Managing Up with Tactical Empathy®

Start with Their World

When I hear “managing up,” my first instinct isn’t to stack arguments, polish a slide deck, or rehearse talking points—it’s to anchor myself in Tactical Empathy®: the ability to make the other person feel truly heard and understood by articulating their worldview, emotions, and dynamics so well that I can play it back to them with precision. 

Tactical Empathy^® isn’t about my title, my logic, or my preferences—it’s about my counterpart. It only works when you show you understand their perspective before you make a case for your own.

My approach to managing up is simple: use Black Swan skills to create outcomes where both sides prosper, with Tactical Empathy^® as the foundation. That applies anywhere authority and expectations exist—in corporations, but also at home or on a team. The sequence doesn’t change: map their world first, then introduce your needs.

Here’s the part many miss: your boss is just as susceptible to the human desire to be heard. They want to know you understand their pressures and constraints so you don’t create turmoil upstream while executing downstream. The same applies to your direct reports—before you issue commands or make requests, show you understand their environment and how whatever news you are going to share is going to impact them

In my book From JetWho to JetBlue, I shared how CEO David Neeleman traveled to cities across the network to experience “the world according to the crew” in each airport; asking about challenges, frustrations, and what was working well. En route, he spoke with passengers, making every conversation entirely about them. After each visit, his team sent a follow-up summary to everyone at that airport—a simple yet powerful habit that earned the loyalty of thousands.

Tailor to Your Boss (Not Yourself)

“Treat people how you want to be treated” is comfortable—and often wrong. Your aim should be to treat them how they want to be treated.

When I worked for an Analyst-type boss, tailoring meant sending a concise pre-read with the exact bullet points they valued and eliminating surprises. By the time we met, they already had the framework they needed to think—leaving space for the conversation we actually needed to have.

Why does this matter? Because preferences aren’t “personality fluff”—they’re operational guardrails. Analysts are methodical, allergic to surprises, and interpret silence as thinking time. They respond to data and clean comparisons, not improvisation. Match that cadence, and you earn attention when it counts.

Build Trust Upward: The Core Four, Delivery, and the Forgiving Nature of the Black Swan Method

Think of Tactical Empathy^® as the slab and Black Swan skills as the bricks. My “bricks” in every direction—up and down—are the Core Four: Labels™, Mirrors™, Dynamic Silence™, and Summaries™. Without the slab, the structure crumbles; with it, you create low-maintenance trust-based influence—trust that makes every future interaction easier.

Delivery is just as important as the skills themselves. Words collapse under the wrong tone. Steady cadence, the right tonality, and sincerity lower defenses and draw out useful details. That’s why how you say something often outweighs what you say. Aim to stay in the Accommodator’s tone (approachable, amenable, friendly) 75–80% of the time.

And don’t stress about getting a skill “wrong.” These skills are forgiving. If your Label or Summary™ misses, people are wired to correct you—which gives you new intel. In high-stakes conversations, progress often comes not from a perfect read but from the useful correction that leaves you smarter than you were a minute ago.

The Payoff

Managing up isn’t politics—managing up is Tactical Empathy^® from the beginning to the end of your interactions. First, demonstrate you understand your boss’s world: what they’re responsible for, what’s at risk and what “good” looks like to them. Then—and only then—share your position/make your ask.

Deliver it in their preferred style so the conversation happens on a channel they trust. Use the Core Four until the relationship carries its own weight. When you do, you don’t just make this conversation easier—you make every conversation easier, because once trust is earned, it lowers the friction on everything that follows.