How to talk to people who have power — from both sides

Executive overview

Most people fail in high-stakes conversations because they focus on how they come across rather than on the person they're serving. Jordan Harbinger's core reframe: in any conversation with a power gap, your job is to advocate for the person who isn't there — your audience, your team, your customer.

Preparation is what makes presence possible. The more you know going in, the more freely you can listen and respond in the moment.

The goal is never to impress the powerful person or befriend them — it's to do your job so well they respect you for it.

Advocating for those not in the room

• Leaders who manage up by telling the boss what they want to hear win short-term, lose long-term.
• Advocating for your team — making sure they're supported and performing — builds results that outlast any single conversation.
• An "agenda mismatch" (wanting your boss to like you while your team needs something else) is the root cause of most leadership friction.
• Delivering tough news or owning a problem is neutral or hard in the moment, but earns long-term credibility.
• People who take management roles as a stepping stone to the C-suite become toxic — their agenda is never their team's agenda.

Preparing to talk to someone more powerful

• Let the celebrity factor wash over you during prep, not during the conversation — research de-glorifies people fast.
• Once you're in the room, your only job is to handle your business; nothing you do will make the powerful person invite you for Christmas.
• Read for controversy, failures, and career ups and downs — it strips away the stardust and gives you real material.
• Interrupting autopilot (scripted talking points, rehearsed "bits") is legitimate and expected — people want you to control the flow.
• Bodily tells signal autopilot: a shift in posture, a familiar story arc, a pivot away from your actual question.
• Confidence in your agenda signals competence; asking "what do you think I should do?" to someone you were hired to advise destroys it.

Closing the power gap when you hold the power

• Go to the lobby to meet them — reverse every signal that announces your status.
• Ask for small, genuine help: "Give me a hand setting this up." It shifts them from nervous guest to collaborator.
• Ask for local knowledge ("where's a good seafood place?") — they give value first, which defuses the need to perform.
• Share a small, real embarrassment from your day; it signals you are human before the conversation begins.
• Dale Carnegie's principle applies directly: mention your own mistakes before anything else.
• Change body language toward open and submissive rather than dominant; don't conduct the meeting from behind your desk.

Preparation as the foundation of curiosity

• What looks like spontaneous curiosity on-air is usually a question written in notes three days earlier.
• Read every word of the book, paper, or public record before the conversation — it gives you faith in your preparation so you can actually listen.
• LinkedIn alone reveals military service, hometown, school, interests, and nonprofits — more than enough to find a genuine point of contact.
• Even five percent of prep puts you in the 95th percentile of people trying to get someone's attention.
• Sending a templated outreach with the wrong person's name ends the conversation before it starts; personalisation is table stakes.
• Reaching out before a conference ("I noticed you play squash — want a game before your talk?") turns a stranger into a collaborator.

Resisting autopilot in yourself and others

• Everyone has "bits" — pre-planned talking points they default to under pressure. Recognise them in others and in yourself.
• Scripted meetings deliver polished information but no real exchange; if you want a genuine conversation, you have to give something unplanned.
• Letting the other person run the agenda means getting the corporate line, not the real conversation.
• Running someone down past their prepared material — giving them time to exhaust the script — is one way to reach authenticity.
• A 15-minute meeting for information delivery is fine on autopilot; anything requiring trust or real dialogue is not.

Lessons from starting over

• Harbinger ran the Art of Charm for years under a brand and business model misaligned with his goals — he kept solving fires instead of auditing what he actually wanted.
• Being a team player to the point of being a pushover for partners who were monetising the audience rather than serving it cost him years.
• The pattern: "I'll focus on what I want once this problem is solved" — repeated indefinitely — is how a career ends without intentional choices.
• Leaving with 90% of his team and starting from scratch was the right call; delaying it was the mistake.
• Take inventory of your own goals regularly — don't wait for a breaking point.