managing-up

- Building a proactive partnership with your manager (vs waiting to be managed)

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Install skill "managing-up" with this command: npx skills add oldwinter/skills/oldwinter-skills-managing-up

Managing Up

Scope

Covers

  • Building a proactive partnership with your manager (vs waiting to be managed)

  • Setting a clear upward communication system (async updates, 1:1 structure, decision memos)

  • Leveraging leaders to remove blockers and accelerate decisions (clear asks + escalation triggers)

  • Communicating trade-offs and context so leadership can make good calls

  • Creating a “seat at the table” path: showing business-level perspective before you’re invited

  • Setting boundaries when leadership pace/expectations are misaligned (without being adversarial)

When to use

  • “Help me manage up with my boss—set a cadence and a weekly update template.”

  • “My exec stakeholders feel out of touch—help me communicate context and trade-offs better.”

  • “I need a clean escalation plan and how to ask my leader for help without sounding needy.”

  • “I want more influence / a seat at the table—create a plan and artifacts.”

When NOT to use

  • You need HR/legal guidance (harassment, discrimination, retaliation, threats, investigations) — follow your company process and involve HR/legal.

  • You’re negotiating compensation/title or a formal performance process — use your company process; this skill can help with communication artifacts but not with policy/legal strategy.

  • You have a personal safety or mental-health crisis — seek professional help and follow company policy.

Inputs

Minimum required

  • Your role, scope, and current priorities (what you own; what “good” looks like in the next 4–8 weeks)

  • Who you’re managing up to (manager level; decision power; relationship stage: new/stable/strained)

  • Current friction (2–5 concrete examples) and desired outcome (clarity, autonomy, speed, influence, boundaries)

  • Communication environment (remote/hybrid, time zones, tools, meeting cadence)

  • Constraints (sensitive topics, confidentiality/PII rules, upcoming deadlines)

Missing-info strategy

  • Ask up to 5 questions from references/INTAKE.md (3–5 at a time).

  • If details are missing, proceed with a default managing-up operating system and clearly label assumptions.

  • Do not request secrets (passwords/tokens) or sensitive personal data; use anonymized summaries.

Outputs (deliverables)

Produce a Managing Up Operating System Pack in Markdown (in-chat; or as files if requested):

  • Context snapshot (role, goals, constraints, assumptions)

  • Manager profile (“How my manager works” + what they optimize for)

  • Upward communication cadence (1:1 structure + async update rhythm)

  • Weekly update template (exec-ready; “no response required” default)

  • Decision/trade-off memo template (for major decisions / escalations)

  • Escalation + ask plan (leader leverage map, escalation triggers, ask ladder)

  • Working agreement + boundary script (how to reset expectations respectfully)

  • Influence / seat-at-the-table plan (pre-wiring, strategic contribution loop)

  • Risks / Open questions / Next steps (always included)

Templates: references/TEMPLATES.md

Expanded guidance: references/WORKFLOW.md

Workflow (8 steps)

  1. Intake + objective + boundaries
  • Inputs: user context; references/INTAKE.md.

  • Actions: Clarify the outcome (autonomy, clarity, influence, speed, boundaries) and define what “better” means in 4–8 weeks. Identify constraints (HR/legal/PII). Choose pack scope (full pack vs subset).

  • Outputs: Context snapshot + assumptions/unknowns list.

  • Checks: Goal is measurable enough to evaluate after 4 weeks.

  1. Build a manager profile (what they optimize for)
  • Inputs: org context, manager level, prior interactions.

  • Actions: Draft “How my manager works”: success metrics, incentives/pressures, decision style, risk tolerance, communication preferences, and common failure modes.

  • Outputs: Manager profile (draft) + validation questions to confirm in 1:1.

  • Checks: Profile includes at least 3 actionable implications (what to do differently).

  1. Design the comms operating system (what goes where)
  • Inputs: current cadences, meeting load, tools.

  • Actions: Define channels: async weekly update, 1:1 agenda, decision memos for big calls, and escalation path for urgent issues. Decide what does not belong in 1:1s (pure status, unless required).

  • Outputs: Cadence plan + “what goes where” map.

  • Checks: System reduces surprises and reduces “drive-by” requests.

  1. Write the weekly update + exec-ready narrative
  • Inputs: priorities, milestones, risks, dependencies.

  • Actions: Create a weekly update that is skimmable: TL;DR, progress vs plan, decisions needed, risks, explicit trade-offs, and clear asks. Default to “no reply required unless…”.

  • Outputs: Weekly update template + example filled-in update (anonymized).

  • Checks: A leader can understand status and decision needs in ≤ 60 seconds.

  1. Create an escalation + ask plan (use leaders as resources)
  • Inputs: blockers, dependencies, stakeholders.

  • Actions: Define escalation triggers, pre-wire plan, and an “ask ladder” (from lightweight FYI → unblock → sponsor → decision). Translate blockers into specific leader actions.

  • Outputs: Escalation triggers + ask ladder + leverage map.

  • Checks: Each “ask” is actionable and time-bounded, not a vague request for help.

  1. Align expectations + set boundaries (respectfully)
  • Inputs: mismatches (pace, scope, availability), examples.

  • Actions: Draft a working agreement and boundary script: clarify expectations, propose alternatives, and secure explicit agreement. Prepare “pushback” language for unreasonable requests (times, scope, urgency).

  • Outputs: Working agreement + scripts (short, copy/paste).

  • Checks: Boundaries are framed as protecting outcomes (quality, speed, sustainability), not personal preferences.

  1. Build influence: seat-at-the-table loop
  • Inputs: strategy calendar, decisions, adjacent teams.

  • Actions: Create a plan to contribute at the business level: pre-reads, crisp POVs, trade-off framing, and consistent pre-briefs. Identify 1–2 high-leverage forums and how to earn invitation.

  • Outputs: Influence plan (30 days) + artifacts to share (POV note, decision memo).

  • Checks: Plan includes at least one recurring “strategic contribution” touchpoint per week.

  1. Quality gate + 4-week pilot + iteration plan
  • Inputs: full draft pack.

  • Actions: Run references/CHECKLISTS.md and score with references/RUBRIC.md. Add Risks / Open questions / Next steps. Propose a 4-week pilot and a retro prompt set.

  • Outputs: Final Managing Up Operating System Pack.

  • Checks: Pack is immediately usable; next interactions are scheduled (cadence + checkpoints).

Quality gate (required)

  • Use references/CHECKLISTS.md and references/RUBRIC.md.

  • Always include: Risks, Open questions, Next steps.

Examples

Example 1 (new relationship): “I started a new PM role. Help me manage up with my manager: create a manager profile template, a weekly update format, and a 4-week pilot cadence.”

Expected: manager profile + cadence + weekly update template + pilot plan + risks/open questions/next steps.

Example 2 (exec misalignment): “Our exec team keeps changing priorities and feels out of touch. Create an exec-ready weekly update and a trade-off memo template so I can escalate issues early and frame decisions.”

Expected: weekly update + decision/trade-off memo + escalation triggers + comms map.

Boundary example: “My manager is retaliating against me and I need to document it.”

Response: recommend HR/legal/company process; offer to create a factual incident timeline template and a neutral summary, but do not provide legal advice.

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