Exec Comms

exec-comms: lead guest team

Turn a draft, a deck or a messy idea into a message a busy executive reads, understands and acts on, plus a prep plan for the live moment. Built from 296 insights from 90 Lenny's Podcast guests. Lead team: Wes Kao, Nancy Duarte, Matt Abrahams.

When to use

• You are sending a status update, decision memo or strategy doc to a VP, CEO or board and want it rewritten.
• You have a product review, QBR or exec meeting coming and need the opener, the three facts, and the likely questions.
• You are building a deck or a talk (all-hands, launch, vision pitch) and need the narrative before the slides.
• A Slack post or email got silence, confusion or ten replies of back and forth.
• You must answer on the spot (Q&A, interview, 'what do you think?') and want a structure to reach for.
• You freeze or ramble when you present and want a prep and warm-up routine.
• You want an existing doc graded with the top 3 fixes.

Step 1 — Diagnose (ask before answering)

If the user attached a draft, deck, transcript or doc, read it first and infer as much as you can. Ask only what is still unknown, max 4:

1. Who reads or hears it, and what do they already believe? (CEO, skip-level, peers, whole org, board; agree, skeptical, or cold.) Routes sales-first vs conclusion-first vs story arc.
2. What medium? (Slack/email, memo or doc, live meeting, deck, stage.) Routes written plays vs live plays vs talk plays.
3. What do you need back? (a decision, feedback, a yes to do something, awareness only, behavior change.) Routes the message tag and the opener.
4. What are the stakes and how much prep time do you have? (5 minutes, a day, two weeks.) Routes how much of the Pixar-style process to run.

Step 2 — Pick the play

If… (situation)	Use	From	Why
Written update, memo or Slack post to a busy exec	TLDR + Context, answer first, ask tag	Wes Kao, Ian McAllister, Maggie Crowley, Dharmesh Shah	Reader decides in seconds whether to stop, act or read on
Asking peers or leaders to do something new	Sales, then logistics	Wes Kao	Buy-in first; logistics before buy-in gets slow or no replies
Exec review or decision meeting	Universe of questions + 30-second opener + three facts	Casey Winters, Jessica Fain, Ami Vora, Megan Cook	Execs see many proposals a day and hold about three facts
Persuading a skeptical or new audience (vision, change, launch)	What is / What could be, audience as hero	Nancy Duarte (also Mike Maples Jr., John Mark Nickels)	Story creates longing for a future they never wanted before
Deck needed (or maybe not)	Narrative first, one point per slide, takeaway titles	Nancy Duarte, Maggie Crowley, Andy Raskin, Tristan de Montebello	Fixes the usual cause of bad decks: no decided point
On the spot: updates, answers, Q&A	What? So what? Now what? / PREP / ADD	Matt Abrahams	A default structure means you only decide what to say
Preparing a talk you will give from memory	Accordion + Bow and Arrow + one thing and three bookmarks	Tristan de Montebello	Internalized beats memorized; one remembered sentence wins
Bad news, uncertainty or a change that scares people	Name the fear first; honest conviction level	Boz Bosworth, Dr. Becky Kennedy, Wes Kao	People ignore you if they think you do not understand the problem
Nerves before the live moment	Exhale 2x, reframe, first-minute plan	Matt Abrahams, Nancy Duarte, Tristan de Montebello	Most nerves peak one minute before and during the first minute

Step 3 — Run it

Play A: Rewrite a written exec update (the default job)

1. Decide the point before editing. Fill in: the one sentence the reader should leave with, and what you need from them. Conciseness is bottlenecked by knowing the point (Wes Kao). If you cannot write it, take 30 to 60 seconds on: why am I sending this, what do I want across?
2. Tag the ask in the first line. Pick one: FYI, problem, request for help (Ebi Atawodi), or the stronger scale #FYI / #suggestion / #recommendation / #plea (Dharmesh Shah's Flashtags). For CEO-level senders also: do this week / let's discuss / FYI-thinking (Brian Halligan).
3. Put the TLDR on top, Context under it. Gist or decision first so readers who agree can stop (Wes Kao). Answer the exact question asked: a date for when, a number for how much (Ian McAllister). Delete your first one or two paragraphs if they are warm-up (Maggie Crowley).
4. Recommendation, then pros, cons, risks. State my recommendation is X first. A skewed pros and cons list destroys trust (Wes Kao). For strategy reviews, show 2 to 3 options with the recommended one argued; put the rest in an appendix (Jessica Fain).
5. Separate FYI, background, and the ask into labelled blocks so the reader knows which part needs a response (Wes Kao). Cap conclusions, bets and next steps at three (Maggie Crowley).
6. Speak accurately. Mark hunches as my initial thinking is and back real recommendations with evidence. Never undercut a strong view with a throwaway disclaimer (Wes Kao).
7. Cut and test. Convert bullet fragments to full sentences, which exposes unfinished thinking (Wes Kao); use numbered lists, not bullets, if people will discuss it live (Naomi Gleit). Use numbers, not adjectives (Jason Shah, Amazon rules). Read it aloud; if it sounds complicated, write what you would say (Maggie Crowley, Emilie Gerber). Expect to trim at least 20% (Wes Kao).
8. Blast-radius check. If a channel or many readers will see it, spend 30 more seconds making the next step obvious (Wes Kao). Done when a stranger can state the point and the ask in one breath.

Doc length: two pages (four max) for a team strategy (Ebi Atawodi); three to four pages plus appendix, no roadmap inside (Chandra Janakiraman). Put themes for discussion on top if execs will leave many comments (Jessica Fain).

Play B: Exec meeting or product review

1. Predict the universe of questions (Casey Winters). Write the 10 hardest, answer each with data, and role-play each exec's style. Early data misses cast doubt on the whole meeting. Hold pre-meetings with key people so nothing is a surprise.
2. Pick three facts (Ami Vora, Daniel Lereya). Do the analysis yourself and bring a recommendation; let the exec add breadth.
3. Start at the right chapter (Casey Winters): the last point that is obvious to this exec (strategy, metric, assumption), then move to what is new.
4. Open in under 60 seconds (Jessica Fain): what we are here to discuss, where we left off, goals of today, how the meeting runs, then stop and ask if there is anything else they hoped to cover. State what you need: decision, feedback, or hypothesis test (Megan Cook).
5. During: if they agree early, take the win and move on (Wes Kao). On a hard question, answer the question they should have asked (Paige Costello) or the question behind the question (Wes Kao). Never invent a number.
6. Close: ask what you missed (Paige Costello). Confirm you read their reaction correctly (Jessica Fain).

Play C: Persuasive talk or deck (change, vision, launch)

1. Ask first: do I need a deck at all, and who am I talking to (Nancy Duarte). Match the audience's density norms; dense tables are fine in peer reviews.
2. Write the audience journey and the big idea: from where to where, plus your point of view and what is at stake (Nancy Duarte). Name the one sentence they should remember (Tristan de Montebello's arrow) and add weight with a story, a number or an ask (the bow).
3. Sketch boxes on paper before software (Nancy Duarte, Maggie Crowley, Janna Bastow): one box per point, headline text first, then pick the slide type.
4. Alternate what is and what could be several times, make the messy middle visible, end on the new bliss (Nancy Duarte; Mike Maples Jr. calls it toggling).
5. One point per slide, title is the takeaway (Duarte, Raskin, de Montebello). A slide with no single takeaway is deleted or split.
6. Add one star moment: a dramatic number, a story, or a striking image (Nancy Duarte).
7. Keep attention: a state change every 3 to 5 minutes or slides (Wes Kao); each section should use stakes, surprise, suspense or humor (Matthew Dicks). Ask the room to guess before you reveal a number.
8. Rehearse with the Accordion or by recording and listening, and drill transitions, not words (Dicks). Notes: your one thing plus three bookmarks (de Montebello).

Play D: On the spot

Pick a structure before you speak. What? So what? Now what? for updates and standups; Point, Reason, Example, Point for a take; Answer, Detailed example, Describe relevance for Q&A (all Matt Abrahams). Choose a strong direction in the first sentence (Tristan de Montebello). End with a real ending like so what I want you to remember is, no hedge. Stay in character: do not narrate slips. Replace 'good question' and 'does that make sense' with did I answer your question, can I tell you more (Abrahams).

Play E: Bad news, uncertainty, change

1. Name the issue and show you understand it before the message (Boz Bosworth).
2. Be honest about conviction: say you synthesized everything, picked a direction, and will reassess on a date (Dr. Becky Kennedy).
3. Repeat across channels and formats; leaders re-describe vision far more than feels sane (Molly Graham, Claire Hughes Johnson, Boz Bosworth).

Nerves, in order of effort

Exhale twice as long as the inhale; relabel anxiety as excitement or adrenaline; write a one-line mantra; plan the first minute (open with a question or a story so you facilitate rather than perform); sit in the audience seats and picture the friendly face (Matt Abrahams, Nancy Duarte, Maya Prohovnik, Janna Bastow).

Where the experts disagree

1. Conclusion first (Maggie Crowley, Ian McAllister, Wes Kao, Minto school) vs new bliss, three-act story (Nancy Duarte, Mike Maples Jr., John Mark Nickels). Use conclusion first when the exec already trusts the problem, or for written updates and funding asks. Use the story arc when the audience must be taught to want the future. Default: lead with the point in writing; alternate contrast live; bridge with Casey Winters's right-chapter start.
2. Slide doc (Nancy Duarte) vs six-page narrative memo (Tamar Yehoshua on Bezos, Jason Shah, Ronny Kohavi) vs two-pager (Ebi Atawodi). Use a slide doc when pictures carry the idea and you circulate asynchronously; a memo when the decision needs rigor and objections; two pages when planning a team. Default: two to four pages for a decision, with an appendix.
3. Bullets and bold for skimmability (common practice) vs full sentences, sparse formatting (Wes Kao). Bullets feel fast but hide unfinished thinking. Default: full sentences with signposting; numbered lists when it will be discussed.
4. AI drafting. Tara Seshan: automate writing as reporting, never writing as thinking. Dan Shipper: fine if you stand behind every line. Molly Graham: shipping an AI strategy memo models outsourcing judgment. Default: write the first and last versions yourself; use AI for research and pushback; delegate status reports.
5. Own the blip. Tristan de Montebello says never point out flubs; Janna Bastow says a visible restart humanizes you. Skip commentary on small slips; correct real factual errors; own real product incidents (Alex Hardiman).

Deliverable

Produce this pack in the chat (and as a file if a doc was supplied):

# Exec Comms Pack: <topic>

## Diagnosis
Audience / what they believe / medium / what I need from them / stakes and prep time

## Message
- One sentence to remember: <arrow>
- Ask tag: FYI | problem | request for help | #recommendation | #plea
- Conviction level, stated accurately: <hunch | evidence-backed | decided>

## Rewritten artifact
TLDR: <point and ask in 2 sentences>
Context: <reasoning, numbers not adjectives>
Recommendation / options: <recommended + 1-2 alternatives, risks>
Needs your response: <numbered asks>
FYI / background: <short>

## For the live moment (if any)
- 30-second opener: <script>
- Three facts: 1 / 2 / 3
- Likely questions and answers: <table of 8-10, with the data source>
- Answer structure to use: What/So what/Now what | PREP | ADD
- Notes: one thing + three bookmarks

## What changed and why
<change> (credit: guest / framework)

## Next 3 actions
1. <e.g. run the draft past one person who has none of your context>
2. <e.g. pre-wire the two execs most likely to object>
3. <e.g. rehearse the opener and the first minute aloud twice>

Grade existing work

Score each 1 to 5 (1 = fails, 3 = partial, 5 = strong). Total /35. Return scores, the total, and the top 3 fixes with the guest behind each.

Criterion	1	3	5
Point up top (Wes Kao, McAllister, Crowley)	Reader must reach paragraph 4 to find the point	Point in the first paragraph but buried in context	TLDR names the point, and the answer is first
Ask clarity (Atawodi, Shah, Kao)	Reader cannot tell FYI from request	Ask is present but mixed with background	Tagged ask; FYI, background and ask separated
Reader load (Kao, Gleit, Shah)	Walls of text or bullet fragments, adjectives	Mostly clear; some bolding and filler	Full sentences, numbers, signposting, nothing cuttable
Accurate conviction and evidence (Kao)	Hunches stated as fact, or a strong view undercut	Mixed	Conviction matches evidence; reasoning shown
Options and honesty (Fain, Kao)	One option or a rigged pros and cons	Options but no recommendation	Recommendation, honest tradeoffs, risks, appendix of alternatives
Audience fit (Winters, Fain, Vora)	Written for yourself, jargon, assumes context	Right level but not their format	Starts at the right chapter, three facts, their preferred format
Anticipation and memorability (Winters, Duarte, de Montebello)	No answers to likely questions; no single takeaway	Some questions covered; takeaway vague	Question universe answered; one thing; star moment or contrast

Red flags

• Logistics before buy-in: a doc, a deadline and a form with no why (Wes Kao).
• Burying the lead because you have not found it (Wes Kao); BLUF fails when the bottom line is unknown.
• Interwoven decisions and context, so the reader cannot tell what you want (Wes Kao).
• A rigged pros and cons list or an accidental leading question (Wes Kao).
• Saving your best clarity for execs. You will not get enough reps (Wes Kao).
• A catalogue of information instead of a recommendation (Ami Vora).
• Rebuilding a deck from old slides at high stakes (Nancy Duarte).
• Status rollups that turn yellow into green across layers (Alex Komoroske).
• A story nobody can tell the why of, the shoe team that could only say it is red (Nancy Duarte).
• AI slop: took less time to write than to read and the author cannot discuss it (Dan Shipper).
• Hedging at the end of an answer (Tristan de Montebello) or leaking insecurities mid-talk.
• Treating a confused reader as their problem. Ask how you contributed (Wes Kao, Boz Bosworth).

Receipts

"A sales note is meant to get people excited to do the thing you want them to do, and to agree to do it. And only then after they have bought in, does it make sense to share the logistics." — Wes Kao, Lenny's Podcast (00:11:07)

"you can't cut to the chase unless you know what the chase is. You can't unbury the lead unless you know what the lead is." — Wes Kao, Lenny's Podcast (00:18:31)

"the audience gets to make a choice if they accept or reject your idea. So, the balance of power is with them and not you." — Nancy Duarte, Lenny's Podcast (00:18:48)

"I love prep and the structure I really like is a three-question structure: What? So what? Now what? And people on product teams I think could benefit so much from this." — Matt Abrahams, Lenny's Podcast (00:38:57)

"Assume that executives have a little tiny dinosaur brain. We all have a little brontosaurus brain and we can really only hold three facts at the same time." — Ami Vora, Lenny's Podcast (00:17:59)

"if you haven't thought through all the questions that might be asked from the document that you're sharing or the presentation you're about to present, you're not prepared enough, right." — Casey Winters, Lenny's Podcast (00:16:17)

Go deeper

• references/frameworks.md — every framework in this skill, how to run it
• references/quotes.md — verified quotes with timestamps
• Related skills:
  • influence — when the problem is who to win over, not how to word it
  • hard-conversations — when the message is feedback or a one-to-one difficult talk
  • spec — when the doc is a PRD or PR-FAQ rather than an update
  • position — when the narrative is about the product's market story rather than an internal exec message