Persuasive communication, managing up, and teaching effectively

Executive overview

Most people write and present too much context, too little "how" — and treat their boss as someone who should manage them rather than the other way around. Wes Kao shares a set of practical frameworks that sharpen writing, meetings, and upward relationships.

These frameworks work because they replace vague good intentions (communicate more, engage your audience) with specific mechanics.

The core insight: specificity and proactivity are the levers — in writing, in meetings, and in your career.

The super specific how

• Most writing overinvests in what and why; readers already agree with the premise.
• The value is in the how: edge cases, nuances, concrete application steps.
• Cut preamble ruthlessly — start right before you get eaten by the bear.
• Scope creep backstory (booking the campsite, stopping at the gas station) kills momentum; open at the moment of tension.
• The content hierarchy of BS: one-directional formats (tweets, keynotes) allow more unfounded claims; cohort-based courses allow almost none because students challenge you live.
• Use this hierarchy to hold your own work to a higher standard regardless of format.

The state change method

• Most Zoom meetings are one person monologuing; this drains attention fast.
• State changes punctuate monologues and re-engage the audience.
• Examples: Zoom chat prompts, polls (ask people to guess before revealing), screen-share switches, breakout rooms, popcorn sharing, unmuting for live responses.
• Rule of thumb: insert a state change every 3–5 minutes or every 3–5 slides.
• Forcing yourself to scan your material at those intervals almost always surfaces a natural opportunity for one.

Eyes lighting up

• Polite nodding is noise; genuine interest shows on the face before it shows in words.
• Track the moments when someone's expression or energy shifts — that's signal.
• Pattern the triggers: numbers, upside framing, low-effort framing — whatever reliably lights that person up.
• Cut content that produces dead eyes; expand content that produces lit-up eyes.
• Applies to sales pitches, presentations, internal meetings, and 1:1s with managers or reports.

Managing up

• Resentment toward managing up ("they get paid more") is common but costly — the people who manage up best are typically the ones who get promoted.
• Senior people are already doing it; it's not a junior-employee skill.
• Keep your boss in the loop on decisions and work in progress, calibrated to reversibility: irreversible or expensive decisions warrant more context, reversible ones less.
• Proactive communication means your boss doesn't have to chase status — that builds trust.
• A simple weekly "State of [Name]" email covering current priorities, blockers needing help, and things on your mind handles most of this.
• Avoid surprises: in work, surprises are almost always negative.
• Over-communication feels excessive to the sender and correct to the recipient — err on that side, especially in remote work.
• Structure long messages so agreement is visible at the top (TLDR / bottom line) and supporting context follows for those who need it.

Saying no and protecting bandwidth

• Saying no outright triggers "are you a team player?" anxiety; reframe as trade-offs instead.
• "Yes, I can do that — it means X gets delayed until Friday. Does that work, or should I keep X first?"
• This shifts the conversation from compliance to prioritisation, and puts the requester in control.
• Pair it with prioritise and communicate: assign the new request a slot in your priority list, tell the requester where it sits, and ask if they agree.
• The outcome (protecting bandwidth) is the same as a flat no, without the friction.

Writing craft

• Learn mechanics, not just style-by-imitation: recommended books are It Was the Best of Sentences, It Was the Worst of Sentences (June Casagrande) and Better Business Writing (Harvard Business Review Press).
• Unintentional point of view leaks into writing — a slanted pros/cons list signals bias and erodes trust.
• If you have a recommendation, state it explicitly at the top; then list risks or trade-offs. This builds trust rather than undermining it.
• Structure: conclusion first (Minto pyramid), then supporting reasoning. Burying the conclusion in context wastes readers' time.
• Mixing action items, FYIs, and background context in one undifferentiated block is the most common structural failure — separate them clearly.