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 going to be a bunch of back and forth. Whereas if you had just taken another look at it, those 15 people would be off to the races. You have an awesome framework called MOO. MO 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 2 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 going to be able to anticipate every single objection? No. But can you anticipate the obvious ones? Absolutely. [Music] Today my guest is Wes Ko. Wes co-created the AltNBA program with Seth Goden. 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, if you listen to what Wes suggests, you will be a lot closer to becoming a worldclass 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, Superhum, Notion, Linear, and Granola. Check it out at lenny'snewsletter.com. With that, I bring you Wes Ko. This episode is brought to you by WorkOS. If you're building a SAS app, at some point your customers will start asking for enterprise features like SAML authentication and skim 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

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OS. It's a drop-in replacement for Ozero 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 SOCK 2, ISO 27,01, HIPPA, and more with a single platform, Vanta. Vanta's marketleading 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 venta.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. Uh, no pressure, but I think this is going to be one of the highest leverage episodes I've done. And let me tell you why I think that's the case. uh in the newsletter and on the

podcast I often talk about just how important and how leverage the skill of communication is to product leaders to leaders just to like people in general. There's this quote that Bos 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 communicator 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?" So, let me read a few quotes about you in regards to your communication skills from folks that

have worked with you. And 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. Great. 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 that's amazing. I'm 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 uh there's skepticism, there's apathy, there's a lot of avoidable questions and uh 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, u I'm a big proponent of agency and uh realizing that we can only control our own behavior. Um, 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're having a hard time people buying 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 a issue with your ability to communicate. It's probably not their their fault. Yeah, I would say so. You know, you can't you can't solve everything with improving your communication. Uh but uh there's you can increase the likelihood of getting what you want. Cool. Okay. Uh, 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 my course and really kick off with is um 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. 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 chance to practice. So, um, 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 report's time. So that's something else that um 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, um 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 like, you know, 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 buyin or making a good decision as a team or, you know, 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've that you teach

uh 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 uh 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, uh, a common mistake that I see is overestimating the amount of buyin 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 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 than that person will want to do it uh 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 uh and to agree to do it and 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, um you will likely uh get a slow response or just no response, right? We've all put a Slack message in a channel and got crickets and tumble weed. Um 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 the 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 uh is a head of operations, and she was trying to get the rest of her uh 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 uh it was going to shine a light on folks. and she led with the logistics of which document to send, you know, to 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 like we're all supposed to do now. Like, yay, right? Um and so she 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 uh 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. Uh for them to feel motivated and to feel like the rest of the company really sees them and understands what they're doing. uh and this is all uh something that that uh 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 etc etc. 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 2 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 a bit 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 1 to 2 minutes, even a couple sentences, and then transitioning into the main thing you want to talk about. So I am a huge proponent of doing that and uh basically reminding people why are we

doing this? Why are we here today? Why does this 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 here's why we think this is important. And I think that's such a good point because because a lot of times it's like a leader is looking at this thing you're asking them to do and you're like 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 going to 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 um 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 uh or stating what I need from the other person upfront. So saying, you know, hey, we're here today because uh 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. Um, what I'm looking for from you is feedback on the changes and if you agree. So, like 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 I think there's like an implication here that maybe is worth

sharing of just and this is a lot of this is about work 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. Uh maybe just share like why this is so important like what the state of mind of a leader is that uh you need to kind of break through. Yeah. So I call it the yes yes yes 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 uh 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 has already agreed, um, 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 agreeing. Yeah. Okay. You mentioned being concise. Let's talk about that. You have some really good advice on just how 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 300word memo that's meandering and long-winded and a thousandword memo that is tight and concise. And so uh not equating concision with with briefness I think is is a really uh big one to understand. The second thing is a lot of advice about being concise I think misses

an important point. So, uh, 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 piffy apherisms assume that you actually know what your core point is. So, you can't cut to the chase unless you know what the chase is. You know, you can't unberry unless you know what the lead is. And so that I found is the bottleneck to being concise. It's it's actually not really being clear of what you were thinking. That's

what's leading to being long-winded. And you can kind of test this theory because most of us have a go-to story that we've told a bunch of times, right? We're like, you know, exactly when people are going to laugh, you know, when they're going to gasp or hold their breath, right? And why are you so good at telling that story? And you're why are you so concise about it? Because you've told it a bunch of times. you know, you know all of the beats. So in meetings though at work, we are very rarely talking about the

same thing that many times. It's always something new. It's something that we are also probably likely processing ourselves and are in the midst of processing as we are uh in a quick turnaround time telling someone else about it, telling our team about it. And so you are basically asking your brain to do a lot of different processes. uh especially in a real-time conversation, you're listening to the other person, absorbing, making sense of it, processing it, figuring out what you think and how you would react, and then trying to say something cohesive that makes sense, right?

And then trying to be um concise about it. So, it's just a lot of different processes. And so, the only solution I found consistently to being concise is preparation. It's not a very glamorous solution by any means, but the clearer I am going into a meeting, going into a conversation, going into a pitch, the better I am at being concise and being able to uh bring the conversation back to the most important points. Uh at being able to stay flexible, but also firm. Yeah. And and and preparation. I don't mean spending hours and hours preparing

for a weekly meeting. Um even a couple minutes really makes a huge difference. Most of us are so backtoback in meetings that we're doing zero preparation. It's like the meeting has started 30 seconds in and you're still unwinding from the last Zoom call that you were on, right? So most of us are are in that mental state. Um so if you even take 30 seconds to 1 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 much more focused and so much more able to be concise. So the advice there, so this is for meetings and I want to talk about writing also, but for meetings, the advice here is before you get into a meeting, like actually think about why why am I in this meeting? What do I what do I want to get out of it? Instead of in the meeting like figure all out as you go, which to your point, you're just going to ramble and be like, okay, here's what I actually want

to say. Yeah. And what what might I want to share in the meeting, too? you know, especially for more introverted folks, sometimes you need to decide beforehand that you want to speak and you want to make sure you get a certain point across. So, even deciding that beforehand makes a huge difference. Yeah, I found this uh extremely powerful. Just like five minutes before you get into a meeting, and it could happen earlier in the day, right? It doesn't have to happen right before the meeting or worst case, it's right before the meeting. Just, okay, what

do I want to get out of this? What am I here? What do I want to say? and just like giving your brain a little bit of time to prepare super powerful. Uh in writing any is there like any tactics you can share for someone to be a little more concise? I think the main tactic is to remind yourself to be concise. Um and usually when I do that I end up trimming 20% at least of what I wrote, tidying up some sentences. I also ask myself how might I be um adding cognitive load to

whatever it is that I'm saying. So, you know, is there a tighter, clearer, cleaner way that I can ask what I'm asking or present the information I'm presenting or the, you know, make the recommendation that I'm making. And usually, if you even ask yourself that, your brain automatically comes up with stuff. you just see whatever you wrote differently and you're like, "Oh I should trim this entire paragraph cuz like that's secondary, you know, and maybe you have your primary message in Slack and then within the thread add, you know, some of the secondary stuff, right?"

So, I find that most of us it's it's reminding yourself to be concise and once you think of it, your brain naturally will see places where you can trim. There's a layer of advice under this that you're not saying that I'm going to say, which is actually look at the thing you wrote at least once before you share it. Because I used to be really bad at this. I just like, okay, I don't have time. I wrote this doc, send it, get feedback. All right, let's send this amount of time to like read this email.

And I find just forcing yourself to look at it solves so much of this. Oh, yes. Yes, definitely. I was I was assuming before doing that, but you're right. The pro, you know, some people may not be. Yes, definitely reading your own message first is huge. And uh yeah, I find that even even doing that, you can often spot a lot of uh a lot of uh lowhanging fruit, right? Like you'll find the typos and grammar issues and you'll be like, "Oh, I don't need this word." Along those lines, let me share two books. People

always ask me, "How did you how did you learn to write?" I'm like, "I'm not a writer. I don't know what I'm doing." But two books really helped me uh write more effectively. And one is specifically to help you write more concisely called on writing well. And I don't know if you've read that. Yeah. Okay. And it's basically like chapter after chapter of here's what you can cut and you can cut more and look what more you can cut and cut this stuff. And he has like images of like screenshots of essays that students have

written in his class and he's like look at all those words you cut and nothing is has changed. It's exactly the same message and even is better with like 40% of the words cut. Is this by Soul Stein or or another author? I am I don't have it. It's somewhere in my bookshelf. So, we'll look it up. Yeah, there's there's there's a writing book by um Soul Stein that I absolutely love and I feel like it might be called on Writing Well, but there also I could see there being multiple books called On Writing Well.

There's also Writing Well, I think by Stephen King that's like another one that people love, but there on Writing Well is the one I really loved cuz it's very like tactical. Um, going back to something that that you were saying earlier with uh rereading what you wrote, um, I think the blast radius of a poorly written memo is way bigger than most people think. So, if you're 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. Like all 15 of these people are reading this being like, "Okay, what do I do with this?" Whereas if you had just taken another look at it, um those 15 people would be off to the races, like they would have read your message and then known exactly what to do next or what their part was or what you were looking for from them. Um so I think about that a lot too. It's not just, you know, me writing this and sending it off. It's who are all the who

are all the people who are going to come in contact with this message, who are going to refer to it and use it. And if I just take 30 more seconds to make sure that it's clean, how much can I unblock from their work? That's such a good point. I like that. I love that that term blast radius. It's such a good point. Just like there's so much negative leverage in writing inefficiently and in concisely if you spend like inconsisely. I don't know the word is there, but uh if you just spend like three minutes

spending a little more time making it more clear just like the impact and leverage that has. That's such a good point. I looked up the books. It's so funny. Okay. So, there's on writing well by William Zissner. There's Stein on writing by soulstein which is what you said you were talking about and then Stephen King has a book called on writing. Oh my god everyone not uh not ideal for SEO but on writing well is the one that I love by William Zner. There's also one called a series of sing of short sentences. If you

haven't seen that one it's a really good rate too. It's just like how to write short sentences and just the the power of just keeping sentences short which I struggle with. Yeah I like that. Okay, back to our agenda. There's another framework/tactic that I've heard you recommend. It's called signposting. What is signposting? Signposting is using certain words, phrases, formatting, and an overall structure in your writing that helps guide your reader and uh signals what is coming in the rest of the post. So, this is especially helpful if you have a long memo. Uh, it adds

structure to where are we going and uh what certain sections of paragraphs are about. So, some of my favorite signposting words are for example shows that you're about to show an example because shows that you're about to share your logic and rationale behind something. As a next step is a great one. People's eyes kind of automatically zoom to as a next step. even first, second, third, kicking off a paragraph with that. Um, you're not needing to rely on rich text formatting with bolding, italics, underlines, and all that craziness. If you kick off sentences with signposting

words, you can often signal, here's what I'm about to talk about in this paragraph. These are like power words for clarity. Like there's this whole concept of power words like free and uh yeah, a gift gift. Yeah. For like copyrightiting. And I these are basically power words for helping your brain see the structure and get to the thing you want to pay attention to. So I'll read back the words you just used. For example, because as a next step and then first, second, third. Yeah. Yeah. You can use signposting um in writing and verbally too.

So if you're doing a product demo, you might say something like the most important part to pay attention to is blank or the part that we were most surprised by is blank or the you know the part that customers are etc. Right? So it's you're signaling that whatever comes after this thing is something that you may want to pay attention to. So, it's a great way not only to add structure, but to also grab people's attention back if it has strayed sometime as they were either listening to you or or reading. Along those lines, I

find I find formatting really helpful here, just like bold and bullets. I know you have a pet peeve with too much formatting. How much is too much formatting? I really hate excessive formatting. So, you know, I've seen memos where 30% of the note was bolded and that just negates the entire point of bolding because if everything is bolded, then none of nothing is is being highlighted, right? So, I think using formatting in general more sparingly than you think you have to is probably a good rule of thumb. I also dislike when people uh overuse bullets

and sentence fragments, phrases in bullets, when they should use complete sentences that actually show the connective tissue between ideas that show the logical flow of what it is that you're saying. And you know, it's it's it feels faster and more concise to put bullets and and fragments, but a lot of times your reader on the other end of that is needing to decipher and interpret and guess what you actually meant. Um, so it net net takes longer. And I also think that it can be a little bit of a crutch. It can be a little

bit lazy because you are telling yourself that you're being concise when really if you had to turn your sentence fragment into a full sentence a lot of times like it actually is harder than you think because you realize that you actually didn't really know exactly what you meant. So as you're trying to turn it into a full sentence, you're actually needing to use brain power. So that's like I think a great limus test of like was that were was that idea fully thought out? because if it was, you should be able to really quickly turn

it into a complete sentence, a complete sentence. Um, and and many times you actually aren't. So, I see people like basically think, oh, I want to make this easier to read, more skippable. I'm just going to throw a bunch of formatting and bullets and turn, you know, turn everything into bullets and and it's not quite that easy of a solution. This is very much along the lines of the whole Amazon six-page memo where Jeff Bezos just kind of realized if you can't write it out as a long memo and explain yourself in pros you you

don't actually know what you're saying and it's a really good filter for helping people actually crystallize and and know themselves. Okay, I see I don't actually know what I'm doing here. And I love this is like a microcosm of that. Can you just like make a bullet point a real sentence versus a fragment of a sentence? M I'm thinking about as a listener being like, "Okay, how do I actually get better at this?" So, maybe take let's take a tangent. I know that you teach a whole course, you do all this stuff hands-on with people

to help them actually build these skills. For someone that hasn't taken the course or isn't taking it, what do you how what's like a good way to start practicing these skills and know if what you're writing is getting better, is good. Is it like find a mentor, find someone that you think is a great writer and have them review stuff? Any tips there? Yeah. So, I have a pretty first principles driven approach for this, which is to think about how long does it take me right now to get to the reaction I'm looking for from

my recipient. If it takes a bunch of back and forth and a bunch of um friction, then that's kind of my baseline. And once you start practicing some of these communication skills, how does that speed up? If you would have had seven different touch points of back and forth, does that shrink to two to three. Not every point of friction is going to be avoidable, but a lot of it is if you get better at communicating. So, I like watching for the reaction and um how quickly and how enthusiastically I'm able to get that reaction.

And for the things that are working, do more of that. For things that are not working, adjust your execution. Cuz it might not be that the tactic doesn't work. it might be your execution of it, you know, wasn't great and uh and you know, keep keep trying basically. So the advice here is just uh see how well your writing slashme slash suggestion goes, how well it does. And if it's not like there's like the ideal immediately, yes, let's do it. And then there's the I don't really understand. There's like the spectrum of response. And what

I'm hearing is just pay attention to if the speed to getting what you want is increasing in general. Yeah. Yeah. I don't think that there's any single shortcut on how to get better besides that. Um I do think that being fascinated by a topic and being excited about it makes it more likely that you're going to find it fun to try all these different things and try different ways to um to get through to people. So, um, I would approach it with a a hypothesis-driven experimental mindset and almost like a game, like when I do

this, how does that other person react? You know, if I frame it this way, do I get a different reaction? When I try this, am I able to, you know, cut through the noise more? Um, so yeah, so I I really think it's about practicing. Um, and I will say that the way not to do it is to try to incorporate 30 different tactics at the same time and then beat yourself up when you don't remember to do them. You know, it's really easy when you are learning a new field or function to um get

overwhelmed when you when you're learning a new skill. And uh the way to build a habit is usually not changing so many different things at once. It's picking one thing that you want to try and keeping that top of mind, trying it in a bunch of different settings in different ways and then um and then getting better at that thing before moving on to the next thing. So that's like a really common thing I see in my course is people feeling overwhelmed and um I always remind folks that you are building a new habit here.

Uh and you know take it be patient with yourself, take it step by step. There's a lot of stuff we're talking about here that a lot of people might be like this is so minor like what I just bullet point sentences uh like be a little like tell them the why at the beginning and I just want to share in my experience the biggest jump I made in my career was actually getting better at these very specific skills. I have this manager, Vlad, who's been on the podcast, and I talk about him regularly, who was

such a stickler about communicating well and being very clear and concise and thinking and just spending more time on documents, on emails, on strategy docs, just like, "No, this isn't ready. Spend more time. Here's something that's not clear." And just doing that was such an accelerant for me. And it's all these little things. That's what's interesting about it. It's like everything seems really minor, but it all adds up to a lot of impact because to your point, people see it. Okay, cool. I get it. Let's go. Versus like, uh, I don't like this idea. And

then it's like it all falls apart. So, I guess any reactions to that? Yeah, all these little things compound and make a big difference. I often hear people think, well, you know, this individual instance, this individual email, the Slack message is not worth spending a couple more minutes on. it's just an email or it's just a Slack message. The problem with that line of thinking is that no one instance of something is ever going to feel important enough to spend a little bit more time on then. And then but when you zoom out that's like

well that's all your work then. This is like literally everything you've touched. This is all your work output then cuz every you know any piece of that process you thought wasn't you know wasn't worth uh spending time on and now this is just the the quality of your work and it's not as good as it could be. So yes, like these might seem minor but a it compounds um and also b all the quote unquote big things everyone else is already doing. So there's not a lot of alpha in that. Whereas if you are paying

attention to skills that people think are boring or too basic and realizing that there is that's a lever that you can pull that you know someone else thought, oh, we're hitting diminishing returns on that. I'm not going to I'm not going to spend more time on that. But you realize that there's actually more juice left to squeeze there. And you decide to squeeze that juice. Well, now you have extra juice, right, that the other person doesn't have. So yeah, in in my experience, I find that people claim the point of diminishing returns way too early.

And this isn't just for communication. This is for strategies, tactics, etc. Like they'll try something once, you know, a mediocre attempt and be like, "This channel doesn't work. This tactic doesn't work." You know, it's like really cuz it's working for a lot of other people who are getting really creative with it. You know, I'm not saying that everything has to work for you, but like for you to claim this thing just doesn't work feels a little bit intellectually dishonest. Like, it's more likely that your skill level, your creativity, your execution ability was not good enough.

And that's fine. Like, let's admit that to ourselves because if we admit that, then we can do the hard work of getting better at those things. It feels like at the like if you really boil this down, it all the advice kind of comes down to just spend a little more time on all these things you're putting out. I like thinking about it as a little bit more upfront investment. And it is an investment. It's not just time. It's an investment because yes, it takes a little bit longer to make a Slack message a little

bit better. But net net, if you save a bunch of questions and back and forth and people asking you things that you don't think they should be asking, then by investing a little bit of upfront effort, you've prevented all that from happening. So yeah, it it it is a little bit more time in the moment, but reaps a lot of benefits down the line. Today's episode is brought to you by KOD. I personally use KOD every single day to manage my podcast and also to manage my community. It's where I put the questions that I

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of the team plan. k cod.io/lenny / Lenny, you mentioned Slack. I have a great quote also about you that I didn't read that I'm just going to read right now from someone that worked with you. She said she searched the the Slack channel at the company you worked at for old posts from Wes for inspiration for what to ask you. And she said zero you had zero halfbaked thoughts, 100% complete sentences, perfect punctuation, clear takeaways at the top of every message. It's the kind of thing you don't notice in isolation, but once you see everyone

else's messages in a remote first company, it's a stark contrast. Yeah, thank you. I will also say that, you know, as someone who tries to walk the talk, I feel like I get a pretty good response rate pretty quickly for the things that I ask for, for the recommendations I'm making. It's not, you know, it's not instant. It's not 100%. But over time, I've realized that improving my communication has led to people receiving my ideas better. You know, ideas that used to be locked in my head that I would get frustrated that no one else

understood, people were now understanding. And that feels really good. That's very, very exciting. And it made me want to do it more, you know, and pay more attention to that. So, that's kind of going back to to what I said earlier about uh watching for what's working. You know, there's there's momentum is is really encouraging. And I and I totally feel that if it starts like if you start getting the things you want that feels great. Okay, cool. Do more of that. Yeah. And again, it's like very minor things like it's you know it's like

a couple more minutes on the Slack message, a couple more minutes on email. Very doable like Yeah. which everyone can do. There's no like magic here. It's just spend a little more time and use some of these tactics that we're talking about. Speaking of that, let me talk about another tactic you have. Apparently, you have some really good advice on finding the right level level of confidence in what you're saying. There's always this like question if I come to leader, how like confident should I be about this is the answer versus like here's a bunch

of ideas. What do you think? What's your advice there? I find that people tend to naturally be on the spectrum uh a little bit too confident as a baseline or not confident enough. So people who are too confident might state hypothesis as if they are fact. So that really bothers me. That's another one of my pet peeves where you know if you say this is X or this will X that is different than saying this could X or this might X or this will increase the likelihood of X. So 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. It's okay for something to be an initial hunch. Say it's an initial hunch. Don't act like this is something that you are super sure about. you've proven out, you know, that this is absolutely, you know, this way because the rest of your team is is listening to you at face value and y'all might spend real headcount and dollars pursuing something that you have advocated for in a way

where you kind of overreached uh with your level of confidence. So, so that's for people who are overconfident. Um, it's equally a problem if you're underconfident. So, I have some clients who, you know, their CEO asks them to uh share some recommendations with another team because, you know, they've run something before and so they share all this amazing information and at the end they're like, "Oh, but you can ignore everything I just said. You know, obviously make your own decision. Do what you think is best and like if you want to just ignore everything that's

totally cool, too, you know." And it's like, you just didn't have to say that, you know? You could say make your own decision. like take all this into account, you know, but like you don't have to diminish to that degree. And so again, speaking accurately, like if you have really strong reasons to recommend something to, you know, to a cross functional team, it's almost irresponsible to act like you are not really sure and it's just this like random idea. Hey, try it if you want to, try, you know, like we might lose a lot of

money and time if you if we don't take this idea, right? So again speaking accurately is um so so important is a simple way to think about then kind of the the right balance is have a point of view have a recommendation present accurate facts and be clear when you are not it's not actually 100% true but here's a hunch I have or here's a theory we have yeah I think sharing a point of view sharing a recommendation and then backing it up with evidence with logic with first principles with examples uh with data if

you have it. You know, you're not every situation you're going to have data for, especially if you're building something new. So, this is where first principles comes in. Like even explaining how you got to where you got to and why you think this is going to work. That all gives your team, your manager, something to push back on, to poke holes on, or to align on and say, "Yeah, I agree here, but I disagree on this part." So you can talk about ideas with a lot more specificity when you share your thought process and you

can you can frame it all kicking off saying my initial thinking is or you know based on what we know my hunch is blank. Right? So speaking accurately and then still bringing up those facts so that we can all make as informed of a decision as we can make given what we know. advice I got that really helped here for me was uh to try to not be super try not to be biased with how you frame everything. You have your uh suggestion for how to do something. It's easy to just bias all of the

data to point in that direction and I think it's and if people notice that they're like okay well I can't really trust this because I see you're just like you clearly have an agenda. So it's a little bit like have an agenda and a POV but be clear about what is actually true. be accurate. Yeah, I think anytime people have to discount what you're saying because you are biased in this way uh is is not great. Is there an example by by any chance that highlights what you're describing here? Yeah. So, in my course, I

talk about not being a single-minded martyr. So, a single-minded martyr is someone who very much has an agenda, who wants their recommendation to go through and is presenting a bunch of evidence supporting that direction. Um, and then gets really frustrated when other people are not seeing it or are skeptical. And so, one of my clients was a single-minded martyr in uh a recommendation she was making. So she uh was on the growth acquisition side of her company and was having trouble with cross functional team members lending headcount to her project. And so everyone would say

like oh yes we believe in this this is important but wouldn't want to actually give her you know half of their engineer for 2 weeks. And we were talking about it and as we were talking she revealed that the CEO had at the beginning of the year said that the companywide goal is retention that year that their biggest challenges and areas of opportunity were in retention not necessarily in growth. And once she zoomed out and realized this she was able to put her recommendation in context and realize that you know it's not just you know

I'm the only one who cares about this company. everyone is a hypocrite. They say they believe this but like don't actually want to work on it. You know, before that was that was kind of her narrative. But once she zoomed out and and realized she was being a single-minded martyr, um she could better fit her proposal in the context of what else was happening in the organization. I think actually this is a really big difference between more junior people versus more senior people. More junior people are like, I need a win. Like I need to

get a yes for this proposal and I'm going to keep advocating for it until I get a yes. Whereas really sometimes the best decision for the company is not right now. Like this doesn't actually fit our priorities right now, right? Or maybe yes, but let's rightsize the level of investment. So it might look like half whatever the proposal, you know, the the the size of what that recommendation actually was. And having the maturity to realize that, to put your idea into context is huge. Like that took me a really long time to learn. And uh

I think that goes under the umbrella of always do what's best for the company, not necessarily what's best for me, my career, my team, my wins. You know, if you if you prioritize what's best for the company, that that helps you have uh a more right-sized way of still, you know, advocating for your ideas, but um doing it with a bit more equinimity. And also just uh connecting to what the company is just this idea of if the thing you're pitching is not aligned with what is important to the company right now, it's unlikely to

be prioritized. Like it makes sense. this is why leaders choose. Here's what matters most. We got to do the things that are going to help us drive this thing right now like retention or uh or revenue. And so that's just I think a sub goal sub tactic there is just whenever you're pitching something, connect that to the goal of the person you're pitching to so that they're like, I see how this is going to help me. That's great. Let's do it. Great advice. Uh and I think this is something a lot of people run into

is just why aren't they listening to me? Why don't they want such a good idea? Mhm. They hate me. It's something. Oh, I bet they hate me. They don't trust me. When it's just like, okay, this isn't a priority right now. Let's come back to it another time. Okay, I'm going to get to a couple more tactics and then I'm going to shift directions to talk about managers and being a manager. You have an awesome framework called MOO. What is Moo? What does it stand for and what is it all about? MOO stands for most

obvious objection, M O. And the thought there is that a lot of times we're surprised by the questions that we get especially in meetings where you know we feel blindsided that was unexpected and then we're we're on our back foot when really if you thought for even 2 minutes about what are obvious objections that I'm likely to get when I share this. You often immediately come up with what some of those things are. So are you going to be able to anticipate every single objection? No. But can you anticipate the obvious ones? Absolutely. Um and

so this is where knowing your own argument in and out including counterarguments becomes so important. So knowing your counterarguments as well as you know the arguments for doing the thing. When you do that when you when you you know have prepared in that way you're less likely to to feel caught off guard. when you hear you talk about this, it's like obviously I should do this, but nobody like very few people actually do this. Like actually spend a couple minutes, okay, here's what I'm gonna pitch. Even a couple seconds really like really like even a

couple seconds, your brain will will think of something. Is there is there a story or an example this that you share that highlights this idea of the power of Moo? I use Moo multiple times a day every day. Every single day. Like literally whatever I'm about to say, I think how might someone disagree with this or what might an objection be? So whatever it is I'm writing, saying it's a really good mental filter because it encourages you to think a couple steps ahead in kind of a structured way, right? Like if I'm about to say

this, the person may then say this to me. Well, if I take that into account, I can I can volunteer that, you know, that information upfront or I can frame it in a way where they're less likely to think that that's an issue. And so, it's it's it's muscle memory for me at this point, but you know, this might be something we we include at the end as something to start with, but putting moo on a post-it most obvious objection. You know, what what is someone likely to object about? And then just keeping that top

of mind. It's a great way to train yourself to be uh to empathize with your audience and with your recipient. We all say that and we all know we should do it, but for me, this is a really tactical, concrete way to do it. I think what's great about a lot of the tactics you're sharing is not only is it going to help you communicate it better, but it helps you actually think and crystallize it better for yourself because you may realize, oh, that's a really good objection. like, oh, oh, the objection is probably going

to be this won't drive enough impact for the business. Oh, that's a great point. Maybe I should not pitch this right now. Yeah, it definitely helps shape your own thinking. Um, I think communication and thinking are so much more interrelated than we think. You know, I think people think there's a thinking as phase one and then communicating the thinking and the reality is a lot more intertwined. Uh, and and I loved your example there that thinking ahead to what might be the most obvious objection actually then prompts you to realize that maybe there was a

gap in in what you were planning to present and then you now have an opportunity to strengthen that pitch before you say it out loud. There's a quote I have highlighted on this podcast a number of times that I love that is exactly along these lines by Joan Ddian. I don't know what I think until I until I write it down. That's I know exactly that feeling. Okay, so there's a couple more things that people have shared uh that you are amazing at helping them get better at. One is just keeping your cool and staying

calm during very high stakes real-time conversations when things maybe aren't going your way or you disagree with someone. Any advice on that? Feels like you're really good at this. I think one thing that um tends to to throw people off is putting a lot of pressure on themselves to get the exact right answer. So if they are asked a question and they don't know the answer, you know, a lot of people will then kind of freak out and I was taught early in my career that if you don't know the answer, you should say, "Let

me look into it. I'll get back to you." So that's a fine approach. It's definitely better than making something up, right? So, so definitely don't make something up. But if you are more experienced and have some confidence in your subject matter uh area, just saying I'll get back to you is sometimes a missed opportunity. You can ask for a bit more information to be able to continue the conversation in that moment. So, you know, let's say that your exec says, you know, what percentage of users came from mobile last month, and you don't have that

number off the top of your head. So, person A says, I'll get back to, you know, let me look and I'll get back to you. Person B might say, 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. So, mobile is is now, you know, a bigger part of our business, etc. are you wondering if we are investing in mobile appropriately or like where's that you know where is that question coming from basically right and so

being able to answer a similar question in the direction you think the person is asking about and then validating why they are asking that question allows you to still continue that conversation in the moment and so I call it the question behind the question sometimes you get a question but underneath there's a deeper underlying concern and many times people don't even know that it's there, right? Subconscious. So, it's not nefarious. They're not withholding anything from you. But, uh, when you are explaining something and you're kind of getting multiple questions on the same thing, it's a

good sign that there might be a deeper question and it's our responsibility to figure out what might that be. Um, and so probing, asking for a bit more information, answering in that general direction, and then validating. These are all techniques you can use when you are in the moment, um, without feeling like, oh, I must have, you know, every single thing prepared, and the moment that I'm caught off guard, you know, everything goes to Another tactic along these lines that's very similar to what you're describing, but I'll I'll share that I learned that was really

helpful is just uh if you're not sure what to say, basically just reflecting back their question and just just being like, "Let me just make sure I understand what you're thinking, what you're looking for." You want to understand monthly retention for and then maybe clarify. And that one gives you time to think about it as you're talking. Two, it helps the person recognize, oh, he he hears me great. Okay, this is good. He's thinking about this. And then at the end of that, you could be like, "Okay, I don't actually have that specific number. Uh,

let me think about." Oh, or I have the quarterly number. Okay, there. That's what I know. So, there's like there's like an interim step almost that I uh I'll add into your piece of advice of just Yeah, I love that. Reflect back their question, just like better understand what they're looking for. Awesome. Okay, let's go back to what I said we do. Let's pick one tactic that you think people should try first. Maybe one or two. So, let me read the ones we've gone through and then see what you think would be a good first

step. So, one is starting with sales before getting to logistics and giving people the why. Signposting, using specific words to help people guide the the doc and not get overwhelmed. Finding the right level of confidence, having a POV, that sort of thing. Getting better, being concise, moo, not overusing formatting, something else you shared. And then this idea of when you don't know the answer, not saying I'll get back to you as the default, maybe giving them a different answer, maybe asking them more questions. Okay, across those, which do you think someone should try to like,

okay, let me start here. I would start with most obvious objection and also framing your conversation up front. And that kind of relates to using signposting words if needed to help you frame that conversation. Sweet. That's such an easy one to remember. Just move. Okay, so stick a post-it somewhere when you're about to share something in Slack and ask someone for something. Present in a meeting. Send a strategy. Just think about for a few seconds what might be the most obvious objection to what I'm trying to ask them to do. Great. Okay, so let's talk

about management. And there's kind of two sides to it. Being a manager and being a person reporting to a manager. You have a bunch of really good advice here. One is around managing up. One of my most popular posts in the early days was advice for managing up and just how important it is. uh what advice do you have for someone to get better at managing up? Why is that even so important? Why do you think people maybe underappreciate how important it is to manage up? Manage your manager, let's say. One of the most uh

common myths about managing up uh that I definitely felt early on in my career was that I would have to manage up if I were more junior, but eventually I would outgrow it, that I would get senior enough that I would no longer have to do it. And it was a rude awakening that no matter how senior I got, uh, managing up, I not only had to manage up, it actually became more important. So I think managing up is is one of those skills that if you invest in learning it, it serves you now and

for the rest of your career. And I realized that many senior people uh are actually the best at managing up. That's partially how they got to be so senior in the first place, but also, you know, the more senior you get, the less likely that your manager is going to give you really well-defined tasks and problems on a silver platter and ask you to solve them. You're going to be dealing with more ambiguity. Uh, and you're going to be dealing with sometimes a mandate like make this number go up or like create this division, right?

where you need to manage up and make sure that your leader, your manager is in the loop about what you are about to try and what you're about to do and uh make sure that they're aligned. And so for me, realizing that managing up is something that uh is is ongoing and that it it shifts and evolves and looks different uh as you go in your career. Um that was a big unlock for me just that even as you like if you become even a VP if you become a director and still something you want

to invest in any specific tactic or advice for how to manage up well the biggest one is to share your point of view. So, this, you know, some people are surprised by because they think I'm going to say do a weekly recap of the tasks that you worked on or like, you know, what you contributed. And that is a good idea. You know, if you want to do it, you can do it. But I think the the more highly leveraged way to contribute and manage up is uh by being more vocal about sharing your point

of view. 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 solution, and then tell you what to do. Whereas, if you instead said, "Hey manager, here's what I think we should do. How does that sound? Where do you see gaps? Am I thinking in the right direction?" You give them something to build off of, and that reduces uh the amount of mental lift that they have they have to uh put

forth. And so sharing your point of view more readily, backing it up with evidence, that's a a wonderful way of making your manager's life easier. And also showing that you are an active, rigorous thinker who is thinking strategically about the business. You're not just waiting to be told what to do. You're not expecting them to figure things out and then tell you. Um, you are actively looking around the corner, trying to solve problems, forming hypotheses in your mind, observing and noticing things. And again, sharing your 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 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 and takeaways. You should look at the report, too, and point out insights and takeaways. So, it's really changing that posture from more reactive and more waiting to be told what to do or kind of staying in this narrow box to being willing to share your recommendation, your point of view, share what

you're noticing. And this is something that even junior people can do. I was going to say exactly that. I think not only is it something junior people can do, this is a really good way to get promoted and to take on more leadership opportunities. You coming to your manager with here's something I think we should do. Here's a perspective I have. Here's an opportunity. cuz that's what like if you if you were in charge you're like how awesome would it be for people to come to me with amazing ideas and have clear recommendations that sound

great like that's exact everyone wants that so if you can do that amazing who wouldn't want that but then it's interesting is similar to how writing helps you crystallize your thinking you coming in with a recommendation forces you to really think deeply about it because that's putting your reputation online so there's like a second order effect of it makes you actually spend more time on the thing and be clear about why you think this is a good idea and do more research. So, a lot of wins here. There are a lot of situations where you

might have the most visibility into a problem. You might have the most proximity into an issue. And so, if you're not speaking up about it and sharing what you're observing, sharing what you're noticing, your manager doesn't necessarily have visibility into that. And so I've heard so many managers say that they want their junior people to speak up more because uh their junior people have uh often close contact with customers with support tickets with you know cleaning data with you know a bunch of things where the manager would love to hear insights from that. And if

you're finding not s if you're not having success with this if you're if you're like hearing this and being like but it never work cuz my manager doesn't listen to me. listen to the rest of this podcast we just did, which is basically advice on how to effectively convince someone of a thing. It's like tell them why this is a problem, be really concise about it, signpost words, all these things. That's exactly what this whole conversation has been about. Okay, let's see. You have a couple more really cool uh tactics that people have suggested we

talk about. One is how to give feedback. Well, how to do better, how to be more effective at giving feedback. What's your advice there? I have a framework called strategy not self-expression. And so the idea here is that most of the time by the time we are giving feedback to someone we have been frustrated for a while. You know I used to be very conflict averse. So I would wait and try to convince myself that I wasn't bothered by something until I really couldn't hold it in anymore. Then I would schedule a one-on-one with a

co-orker to, you know, to tell them the feedback. And it would inevitably turn into a venting session where I was in the name of sharing the impact of what they did uh would share all my frustrations and all the ways that they have basically harmed me and made my life difficult. And this would be very counterproductive because the person would either feel like and feel really demoralized or they'd get really defensive and they'd want to argue with me about how what they did actually was like not that bad or it was partially my fault too

or whatever. 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 were about to say that does not actually contribute to that goal and only keep the part that will make the person want to change, help them understand the benefit to, you know, them as well as to the people around them. And so usually for me that's trimming 90% of the initial stuff that I want to say and really keeping only that

10%. And that's made a really big difference whenever I am giving constructive feedback of any kind I always keep that in mind and when I don't do it I almost always regret it. someone close to me in my life uh is very uh needs is is some is working on the skill which is like there's just like a I want people to know how mess they messed up justice I need this to be fair and there's like a like what I always recommend is just think about what you want to get out of this conversation

like what do you want from them and then okay what's the best way to get that versus just making sure they hear you and making sure they understand how screwed up this was and that's basically So what you're saying right is like focus on the outcome you want to achieve not like uh something that's useful like some something that will make you just feel better. Yeah. I definitely think that having a space to vent and to share those frustrations is important. So you want to get that out before you go into the conversation with your

counterpart. So whether it's talking to your therapist or your partner or friend, you want to basically get all that energy out because otherwise you bring it into the conversation and it doesn't take much to set you off. Like you might have a whole script, you're, you know, you're controlled, you're calm, and then you start talking and the other person raises an eyebrow and it's like, you know, acting a little incredulous at what you're saying and that's all it takes for you to snap and be like, "You're surprised. You're incredulous. Why are you incredulous?" Like, right?

Like, and then and then you're off, right? So yeah, getting that getting that energy out I would say is step one so that you can go into the conversation clear, grounded, setting that emotional tone that is more positive and that allows you to stay focused on only the part that will get them to behave in the way you want them to behave. Such good advice. And I think we come back to are you getting the outcomes you want? If you're not, this is another reason it might be the case is you're just like you just

need them to hear your mind. I just need you to know. And I think a lesson here is that may not be what the best path to getting what you want, but it may feel good. Maybe people like, "H, but I really want them to know this." There's that great Einstein quote about insanity being repeating things that you're doing, expecting a different outcome. And I feel like that applies so much to the workplace and communication, you know, like most of us have certain patterns that we're used to and certain ways of responding. And if that's

if you if you believe that there is uh untapped upside that like what whatever you are at is kind of a local maximum and that there's more there's better out there then that's where switching things up could be useful and just not not just doing everything that you've been doing and getting the same result that you might be getting. this um resonates with Toby Lucky when he's on the podcast talked about how he had this quote that I love that just no human in history has come anywhere near their potential and everyone is way way

way better than they think they are and these are really cool tactics and really effective ways to actually get closer to your potential. Okay, two more things I want to talk about real quick. One is your advice on delegating but also continuing to have high standards. This something I spent a lot of time on because a lot of people don't delegate because they're afraid it's not going to be as great. They want to just I just want this to be really good. I don't trust that it's going to go as well. If I if I

did it my my way, it would be great. So, just advice on how to delegate effectively while maintaining high standards. Yeah. I have a framework called CEDAF. C D A all these acronyms. These are It's kind of like Cedar but with an F at the end. I need acronyms for myself. Like all of these are are really reminders for myself because I need a short way to remind myself. So um CAD stands for the C is comprehension. So have I given this person that I'm delegating to everything that they need to understand what it is

that I want them to do? uh that includes more simple things like login to all the right software tools that they need to look up whatever you need to look up and understanding you know what the end result should look like right so that's all under C for comprehension um E is excitement am I explaining this in a way that is making this as exciting as it could be there are a lot of tasks that aren't inherently that exciting but by explaining the why behind why we're doing this or why it's important to the project

we're working on that makes people more likely to understand and be excited about how this fits into everything. So E is for excitement. D is for derisk. Am I derisking any obvious risks from delegating this? So usually when I ask clients this, they immediately think of something. They're like, "Oh, yeah. I wouldn't want my direct report to spend, you know, a ton of time going in the wrong direction filling out a hundred rows of the spreadsheet if like actually it took longer than we expected." Okay, great. If that's a risk, then maybe you have them

do 10 rows, see how long it takes, see if we need all the information that they're actually gathering, and then regroup, right? So, what's an obvious risk? Another might be, you know, I can see this person misunderstanding and thinking I'm looking for this where I'm really looking for that. Okay, perfect. Just tell them, you know, when I explain this, you might think I mean this, but really I don't want that. I actually want this, right? So, just vocalize it. The A is for align. So, am I giving the other person a chance to speak up

and make sure we are actually aligned? That they are picking up what I'm putting down, right? Right? Cuz you might you might be explaining a bunch of stuff, but how much are they actually absorbing? You won't ever know if you wrap up your little spiel and then say like, "Okay, go off." Like, "Come back to me when you're done." Right? So, give people a chance to ask questions to see what parts are resonating, what parts they, you know, might be a little bit confused on. Usually, when I do this, it's amazing because my team member

will say, you know, what did you mean by this this part or like, "How does this part fit in?" And I'm like, "Oh my god, I totally forgot to like mention this thing." or oh yeah I I didn't even really explain that well okay so let me let's go into that right and then F is feedback so how can you have the shortest feedback loop possible I am a huge fan of shortening the feedback loop as much as possible and then shortening it again so even within that initial conversation where I'm delegating something instead of

waiting a week what if we waited a day and checked in on the initial direction that person was going and let's do it even more what if after I finish explaining at the end of that conversation we brainstormed a couple things that that person wants to do. So within this same conversation I'm delegating I'm already getting a sense of you know where do you want to go with this once you start like do you see any bottlenecks you know and so just really keeping that feedback loop super tight. I found that when I run through

the CDF acronym, there's usually one letter that I could amp up a little bit more. Like, oh, like I didn't really put much thought into making this exciting for the person. How can I connect this to their career goals or to the company's uh priorities this quarter or to something else, right? So, um it's a nice mental checklist. So much of your advice comes back to this idea that we've touched on a couple times, which is spend a little bit more time upfront. Is that how you described it? a little more time up front, a

little bit more time, a little bit more of an investment up front to save you tons of time later. Okay. Uh Okay. So, as you describe this, I don't know if you're realizing this, but you're basically just helping people work better with AI and agents like this framework is exactly I think what people need to effectively delegate to this future world of this agent world of society of agents doing work for us. It's like exactly what you like. It's basically you're going to be delegating to these agents in the future and this framework is a

really cool way to frame it. So think about am I is am I communicating this well? Comprehension. So CDF comprehension is comprehension again just like can I make this clear? Is that the way to think about that? Yeah. Can I make this clear? Does this person have everything they need to be able to accomplish? Okay. What I am asking them to do? And then it's communicate why you're excited about this. Basically the why. And it's interesting there's this funny prompt technique I've learned uh prompting engineering technique of just telling the AI this is very important

to my job just using that sentence it doesn't matter interesting yeah it takes it more seriously that's it's so weird right it's like I have a post about this and that's one of the pieces of advice just tell why this is important okay I think people take it to the extreme is like someone will die if you don't get this right like people that actually works that that is extreme it's it's wild okay so caf comprehension excited derisk. Think about ways you're you can derisk which is moo basically what's the most it's like a similar

concept just like think ahead to what might be go wrong uh make sure you're aligned which is quite important in the AI space make sure you're aligned and feedback get a quick feedback cycle and it's interesting with like deep research and some of these AI tools now it's like I'm off for half an hour see you and I imagine more and more of them will check in with you as it's going and ask you questions I I used deep research recently and it's really good at just like okay let me have five questions for you

before I go off and do this work just to clarify what you want. Yeah, I found that um AI will often um shorten the feedback loop and align with you as well. Like when you prompt it, when it comes back, it will not do the entire task for me. Sometimes it'll say like, you know, I've done the first part of this. Does this sound right? You know, is this is this what you're looking for? If so, I will complete the next section. And then the and then sometimes I'm like, do the whole thing. just stop

trying to conserve energy and just do I want you to do the whole thing, you know. Uh but that's what it's doing. It's it's breaking it into smaller chunks to derisk that you know it's going to use all this bandwidth to process this thing and I'm going to say oh that's not what I was looking for. I want to come back to AI real quick but before I do that I have one more question for you but let me just say I feel like we've discovered an AI version of your course now. Basically how to

delegate well to AI agents that I think people are going to find really valuable. Planting a seed. Okay. Uh before we get back to AI, you have this other concept that I love that I actually learned from you years ago when I was working on my course called the swipe file. Swipe file. What is a swipe file? What is that about? What can I help you with? Why should people be doing this? Yeah, so swipe files are really common for marketers and I think other functions haven't caught on as much, but I think is uh

really really useful. And basically swipe file is collecting inspiration that you can refer back to later on. So you know some markers will collect examples of copy landing pages ads etc. For me I have a file an Apple notes file called smart things people have said where I will basically paste in phrases words you know things people have said that I thought were well articulated or sounded really intelligent or uh sounded strategic. And I don't actually go back and look through my swipe file very often. I think other people do, but for me, even the

act of adding it to my swipe file, I've already gotten value from it because it's training me to be more alert to noticing when something is working well. I think there's so much happening around us all the time that, you know, your coworker says something smart and like, "Oh, that was nice." And then you keep you keep moving on, right? But when you stop and pause and think, "Oh, that was really effective." Like, "Let me add it to my file." and also think about why was that effective and is that something I can borrow. So

in my course I uh encourage folks to create a work journal where they can jot down some of these observations, some of these phrases and basically encourage yourself to be more alert to things you can borrow from other people all around you. Something else about the swipe file like you use quotes. It could be screenshots of cool designs. It could be strategy docs you found to be really effective. It could be uh conversion flows that are really cool, right? It could be just like whatever you're interested in. Yeah. And the great thing about that is

you can then go back and analyze it and break down the structure, break down the argument, break down why was this so effective. Uh whereas if you're if you're not capturing it, it's it's easy to just move on to the next thing. Yeah. Cool. And I I did this for a while. I stopped to be honest, but I I really want to be doing this. But so this is some maybe some homework for someone because I know a lot of people uh stick with it is just start like a folder or a notes notes note

whatever you note takingaking and just start throwing stuff in there. And it's like it could be messy, right? It's just like throw it. It could be super messy. I was going to say my backend system is super messy and it's fine. I am not, you know, it's not a problem I need to be solving. Um, it works. I find things I need to find. So, I like having as simple of a process as possible. So, Apple Notes, like I open it. It's just, you know, on my home screen. I just add something. I'm not tagging

anything. I'm not putting it in certain rows and filling information out. I'm just including in a file and if I want to go back and look at it, it serves it purpose. Awesome. Okay. So, last question. AI. I'm going just come back to this briefly. We have a segment on the podcast called AI Courtner and we touched on this already, but I'm just curious how you have found AI to be useful in your work or your life, whether you've it's helped you become better communicator. Is there anything you can share might be helpful to folks?

Yeah. Um, I love Claude. Uh, there are days when I talk to Claude for like three or four hours prompting as a thought partner. So, yeah, I think that that AI is really helpful for an initial draft of something to to bounce off of. Um, sometimes I'll paste in an email that I am not quite sure how to respond to and ask Claude, uh, tell me draft reply and I'll usually give it some direction. So, I found that sharing my point of view makes the output way better. If I just give it something and say

like what would you say? It's just not as good. Whereas if I say you know I am not sure about how to tell this person no because you know I previously kind of said yes and so I kind of feel on the hook but you know the sit has changed and so like is there a nice way where I can be really respectful of our relationship and also make them feel seen and heard but but like decline. So, if I explain like that's the problem I'm dealing with and like here's what I would ideally like

to be able to do. Claude comes back with something that's like pretty good and then from there I'll edit it to my voice because usually it's it's a little bit too formal sounding and so I'll I'll make some edits and then I'll share it back to Claude and say, "What do you think of this version? Would you make any improvements?" And then we kind of go back and forth from there. Wes, this is the most useful thing I've ever heard. I need this. I need this immediately. just like nice ways to say no to stuff.

This needs to be like an extension that I can have in my browser just like help me say no to this, please. Wow, such a great idea. Okay, good one. Okay, great. Wes, is there anything else that we we we've gone through a lot. I imagine the answer is no. But before we get to our very exciting lightning round, is there anything else that you wanted to share or leave listeners with? Um, no. I feel like we covered a bunch of great frameworks, principles. So, lots for folks to get started, all the things. And I

I think I I love that so much of this will apply to being more effective with AI tools. And I feel like people can go through this again and just through that lens of how will this help me get more out of Claude and ChatgBT. I bet so much of this will actually apply and I feel like there's an interesting course there. With that, Wes, we've reached our very exciting lightning round. All right. Are you ready? Let's do it. Okay. First question. And what are a couple books that you recommend most to other people? One

is High Output Management by Andy Grove, which is a classic. Another one is Your brain at work by Dr. David Rock. And that one is all about better understanding your own brain and attention span so that you can allocate your mental resources appropriately. So, that one's great. Ever since reading that, I hide my phone from view because there have been studies that show that even seeing your phone in the corner of your eye kind of changes. It's distracting. And uh I do the hardest things earlier in the day when you still you have, you know,

more cognitive resources available. So that one's really good. Um yeah, those two. These are great. I completely get that phone thing. I'm just looking at my phone. I'm like, Dan, get out of here. Just like go away. I will like stick it under my pillow like on the couch or like hide it under a notebook. It's a It's huge. I'm always hiding my phone so it's not in my line of sight. I think uh Ariana Huffington has a product you can buy that's like a little bed for your phone that you put to bed before

you go to bed in a different room and it has a charger attached. Oh, that's cute. So cute. So cute. I don't know if I need a separate bed but for my phone but you know. Yeah. But it's like a ritual, I guess. You know, there's some theory behind it. Okay, next question. favorite recent movie or TV show you really enjoyed? I love anything by Harlon Coin on Netflix. Basically, I don't even remember any specific movies or or a TV series. Um, but anything he puts out, he's an author and then they, you know, uh

they've turned a lot of his books into mystery, thriller, TV series, and anything he puts out becomes number one on Netflix. And I appreciate that he gives the people what they want, that he knows his craft, he knows his genre, and uh yeah, he just has so many bangers and like I don't remember any specific one, but if it's a if it's a Harlon Coben show, I know it's going to be good. I'm looking at a list now. I just Googled real quick. So, it's all like scary stuff, right? Yeah. They're like mystery thrillers, and

I think he does a good job playing with time and revealing information over time. And like it's usually something about someone's past that is like now coming to haunt them. And so he'll go he'll skip between present day to the past and then like slowly reveal stuff and there's always a twist at the end. There's a page the Harland coin collection on Netflix that we'll link to that has all this stuff. I've never heard of this so this is great. Next question. Do you have a favorite product you recently discovered that you really love? I

recently started using an electric toothbrush and it's been kind of life-changing. So, my husband got one and then a couple weeks later he gifted me one and I was like, "Wow, this is actually really nice." Are you a sonic care person or Oral B person or something else? It's Oral B, but I've not tried any other brand. That was one that um my our dentist gifted my husband this electric toothbrush because he did Invisalign. And I'm sure Invisalign is like every dentist's dream, right? Yeah. I feel like every time I go I get a cleaning,

the dentist is like, "So, have you thought about are you interested in Invisalign?" I'm like, "No." You know, and so like when they get a yes, I'm sure they're really excited. Um, and then they lock you in with with uh or the brand locks you in with these replacement toothbrush heads that are way more expensive than they should be. So, it's a whole razor and blades ink cartridge and printer model here. So, I was kind of horrified by how expensive these replacement heads were, but but you got a free toothbrush. Um, uh, I think they're

all B is what I use, but it's I think that's the wire cutter recommended, but it's so loud. I don't know if like one of them is just really loud. I think it's the oral B, but it's better apparently. So I I I went with wire cutter, but it's like ah it's so loud. I feel like there needs to be a wire cutter for like good design and experience versus just the optimal efficient version. Anyway, let's keep going. Do you have a life motto that you often find useful in work in life that you repeat

yourself? share with folks. Yes, I have I actually have many, but I'll share two. Um, one is everything takes longer than you think. So, this applies whether you are calling customer support for something or running an errand or building your career, building skills. I find it's useful to add buffers for yourself. Uh, and this applies for launches too, right? Everything just assume it will take longer than you think. Um, and you'll be less stressed. that connects everything we've been talking about. Just spend a little more time up front to make it and maybe maybe if

you spend more time up front, it'll take less time than you think. The other one is a riff on always be closing by Glenn Gary Ross. It's always be selling. So, this does not mean pawning your wares, but rather putting forth effort into convincing the other person of whatever your recommendation is. Love them. Okay, final question. So you've been a longtime I hate this word operator but I guess that's the way people describe this where you just been working at companies building companies and you recently left that just become creative person started a c course

on Maven you do executive coaching things like that any just lessons or a lesson from that jump that might be helpful to folks that are maybe thinking about that I think when you are an in-house operator there's a lot about your role that you have a little bit less control over basically like there's there's just certain things you have to do because it comes with the territory. Whereas when you are a solo operator, you know, running your own business, doing your own thing, you have a lot of freedom to craft your work around only your

strengths, only the part that you are really good at that adds a lot of value for other people where there's market demand. And so for me there was a bit of a shift where uh uh when I realized that I could craft my business, my work around only the part that I'm best at and that can be a narrow ass slice. Like that's actually really really freeing. And so I would encourage folks to think about what is the thing that you are, you know, extremely good at that people find super valuable, the part that you

love doing most. if you could, you know, not do all the other stuff you don't want to do. Um, and how can you think about doubling down on that? That's such an important point and that can the the claw tip you shared of how to say no well is such a important ingredient into that because so many things come at you and are interesting and enticing that it's hard to decline that you realize why the hell am I doing this? I can actually control where I spend time and why did I say yes to this?

I actually um credit you with helping me come to this realization. Um I mentioned you on a podcast the other day um about this because do you remember when Maven was uh launching an important feature I think it was like our marketplace or something and I had asked you if you wanted to go on Clubhouse uh to be part of I don't remember that but I'm sure I said no. Okay. Yeah. You said no. You said no. And and I was like, wow, you know, out of curiosity, what's the thought behind it? And you said,

I'm going to bastardize this, but but you know, you can correct me, but you essentially said, I don't really like doing live um public speaking type things. And I've been fortunate enough to to build a career where um I can write, you know, I do my podcast and kind of work only on the part that I love doing. Um and so I'm I'm okay saying no to these other, you know, really interesting opportunities. And I remember at that time thinking it was so groundbreaking that like you could say no to something that was legitimately a

cool opportunity um and and be really confident about it because it wasn't your core competency. It wasn't like the thing you are best at. And I've really kept that in mind when opportunities come my way of like am I excited about this? Is this what I'm really good at? Can I shine in this setting? Um because when you are solo like you get to choose the settings that you want to be in. That's such a cool story. I don't exactly remember that, but I'm zero% surprised that what I said and I what I what the

way I put it now when I folks invited me this stuff like this is just I just find the ROI on my time is so not worth doing a talk, doing a a fireside thing, doing another podcast. It's just just like if I can spend more time on this newsletter and the podcast, the leverage is so much higher than just doing a talk because that takes so much time. And so, so I just have this like template now that basically says what I sent you that is that helps. And that's but it's tough. It's so

hard to say no. It's like sometimes these opportunities are so interesting and the person is like, "Wait, what?" Cuz I don't think the people asking you for stuff know that I'm getting like 10 of them a day and they're like, "Oh, he said no to my talk. He doesn't want to be on my podcast. What a jerk." That's what I think. I don't know if that's a big thing, but anyway. Okay, that's great. Yes. Uh, and I think I just I just had a post about reaching a million subscribers a newsletter and actually had this

uh image of the eeky guy concept which is exactly what you just described which is you want to try to find the thing that you love doing that people value and that uh you can make money doing that's like the dream and that's exactly what you have done as well. So thank you for being here Wes. This I like I actually think we delivered on what I thought we would. I think this is going to be one of the most high highest leverage conversations we've had. So, two final questions. Where can folks find your course?

I know you also do executive coaching. So, where can folks learn more? And final question is just how can folks be useful to you, Wes? You can find out more at wesko.com. I linked to my course to my coaching from my main page. Uh I also post on LinkedIn as well, so you can follow me there. And uh I'm always looking to meet fellow operators who nerd out about communication. So if you put any of these principles into practice, uh I would love to hear about it. Awesome. And then we'll do that in the comments.

They can DM you. I don't know what's the best way to reach you on the website or Twitter. Yeah. Um bunch of platforms, website, all the places. Cool. LinkedIn, DM me. Yeah. There we go. There we go. Wes, thank you so much for being here. Yeah. Thank you so much, Lenny. Bye. This is fun. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners

find the podcast. You can find all past episodes or learn more about the show at lennispodcast.com. See you in the next episode.