/stakeholder-engagement-advisor

name: stakeholder-engagement-advisor
argument-hint: "[stakeholder and situation]"
description: Plan engagement for a specific stakeholder. Use when preparing an outreach, navigating resistance, or aligning a critical relationship before a key milestone.
intent: >-
  Guide per-stakeholder engagement planning through the Adaptive Decision Ladder:
  three targeted questions diagnose the stakeholder's profile, power/impact quadrant,
  and your engagement context, then deliver a tailored approach — key message framing,
  recommended medium and cadence, what you need from them versus what they need from
  you, and a named next action with owner and deadline. Treats both sides of the
  relationship, not just yours.
type: interactive
best_for:
  - "Preparing to engage a powerful executive sponsor whose support is critical but whose motivations are unclear"
  - "Planning outreach to a resistant or skeptical stakeholder who could block your roadmap"
  - "Navigating first contact with a newly identified stakeholder mid-initiative"
  - "Designing inclusive engagement for a Q1 (high-impact, low-power) user community that needs more voice"
  - "Aligning cross-functional engagement strategy before a high-stakes roadmap review or launch"
scenarios:
  - "Help me plan how to engage [stakeholder] before my roadmap review"
  - "I have a resistant stakeholder — how do I approach them?"
  - "I need to bring a new executive sponsor up to speed quickly"
  - "How do I engage frontline users who've been excluded from our feedback loops?"
  - "Help me prepare a 1:1 with someone who could block this initiative"
sources:
  - "MITRE Innovation Toolkit — Quickstart Stakeholder Engagement Canvas: https://itk.mitre.org/toolkit-tools/quickstart-stakeholder-engagement-canvas/"
theme: stakeholder-comms
estimated_time: "15-25 min"

Stakeholder Engagement Advisor

Purpose

Plan how to engage a specific stakeholder — before a critical conversation, milestone, or relationship repair. Generic stakeholder engagement fails because it treats all stakeholders with the same message, medium, and cadence. An executive sponsor who privately disagrees with your direction needs different handling than an impacted frontline user who's never been consulted. This skill diagnoses the specific stakeholder relationship you're managing and delivers a tailored engagement approach that accounts for both sides of the conversation — their motivations and yours.

Run this skill once per priority stakeholder. Priority stakeholders are those in the "manage closely" quadrant from stakeholder-mapping, every Q1 (high-impact, low-power) stakeholder regardless of Power × Interest placement, and anyone who has the potential to block, delay, or fundamentally reshape your initiative.

Input

**Works best with:** The specific stakeholder and the situation — the conversation, milestone, or tension you're preparing for. **Also useful:** Their power/interest read, history with you or the initiative, and what a good outcome looks like.

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 advisor opens by asking who the stakeholder is and what's coming up with them.

**Example invocation:** `Plan engagement: our VP Sales publicly supports the replatform but keeps escalating exceptions — QBR in 2 weeks.`

Key Concepts

**Stakeholder Motivations vs. Your Motivations** — The most common engagement failure is planning only your side of the conversation. Effective stakeholder engagement requires mapping what the stakeholder needs, wants, and fears — separately from what you need from them. Where these overlap, you have an alignment path. Where they diverge, you have a negotiation to prepare for.

**Proxy** — A credible representative who speaks for or stands in for a stakeholder who is hard to reach, part of a large group, or represents a community rather than an individual. A good proxy is validated: they understand and can speak for the people they represent. A convenient proxy — the person who shows up to meetings — often cannot. Name the proxy explicitly and verify their representativeness before relying on their input.

**Analysis Before Action** — The engagement plan has two phases: diagnosis (who is this person, what drives them, what is the relationship history?) and planning (what will you say, through which medium, with what desired outcome?). Teams that skip directly to planning produce tactics without foundation — a message crafted for the wrong motivation, a medium that signals the wrong level of importance, an ask that misreads what the stakeholder actually controls.

**Equity Lens in Engagement** — High-impact, low-power stakeholders (Q1 from stakeholder-mapping) require proactive engagement design, not an open-door policy. An open door serves the people who already know they have a seat at the table. Q1 stakeholders typically need you to go to them: structured research recruitment, named roles in review processes, and deliberate inclusion in decisions that affect them.

**Next Action Commitment** — Every engagement plan must end with a named next action: who does what, by when, through which medium, with what key message and desired outcome. Engagement plans without this commitment are intentions, not plans. The next action is the only part that actually moves the relationship forward.

**Engagement Context** — The situational frame around the engagement matters as much as the stakeholder profile. Preparing for a first contact requires different framing than recovering from a conflict, securing buy-in before a launch, or maintaining an already-aligned relationship. The context shapes the message, the medium, and the desired outcome.

Application

This skill runs as a guided conversation. Answer each question; the advisor synt