Sell Before You Tell: Wes Kao's Tactics for Communication That Actually Lands

Wes Kao opens with the observation that operators who explain things poorly are often shocked and horrified when the response is confusion, skepticism, or apathy. Rather than blaming the audience, she asks herself a short set of questions: if I'm not getting the reaction I'm looking for, how might I be contributing, how could I explain this more clearly, how could I be more compelling, and how could I anticipate the questions they might have? She describes herself as a big proponent of agency — the recognition that we can only control our own behavior. Lenny restates the implication bluntly: if people don't buy in or don't do what you asked, it's probably a communication problem, not their fault; Kao agrees, with the caveat that better communication can't solve everything but reliably increases your odds.

Her second principle is to practice like it's game day. She sees many operators save their best behavior for executives — shining in front of senior leadership while, in her words, kind of calling it with everyone else. The arithmetic doesn't work: most people present to executives once a month or a couple of times a quarter, which is nowhere near enough reps to get good at executive communication. Treating every stakeholder as important is both better practice and better manners, because you shouldn't waste your CEO's time any more than your cross-functional peers', your manager's, or your direct reports'.

Kao divides the territory into two mediums: verbal (meetings, conversations, presentations) and written (emails, strategy docs, Notion docs, Slack messages, texts). She also insists that communication is a means to an end rather than an end in itself, even for someone who teaches a course on it — the end being the outcome you want, whether that's buy-in, a better team decision, or simply moving to the next step. Lenny frames the stakes with a line from Boz, Meta's CTO, that communication is the job: true for product people, Kao's framing suggests, and for basically anyone in a leadership role.

The most common mistake Kao sees is overestimating how much buy-in you already have. Operators jump straight into logistics — the how, the process, the details — when the audience hasn't yet decided whether they want to do the thing at all; when the response is tepid, they go even deeper into the how, assuming more explanation will create desire. It won't, because a sales note and a logistics note do different jobs: the sales note gets people excited and gets them to agree, and only then does the logistics note make sense. Switch the order of operations and you get a slow reply or none at all — the Slack message that lands in a channel and is met with crickets and tumbleweed.

One of her clients, a head of operations, wanted her fellow executives to submit weekly wins so the company could celebrate them. She led with the logistics — which document to use, what time to submit, what format — and got almost no response, which Kao says makes sense: it read as one more checklist item, another process everyone was now supposed to do. The same request framed as a chance to shine a light on team members doing great work, to make them feel seen and motivated, would have been in service of the executives and their teams rather than a favor to the requester.

Lenny pushes back on behalf of executives who say just get to the point, and Kao's answer is that you should always do a little selling, even when people have broadly bought in. Everyone has a lot going on: even if I agreed two weeks ago, by the time you raise it again I've thought about a billion other things, so reminding me why we're talking keeps the conversation from stalling at a cold start. This doesn't require spending 15 minutes of a 30-minute meeting selling — a minute or two, or a couple of sentences, is enough before transitioning into the substance.

Her template is short: say why we're here, what problem this solves, and what you need from the other person, then move on. In her microcopy example the whole frame takes about 15 seconds — two weeks ago we reviewed the product flow, a couple of parts were confusing, I rewrote the microcopy, I want your feedback on the changes and whether you agree — after which the listener knows exactly what kind of feedback to give. She also names the executive mindset as yes, yes, yes, next, next, next: she has presented 15-slide decks where executives made the decision by slide four, and the lesson was to take the win rather than insist on slide 13. If you've sold them, stop talking; you might otherwise talk them out of agreeing.

Kao's pet peeve is people who equate being concise with being brief. Concision, she argues, is not about absolute word count but about economy of words and the density of the insight you're sharing: a 300-word memo can meander and a 1,000-word memo can be tight.

The usual advice — don't bury the lead, bottom line up front, cut to the chase — quietly assumes you already know what your core point is, and that is the real bottleneck. You can't cut to the chase if you don't know what the chase is; long-windedness is usually a symptom of unclear thinking. The proof is the story you've told a hundred times: you know exactly where the laugh or the gasp lands because you know all the beats. At work it's different — you're usually explaining something new while simultaneously listening, absorbing, deciding what you think, and trying to be concise.

The only consistent solution she has found is preparation, which she cheerfully admits is unglamorous. It doesn't take hours: 30 seconds to a minute before a meeting to ground yourself on why you're there and what you want to get across changes the quality of the conversation, especially because most people are back-to-back and still unwinding from the previous Zoom call when the meeting starts. Deciding in advance that you want to speak — particularly useful for more introverted people — is part of the same move.

In writing, the main tactic is simply reminding yourself to be concise, which typically trims at least 20% of a draft, and asking how you might be adding cognitive load to what you're saying. Primary messages can live in the Slack message with secondary detail moved into the thread, and, as Lenny adds, you should read your own message at least once before sending it. Kao thinks the blast radius of a poorly written memo is much bigger than most people assume: a confusing message to a 15-person channel produces back-and-forth from all 15, whereas 30 more seconds of editing would have sent them off to the races. Lenny recommends William Zinsser's On Writing Well for this — its exercise is cutting and cutting again, with 40% of the words gone and the message intact or better.

Signposting is the use of specific words, phrases, and structure that tell the reader where the argument is going. Kao's favorites include for example (an example is coming), because (here comes the logic), as a next step (people's eyes zoom to it), and first, second, third to open paragraphs, which adds structure without relying on bold, italics, or underlines. In a long memo these are power words for clarity — the copywriter's power words, aimed at helping the brain see the structure. The same works verbally: in a demo, the most important part to pay attention to is… or the part we were most surprised by is… signals that what follows deserves attention, and pulls back listeners whose attention has strayed.

Her counterpart warning is against excessive formatting. She has seen memos where 30% of the text was bolded, which negates bolding entirely: if everything is highlighted, nothing is. She also dislikes bullets made of sentence fragments where complete sentences would show the connective tissue and logical flow between ideas — fragments feel faster, but they push the work of interpretation onto the reader, so net-net they take longer.

She goes further and calls fragment-heavy writing a crutch, because turning a fragment into a full sentence is a litmus test for whether the idea was fully thought out — and often it's harder than expected, which reveals that you didn't actually know what you meant. Lenny connects this to Amazon's six-page memo culture and Jeff Bezos's view that if you can't write it out in prose, you don't know what you're saying. Kao's version is the microcosm: can you turn that bullet into a real sentence?

On getting better, Kao suggests a first-principles measure: how long does it take right now to get the reaction you want from a recipient, and does that time shrink as you practice? Friction won't disappear entirely, but going from seven back-and-forths to two or three is the signal to watch, and you should do more of what works while adjusting execution rather than abandoning the tactic. The wrong way is to attempt 30 tactics at once and then beat yourself up for forgetting them; pick one thing, try it in different settings, and only then move on. Zooming out, no single email ever feels important enough to justify two extra minutes, which is exactly how your work output ends up being the sum of everything you didn't bother to improve — and people claim diminishing returns far too early, when the more honest explanation is usually that execution wasn't good enough yet.

Kao finds that people tend to sit at one end of a confidence spectrum by default. The overconfident state hypotheses as fact — this will increase X rather than this could increase X, or this will increase the likelihood of X — and the cost is real: the team takes you at face value and spends headcount and dollars pursuing something you overstated. Speaking accurately about your conviction and the evidence behind it avoids a lot of problems.

Under-confidence is equally a problem. She describes clients who share excellent recommendations with a cross-functional team and then add, but you can ignore everything I just said, do what you think is best — a diminishment they didn't need to make, and almost irresponsible when the idea is strong and could save money and time. Her prescription is to share a point of view and back it with evidence, logic, first principles, examples, or data where available, framed honestly as my initial thinking is or based on what we know, my hunch is. That gives your manager or team something specific to push back on: I agree here, I disagree there. Lenny adds that people discount your evidence the moment they sense you've curated it to support a predetermined agenda.

The anti-pattern is the single-minded martyr: someone with an agenda who presents only supporting evidence and then feels frustrated that others are skeptical. One client on the growth acquisition side couldn't get cross-functional partners to lend her engineering time; the breakthrough came when she remembered the CEO had declared retention the company-wide goal for the year, which reframed her narrative from everyone says they care but nobody will help to here's how my proposal fits what the company is actually prioritizing. Kao frames the shift as junior versus senior: juniors need a yes, while seniors can conclude that this isn't the right moment or that the investment should be right-sized — doing what's best for the company rather than what's best for their own win.

MOO stands for Most Obvious Objection. Kao's observation is that people feel blindsided by questions in meetings — caught on the back foot — when two minutes of thinking about the obvious objections would have surfaced most of them. You will never anticipate every objection, but the obvious ones are absolutely predictable, which is why knowing your counterarguments as well as you know your arguments matters.

She uses MOO multiple times a day as a mental filter: before saying or writing anything, ask how someone might disagree, then volunteer that information up front or frame the point so the objection is less likely to arise. It has become muscle memory, and she suggests putting MOO on a post-it as a training device — a concrete, tactical way to practice the audience empathy everyone claims to value. Lenny notes the secondary benefit: anticipating an objection can expose a gap in the plan itself, since thinking and communicating are far more intertwined than the think-first-then-communicate model implies.

Staying calm in high-stakes conversations starts with taking pressure off yourself to produce the perfect answer on the spot. Let me look into it and get back to you is acceptable and far better than making something up, but for someone with real subject-matter confidence it can be a missed opportunity to keep the conversation moving. Asked what percentage of users came from mobile last month, a stronger response offers directional context — I don't have that number off the top of my head, but last quarter it was 60 to 70% and it's been growing — and then checks the intent: are you wondering whether we're investing in mobile appropriately?

Kao calls this the question behind the question: multiple questions on the same topic usually signal a deeper, often subconscious, concern, and it's the communicator's job to probe for it and answer in that direction. Lenny adds a technique he relies on — reflect the question back, let me make sure I understand what you're looking for — which buys thinking time and signals to the questioner that they've been heard. Asked which single tactic to start with, Kao picks MOO plus framing the conversation up front, using signposting phrases as needed to make that frame land.

Kao's early belief was that managing up was a junior person's burden to outgrow; the rude awakening was that it only became more important, and that many senior people are excellent at it — partly how they got senior. The higher you go, the less your manager hands you well-defined problems on a silver platter and the more you operate amid ambiguity, with mandates like make this number go up, which makes alignment with your leader a continuous job rather than a phase. Her highest-leverage advice isn't a weekly recap of tasks but sharing your point of view: here's what I think we should do, where do you see gaps? instead of what should we do?, which spares your manager the work of framing the problem, generating a solution, and instructing you.

Sharing a point of view marks you as someone looking around the corner rather than waiting to be told what to do, which is how people get promoted — and it has a second-order benefit, because putting your reputation behind a recommendation forces you to think it through properly. The same applies to reports: surface the insights instead of forwarding the dashboard. Junior people often have the most proximity to customers, support tickets, and messy data, and managers consistently say they want to hear what those people are noticing; if it isn't landing, the fix is the communication toolkit covered earlier in the conversation.

Her feedback framework is strategy, not self-expression. Because most feedback is delivered after long frustration, it turns into a venting session about how the person harmed you, which leaves them either demoralized or defensive and arguing about whether it was really that bad. If the goal is behavior change, trim everything that doesn't contribute — she says that's often 90% of what she initially wanted to say — and keep only what helps the person see the benefit to themselves and to the people around them. Vent first, with a therapist, partner, or friend, because otherwise one raised eyebrow in the conversation is enough to set you off.

Delegation gets its own acronym, CEDAF: comprehension (does the person have everything they need, including logins, to understand the end result), excitement (explain the why so a mundane task connects to something that matters), de-risk (name the obvious risks — have them do 10 rows before a hundred, or say you might think I mean X, but I actually want Y), align (give them a chance to ask questions, which reliably surfaces what you forgot to explain), and feedback (shorten the loop, ideally starting inside the delegation conversation itself). Kao says one letter usually turns out to be the weak spot when she runs the checklist. Lenny points out that CEDAF doubles as a recipe for delegating to AI agents, and notes that Claude-style tools already shorten the loop by asking clarifying questions before starting — a pattern he reinforces with the prompt this is very important to my job.

A swipe file is a collection of inspiration you can refer back to — standard practice among marketers, who keep examples of copy, landing pages, and ads, and underused elsewhere. Kao keeps an Apple Notes file called Smart Things People Have Said, where she pastes phrasing, words, and arguments that struck her as well articulated or strategic. She rarely rereads it, because the value is in the act of adding, which trains her to notice when something is working and to ask why it worked and whether it can be borrowed. Strategy docs, conversion flows, and screenshots all qualify, since capturing them is what lets you break down the structure or the argument later.

The system should stay deliberately messy — no tags, no rows, no metadata, just a note on the home screen you can add to in seconds. Kao also uses Claude heavily, sometimes three or four hours a day, as a thought partner: she pastes in an email she doesn't know how to answer and asks for a draft reply, but only after explaining the situation and what she'd ideally achieve. Giving it her point of view makes the output much better than a bare what would you say — for example, I said yes earlier, circumstances have changed, I want to decline respectfully while making them feel heard. She then edits for voice, sends the revision back, and iterates.

In the lightning round she recommends Andy Grove's High Output Management and David Rock's Your Brain at Work, the latter for understanding attention and allocating mental resources — since reading it she hides her phone from view, because even a phone in peripheral vision is distracting, and does the hardest work earlier in the day. Her life mottos are that everything takes longer than you think, which argues for building in buffers, and a riff on always be closing: always be selling, meaning put real effort into convincing people of your recommendation rather than peddling wares.

Reflecting on leaving an in-house operator role, Kao says the shift was realizing she could craft her work around only the part she is best at — a narrow slice — and that this is freeing rather than limiting. Lenny credits her with a lesson he has repeated since: when Maven was launching, he invited her onto Clubhouse for the launch and she declined, explaining that she doesn't enjoy live public speaking and has built a career around writing and podcasting, so she was comfortable saying no to even legitimately cool opportunities. Now on the receiving side of such requests, Lenny notes that the people asking don't see the ten invitations a day, and that having a graceful template for declining has become essential to protecting the work that compounds.