This is Part 1 of a two-part series on executive storytelling. Part 2 will cover directness, clarity about objectives, and tying it all together.
I have been a part of more executive briefings than I can count. Some land, several don’t. The ones that fail? They fail the same way every time: too much information, too much hedging, too little clarity about what actually matters.
Executives are drowning. Strategic priorities, fires to put out, politics to navigate, high-stakes decisions with incomplete information. The last thing they need is another 30-slide deck or 15 minutes of being talked at. What they need is a signal through the noise — make it easy for them to understand, decide, and act.
So how do you level up your storytelling and influence when the stakes are high and attention spans are short? Four principles. In this post, I’ll cover the first two: knowing your audience and cutting the noise.
Know Your Audience (And What They Actually Need)
Before you talk or share a single slide, answer one question: “What does this specific leader actually need from me right now?”
This is pattern matching at its core. Not every executive needs the same thing, and not every conversation calls for the same approach. Some leaders want context and narrative. They need to be brought along on the journey so they can understand the stakes and make an informed decision. Others just want the bottom line. Give me the cost projection, tell me the risk, let me move on.
If you don’t know which type of conversation you’re walking into, you’re guessing. Guessing wastes everyone’s time and can jeopardize your desired goals.
Patterns
Here are a few patterns I’ve learned to recognize:
The Strategist
This executive wants to understand the why behind your recommendation. They’re thinking three moves ahead. They need to see how your proposal fits into the bigger picture. Lead with context, connect the dots to broader goals, frame your ask in terms of long-term impact.
The Firefighter
This executive has 10 minutes and three other active fires to put out. They don’t need the full story. They need the headline, the tradeoff, your recommendation. Open with the conclusion and hold the supporting details in reserve unless they ask.
The Questioner (sometimes called the “Thinker“)
This executive wants to pressure-test your thinking. They’ll ask follow-up questions, poke holes, challenge assumptions. They’re analytical, methodical, they appreciate precision and thoroughness. Come prepared with backup data, examples, clear reasoning. But don’t lead with all of it- let them extract it through their questions.
The Relationship Builder (often referred to as the “Relator“)
This executive cares about people and process as much as outcomes. They want to know who’s on the team, how stakeholders are aligned, whether everyone’s bought in. They value interpersonal relationships, stability, and genuineness. Emphasize collaboration, acknowledge concerns, show that you’ve done the human work alongside the analytical work.
Note: These patterns are informed by well-established communication frameworks like the four behavioral styles (Director, Relator, Socializer, Thinker) that have been studied extensively in organizational psychology, communication and leadership research.
The key? Read the room and adapt in real time. If you walk in planning to tell a story and the executive cuts you off with “Just give me the cost,” stop storytelling. Pivot. Give them the number. If they want more context, they’ll ask for it. If you ignore their signal and plow ahead with your prepared narrative, you’ve lost them and likely your desired outcome.
Pattern matching is about respect. Recognizing that different people process information differently, have different priorities, operate under different constraints. Your job is to deliver the right message to the right person at the right time. And honestly, this is one of the hardest skills to develop. It requires paying attention to what you’re saying and how the other person is receiving it. Are they leaning in or checking their phone? Asking clarifying questions or giving one-word answers? Engaged with your reasoning or just waiting for you to get to the point?
Ask!
If you’re not sure what an executive needs, ask. Before the meeting, send a quick note: “I have an update on the project. Do you want the full context or just the key decision and recommendation?” Most executives will appreciate the clarity and tell you exactly what they’re looking for. If you’re already in the room and sense a mismatch, pause. Say, “I can go deeper on this or just give you the high-level takeaway. What’s most useful for you right now?” Or even better, start with your intent for the call and then ask directly what they want to get into.
The best storytellers can read their audience, adapt on the fly, and deliver exactly what’s needed in the moment.
Cut the Noise
Hot take: information overload makes you look unprepared.
When you’re presenting to leadership, every word, slide, and data point competes for limited cognitive bandwidth. Executives don’t have much to spare. They’re already overextended, context-switching between meetings, emails, and emergencies. If you bury your message under a mountain of detail, they won’t dig for it… They’ll just move on.
Less is more means doing the hard work of synthesis yourself. This is where the inverted pyramid communication style becomes invaluable. Popularized by Barbara Minto at McKinsey and widely used in journalism, the principle is simple: start with your conclusion, then provide supporting arguments, and finally share the underlying data and facts.
Look at the difference:
- “Here are 15 metrics and 4 epics that we’re tracking across three workstreams with varying degrees of confidence.”
versus
- “Revenue is up 12%, but churn is rising. We need to decide whether to invest in retention or keep pushing growth.”
One makes them work, and the other makes them think. That’s the shift.
I’ve learned this the hard way, at times thinking that comprehensiveness was impressive. I’d walk into a meeting armed with every possible answer, every scenario, every contingency. What I didn’t realize was that I was offloading my analytical burden onto them. They didn’t need me to present the buffet. They needed me to recommend the meal.
As Minto’s Pyramid Principle teaches: “You think from the bottom up, but you present from the top down.” When an executive asks, “What should we do?” you should answer that question directly with, “You should do X.” Only then do you delve into the reasoning. So ask yourself: what’s the one thing they need to know? What’s the decision they need to make? Start there. Everything else is optional context, and most of it can be stripped away or held in reserve for questions.
Executive Storytelling That Actually Works
That’s it for Part 1. In Part 2, I’ll dig into the other two principles: directness and naming what you’re optimizing for. These are the moves that separate good communicators from great ones. Skills anyone can develop with practice. Stay tuned!