Influence: Stakeholder Map and Influence Plan

Turn I need buy-in from these people into a mapped, sequenced plan with scripts, ready to paste into a doc. Built from 328 insights from 140 Lenny's Podcast guests. Lead team: Jessica Fain, Jeffrey Pfeffer, Hilary Gridley.

When to use

• You must get a plan, budget or headcount approved by an exec, founder or board-facing leader.
• You disagree with a CEO, founder or boss and still have to lead the team through it.
• A founder or exec keeps pushing a pet idea or dropping drive-by asks.
• Requests from sales, execs or partners are piling up and you cannot say yes to all of them.
• You are new (to a company, team or level) and nobody trusts your judgment yet.
• A cross-functional launch or platform change touches many teams (eng, legal, sales, marketing).
• You have a doc or deck and want it graded for how it will land with a specific leader.

Step 1 — Diagnose (ask before answering)

If the user attached a PRD, deck, Slack thread or meeting notes, read it first and pull out: who is named, what is being asked, and the tone of any pushback. Then ask only what you cannot infer (max 4):

1. Who is the target and where do you stand with them? (new / low trust vs established; above you, peer, engineering, legal, sales) — routes to trust-building vs pitching plays.
2. What exact decision or action do you need, by when? (approval, resources, stop blocking, change a mind) — a vague ask cannot be planned.
3. Do you disagree, and what evidence do you hold? (none / opinion / data / a prototype) — routes the disagreement ladder.
4. What kind of org is it? (founder-led with strong opinions, doc culture vs slide culture, AI-native bet with uncertain outcomes) — routes founder plays and the shrink-the-change play.

Step 2 — Pick the play

Step 3 — Run it

Play A — Stakeholder map (always run first)

1. List every person or group who can approve, block, fund, build, or publicly criticize your initiative. Include the exec's chief of staff or EA, legal, finance, sales leads and the engineering partner.
2. Flag who is on your critical path (Pfeffer). For each, the only judgment you make is that you need their cooperation. Do not leak disrespect; senior people hide what they think of you, but cooperation odds still collapse.
3. For each person fill in: stance (ally / neutral / blocker), what they are accountable for beyond your area (Bangaly Kaba: ICs optimize a local maximum), their likely failure fear, and what kind of evidence moves them (Casey Winters: other CEOs, operators, customers, experiments).
4. Map allies and blockers, then test a safe person first with a low-stakes ask before the vulnerable one (Phyl Terry's positive politics).
5. Ask the people around them: the EA, chief of staff, anyone who pitched them successfully. Ask what worked, and what they worry about (Fain).
6. Done when every critical-path person has a stance, a failure fear, an evidence type and a named first move.

Play B — Exec as key user, before the pitch (Fain, Gridley, Janakiraman)

1. Book Office Hours or a 30-minute session before you write the one-pager. Run it as a user interview, not a pitch. Go in to learn and strengthen the plan, not to get approval.
2. Replace the generic what's top of mind with sharper questions: Tell me what the board is pushing you on. What are the key inputs to your success? What are you scared of messing up?
3. For leadership interviews ahead of a strategy (Chandra Janakiraman): ask what success feels like, what failure looks like, the measure of success, guiding principles, and their pet ideas.
4. Use Gridley's magic questions: state your view and ask is that right? or do you agree? instead of open-ended questions. Calibrate against their reaction and stay open to being wrong.
5. Simulate them: feed an LLM your notes on what they said (or past review transcripts) and ask for the 10 criteria they will use to judge a recommendation and the top 10 ways they will object (Gridley, Fain, Aparna Chennapragada's WWXD).
6. Reset context at the top of every meeting. The exec's calendar is a strobe light: finance, hiring, legal, product. They have not been thinking about your problem (Fain).
7. Ground the pitch in beliefs they already hold. If it contradicts a strong belief, check once or twice, then pick one of your other ideas (Fain).
8. Show how the proposal moves their metric, OKR or board pressure. Put the method and research in an appendix; lead with conclusion and options.

Play C — Pre-wire and sequence the buy-in (Cook, Seshan, Schaffer, Janakiraman)

1. Order the stakeholders: gatekeepers first (2-3, one-on-one), then key stakeholders (async or group review), then roadshows of 8-10 people (Janakiraman). The aim of the last stage is to land the plan, not reopen it.
2. Take a 70% draft to each person who needs to buy in. State what is missing: 70% done; the missing 30% is these three things (Seshan, Costello). Fold in their concerns and return as designs, data and tests develop (Cook).
3. For a net-new idea, recruit a respected ally close to the decider so the meeting before the meeting is already done (Schaffer). Win cross-functional advocates and prototype a messy V1 so the funding is hard to refuse (Fain).
4. Write the Most Obvious Objection on a sticky note before you send anything (Wes Kao's MOO). Volunteer the answer or reframe. If the objection is fatal, rethink the pitch.
5. Show options, not a single plan: three options, the trade-offs, one recommendation (Matt LeMay). A single option invites hole-poking.
6. Publish the vision doc as comment-only, not view-only or editable, so anyone feels heard without derailing the narrative (Ebi Atawodi). Evangelize in circles: your own team, adjacent teams, then leadership.
7. Done when each critical-path person has seen the idea at least twice and no one will first hear a major element in the decision meeting.

Play D — Disagreeing with a leader: the ladder

Climb one rung at a time; stop when it resolves.

1. Pause, then get curious (Ami Vora). Feel the reaction, reinterpret it as a chance to learn. Ask: Am I hearing you right that this is your prior? What context am I missing? (Tom Verrilli). Exec certainty often comes from deciding fast on little information; ask what led you to believe that? (Fain).
2. What would have to be true for them to be right? Complete this makes sense if… statements (Gridley). Surface the unstated foundational assumption where views diverge (Tobi Lutke).
3. Find their objective. Ask what they want for the user and the business, restate it, then return with better options (Zhang, Gupta, Jason Shah). Do not use the word pushback; shift direction instead.
4. Decompose into hypotheses and propose the smallest test, such as one market before fifty states (Julie Zhuo).
5. Bring a concrete artifact: a prototype bake-off of options A and B, or a quiet small experiment, rather than opinions (Merci Grace, Dylan Field, Gilad). When the founder believes from three customer chats, ask where's your evidence? without shutting them down.
6. If the exec dictates a design, build exactly what they asked plus two alternatives you believe in and debate the three (Fain's Stuart plus two more).
7. Still disagree? Advocate once, well, with data and qualitative evidence (Gridley's obligation to advocate). If you lose, update, then give the decision your best shot. Explain their rationale to your team separately from your own opinion. Decide which hill is worth dying on (Gupta).
8. If there is only opinion on both sides and no data, the CEO's opinion wins and that is fine (Verrilli). If the disagreement is about the goal itself, escalate together to whoever can decide (Molly Graham).

Play E — Overload, urgency and trade-offs

1. When an exec floats an idea, ask how strongly do you feel about this? and is it more important than these three projects? (Fain). Do not over-react to passing ideas; do not ignore repeated breadcrumbs either.
2. When the ask is real, show a menu of trade-offs: what you do, what you do not, why, which would you pick. Frame it as increasing velocity, not pushback (Geoff Charles).
3. For a boss who pings constantly, run schedule syncing: 10 minutes on Monday with your time-boxed calendar plus a list of asks you cannot fit; ask them to prioritize (Nir Eyal).
4. For a service-style team, ask requesters is this more important than these three things, yes or no? Review prioritization weekly; knock out an occasional quick ask for goodwill (Jessica Lachs).
5. When your investment is scary, shrink it: a one-week proof of concept, milestones every month or less (Fain, from Switch). Ask the exec what would a failure state look like for you in this experiment? and design the test around it.
6. When you cannot promise outcomes, promise the next check-in date and what you will know by then (Fain).

Play F — Build trust from zero (Liu, Idiodi, Costello, Gupta)

1. Run a 30-day listening tour; write a state of the union of challenges and wishlists, and report back when you finish someone's wishlist item (Deb Liu). Ask each new team what is one thing I can do to help you this week?
2. Find the most influential person who knows the business, get your manager's blessing and ask them to teach you, or offer to help them (Idiodi). They extend their trust and become accountable for your growth.
3. Bring insight to every meeting: know your customer, market, competitors, numbers and product (Costello). Trust is credibility plus reliability plus authenticity, over perceived self-interest. State your intent: you care about company success and do not need to own the idea (Chris Hutchins).
4. With a difficult personality, learn what drives them, ask people who have worked well with them, and connect your goal to what they care about (Gupta).

Play G — Trust loop (ongoing)

1. Send a short heartbeat to your manager: progress, blocker, plan, no response required (Boz Bosworth). When blocked, hand over a drafted email or a yes/no question so helping is cheap.
2. Say you will do it, say you are doing it, say you did it (Peter Deng). Follow up on meeting actions in days, not a week, and follow exec breadcrumbs with a concrete first answer, such as a Loom within an hour (Fain).
3. Ship, report results back to the person who gave feedback, and kill your own underperforming work with criteria and a decision date (Fain).
4. After any leadership review, post a five-minute recap in Slack: what was presented, the feedback, what changes (Nickey Skarstad). In meetings, summarize what you heard and name each contribution; people treat good summaries as strategy (Anneka Gupta, Bangaly Kaba).

Where the experts disagree

1. Say no vs never say no. Camp A: give options and trade-offs, never a flat no (Matt LeMay, Nir Eyal, Geoff Charles). Camp B: the PM's job in many cases is to say no early, with data, as an owner (Jag Duggal). Use A when the requester has formal authority or information you lack; B when a proven-bad bet is about to scale and you will be blamed later. Default: options plus a recommendation; reserve the explicit no for unproven bets under top-down scale pressure.
2. Consensus vs a decider. Camp A: buy-in is a long journey of early partnering (Megan Cook, Chandra Janakiraman). Camp B: alignment is an illusion; surface disagreement, then decide and say nevertheless (Annie Duke), and someone with authority must choose (Richard Rumelt). Use A for cross-team changes you cannot ship alone; B when a single decision maker exists and the debate is looping. Default: pre-wire the people who must execute, then decide.
3. Data vs opinion and relationships. Camp A: evidence is how smaller people challenge leaders (Itamar Gilad, Merci Grace). Camp B: PMs over-rely on data; your opinion and relationships are often enough (Kenneth Berger). Use A against a skeptical or senior decider; B in low-stakes calls and when no data can exist. Default: voice a labeled opinion early (Mihika Kapoor: state your confidence), then bring evidence if it persists.
4. Be liked vs be respected. Camp A: do not prioritize being liked; competence and respect win, and success excuses flaws (Jeffrey Pfeffer). Camp B: appeal and trust matter more than ability, so first ask what kind of experience you are (Evan LaPointe), and people do not care what you know until they know you care (Shaun Clowes). Use A when you must make unpopular calls; B when you depend on voluntary cooperation. Default: be reliably respectful, never gratuitously disliked, never conflict-avoidant.
5. Protagonist vs advocate. Gridley says you are probably not the protagonist: understand the CEO's vision and operationalize it. She also says you have an obligation to advocate. Advocate on execution and in your lane; do not fight over the five-year worldview.

Deliverable

Produce this document (fill every cell; mark unknowns as to learn):

# Influence Plan: <initiative>
**Decision needed:** <exact ask> | **Decider:** <name> | **Date needed:** <date>

## 1. Stakeholder map
| Person / group | Role in decision | Stance | Critical path? | Cares about / failure fear | Evidence that moves them | My ask of them | Play | First move + date |
|---|---|---|---|---|---|---|---|---|

## 2. Intel and pre-wire sequence
1. Gatekeepers (1:1): <names, date, what I will ask>
2. Key stakeholders (draft at 70%, missing pieces named): <names, date>
3. Roadshow / wider circle: <audience, date>
Most Obvious Objection: <objection> -> my answer: <answer>

## 3. The pitch (one page)
- Conclusion and ask:
- Link to their metric / OKR / board pressure:
- Options (3) with trade-offs and my recommendation:
- Appendix (method, data):
- Shrink-the-change version (1-4 week test) and the failure state it tests:

## 4. If they disagree
- Their likely position and the assumption underneath it:
- What would have to be true for them to be right:
- Artifact or test I will bring:
- Hill I will and will not die on:

## 5. Trust loop
- Heartbeat cadence and format:
- Next check-in date and what I will know by then:
- Recap channel and date (within 24h of the decision meeting):
- What I will kill or deprioritize, and the criteria:

## Next 3 actions
1. <this week, with a named person>
2. <this week>
3. <before the decision meeting>

Grade existing work

Score an existing stakeholder map, pitch, pre-read or influence plan. Return a score per criterion, the total (out of 35), and the top 3 fixes with the guest behind each.

Red flags

• Walking in only to get approval; the exec becomes a rubber stamp (Fain).
• Bringing all the research to prove homework; the baseline is that you did your job, so use the appendix (Fain).
• Arriving with a polished, finished design nobody has seen; bring a 70% draft and let people fall in love with it (Baxley, Seshan).
• Hunting for a green light in reviews, which distorts truth-seeking (Tom Verrilli: listening for yes).
• The single-minded martyr: one-sided advocacy that resents skeptics and ignores company priorities (Wes Kao).
• Saying no to a boss without exposing the trade-off; or telling an unhappy stakeholder that everyone else is happy (Eyal, Camille Fournier).
• Competing with the founder for vision, or doubling up as a second parent on a topic they own (Verrilli).
• Waiting a week to follow up on meeting actions; the exec has moved on (Fain).
• Disguised asks and cold requests with no homework (Phyl Terry); villain stories about peers instead of mapping incentives (Will Larson).
• Walking in certain you are right and they are wrong (Kenneth Berger).

Receipts

• "Politics is manipulating outcomes and people for your own gain. Influence is about increasing the odds that your good ideas survive." — Jessica Fain, Lenny's Podcast (00:13:24)
• "if somebody is on your critical path, the only judgment you should make is they're on my critical path." — Jeffrey Pfeffer, Lenny's Podcast (00:09:46)
• "in the story of your work of a company, you are probably not the protagonist." — Hilary Gridley, Lenny's Podcast (00:50:56)
• "if you're doing product management really well, you never have to say yes and you never have to say no. You're giving people options and you're helping them understand the trade-offs." — Matt LeMay, Lenny's Podcast (01:08:24)
• "I think one of the biggest things you can do to build trust is kill things, deprioritize things. That is a very, very senior way of thinking" — Jessica Fain, Lenny's Podcast (01:00:53)
• "This is a 70% cut. 30% of this is missing or incorrect, and that's why I'm coming to you early." — Paige Costello, Lenny's Podcast (00:38:52)

Go deeper

• references/frameworks.md — every framework in this skill, how to run it
• references/quotes.md — verified quotes with timestamps
• Related skills:
  • exec-comms — when the pitch itself needs rewriting as an exec memo or update.
  • hard-conversations — when the next step is a direct feedback or conflict conversation.
  • decide — when the group needs a decision memo, pre-mortem or DACI-style ownership.
  • strategy — when the thing you are trying to sell is the strategy and it needs a stress test first.