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Lenny's Podcast

Become a better communicator - Wes Kao

Skip the fluff. Hear the best bits.

Just 5 minutes. All value, no filler.

📓 Key Takeaways

📘 If you're not getting the response you want, start with yourself. Most confusion, apathy, and skepticism stems from unclear communication. Instead of blaming others, ask: How can I explain this better? What might be unclear? What’s the most obvious objection someone might have? The onus is always on the communicator to close the gap.


📘 Don’t save your best communication for the exec meeting. You don’t get enough reps if you only practice when it counts. Treat every Slack message, every 1:1, every doc like a high-stakes opportunity. You’ll build muscle memory fast.


📘 Don’t assume buy-in. Most people jump into the how when their audience hasn’t bought the why. Lead with a sales note...what problem are we solving, why now, why this matters. Only then move to the logistics.


📘 Concise doesn’t mean short. It means dense with insight. You can’t cut to the chase if you don’t know what the chase is. Take time to prep - even 60 seconds before a meeting will dramatically improve clarity. Read your Slack message before you send it. Trim 20%. Then trim again.


📘 This is the shortcut to avoiding “surprise” pushback. Take 30 seconds to think: What’s the most likely question, concern, or challenge someone will raise? Address it upfront. You’ll get fewer “Actually, what about…” moments...and way more alignment.


📘 If you’re delegating, shorten the cycle. Instead of checking in a week later, ask for an early peek at direction or first draft. You’ll de-risk the work and raise the bar faster.


📘 Don’t understate or oversell. Instead of “This will work,” say “This increases our chances.” Instead of “I think this might be okay,” say “Based on X, here’s my recommendation.” Clarity wins over certainty.


📘 When giving feedback, focus on one thing: behaviour change. Trim the 90% that’s about your frustration. Keep the 10% that will help the other person change. Vent somewhere else first. Then show up calm and clear.


📘 A well-written memo saves 15 other people from wasting 10 minutes. A Slack message with no context adds 5 replies. Multiply the cost. Rewriting takes 60 seconds. Do it.


📘 Great communicators don’t just present ideas. They sell them. Frame every pitch with the company’s goals. Show why it matters. Be clear about the benefit. Don’t assume others will connect the dots. You do it for them.


📘 Start a swipe file. Anytime someone communicates brilliantly - in a doc, a slide, a Slack. Save it. Reflect on why it worked. The more you notice, the faster you level up.


📘 You don't need a new job to feel like a leader. You need better communication. And that starts now.


💬 Top Quotes

Move 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 what are obvious objections that I'm likely to get, you often immediately come up with what some of those things are
I often see operators who explain things poorly and then are shocked and horrified when people are confused or there's skepticism, there's apathy, there's a lot of avoidable questions. And I'm a big proponent of asking myself, if I'm not getting the reaction that I'm looking for, how might I be contributing to that?
I think another big one that I teach in my course and really kick off with is practicing like it's game day, playing like it's game day. So I see a lot of operators who save their best behavior for executives only. So, you know, they want to shine when they're presenting to senior leadership, but with everyone else, they're kind of calling it in
So, a common mistake that I see is overestimating the amount of buy-in that you have from your audience. So, that looks like jumping straight into talking about the logistics, the details of the how to do something of the process, when in reality, your audience is not yet decided if they even want to do the thing
Being brief and 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-winded and a thousand-word memo that is tight and concise
You can't cut to the chase unless you know what the chase is. You can't unbury the lead unless you know what the lead is. And so that I found is the bottom line to being concise. It's actually not really being clear of what you were thinking
The blast radius of a poorly written memo is way bigger than most people think. So if you're just shooting off a message in a Slack channel with 15 other people and it's confusing and you didn't include information you should have included, there's going to be a bunch of back and forth
Sharing a point of view doesn't mean that you have the perfect answer. You can share that, hey, I've noticed this problem popping up in a couple of different places. Here's what I think might be happening. You know, or when you share a report, don't only share the report and expect your manager to come up with insights—the takeaways. You should look at the report too and point out insights and takeaways
Most of the time, by the time we are giving feedback to someone, we have been frustrated for a while. And so I realized that a better way of giving feedback is thinking about motivating the person's behavior change. The goal is behavior change. So if that's the goal, trim everything else that you're about to say that does not actually contribute to that goal
I have a framework called CDF. The C is comprehension—have I given this person everything they need to understand what it is that I want them to do. E is excitement—am I explaining this in a way that is making this as exciting as it could be. D is de-risk—am I de-risking any obvious risks. A is align—am I giving the other person a chance to speak up and make sure we are actually aligned. And F is feedback—how can you have the shortest feedback loop possible