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Wes Kao is an entrepreneur, coach, and advisor. She co-founded the live learning platform Maven, backed by First Round and a16z. Before Maven, Wes co-created the altMBA with best-selling author Seth Godin. Today, Wes teaches a popular course on executive communication and influence. Through her course and one-on-one coaching, she’s helped thousands of operators, founders, and product leaders master the art of influence through clear, compelling communication. Known for her surgical writing style and no-BS frameworks, Wes returns to the pod to deliver a tactical master class on becoming a sharper, more persuasive communicator—at work, in meetings, and across your career. What you’ll learn: 1. The #1 communication mistake leaders make—and Wes’s proven fix to instantly gain buy-in 2. Wes’s MOO (Most Obvious Objection) framework to consistently anticipate and overcome pushback in meetings 3. How to master concise communication—including Wes’s tactical approach for brevity without losing meaning 4. The art of executive presence: actionable strategies for conveying confidence and clarity, even under pressure 5. The “sales, then logistics” framework—and why your ideas keep getting ignored without it 6. The power of “signposting”—and why executives skim your docs without it 7. Exactly how to give feedback that works—Wes’s “strategy, not self-expression” principle to drive behavior change without friction 8. Practical ways to instantly improve your writing, emails, and Slack messages—simple techniques Wes teaches executives 9. Managing up like a pro: Wes’s clear, practical advice on earning trust, building credibility, and aligning with senior leaders 10. Career accelerators: specific habits and tactics from Wes for growing your influence, advancing your career, and standing out 11. Real-world communication examples—Wes breaks down real scenarios she’s solved, providing step-by-step solutions you can copy today Transcript: https://www.lennysnewsletter.com/p/become-a-better-communicator-specific Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny • Vanta—Automate compliance. Simplify security: https://vanta.com/lenny • Coda—The all-in-one collaborative workspace: https://coda.io/lenny Where to find Wes Kao: • LinkedIn: https://www.linkedin.com/in/weskao/ • Website: https://www.weskao.com/ • Maven course: https://maven.com/wes-kao/executive-communication-influence Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Introduction to Wes Kao (05:34) Working with Wes (06:58) The importance of communication (10:44) Sales before logistics (18:20) Being concise (24:31) Books to help you become a better writer (27:30) Signposting and formatting (32:05) How to develop and practice your communication skills (40:41) Slack communication (42:23) Confidence in communication (50:17) The MOO framework (54:00) Staying calm in high-stakes conversations (57:36) Which tactic to start with (58:53) Effective tactics for managing up (01:04:53) Giving constructive feedback: strategy, not self-expression (01:09:39) Delegating effectively while maintaining high standards (01:16:36) The swipe file: collecting inspiration for better communication (01:19:59) Leveraging AI for better communication (01:22:01) Lightning round Referenced: • Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennysnewsletter.com/p/persuasive-communication-wes-kao • Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto • Communication is the job: https://boz.com/articles/communication-is-the-job • Maven: https://maven.com/ • Sales, not logistics: https://newsletter.weskao.com/p/sales-not-logistics • How to be more concise: https://newsletter.weskao.com/p/how-to-be-concise • Signposting: How to reduce cognitive load for your reader: https://newsletter.weskao.com/p/sign-posting-how-to-reduce-cognitive • Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product): https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev • Tone and words: Use accurate language: https://newsletter.weskao.com/p/tone-and-words-use-accurate-language • Quote by Joan Didion: https://www.goodreads.com/quotes/264509-i-don-t-know-what-i-think-until-i-write-it ...References continued at: https://www.lennysnewsletter.com/p/become-a-better-communicator-specific Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.
Wes Kao discusses the common communication mistake where operators fail to convey their messages clearly, leading to confusion and skepticism. She emphasizes the importance of self-reflection in communication, urging individuals to consider how they might improve their clarity and anticipation of questions to foster better understanding.
"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 gett..."
Wes introduces her MOO (Most Obvious Objection) framework, which helps communicators anticipate and address potential objections before they arise. She highlights the importance of taking a moment to think about likely objections, which can significantly enhance the effectiveness of communication in meetings.
"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 yo..."
In this segment, Wes Kao reflects on the critical role of communication in leadership and influence. She shares insights on how effective communication can lead to better outcomes and emphasizes that improving communication skills is essential for anyone looking to advance in their career.
"[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 ..."
Wes discusses the necessity of treating every communication opportunity as important, not just those with executives. She advocates for consistent practice in communication to build skills and confidence, stressing that every interaction is a chance to improve.
"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 brin..."
Wes categorizes communication into verbal and written forms, explaining that both are essential for effective executive communication. She emphasizes that communication should be viewed as a means to achieve specific outcomes, rather than an end in itself.
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Wes introduces the concept of 'Sales Before Logistics,' highlighting the common mistake of diving into details before securing buy-in from the audience. She explains the importance of framing communication to first engage and excite the audience before discussing logistics.
"even the most complex use cases. If you're currently looking to build role-based access control or other enterprise features like single signon skim or user management, you should consider work OS. It..."
Wes provides a real-world example of how a head of operations failed to engage her executive team by leading with logistics instead of the benefits of sharing team wins. She illustrates how starting with a compelling reason can motivate the audience to participate.
"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 questi..."
Wes emphasizes that even when the audience is generally on board, it's crucial to remind them of the context and importance of the discussion. She suggests that a brief reminder of why the topic matters can help maintain engagement and clarity.
"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 ..."
Wes Kao emphasizes the importance of starting conversations with a brief reminder of the topic's significance. She suggests that even when people have previously agreed to something, it's crucial to re-establish context to avoid confusion. This segment outlines how a concise introduction can set the stage for productive discussions, ensuring everyone is aligned and focused on the main points.
"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..."
In this segment, Wes Kao introduces the 'yes-yes-yes next' mindset, explaining how leaders often think in terms of quick affirmations during presentations. She shares her experiences with executives who make decisions early in a presentation, highlighting the importance of recognizing when to move on after gaining agreement. This approach helps maintain momentum and keeps discussions efficient.
"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 thi..."
Wes discusses the common misconception that being concise means being brief. She explains that true conciseness is about the economy of words and the density of insights shared. This segment emphasizes the need for clarity in communication, particularly in meetings, and the importance of preparation to ensure messages are delivered effectively and succinctly.
"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 th..."
Wes Kao stresses the significance of preparation in achieving concise communication. She advises taking a moment before meetings to clarify objectives and key points to share. This segment highlights how even a brief period of preparation can enhance focus and clarity, leading to more effective conversations and presentations.
"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 ..."
In this segment, Wes discusses the importance of clarity in written communication. She explains how a poorly written memo can create confusion and lead to unnecessary back-and-forth among team members. By taking the time to review and refine messages, communicators can significantly improve understanding and efficiency within their teams.
"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 sayin..."
Wes introduces the concept of signposting, which involves using specific words and phrases to guide readers through written content. This technique helps structure communication and signals important points to pay attention to. The segment explains how signposting can enhance both written and verbal communication, making it easier for audiences to follow along and stay engaged.
"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..."
Wes shares practical advice on how to improve communication skills through practice and feedback. She suggests monitoring the time it takes to achieve desired responses from recipients and adjusting tactics based on effectiveness. This segment emphasizes the importance of a hypothesis-driven approach to communication, encouraging listeners to experiment with different strategies to enhance clarity and engagement.
"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 i..."
Wes Kao discusses the importance of building effective communication habits gradually. She advises against overwhelming oneself with multiple tactics at once and instead recommends focusing on one skill at a time. This approach allows for deeper understanding and mastery, ultimately leading to more impactful communication. Wes highlights the significance of patience and persistence in developing these skills.
"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 ge..."
In this segment, Wes reflects on how small improvements in communication can lead to significant career advancements. She shares personal experiences of how focusing on clarity and conciseness in communication has accelerated her professional growth. Wes emphasizes that every piece of communication contributes to overall work quality, encouraging listeners to invest time in refining their writing and speaking skills.
"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 t..."
Wes Kao concludes by discussing the long-term benefits of investing time in crafting clear and effective communication. She explains that while it may take extra time upfront to improve messages, the reduction in back-and-forth clarifications and misunderstandings ultimately saves time and enhances productivity. This segment reinforces the idea that thoughtful communication is an investment in professional relationships and outcomes.
"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 do..."
Wes Kao shares her personal journey of improving communication skills and how it has positively impacted the reception of her ideas. She emphasizes the excitement of seeing others understand her thoughts, which motivates her to continue refining her communication techniques. This segment highlights the importance of momentum in effective communication and the small, manageable changes that can lead to significant improvements.
"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 under..."
In this segment, Wes discusses the balance of confidence in communication. She explains the pitfalls of being either overconfident or underconfident when presenting ideas. Wes advocates for speaking accurately about one's level of conviction and the evidence supporting claims, stressing the importance of framing recommendations appropriately to avoid miscommunication and ensure clarity.
"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 findi..."
Wes introduces the concept of the 'single-minded martyr'—a person who pushes their agenda without considering the broader context. She shares a client’s experience in advocating for a project without aligning it with company priorities. This segment emphasizes the importance of understanding organizational goals and adapting proposals to fit within those frameworks for better acceptance and collaboration.
"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 t..."
Wes highlights the significance of contextualizing proposals within the company's current priorities. She explains how junior professionals often focus solely on getting approval for their ideas, while senior professionals recognize the need to align their suggestions with organizational goals. This understanding fosters a more strategic approach to communication and advocacy.
"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 princip..."
In this segment, Wes discusses the importance of probing deeper into questions during high-stakes conversations. She advises on how to handle inquiries by validating the underlying concerns and responding thoughtfully, rather than feeling pressured to provide immediate answers. This approach enhances communication effectiveness and builds trust with colleagues.
"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. I..."
Wes elaborates on the technique of reflecting back questions to clarify understanding and buy time to formulate a response. This method not only helps in gathering more information but also reassures the questioner that their concerns are being taken seriously. It’s a practical strategy for maintaining composure and facilitating productive dialogue.
"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..."
Wes emphasizes the necessity of connecting proposals to the goals of the audience. She explains that understanding the priorities of decision-makers can significantly enhance the chances of getting buy-in for ideas. This segment reinforces the idea that effective communication is not just about presenting ideas but also about aligning them with the needs and objectives of others.
"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 i..."
Wes addresses common frustrations professionals face when their ideas are overlooked. She reassures that it often isn't personal but rather a matter of timing and alignment with current priorities. This segment encourages listeners to remain patient and strategic in their communication efforts, reinforcing the importance of timing in advocacy.
"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 als..."
Wes introduces the MOO (Most Obvious Objection) framework, which helps anticipate potential objections during presentations. She explains how taking a moment to consider likely counterarguments can prepare communicators to address concerns proactively. This segment highlights the value of preparation in enhancing communication effectiveness.
"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 i..."
Wes shares her daily practice of using the MOO framework to enhance her communication. By anticipating objections, she can frame her arguments more effectively and engage her audience better. This segment illustrates how proactive thinking can lead to clearer and more persuasive communication.
"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 ..."
Wes discusses the interconnectedness of thinking and communication, emphasizing that articulating thoughts can clarify ideas. She shares a quote by Joan Didion that encapsulates this concept, reinforcing the idea that writing and speaking help shape understanding and decision-making.
"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..."
Wes provides strategies for maintaining composure during high-pressure conversations. She advises against feeling the need to have all the answers and encourages asking clarifying questions to keep the dialogue flowing. This segment offers practical tips for navigating challenging discussions with confidence.
"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 co..."
Wes Kao discusses the importance of understanding the underlying concerns behind questions in conversations. She emphasizes the need to validate these concerns and respond appropriately, which helps maintain the flow of dialogue and addresses deeper issues that may not be immediately apparent.
"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 dir..."
In this segment, Wes shares a tactic for effective communication: reflecting back the question posed by the other party. This technique not only buys time to think but also reassures the questioner that their concerns are being heard, fostering a more productive conversation.
"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 ..."
Wes outlines several communication tactics and suggests starting with the Most Obvious Objection (MOO) framework. She explains how framing conversations effectively can enhance clarity and engagement, making it easier to address potential objections upfront.
"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 yo..."
Wes Kao emphasizes the critical skill of managing up, explaining that it is essential at all career levels. She shares insights on how effective management of one's superiors can lead to better alignment and clarity in ambiguous situations, ultimately enhancing career growth.
"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 ..."
In this segment, Wes discusses the value of proactively sharing your perspective with your manager. She explains how presenting your ideas and recommendations can reduce cognitive load on your manager and demonstrate strategic thinking, which is crucial for career advancement.
"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..."
Wes highlights the importance of being vocal about observations and insights in the workplace. She encourages individuals to share their findings with managers to enhance visibility and foster a culture of open communication, which can lead to better decision-making.
"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 contrib..."
Wes introduces her framework for giving constructive feedback, focusing on strategy rather than self-expression. She advises trimming unnecessary details to motivate behavior change and emphasizes the importance of clarity in feedback conversations.
"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..."
In this segment, Wes discusses the significance of focusing on desired outcomes when giving feedback. She advises against venting frustrations during feedback sessions and instead encourages a clear, goal-oriented approach to foster positive behavior change.
"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 opportunitie..."
Wes emphasizes the need to manage emotions before entering feedback conversations. She suggests venting frustrations beforehand to maintain a clear and positive emotional tone, which is crucial for effective communication and achieving desired outcomes.
"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 ..."
Wes shares her CEDAF framework for effective delegation while maintaining high standards. She explains the importance of ensuring comprehension, excitement, and risk management when delegating tasks to ensure successful outcomes.
"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 ..."
Wes Kao shares a powerful quote about human potential, emphasizing that everyone is capable of achieving more than they believe. She discusses effective tactics to help individuals get closer to their potential, particularly in the context of communication and leadership.
"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 ..."
Wes introduces her CEDAF framework for effective delegation while maintaining high standards. Each letter stands for a key principle: Comprehension, Excitement, Derisk, Align, and Feedback. This structured approach helps leaders delegate tasks clearly and confidently, ensuring alignment and minimizing risks.
"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..."
Wes emphasizes the importance of investing time upfront in communication and delegation to save time later. She discusses how this principle applies to working with AI tools, suggesting that clear communication and structured delegation can enhance productivity and effectiveness.
"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."..."
Wes explores how her delegation framework can be applied to working with AI agents. She highlights the importance of clear communication and alignment when delegating tasks to AI, ensuring that the output meets expectations and reduces misunderstandings.
"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..."
Wes explains the concept of a swipe file, a collection of inspirational examples and effective communication strategies. She encourages listeners to maintain a swipe file to enhance their communication skills by analyzing and borrowing effective phrases and strategies from others.
"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 righ..."
Wes discusses how she utilizes AI, specifically Claude, as a thought partner in her communication process. She shares her approach to drafting responses and refining her communication with the help of AI, highlighting the collaborative potential of AI tools in enhancing clarity and effectiveness.
"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 ..."
In the lightning round, Wes recommends two impactful books: 'High Output Management' by Andy Grove and 'Your Brain at Work' by Dr. David Rock. She discusses how these books can help individuals understand their cognitive processes and improve their communication and management skills.
"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, wh..."
In a light-hearted moment, Wes talks about her recent experience with an electric toothbrush, describing it as life-changing. She humorously discusses the marketing strategies behind dental products and the importance of choosing tools that enhance daily routines.
"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 lin..."
Wes shares her life motto: 'Everything takes longer than you think.' She emphasizes the importance of building buffers into your schedule to reduce stress and improve productivity, especially when launching new projects or skills.
"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 h..."
Wes reflects on her transition from being an in-house operator to a solo entrepreneur. She discusses the freedom of shaping her work around her strengths and the importance of saying no to opportunities that don't align with her core competencies.
"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 per..."
Wes recounts a pivotal moment when she learned the value of saying no to opportunities that don't fit her strengths. She highlights the importance of being selective about engagements to maximize impact and maintain focus on what truly matters.
"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...."
Wes discusses the concept of finding the intersection of what you love, what you're good at, and what people value. She encourages listeners to identify their unique strengths and leverage them to create fulfilling careers.
"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 publ..."
Wes shares how listeners can connect with her through her website and LinkedIn. She expresses her eagerness to engage with fellow operators interested in communication and invites them to share their experiences with the principles discussed.
"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. ..."