Become a better communicator: Specific frameworks to improve your clarity, influence, and impact

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. 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? How could I explain this more clearly? How can I be more compelling? How can I anticipate any questions that they might have?

You are one of the best teachers of communication I've ever come across. I made a list of people's favorite tactics and frameworks and approaches that you teach in writing. Any tactics you can share for someone to be a little more concise.

I think the blast radius of a poorly written memo is way bigger than most people think. If you were just shooting off a message in a Slack channel with 15 other people, and it's confusing, you didn't include information you should have included, there's gonna be a bunch of back and forth, whereas if you had just take another look at it, those 15 people.

Would be off to the races.

You have an awesome framework called MOO. 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 what are obvious objections that I am likely to get, you often immediately come up with what some of those things are. Are you gonna be able to anticipate every single objection?

No.

But can you anticipate the obvious ones? Absolutely.

Today, my guest is Wes Cayou.

Wes co-created the ALT MBA program with Seth Godin, She co-founded a company called.

Maven, which I often collaborate with, which makes it easy for people to host.

Live cohort based courses.

She recently left Maven to launch her.

Own course on executive communication and influence. There's a quote that came to mind.

After I stopped recording this conversation with Wes by George Bernard Shaw. The single biggest problem in communication is the illusion that it has taken place. By the end of this podcast, you listen to what Wes suggests, you'll be a lot closer to becoming a world-class communicator. If you enjoy this podcast, don't forget to subscribe and follow it in your.

Favorite podcasting app or YouTube.

Also, if you become a yearly subscriber.

Of my newsletter, you get a year.

Free of Perplexity Pro, Superhuman, Notion, Linear and Granola. Check it out at lenny's newsletter.com.

With that, I bring you Wes Kayo this episode is brought to you by Work OS. If you're building a SaaS app, at some point your customers will start asking for enterprise features like SAML authentication and SCIM provisioning. That's where Work OS comes in, making it fast and painless to add enterprise features to your app. Their APIs are easy to understand so that you can ship quickly and get back to building other features. Today, hundreds of companies are already powered by Work OS. including ones you probably know, like Vercel, Webflow, and Loom. WorkOS also recently acquired Warrant, the fine-grained authorization service. Warrant's product is based on a groundbreaking authorization system called Zanzibar, which was originally designed for Google to power Google Docs and YouTube. This enables fast authorization checks at enormous scale while maintaining a flexible model that can be adapted with even the most complex use cases. If you're currently looking to build role-based access control or other enterprise features like single sign-on, S/KIM, or user management, you should consider WorkOS. It's a drop-in replacement for Auth0 and supports up to 1 million monthly active users for free. Check it out at workos.com to learn more. That's workos.com this episode is brought to you by Vanta. When it comes to ensuring your company has top-notch security practices, things get complicated fast. Now you can assess risk, secure the trust of your customers, and automate compliance for SOC 2, ISO 27001, HIPAA, and more with a single platform, Vanta. Vanta's market-leading trust management platform helps you continuously monitor compliance, alongside reporting and tracking risk. Plus, you can save hours by completing security questionnaires with Vanta AI. Join thousands of global companies that use Vanta to automate evidence collection, unify risk management, and streamline security reviews. Get $1,000 off Vanta when you go to vanta.com/lenny. That's v-a-n-t-a.com/lenny.

Wes, thank you so much for being here and welcome back to the podcast.

Thanks, Lenny. I'm very honored to be a second time guest.

Very rare honor. No pressure, but I think this is gonna be one of the highest leverage episodes I've done. And let me tell you why I think that's the case. In the newsletter and on the podcast, I often talk about just how important And I had leverage the skill of communication is to product leaders, to leaders, just to like people in general. There's this quote that Boaz, the CTO of Meta, he's been on the podcast. He wrote this famous blog post, Communication is the job. And I think that's true for product people, but it's true for basically any sort of leadership role and anyone trying to get ahead. And you are one of the best communicators I've ever met. You are one of the best teachers of communication I've ever come across. You have one of the most popular courses on Maven on Executive Communication. So I'm really excited to have you here and to help people become better communicators, better at influence, and all these things. So thank you again for being here.

Absolutely.

Okay, so something that I often do with guests on the podcast, not even often, always, I ping people that the guests have worked with and ask them, what should I ask Wes? What should I know about Wes? Let me read a few quotes about you in regards to your communication skills from folks that have worked with you. These are three different people. Okay, so first, Wes single-handedly raised the quality of the entire company's writing by like 2x across the board. I always say the best writing course I ever took was working with Wes for a year.

Wow.

Okay, that's one. Wes never just throws things out there. She's precise with her use of language, meticulous about examining her own ideas before bringing them in front of others. and knows how to make her points in a way that people will understand them and buy into them. Okay. And third, Wes includes her reasoning with every proposal and the context behind all of her recommendations so that everyone around her learns in order of magnitude faster. This also makes her an exceptional teacher because she can clearly define what excellence is and why something is the goal and then break down the steps and principles involved. Okay, reactions.

Those are really nice things. That's amazing. Yeah, thank you so much.

And these are played people across different companies. So, okay, so that was just to highlight how good you are at this stuff. And what we're going to be doing with our chat is going through a bunch of your tactics that you teach and that have helped people become better communicators, executive communicators, better at influence. Before we get into the specific tactics, Is there anything that you think is important for people to understand just broadly around the skill of becoming a better communicator?

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? So, you know, instead of blaming other people for not understanding me, I think about how could I explain this more clearly? How can I be more compelling? How can I anticipate any questions that they might have? So, I'm a big proponent of agency and realizing that we can only control our own behavior. And so the best place to start if you're not getting the reaction you're looking for is reflecting on how can I get better at the skill of communicating? And it absolutely is a skill.

So I'm hearing is like, if you are having a hard time people buy into what you're trying to convince them to do, or you're finding people are doing not what you asked them to do, it's likely an issue with your ability to communicate. It's probably not their fault.

Yeah, I would say so. You know, you can't solve everything with improving your communication. But you can increase the likelihood of getting what you want.

Cool. Okay. Anything else along these lines of just things that are important to understand just broadly around communication, executive communication?

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 it. And I just don't think that you're going to be able to get enough reps to actually get good at executive communication if you are only doing it with executives. Because many of us only present to execs once a month, right? Or a couple times a quarter. And that's just not a lot of chances to practice. So, really treating every single stakeholder as if they are important because they are. And you shouldn't be, you know, if you don't want to waste your CEO's time, you also shouldn't waste your cross-functional team members time or your manager's time or your direct reports time. So that's something else that I ask.

Folks to keep in mind. And maybe a last question before we get into the tactics. When people think communication, they think email, they think meeting presentations, things like that. What's like a, how do you think about, when you talk about executive communication and communication in general, what's kind of.

The umbrella of things that includes? Yeah, I would say broadly the two mediums are verbal communication and written. So verbal being meetings, conversations, presentations, and written being emails, strategy docs, notion docs, Slack messages, text messages, those two categories broadly. And I also think about communication as more of a means to an end. which might be interesting for some people because I teach a course on communication, so you would think that's the end in and of itself, but I really see it as a means to an end where the end is getting the ideal outcome you're looking for. So whether that is buy-in or making a good decision as a team or moving to the next step, whatever that might be, communication is really in service of that end goal.

Awesome. Okay, so I made a list of people's favorite tactics and frameworks and approaches that you teach in talking to folks that you've taught and folks that you've worked with. So I'm just going to go through a bunch and let's just help people get better at these things.

All right, let's do it.

Okay, so the first is something you call sales, then logistics. What is that about?

Yes. 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 has not yet decided if they even want to do the thing. So, you know, what, you know, I see operators do in response then is go even deeper into the logistics and the how, thinking that, oh, if I just explain this more, then that person will want to do it. When really a sales note is different than a logistics note. 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. So there's an order of operations here. If you switch the order of operations, you will likely get a slow response or just no response, right? We've all put a Slack message in a channel. and got crickets and tumbleweed. So really starting off with selling the person and making sure that they know why we're doing this, why this matters to the company, why now, and then sharing logistics tends to be a lot more effective.

Is there an example of that that might help illustrate that point or that approach?

Yeah. So one of my clients is a head of operations and she was trying to get the rest of her executive team, which she was a part of, to fill in some wins for the week so that they could share this out with the whole company. And this was going to be motivating. It was going to be, it was going to shine the light on folks. And she led with the logistics of which document to send, you know, to put the details in, what time to put it in by, the format that you should put these wins, and didn't really get much of a response from the leadership team, which Makes sense, right? Because this totally sounds like one of those things that's another item to check off on your list when you already have so many other things to do. And here's this other process that we're all supposed to do now, like yay, right? And so she wasn't really getting a response. And that's because she dove straight into logistics. Whereas what she could have done is start by selling folks, selling the other executives on why are we doing this? Well, we're doing this because this is a chance to shine a light on your team members who are doing amazing work, for them to feel motivated and to feel like the rest of the company really sees them and understands what they're doing. And this is all something that is going to motivate your team, right? So sharing why this is helpful and useful and how this is in service of you and your team versus like, oh, this is a favor that you're doing for me to fill out this form and fill it out this way.

And by this date, et cetera, et cetera.

I know that execs often are often.

Want the opposite where they're just like, okay, I know, like, just tell me what you want to do. Just like, okay, just get to the point. I don't want time for all this context and background. Any advice on when to spend any time on the sales? Like, what are signs that, okay, maybe.

You don't have them sold yet, or what are maybe contexts where you should probably still try to sell them first. Yeah. So I actually think that you should always do a little bit of selling, even for situations where people have generally bought in, because most of us have a lot going on and we're not actively thinking about whatever you're talking about. So even though I agreed to something two weeks ago, by the time you're telling me about it again, like I thought about a billion other things since then, right? So reminding me of, why are we talking about this? Why does this matter? And then getting into it, and framing that conversation up front is way more likely for us to not get stuck in a cold start and not kind of go two steps back, one step forward. The other thing is you can frame a conversation and sell it at the beginning very concisely. So I'm not talking about spending 15 minutes out of a 30 minute meeting selling. I'm talking about one to two minutes, even a couple sentences, and then transitioning into the main thing you want to talk about. I'm a huge proponent of doing that and basically reminding people, why are we doing this? Why are we here today? Why does this matter? And then getting into the meat. I love that.

So basically it's, you can do this really briefly. It doesn't have to be a whole pitch for half an hour. It's just a reminder. Here's why we think this is important. And I think that's the trigger point because a lot of times it's like a leader's looking at this thing you're asking them to do, and they're like, why are we even why am I spending time on this? And just a reminder of like, okay, I see. I forgot. This is gonna be, this is a part of our strategy. This is a big, this has this much impact potential. And, or here's how it could help.

Our team be more efficient. So, yeah.

And you can really do that in like 30 seconds. Is there, is there like a, I don't know, structure to this? Is it just like, why? Like, is there kind of a template you like or some way you recommend of selling first? Is it like, here's why we're doing this, like starting like that? anything along those lines?

Yeah, I think explaining why we're doing this, why this benefits the business, what problem this is solving, again, you can do a lot of this in a couple sentences. And then I also like asking or stating what I need from the other person upfront. So saying, you know, hey, we're here today because two weeks ago we were reviewing the product flow and realized that there were a couple parts that were kind of confusing. So I took a stab at fixing those areas, rewriting the microcopy, and I want to present them to you today, see if you agree with these changes, and then we're going to roll them out. What I'm looking for from you is feedback on the changes and if you agree. So that was like 15 seconds, right? Like super fast. And then now we're all on the same page about why we're here, and you can listen more intently knowing that I'm looking for a certain kind of feedback.

I would love to hear it that way. I think there's like an implication here that maybe is worth sharing of just, and this is a lot of this is about communicating effectively to execs, which will make you communicate better to most people, but especially with folks up the ladder. They don't have a lot of time. They have million things in their head. Maybe just share like why this is so important, like what the state of mind of a leader is that you need to kind of break through.

Yeah, so I call it the yes, yes, yes, next, next, next mindset where, where I'm, you know, if I'm listening to direct reports present something to me, very often I find myself thinking, got it, all right, yes, let's keep going, right? And, you know, on the other side of that, I've often presented to executives where I had a 15 slide deck and execs would do that and I'd be like, whoa, whoa, whoa. Like, I have, I have a whole sequence, I have a whole order. you know, and sometimes they would, they would give me buy or make the decision by slide four, you know, and I'd be like, okay, well, you know, slide 13, I want to show you this, this great graph I put together, right? And, you know, what was really helpful for me was realizing that I should take the win. Okay, if five seconds already agreed, take the win and, and keep it moving, move on. Yeah.

What's that quote? Like, if you've, if you've sold them, stop talking. Right.

Yes. Yeah. You might, you might talk them out of, Agreed.

Yeah. Okay, you mentioned being concise. Let's talk about that. You have some really good advice on just how to effectively be concise and not too concise. What's your advice there?

Yes. One of my pet peeves is when people are too concise and they equate being concise with brief, 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. And so not equating concision with, with briefness, I think is, is a really, big one to understand. The second thing is a lot of advice about being concise, I think misses an important point. So, you know, we've all heard, don't bury the lead, cut to the chase, main point, you know, put the main point at the top, bottom line, not front, right? And all of these pithy aphorisms.