Executive Communication

Master the art of framing, transparency, and decision-ready communication to build trust with leadership.

Help the user with executive communication using insights from 9 guests and posts across Lenny's Podcast and Newsletter.

How to Help

1. Analyze the audience - Identify the specific values and communication styles of the executives involved to tailor the message effectively.
2. Structure the narrative - Use frameworks like SCR or the Pyramid Principle to ensure the core message and conclusion are delivered upfront.
3. Frame the tradeoffs - Present choices in terms of company-wide objectives rather than team capacity to facilitate better prioritization.
4. Iterate on delivery - Refine the medium and language based on feedback to ensure the message is received as intended and project confidence.

Core Principles

Start from the obvious

Casey Winters: "One of the ways I try to frame it to my team is if you're not an executive, whatever you're working on, you're basically writing and telling a story. And when you talk to an exec about that story, you have to start with chapter one, which is what part of the company strategy are you working on? What metrics are you trying to improve? What assumptions are you making that are guiding what you're building?"

Begin your narrative at the last point in the story that is completely obvious to your audience. This ensures everyone is aligned before you dive into new assumptions or complex project details.

Align with leader values

From "A PM’s guide to influence": "It’s often more effective to speak their language and demonstrate how my proposal will help them reach their goals, not mine, because stakeholders are focused on their own problems and are more receptive to proposals that address what’s already top of mind for them."

Overcome skepticism by recasting your proposal to prioritize the leader's specific philosophy. Pivot the framing from internal team metrics to the stakeholder's primary business values.

Control the bad news narrative

From "Communicating bad news - Issue 26": "The trick to sharing bad news effectively is to imagine being on the other side of the table. What would you want to know if you were in charge? If you’re like most people, you’d want to know everything, as soon as possible, plus exactly how to best move forward. So start there."

Ensure stakeholders hear bad news directly from you first. Proactively provide context and a clear path forward rather than just reporting a failure in isolation.

Frame tradeoffs by goals

From "How to communicate tradeoffs so leaders will listen": "While presenting the pros and cons between two priorities, I’d somehow always end up committing to doing both, and in less time than I had planned. As you’d expect, this usually went … badly. I’d burn myself out or, worse, burn out my team."

Force prioritization by framing choices in terms of company goals rather than team capacity. Present clear rankings of what falls above and below the line to make the cost of projects visible.

Take radical ownership of reception

From "Essential reading for product builders—part 2": "But make no mistake, when this happens, it is your fault. You have to sit down and ask questions from a place of humility to hear what they took away from what you said. Take full responsibility for any discrepancy from what you intended and make corrections with your entire audience."

Take full personal responsibility for how your communication is received. Treat any gap between your intended message and the audience's understanding as your own failure to clarify.

Project assertive confidence

From "Getting buy-in": "Presence is a combination of verbal cues, body language, and mindset. One of the actions you can take to improve your presence is to stop saying “sorry” when it’s not warranted."

Build executive presence by replacing submissive qualifiers like 'just' or 'actually' with direct phrasing. Swap apologies for mistakes with immediate commitments to fix the issue.

Structure for decision value

From "Getting buy-in": "Good storytelling means you present a narrative that resonates with your audience. Focus on why stakeholders should care about the idea. For example, prioritizing a recommendation feature will improve conversion or changing the sprint process will free up time to reduce tech debt."

Strip away any context or backstory that does not directly support a decision. Structure the message around the specific value the proposal provides to the stakeholder's own metrics.

Templates & Frameworks

• McKinsey Situation-Complication-Resolution (SCR) Framework (This Week #3: Finding product/market fit, interviewing for a Director of PM role, and structuring discussions with senior leaders) - A storytelling framework for structuring business communications, especially presentations to senior leaders. Can be applied to any medium and many contexts.
• SCQA / Pyramid Principle for Executive Communication (Essential reading for product builders—part 2) - A four-part framework for structuring any executive communication: Situation, Complication, Question, Answer. The answer sits at the top of a pyramid with evide
• Communicating Failure to Leadership — 7-Step Framework (This Week #7: Effectively communicating about a failure to execs, managing founder expectations, and hiring a Director of PM) - A structured approach for presenting a failed project or missed goals to executive stakeholders, including mindset preparation and delivery tactics
• Tradeoff Decision Meeting Facilitation Guide (How to communicate tradeoffs so leaders will listen) - Step-by-step guide for running a meeting where you present a tradeoff decision document to executives.
• Weekly Leadership Update (How to make an impact in your first 90 days) - A regular async written update format for new leaders to build trust and visibility
• Executive Patterns Notes Doc (A PM’s guide to influence) - A running document to track executive behavior patterns—questions they ask, feedback they give—to anticipate reactions in future meetings
• CEO Test for Tradeoff Framing (How to communicate tradeoffs so leaders will listen) - A simple mental model for ensuring your tradeoff communication hits the right level — ask yourself what the CEO would want to know.
• Dinosaur Brain Executive Reviews (Ami Vora) - A framework for structuring product reviews based on the limited cognitive load executives can dedicate to any single project.
• Buy-in Meeting Narrative Structure (Megan Cook) - A framework for opening a pitch or proposal meeting with executives.

See references/artifacts.md for the full list with details.

Questions to Help Users

• "Who is your primary executive audience and what do they value most?"
• "What is the single most important decision or takeaway you need from this interaction?"
• "Have you structured your message to lead with the conclusion rather than a build-up?"
• "How does your proposal directly impact the company's top-level metrics or strategic goals?"
• "If you are delivering bad news, what is your recommended plan of action and timeline for recovery?"
• "Are there any qualifiers or submissive language patterns in your draft that could be removed?"

Common Mistakes to Flag

• The 'Movie Arc' reveal - Building tension for a big reveal at the end wastes executive time and risks the meeting being cut short before the core point is made.
• Focusing on team capacity - Framing tradeoffs as 'we don't have enough people' instead of 'we are choosing Goal A over Goal B' makes the team look like a bottleneck.
• Defensive communication gaps - Treating a misunderstanding as the audience's fault instead of taking ownership of the communication gap undermines your leadership presence.
• Including excessive backstory - Adding context that doesn't directly support the required decision confuses the core message and slows down the operating cadence.
• Using submissive language - Phrases like 'Sorry to bother you' or 'I just wanted to' project a lack of confidence and lower your perceived executive presence.

Deep Dive

For all 20 sourced insights from 9 guests, see references/guest-insights.md

Related Skills

• Product Reviews
• Managing Up
• Running Meetings
• Written Communication