Manage Up, Get Specific, Say No by Trading Off: Wes Kao's Playbook for Clearer Work

Wes Kao began in corporate retail at the Gap headquarters, rotating through Old Navy, Banana Republic and Gap. She says a 40-plus-year-old company was great training in business fundamentals, and she has since moved to progressively smaller companies. Later she worked at a beauty company acquired by Shiseido and an ad tech company acquired by Snap before moving to New York to work with Seth Godin.

With Godin she co-founded the altMBA and grew it from an idea between two people to thousands of students in 45 countries and a team of more than 60. After that she spent a couple of years consulting for course creators who wanted mini versions of it, which convinced her that cohort-based courses could work for experts in many fields. She saw that creators were toggling between half a dozen tools, so she started Maven with co-founder Gagan Biyani.

The Godin job came from a 2014 blog post seeking a special projects lead, with an application that included a three-minute video. Kao recorded hers in one take, expecting thousands of applicants, and got an email back within days. Her lesson is not to take yourself out of the running before you are rejected: put your best foot forward, but do put it forward.

Kao says Godin is even sharper and funnier in person than online, and that his daily blog works because it is insight rich, not because it is short. Internally the team held high standards and shipped work that was fast and still excellent, which raised her bar on strategy, tactics, quality and speed. She says the refusal to accept anything but excellence is something she took into building Maven.

Kao says most writers and course instructors spend too much time on the what and the why and too little on the how. Unless your point is truly controversial or new, most readers already agree with the premise. What they want is how to apply it to their own lives, how to handle nuances and examples that help them internalize it.

Her example is writing about product management communication. Rather than explain why communication matters, which most PMs already know, write about getting buy-in without positional authority, turning chaos into order across stakeholders, or putting forward hypotheses that might not work. Those topics are juicier and more specific than a general claim.

She pairs this with a framework she calls "start right before you get eaten by the bear." In a camping story, skip the trip to REI and the gas station, and begin just before the friend leaves a Clif Bar in the tent. Kao says most people need less context-setting and preamble than they think, and she often writes and then cuts a lot of it afterward.

Kao describes a "content hierarchy of bullshit" as a pyramid. At the bottom, with the most room, are one-directional formats like Twitter, podcasts, short articles and keynote speeches, where you can drop a mic-drop line and walk away without defending it. Higher up are long-form articles and books, where you have to defend and convince.

At the top are courses, especially cohort-based ones with live and asynchronous interaction. Students can ask questions or start a conversation in the Zoom chat saying something doesn't make sense, so instructors must be able to defend what they say. Kao says thinking about the hierarchy helps hold yourself to a higher standard even when a format would let you get away with less.

She adds nuance: contents matter more than format, so some books could be ten-page blog posts while others earn every page. Lenny says it explains why Twitter threads can feel cringe, since they sound wise with little depth. Having built a course himself, he agrees there is no room for filler because of the time to fill and the questions students ask.

Kao says most Zoom meetings are one person talking while everyone else sits still and tries to look focused, which is draining. Her state change method is to punctuate monologues with anything that shakes the audience awake: a prompt in the chat, switching from gallery view to screen share, having someone else speak, breakout rooms, popcorn-style sharing or polls.

Any moment when you would simply share a fact is a chance to ask people to guess first. In her Maven Course Accelerator she asks students to guess the average attention span, with answers ranging from an hour to three seconds, before revealing two to four minutes according to some research. Nathan Barry of ConvertKit puts a state change every three to five slides, and Kao wants engagement to be more science than art.

Her "eyes light up" idea is that people being polite will nod, but there is usually a moment when their eyes light up with genuine interest. She says to treat boredom and excitement as data, not accept words at face value, and trim what makes people go dead in the eyes. It works for sales pitches, courses and internal meetings, including with your boss, whose energy tells you which angle to lean into, such as numbers, upside or low effort.

Most people assume their boss has to manage them and resent the idea of managing their boss, Kao says. She argues that if you manage up, your boss appreciates you more, you get more opportunities and trust. She adds that there is no seniority level where it stops: the most senior people are best at it because they learned what worried their bosses and took it off their plate.

Her main tactic is to keep your boss in the loop on decisions and work with the right level of context, using judgment about whether a decision is reversible or expensive to reverse. Lenny shares his weekly "state of Lenny" email to his manager with priorities, blockers needing help and things on his mind. Both prefer avoiding surprises and erring toward overcommunicating, which Kao says often turns out to be the right amount, especially in remote work.

Kao structures messages with the key point and decision at the top, then "Context:" with paragraphs for anyone who wants the reasoning. Lenny says he teaches a bottom-line-first format that came from military writing, though one student found it too aggressive with a customer and softened it. The idea is that people who already agree can stop reading, and others can continue.

Kao says many people learn writing by mimicking others on social media, which is useful only up to a point. She recommends studying the craft away from social, naming It Was the Best of Sentences, It Was the Worst of Sentences by June Casagrande and Better Business Writing from Harvard Business Press. She gives them to new team members because they cover sentences, paragraphs, arguments and logic.

Her example is a teammate's Slack message about changing a WeWork location for an offsite, phrased so that the obvious conclusion was to keep the current one. Kao asked whether that was really her recommendation, because otherwise the leading question skews the answers. They revised it so any recommendation was intentional. She also points to technical issues, like a "which" clause that attaches to the wrong noun.

On pros and cons lists, Kao says the structure implies equal, objective weight, so skewing them makes readers suspicious. Better to state your recommendation first, then list pros and cons or risks, which builds trust. Lenny relates this to the pyramid principle of leading with the conclusion, and Kao warns against mixing action items, decisions and background so readers can't tell what you're asking for.

Lenny says saying no is an under-taught skill and asks for advice. Kao, a recovering people pleaser, says it depends on the relationship: a manager or cross-functional colleague is different from a stranger sending a DM. For ongoing relationships she prefers to talk about trade-offs, a technique she learned from Alex Peck, her design counterpart at altMBA.

When she asked Peck to design things, he would say yes, he could do the PDF, but the page redesign he planned for today would slip until later in the week, and ask whether that was fine or whether she wanted the original project first. That made her feel in control and turned the question into how to get the right things done. Kao says it protects bandwidth and mental health without ever saying the word no.

Lenny adds a related framework from a former manager called "prioritize and communicate." In a two-by-two, you can prioritize without communicating, or communicate without prioritizing, but the right move is to do both: tell the requester where it sits in your list, say it is third, and ask whether that seems reasonable. Kao calls it a fantastic two-by-two.