Executive Communication

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.