retiring our legacy reporting module.
• Who do I talk to, in what order, about sunsetting a hardware line with 8 resellers?

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Key Concepts

The Sequencing Principle

Talk to the people who can kill the plan before you talk to the people who have to execute it.

Each conversation should inform the next. Legal exposure first, because a contract term can end the discussion. Financial impact second, because it sizes everything downstream. Then revenue-facing teams, then customer-facing teams, then the technical teams who will carry it out.

Get this backwards — brief Support first, Legal last — and you will have told forty people about a plan that a single contract clause invalidates.

Right-Size the Sequence

Not all EOLs play out the same. Most land in the middle:

Level 2 is the default. Recommend a level, say why, then let the user move it. Never default to the heaviest sequence — a ten-stop tour for a feature deprecation burns credibility you'll want for the sunset that actually needs it.

If someone dials down, name the stop they're dropping and what it typically catches. Dropping Legal on a product with contracts is the one worth pushing back on once — then honoring their call.

The Canonical Order

Filtered by level, but the relative order holds:

Level 1+

1. Engineering — what depends on this technically
2. Support — what changes for support operations
3. Affected users or internal teams — who feels it first

Level 2+ (inserted ahead of the above)

1. Legal — contractual and regulatory exposure
2. Finance — revenue impact and forecast changes
3. Sales — pipeline, bundles, and promises made in the field that never found their way into a contract or a ticket
4. Marketing — you do not want to discover they just bought a quarter's worth of demand gen for the thing you killed
5. Customer Success — they will bear the brunt of this; work with them, not around them
6. Your most difficult customers — they will find the three things you forgot that would have blown up six months later

Level 3+

• Executive leadership — strategic approval
• Channel partners — inventory, commitments, and their own customer relationships
• Regulatory bodies — filings and compliance
• Key accounts — individual transition conversations

Why Your Most Difficult Customers Belong in the Sequence

Counterintuitive, and the stop teams skip most often. The customer who files the most tickets and pushes hardest in QBRs has, by construction, the deepest and weirdest usage of your product. They will find the integration you forgot, the contract term nobody read, and the workflow that has no equivalent in the replacement.

You can learn that from them in a scheduled call now, or from them on a public forum later.

What You Need / What You Owe

Every stop has two directions. Skipping the second turns stakeholders into an audience:

• What you need FROM them — the input, approval, or knowledge only they have
• What you owe TO them — the context, commitment, or lead time they need to do their job

A conversation that is all extraction gets you compliance. A conversation that runs both ways gets you the thing they weren't asked about.

The Sticky-Note Rule

Every bullet is 4 to 8 words. Sequences get read in hallways, before meetings, on phones.

Anti-Patterns (what this is NOT)

• Not a stakeholder map. No power/interest grid. This is an ordered itinerary.
• Not a broadcast plan. The customer announcement is a different artifact.
• Not parallelizable by default. The order is the value; parallelize only where noted.
• Not a RACI. Decision rights are a separate question from conversation order.

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Application

Step 1: Set the level

Recommend from blast radius, present all three, let the user choose. If unclear, ask:

"How complex is this sunset?

1. Light — a feature or internal tool. Few users, all reachable.
2. Standard — a commercial product with paying customers and contracts.
3. Heavy — revenue-critical, hardware, channel partners, or regulated.

Most are Standard. Which sounds like yours?"

Step 2: Order the stops

Apply the canonical order, filtered by level. Two adjustments worth making:

• Move a stop earlier when history demands it. If Sales was blindsided last time, brief Sales earlier than the template says and note why.
• Split a stop when one function holds two different conversations. "Legal (contracts)" and "Legal (regulatory)" are often different people with different answers.

Step 3: Build each stop

For every stop, fill five fields:

1. When — before or after which milestone or other stop
2. Why this stop matters for EOL — in 4-8 words
3. What you need FROM them — specific questions, not "input"
4. What you owe TO them — context, lead time, commitments
5. Red flags to watch for — the signals that this stop just surfaced a blocker

Then state the output: the decision, approval, or artifact the conversation must produce. A stop with no output is a status update, not a stop.

Step 4: Mark parallel vs. sequential

Say which stops must be strictly sequential and why, and which can safely run in parallel. Being explicit here is what lets a team compress a ten-stop sequence into three weeks without breaking the dependency that mattered.

Step 5: Assumptions

Close with what you assumed — who you think knows, what you think the contracts say, which relationships you think are intact.

Final Step: Offer what comes next

"Where next?

1. Build the phase-gated checklist — the operational plan (Recommended)
2. Draft talking points for the three most sensitive stops
3. Build the internal enablement pack — support FAQ, sales talking points, objections
4. Draft the customer announcement — see eol-message

Reply with a number, a combination ('1 & 3'), or your own path."

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Examples

• examples/sample.md — Fieldlight Classic Dispatch (SaaS, Level 2, eight stops)
• examples/sample-industrial.md — NFA-200 controller line (industrial, Level 3, eleven stops)

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Common Pitfalls

Pitfall 1: Announcing Before Asking

Symptom: The sequence starts with a company-wide email.

Consequence: Every subsequent conversation is a negotiation with someone who found out the wrong way and is now defending their turf instead of helping you.

Fix: The announcement is the end of the internal sequence, not the beginning.

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Pitfall 2: Legal Last

Symptom: Legal gets looped in once the plan is built, "to review."

Consequence: A contract term or regulatory obligation invalidates a plan forty people have already committed to. Now you're relitigating instead of executing.

Fix: Legal is the first Level 2+ stop. A five-minute "are there commitments here?" beats a five-week replan.

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Pitfall 3: Treating Sales as Recipients

Symptom: Sales is informed of the EOL date rather than asked what they've promised.

Consequence: Field commitments that never made it into a contract surface after the announcement, from the customer's side, as accusations of bad faith.

Fix: Ask Sales explicitly: what has anyone promised about this product's future? Ask before you tell.

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Pitfall 4: Skipping the Difficult Customers

Symptom: The sequence covers internal functions and stops.

Consequence: Your edge cases are discovered by the people least inclined to be quiet about them.

Fix: Two or three of your hardest customers, under NDA if needed, before the public announcement. Budget for what they'll find.

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Pitfall 5: Extraction-Only Conversations

Symptom: Every stop is a list of things you need. Nothing is offered.

Consequence: Stakeholders answer the questions asked and volunteer nothing. The thing that sinks you was the thing nobody thought to ask about.

Fix: Fill "what you owe them" for every stop before you hold it.

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References

Related Skills

These stand on their own — none is a prerequisite for this skill, and this skill isn't a prerequisite for them. If you already chose a level elsewhere, say "Level 2" and this skill builds to it.

• eol-checklist — the phase-gated operational plan
• eol-internal-enablement — what customer-facing teams get after these conversations
• eol-readiness-advisor — if the decision still needs a case
• eol-message — the customer-facing announcement
• stakeholder-map — general power/interest mapping for non-EOL work

External Frameworks

• Mendelow's Matrix — power/interest prioritization, useful for choosing depth per stop
• DACI / RACI — decision rights, a separate question from conversation order

Provenance

• Adapted from prompts/eol-stakeholder-sequence.md in the https://github.com/deanpeters/product-manager-prompts repo.