Wes Kao

LLM outputs improve drastically when you provide your specific point of view and desired constraints in the prompt.

"I found that sharing my point of view makes the output way better. If I just give it something and say, 'What would you say?' It's just not as good. Whereas if I say, 'I am not sure about how to tell..."

Audience engagement in presentations can be systematized by scheduling interactive elements at regular intervals.

"anytime he does a presentation now, every three to five slides, he'll put in a state change. So the idea of every three to five minutes, every three to five slides, go ahead and put in a stage change...."

Effective communication focuses on the 'how'—the specific application and nuances—rather than justifying the 'what' or 'why'.

"The idea of the super specific how is that most writers, most course instructors spend too much time on the what and the why and not enough time on how. So if you think about people who are reading yo..."

Engagement is maximized by cutting the preamble and starting the narrative at the point of highest tension or relevance.

"I have a framework that I call start right before you get eaten by the bear. And the idea is that if you're telling a story about camping, don't start talking about going to REI to buy a Patagonia jac..."

Mastering the technical mechanics of writing prevents accidental leading or misleading of the reader.

"more people should learn the craft of writing and the technical aspects of writing, not just look at what other people are doing to try to get audience engagement, but to actually improve your ability..."

Business communication should follow the pyramid principle: lead with the conclusion to respect the reader's time.

"in business, you often want to start with here's my conclusion, and then here's why, versus here's all the things I've done, here's all my thinking, here's all my data points, and then now here's my c..."

Concision is defined by the density of insight and economy of words rather than a simple character count.

"Being concise is not about absolute word count, it's about economy of words. It's about the density of the insight that you're sharing. And so you can have a 300 word memo that's meandering and long-w..."

Poorly written communication creates significant negative leverage through confusion and unnecessary back-and-forth for the entire team.

"I think the blast radius of a poorly written memo is way bigger than most people think. If you are just shooting off a message in a Slack channel with 15 other people, and it's confusing, you didn't i..."

Using specific transition words helps guide the reader's attention and reduces cognitive load.

"Signposting is using certain words, phrases, formatting, and an overall structure in your writing that helps guide your reader and signals what is coming in the rest of the post."

Over-reliance on bullet fragments can hide gaps in logic; full sentences force clearer thinking.

"I also dislike when people overuse bullets and sentence fragments, phrases in bullets when they should use complete sentences that actually show the connected tissue between ideas, that show the logic..."

Reading visceral physical reactions (like eyes lighting up) provides more honest data for alignment than verbal feedback.

"watch for these different eyes light up moments because their face can't lie... those are great fodder for content that you might want to write about, for the angle of your sales pitch, for how you mi..."

Aligning with stakeholders on new requests is more effective when framed as a trade-off between existing priorities rather than a simple 'yes' or 'no'.

"Alex would always talk about trade-offs and he'd say, 'Wes, yes, I can design this PDF for you. That means that the thing that I was going to work on today, which was redesigning this page on the site..."

Always secure buy-in on the 'why' (sales) before diving into the 'how' (logistics).

"A sales note is meant to get people excited to do the thing you want them to do, and to agree to do it. And only then after they have bought in, does it make sense to share the logistics."

Communicating the precise level of certainty prevents teams from over-investing in unproven hunches.

"I'm a big proponent of speaking accurately. You can avoid a lot of problems if you speak accurately about your level of conviction and about the actual amount of evidence that you have for something."

Anticipating the most likely pushback allows you to address concerns proactively and stay on the front foot.

"MOO stands for Most Obvious Objection. A lot of times we're surprised by the questions that we get especially in meetings, we feel blindsided. When really, if you thought for even two minutes about wh..."

When you don't have a specific answer, provide directional data and probe for the 'question behind the question.'

"I don't have that number off the top of my head, but in the last quarter the number has been 60 to 70% and it's grown in the past year... Are you wondering if we are investing in mobile appropriately..."

To maintain engagement in virtual meetings, you must break up monologues with frequent shifts in activity or visual perspective.

"the state change method is that you should punctuate your monologues with state changes. So state changes are anything that shakes your audience awake and adds some variety. So it might be asking peop..."

Brief mental preparation before a meeting significantly improves focus and concision.

"If you even take 30 seconds to one minute to ground yourself on why am I in this meeting? What do I want to share and make sure I get across in the time that we have, you're going to go in there so mu..."

Feedback should be a strategic tool for behavior change, not a vehicle for emotional venting.

"I have a framework called strategy, not self-expression... the goal is behavior change. So if that's the goal, trim everything else that you were about to say that does not actually contribute to that..."

Successful delegation requires ensuring the recipient understands the task, is motivated, and has a tight feedback loop.

"CEDAF stands for the C is comprehension... E is excitement... D is for de-risk... A is for align... and F is feedback."

Managing your manager is a proactive career strategy that builds trust and opens up more opportunities than waiting to be managed.

"I think that most people assume that their boss has to manage them and they feel a little bit resentful that, why should I manage my boss? They're getting paid more. They are my manager. They have mor..."

Seniority is often a result of effective managing up, specifically by identifying and solving the manager's primary concerns.

"the most senior people are best at managing up. This is why they got promoted in the first place because they were great at managing up to their bosses to understand what was worrying their bosses, wh..."

Effective managing up requires providing the appropriate level of context based on the risk and reversibility of the decision.

"proactively giving the right amount of context for your manager to be able to weigh in on what you're doing and to be able to give feedback, I think that's super, super important. And then thinking ab..."

A structured weekly update email ensures alignment on priorities and surfaces blockers without requiring a meeting.

"I sent my manager a state of Lenny email every week, just titled the state of Lenny. And it had basically three sections, my priorities currently, blockers that I need their help with, and maybe that..."

Effective managing up involves bringing recommendations and points of view rather than just problems.

"When you just ask your manager, 'Hey manager, what should we do?' You're putting a lot of cognitive load on your manager to need to think about the problem, think about potential solutions, craft the..."

High-velocity shipping can coexist with high quality if there is an obsessive commitment to craft and excellence.

"the speed that we shipped at Seth HQ was just beyond. It just blew away what I think normal people think of as fast, but it was also still so good. And so I think that rigor and that refusal to accept..."