Summary

This in-depth guide helps entrepreneurs master the art of communication using proven frameworks from Wes Kao. You’ll learn how to get buy-in with the “Sales, Then Logistics” method, handle objections using the MOO framework, delegate effectively with CEDAF, and write sharper, more persuasive messages. The guide includes real-world scripts, actionable tactics for meetings, feedback, Slack, and email, plus career-boosting communication habits and AI-assisted tips. Whether you’re managing up, pitching, or leading a team, this guide will help you communicate with clarity, influence, and confidence.

Become a Better Communicator: A Comprehensive Guide for Entrepreneurs

Communication is one of the highest-leverage skills in any entrepreneur’s toolkit. As Wes Kao (coach and co-founder of Maven) emphasizes, if you’re not getting the reaction you want from your team or stakeholders, resist the urge to blame them for “not getting it.” Instead, take ownership of explaining your idea more clearly and compellingly . This guide is a hybrid playbook and in-depth article, drawing on Wes Kao’s proven frameworks from her interview on Lenny’s Podcast, to help you sharpen your communication.

We’ll cover practical frameworks (MOO, “Sales-Then-Logistics,” CEDAF), tactics for concise and impactful messaging (signposting, managing up, executive presence, giving feedback), and real-world examples of better vs. worse communication. You’ll also find step-by-step instructions, templates, and tips — including how to leverage AI tools like ChatGPT — to refine your emails, Slack messages, and presentations. The tone is direct and actionable, geared toward startup founders, solopreneurs, and team leaders who need to get buy-in, align teams, and increase their influence through better communication. Let’s dive in!

“Sales, Then Logistics”: Sell the Idea Before You Share the Details

One of the biggest communication mistakes is diving into details (“logistics”) before your audience is sold on the idea. Most work communications involve both aspects: you need buy-in (sales) and you need to share how-to details (logistics) . The key is to sequence them correctly. As Wes Kao notes, many people over-focus on the “how” too early, assuming others already care – when in fact, “you often have less buy-in than you think.” No one will care about the step-by-step plan (logistics) if they aren’t yet convinced why it matters .

Sales vs. Logistics: “The goal of a sales note is to get your recipient excited to take action,” whereas “the goal of a logistics note is to share the ‘how’” . In other words, sales messaging answers “Why should we do this?” and logistics messaging answers “How do we do this?”. Both are important, but timing is everything.
Order of operations: Always sell them on the why before diving into the how. If you’re 100% sure your audience is already bought in, you can jump straight to logistics. But be cautious – it’s easy to overestimate their buy-in . Even busy executives who seem impatient need 30-60 seconds of context for why something matters now . Once a person is convinced, they will find your how-to details far more relevant .
Consequence of skipping “sales”: If you treat what should be a sales message like a logistics dump, you’ll wonder why people aren’t taking action despite all your detailed instructions. You might respond by adding even more details – solving the wrong problem . The real fix is to make them care first, then present the plan.

Example – Announcement (Worse vs. Better): An engineering lead needs company-wide input for a weekly all-hands update. Here’s how they might communicate it:

Worse (Logistics-first): “Morning! I’d like to get more input from across the team on wins to include in the all-hands meeting each week… ➡️ If you have a win to share, can you please add to this deck and tag me by Sunday night?…” (The focus is on what the sender wants and the process details, making it feel like a favor being asked.) This message, as Wes Kao says, “feels like you’re adding yet another process to everyone’s plate,” and the me-focused tone (“I’d like…”) underplays what the recipient gains .
Better (Sales-first): “Morning! At our all-hands each week, we’re going to start highlighting wins from across the company. Participation isn’t mandatory, but this is your team’s chance to get recognized for their hard work. The goals are two-fold: (1) help everyone get a high-level view of wins beyond their own org, and (2) boost morale by celebrating small wins, so your team feels motivated as we push toward big milestones. ➡️ To have your team’s win included, just add it to [the deck] and tag me by Sunday 8pm. I’m excited to showcase the great work you and your teams are doing!” (This version frames the request as a benefit to the reader, highlighting visibility and morale, and only then gives the how-to. The tone is confident and you-focused.) The logistics (where to add wins and by when) appear after explaining why it’s worthwhile. The result is a message that’s “more confident, persuasive, and powerful,” where recipients feel that by contributing, they benefit (their team gets recognition), not that they’re doing the sender a favor .

Tips to apply “Sales-Then-Logistics”:

Lead with the “Why”: Start your email or pitch by answering: Why should your audience care? How will your idea/project help them or the organization? Use a confident, you-oriented tone. Save the step-by-step or technical details for later in the message (or an attachment).
Make it about them: Scan your draft for a high ratio of “you/your” vs. “I/we”. A sales-first message focuses on the reader’s gain or interest. In the example, saying “this is your chance to shine a light on your team’s work” flips the dynamic – it signals I’m helping you, rather than asking you to help me .
Assume buy-in, show enthusiasm: Write as if you expect people will be on board. For instance, avoid weak phrases like “If you want to participate…” and instead assume they do (fear of missing out can motivate). Also, express excitement for the positive outcome (“I’m excited to highlight your team’s wins” sets an enthusiastic tone). Enthusiasm is contagious when it’s framed as helping the audience, not just excitement for your own sake .
Then get to “How”: After you’ve sold them on the idea, provide the necessary logistics: what actions they need to take, deadlines, resources, etc. Keep this part clear and concise, since by now the reader understands its relevance .

By selling first and sequencing information properly, you’ll notice your ideas gaining much more traction. Readers or listeners will lean in, already nodding at the why, by the time you spell out the what/how. As Wes Kao puts it, when done right, “recipients realize you are doing this in service of them,” and they become eager to comply .

Anticipate Pushback with the MOO Framework (Most Obvious Objection)

Even the best idea can get derailed by an objection or concern you didn’t foresee. That’s where MOO – Most Obvious Objection – comes in. Wes Kao’s MOO framework is a simple habit: Before you present an idea or send a proposal, take 2 minutes to think about the most obvious objections or questions your audience might have, and address them proactively.

“MOO stands for Most Obvious Objection.”

But if you pause to consider what the obvious objections might be, you’ll usually anticipate the key concerns.

cover the most likely ones

How to use MOO: Put yourself in your audience’s shoes and ask, “What’s the first question or doubt I would have about this idea, if I were them?” The “obvious objection” is usually something about feasibility, cost, timing, or alignment. Once identified, weave the answer into your initial communication. For example, if you’re pitching a new product feature and you suspect the most obvious objection will be “But will this distract from our roadmap timeline?”, you might preemptively say: “This proposal won’t delay our core roadmap – we’ve scoped it to fit in one sprint by reassigning X, so it stays on track with our timeline.” By doing this, you disarm the objection before it’s voiced.
Benefits of anticipating objections: First, it instills confidence – your audience sees you’ve done due diligence and thought things through. Second, it keeps momentum: instead of getting stuck on a concern, the discussion can move to how to execute. Third, it calms your nerves; you’re less likely to be thrown off by tough questions, since you’ve already considered them. It’s a tactic to communicate with poise under pressure, contributing to your executive presence (more on that later).
Make it a habit: This need not take long. As Wes suggests, even a couple of minutes of anticipation can surface the biggies . You can jot down 2-3 objections and ensure your presentation or email addresses them. Over time, you’ll start doing this mentally on the fly.

Real-world scenario: A solopreneur preparing a proposal for an investor might identify the obvious objection: “Is there really market demand for this niche?” Using MOO, she decides to open her pitch by highlighting traction and customer testimonials (preempting the demand question). In a team meeting context, a product manager proposing a process change might anticipate the objection “This will add more work for engineers” and proactively clarify how it actually saves engineering time in the long run. These preemptive answers prevent the “Gotcha!” moment and convey credibility.

Bottom line: Don’t let predictable questions catch you off guard. Incorporate the MOO framework in your prep: identify the likely pushback, and address it upfront. It’s a small step that consistently elevates the clarity and persuasive power of your communication .

Mastering Concise Communication (Say More with Less)

In leadership, how you speak often matters as much as what you say. Being concise is a hallmark of great communicators – it respects people’s time and makes your messages punchier. But “concise” does not simply mean short. It means dense with insight. As Wes Kao explains, “Being concise is not about absolute word count. It’s about economy of words and density of the insight.” Often, the bottleneck to brevity is unclear thinking . If you haven’t crystallized your own thoughts, it’s easy to ramble. Here’s how to achieve clarity and brevity together:

Framework for Conciseness: Before speaking or writing, do a mini prep using the following tactics (drawn from Wes Kao’s techniques for concise communication):

Know Your Main Point: “Figure out your main point” ahead of time . This involves quickly organizing your thoughts: What is the core message or ask? If you can’t answer that in one sentence internally, pause and sort out your thinking. Even a few seconds of reflection (e.g. jotting a keyword) can prevent a meandering explanation. Ask yourself: What do I need from my audience? What do I want them to remember? Focus on that.
Lead with a Summary (BLUF): Use the BLUF technique – Bottom Line Up Front. Try to state your high-level point in the first 2-3 sentences of an email or the first 30 seconds of speaking. For instance, instead of walking someone through a chronological story (which buries the point), start with: “__Here’s the headline: We should expand our pilot to 50 more users next month. I’ll explain why and how next.” This frames the conversation and “buys you time” with your audience because they now know where you’re going . Listeners can relax and follow the details more easily once the destination is clear.
Avoid Chronological Dumping: Don’t recount every step you took or the whole backstory in the order it happened. That’s a common pitfall when explaining complex situations. Instead, state the conclusion or key issue first, then only the relevant supporting context. As Wes advises, “When you say your punchline upfront, you instantly seem more competent, strategic, and organized.” Skip the play-by-play unless asked . For example, rather than: “So first I tried A, then B happened, then I talked to X, which led me to think about Y…”, say: “The main issue we need to address is X. Here’s what happened and how I reached this conclusion…”
Keep a “Conciseness Meter” Running: Develop an internal editor that monitors you in real-time. While speaking, silently ask yourself: “Is this the shortest way to explain this? Have I drifted off-point? Can I omit this detail?” . This meta-awareness takes practice but can significantly tighten your delivery. It’s like having a little coach in your head reminding you to land the plane. If you notice you’re on a tangent, gracefully steer back: “Anyway, the key point is…”

• Pause and Check In: Especially in verbal communications (meetings, calls), pause sooner than you naturally would. Concise communicators don’t monologue nonstop. They pause and allow the other person to engage. Watch for cues – if eyes are glazing over or people look lost, don’t ignore it. Invite interaction: “I’ll pause there – does that make sense?” or “Any questions so far?” This not only shows respect, it also prevents you from over-explaining. Wes notes that people who speak in endless run-on sentences tend to come across as more junior; seasoned leaders take breaths and create rhythm .

Don’t Omit Too Much: Conciseness is a balance. Yes, you want brevity, but don’t omit critical context or caveats that your audience needs. If you cut so much that others have to ask basic questions to understand, you’ve gone too far. “There is some information you should volunteer without being asked… Don’t force others to do the heavy lifting to draw basic information out of you piece by piece.” In practice, this means including essential facts like dates, names, definitions, or a brief background if it’s needed to grasp your point. Being clear is just as important as being concise . Aim for efficient completeness: cover the fundamentals, then stop.
Use “Main Point > Context” in Writing: For written updates or emails that are lengthy, apply a structure where you put the main point or recommendation at the top, and detailed explanation below . For example, start an email with: “__Proposal: Move launch to Q2 to align with new customer timelines. Background: [Then provide reasons, data, etc.].” This way, a skim-reader sees the conclusion immediately and can choose how much of the supportive detail to read. It’s giving the reader control: they can stop after the summary or dive into the context as needed . This tactic, a variant of BLUF, prevents burying the lede.
Offer to Elaborate (Instead of Oversharing): To cap a concise explanation, signal that you have more info if needed. Rather than “Let me know what you want to know” (which puts the burden on them), be specific: “I have additional analysis on A/B testing results and some risk mitigation plans if you’re interested.” That way, you hint at areas they might be curious about . For instance: “I’m keeping this overview brief, but I can share more about the alternative options we considered or the data we gathered, if that would be helpful.” This shows you have depth without unloading it all upfront. It reassures your audience that you’re prepared, and it invites them to direct the conversation to what they care about.

By implementing these tactics, you’ll find your communication becomes tighter and more impactful. Remember, conciseness is about conveying meaning as efficiently as possible. You want to create understanding quickly, which means being clear and compelling as well as succinct . It’s a skill that improves with practice: challenge yourself to explain your idea in half the words, then maybe in half again. As you hone this, you’ll notice people pay closer attention to your words – because every sentence counts.

Guide Your Audience with Signposting

Have you ever read a long memo or listened to a complex explanation and felt lost about where it was headed? Signposting is the remedy. Signposting means using explicit words and phrases to signal the structure of your message and the relationships between ideas. It reduces the mental work for your audience by providing guideposts (like signs on a road) about what’s coming next or why something is being said . Busy readers and listeners love signposting because it lets them navigate your content effortlessly.

According to Wes Kao, using signposting words is one of the most “thoughtful, selfless things you can do” in communication, since “your recipient shouldn’t have to decipher or clarify what you meant” . Clear writing (and speaking) that’s well-structured keeps people engaged, especially when ideas are complex.

How to Signpost Effectively:

Use Transitional Keywords: Simple words like “for example,” “because,” “first, second, third,” “however,” “as a next step,” etc., act as signals. They might seem obvious, but they drastically improve readability. For instance, starting a sentence with “For example,” tells the reader a concrete instance is coming – if they already get it, they can skip ahead; if not, it helps illustrate the point . Words like “because” explicitly tie a statement to its reason, which “makes you more persuasive” just by the nature of cause-and-effect logic . Enumerating points with “first, second, finally” imposes order and hierarchy in text without needing bullet points . These cues “pop when your reader is skimming,” allowing them to see the logical structure even if they’re rushing . In short, signposts are like road signs: turn here, explanation ahead, example follows, important point coming up.

Some Favorite Signposts (and what they signal):
- For example… – an illustration or case is next .
- Because… – a reasoning or cause will follow .
- First, Second, Third… – a sequence of points or steps .
- Up until now… / Going forward… – contrast between past and future, great for showing a change or plan .
- For context… – background info incoming (readers can skip if they’re already aware) .
- At this point… – bringing the narrative to the present moment or current status .
- However / On the other hand… – a contrast or exception is coming.
- Therefore / So… – a conclusion or result is next, shows logical consequence
- This means… – an interpretation or implication of the previous info .
- To be clear… – a clarification or emphasis on a key point (often used to preempt misunderstanding or objections) .
- As a next step… – an upcoming action or request .

These phrases act as connective tissue between your ideas . They prevent the reader from getting lost or guessing how one thought relates to another. In Wes’s words, they “serve as connective tissue between ideas,” ensuring your logic is transparent .

Signpost in Speaking, Too: In written form, readers can glance back at headings or bullet points, but in live conversation or presentations, listeners only have one chance to catch your drift. That’s why it’s important to verbally signpost. Frame the journey at the start: e.g. “I’ll first give a quick overview of the problem, then share the top solution options, and finally recommend one.” This primes your audience to follow along easily . Throughout your talk, drop in signposts: “For context, last quarter we…”, “The most important thing to note here is…”, “As a result, …”. This way, even if someone’s attention dips for a moment, these phrases can pull them back on track. Remember, in verbal settings the audience can’t see the structure, so you have to narrate it to them .
When to signpost: The more complex or longer your message, the more you should signpost. If you’re writing a multi-paragraph email or a memo, try to include guiding phrases in each section. If you’re delivering a project update with multiple themes, explicitly outline the sections (“I have three updates: one on timeline, one on budget, and one on risks”). Signposting is especially helpful when executives are your audience – they often skim documents quickly. Using phrases like “in summary,” “the key takeaway,” “next steps” as labels helps busy readers find what they need (indeed, executives will skim your doc without signposting, and might miss your point ).
Emotional signposting: In writing, also consider words that convey tone – e.g., using “fortunately” or “important” to subtly flag good news vs. serious points. Wes calls this “emotional signposting.” For instance, if a status update has both positive and negative news, explicitly saying “On the bright side,… however, one challenge is…” helps the reader emotionally process the ups and downs. It prevents confusion like “Wait, is this good or bad?” by clearly labeling it .

In practice: Let’s say you’re writing to your team about a complex new strategy. Without signposts, it might read as a wall of text that leaves people wondering “Why am I reading this?” or “What’s the point here?” With good signposting, your intro might say, “Here’s the plan in a nutshell… Because of [market shift], we need to adjust. Here’s what this email covers: First, background on the market change. Second, proposed strategy changes. Finally, next steps for the team.” Already, the reader knows the roadmap. Then you’d use transitions like “For example,…”, “The result is…”, “To be clear,…”, “As a next step,…” throughout. The difference in clarity and reader-friendliness is dramatic.

Always remember: Clarity is kindness. Signposting is a simple way to be kind to your busy reader’s brain by reducing cognitive load . It keeps your audience engaged and ensures your message lands as intended, without them having to play detective on what you mean. Start incorporating a few of these phrases in your next email or presentation and notice how much smoother your communication will go.

Speak with Confidence and Executive Presence

“Executive presence” is often used to describe leaders who command a room and instill confidence through their communication. You might picture a CEO who speaks calmly, clearly, and decisively, even under pressure. The good news is, executive presence is a skill you can build by adopting certain communication habits – chiefly, speaking with clarity, composure, and accurate confidence.

Wes Kao highlights a critical aspect of confident communication: using language that accurately reflects your level of certainty. Projecting confidence isn’t about bluster; it’s about honesty and precision in how you express ideas . Here are strategies to strengthen your presence:

Match your conviction to your evidence: Avoid the two extremes – overstating (making bold claims without backup) and understating (over-caveating or downplaying your well-founded ideas). Both extremes erode trust. For example, saying “This will triple our revenue” (when it’s just a hypothesis) can mislead and later backfire, while saying “I’m not sure, but maybe we could try A or whatever you think” (when you actually have expertise) undermines your credibility. The goal is to be accurate: if you have data or strong experience indicating a decision, state it with confidence; if something is an educated guess, frame it as such. “Don’t make a hypothesis sound like a fact,” and conversely, don’t present a solid fact as just a hunch . Your team will trust you more because they learn that when you sound confident, it’s because you have reason to be, and when you’re unsure, you’re candid about it. This consistency builds your reputation for integrity in communication.
Use a steady, measured tone: In high-pressure meetings or presentations, consciously moderate your pace and tone. Speaking a mile a minute or in a shaky voice can signal nervousness or junior-level anxiety. Executives typically don’t rush; they pause to emphasize key points. Take breaths, vary your cadence, and allow moments of silence for listeners to absorb information. This not only makes you easier to follow, it also conveys that you’re comfortable in your skin and in command of the topic. If you feel adrenaline spikes, remember that speaking slower and clearer actually makes you sound more authoritative – it’s something you can control. (Pro tip: If you tend to talk fast, try inserting deliberate pauses at natural break points. It will feel odd to you but often sounds just right to the audience.)
Choose words that convey certainty (when warranted): Words matter. If you believe in something, say “I recommend” or “We should” instead of “maybe we could”. For instance, compare: “We might possibly consider targeting Segment X…” vs. “I recommend targeting Segment X because our data shows higher retention there.” The second is decisive and backed by reasoning (remember to include the because!). Conversely, if you’re in exploratory mode, it’s fine to use tentative language like “One idea to explore is…” This shows you’re not locked in. The key is that your tone aligns with reality – neither overconfident nor needlessly unsure . Wes Kao cites this balance as critical: “If you have strong evidence of the right approach, you can and should speak confidently. If you’re batting around options… be honest about this.” The result is that “when you speak accurately, your audience can trust what you’re saying.”
Maintain poise under fire: Founders and leaders are often challenged with tough questions (remember MOO!). Part of executive presence is staying composed and solution-oriented when you’re challenged. If someone raises an objection you didn’t anticipate, resist the urge to get defensive or flustered. Instead, acknowledge the point and bridge to how you’ll address it. For example: “That’s a great question – you’re right, the budget is a constraint. Here’s how we can manage that…” This shows you’re not thrown by issues; you tackle them head-on. Also, never fight to “win” a point at the cost of alienating your audience. Presence is also about emotional control. If a conversation gets heated, keep your tone calm and your words factual. It will set you apart as the grown-up in the room.
Body language and brevity for presence: While this guide focuses on verbal and written tactics, remember that nonverbal cues complement your words. Stand or sit upright, make eye contact, and use gestures naturally – these amplify your spoken confidence. Additionally, many points from earlier sections contribute to executive presence: for instance, conciseness (not rambling) and signposting (logical flow) both make you sound more in command. Someone who gets to the point and outlines a clear argument will inherently appear more leader-like than someone who meanders and confuses. In practice, if you implement the tactics on being concise and structured, you’re already halfway to projecting presence.
Show up prepared: Confidence often comes from preparation. Do your homework on both content and audience. That means knowing your material cold (so you aren’t rattled by questions) and understanding what the audience cares about (so you can speak to their priorities). This preparation enables you to speak in a more relaxed, conversational tone because you’re not desperately trying to recall facts or worrying you’ll be stumped. Paradoxically, the more you prepare, the more effortlessly confident you will seem, as if the ideas are just flowing.

In summary, executive presence isn’t about being the loudest voice or having a fancy title – it’s about communicating in a way that exudes clarity and credibility. By using accurate language, a balanced tone, and confident body language, you’ll earn the trust and attention of any room you enter. People will start to say, “Whenever you speak, it’s clear you know your stuff,” which is the essence of executive presence.

Managing Up: How to Align with Senior Leaders

Managing up means communicating with your boss (or higher-level stakeholders) in a way that makes their job easier while also advancing your goals. For entrepreneurs and startup leaders, this could mean managing up to board members, investors, or even early customers whose buy-in is crucial. Wes Kao’s core advice on managing up is to approach every interaction with your higher-ups as an opportunity to demonstrate your own strategic thinking and leadership, not just to get instructions.

A common mistake is constantly asking your manager or investor open-ended questions like “What should we do about X?” or dumping problems on their lap. While it’s fine to seek guidance, if you do it every time, you’re adding to their cognitive load rather than reducing it. Instead, come with a point of view and a recommendation. As Wes says, “Managing up is about sharing your point of view… Present your recommendation with supporting evidence,” rather than simply asking for a plan . This habit builds trust and shows that you’re taking ownership.

Tactics for Managing Up Effectively:

Frame the Context Briefly: When bringing an issue to a senior person, give them just enough context to understand the situation (remember, they might not be in the weeds like you are). Then state the decision or input needed. Example: “Our team is facing a delay in project X due to a vendor issue. I see two options: A (which costs more but stays on schedule) and B (cheaper but extends the timeline). I recommend A because it preserves our launch date, which is high priority. Does that align with your thinking?” Notice this approach does the heavy lifting for them – it summarizes the problem, offers a solution, and asks for confirmation or adjustments. Your manager doesn’t have to start from scratch; they just react to your analysis.

Provide Your POV with Rationale: Make it a rule: never just escalate a problem without a proposed solution (or at least a next step). Even if you’re genuinely unsure, come with a hypothesis: “I’m leaning toward option A because of [reason], but I’d like your take.” This shows you’ve thought it through. Back it up with data or examples when possible. By doing this consistently, you become someone who lightens your boss’s load. Wes Kao emphasizes that this not only helps your manager make a decision faster, it also demonstrates your strategic thinking . Over time, they’ll trust you with more autonomy.

Align with Their Goals: Managing up is also about showing that you get the bigger picture. Tie your recommendations to what’s important to your manager or the organization at large. For example, if you know your CEO cares most about user growth, and you’re proposing a change in the product, mention how your suggestion impacts user growth. “I recommend we prioritize Feature Y next quarter because it could accelerate user sign-ups by addressing feedback we’ve heard (25% of trial users mention this gap).” This shows you’re not just solving your team’s problems in a vacuum; you’re considering the company’s objectives. It earns you credibility as someone who “gets it.”

Don’t be a Bottleneck: If you always wait for explicit direction from above, you can become a bottleneck for your team. Instead, manage up by keeping your higher-ups informed proactively and asking for input only when needed. For instance, send a concise weekly update to your boss highlighting key progress, issues, and your plan for each issue. This keeps them in the loop and gives them the chance to course-correct if they see something off. If they consistently see you handling things, they’ll step in less. In essence, you’re managing their need to micromanage by proving you have things under control.

Clarify Expectations and Preferences: Part of managing up is learning how your senior stakeholders like to communicate. Do they prefer a high-level briefing or a deep dive? Do they love data dashboards or a quick narrative summary? Adapt your style to fit theirs. You can also straight up ask: “Would it help if I provide this report in a different format?” or “How would you like updates on this project?” This signals that you’re eager to make their life easier (which is managing up at its finest). If your boss knows you’re tailoring your communication to their style, they’ll be more receptive and appreciative.

Own the Follow-Through: When you get a decision or advice from your manager, run with it and report back results. For example, if they approve your recommendation to pursue option A, later update them: “We implemented A, and here are the outcomes.” This closes the loop and shows reliability. It also sets up the next cycle of trust – because you delivered well this time, next time they’ll trust your judgment even more. This habit of managing up through completion distinguishes leaders from mere task-doers.

In short, managing up is about being proactive, not passive. It’s demonstrating that you can “manage across and up, not just down.” When you do this well, you’ll find senior leaders give you more freedom and listen more intently to your suggestions. You cease to be just an executor and become a thought partner to those above you – which is exactly how entrepreneurial leaders rise fast. Remember Wes’s point: bringing your own well-considered recommendation whenever you seek guidance not only solves the issue quicker, it also showcases your maturity and strategic acumen .

Giving Feedback that Actually Drives Change (Strategy vs. Self-Expression)

Whether you’re leading a team of 2 or 200, at some point you’ll have to give constructive feedback – to an employee, a co-founder, or a contractor. How you deliver that feedback will determine whether the person gets defensive and nothing changes, or whether they feel motivated to improve. Wes Kao offers a powerful principle for feedback: “Strategy, not self-expression.” In essence, treat feedback not as a personal venting session but as a strategic conversation aimed at behavior change.

“A feedback conversation is actually a sales conversation. You are ‘selling’ and pitching the person on why and how to change.”

Here’s how to apply this mindset to give feedback that works:

Start with your Goal (Behavior Change): Before you initiate a feedback conversation, get clear on what you want to achieve. The goal isn’t to get something off your chest; it’s to help the person perform better for the future. For example, if a team member missed a deadline, your goal might be: “I want them to understand the impact, take ownership, and commit to better planning so it doesn’t happen again.” With that goal in mind, you can steer the conversation toward solutions. This framing turns feedback into a collaborative improvement discussion, not a punitive lecture.
Filter Out Emotional Venting: It’s natural to feel annoyed or disappointed when someone falls short. But don’t make the feedback about your feelings. As Wes bluntly advises, “Write out what you want to say. Then trim 90% of that because it’s probably self-expression, not strategy.” . That 90% is likely the part where you’d be saying “I’m frustrated that you…”, “It really upset me when…”, or rehashing every mistake. Those might be valid feelings, but expressing them fully is rarely useful to the other person. They can lead to defensiveness or shame, and distract from what needs to change. Trim down to the essential message that will help the person improve. One trick: after writing your feedback script, cross out any sentences that are just venting or repeating the same point. What remains should be focused on the future and the desired change.
Make it About Them (and the Future): Feedback should answer: “What’s in it for me to change?” for the recipient. Frame your points in terms of their growth or success, not how they inconvenienced you. For instance, instead of “Your communication is unclear and it’s frustrating,” say, “Being clearer in your emails will help you get responses faster and make the team more effective – it will elevate your impact.” Tie the feedback to something they care about – maybe their professional development, their reputation, or the team’s mission. This aligns with the idea of selling the change: people commit when they see how changing benefits them or the goals they value .
Be Specific and Objective: Describe the behavior and its impact, not the person’s character. E.g., “In the last two client calls, you interrupted the client while they were speaking, which risked making us seem less attentive to their needs.” This focuses on observable actions. Then pivot to the desired behavior: “…Going forward, I’d like you to try letting the client finish and then respond thoughtfully. I think it will showcase your listening skills and build more trust.” This way you’re not labeling them (“you’re rude to clients” – which feels like an attack); you’re pointing out a specific issue and giving a clear route to improvement. Being specific also helps the person know exactly what to do differently.
Keep it Positive and Solution-Oriented: Using a positive or constructive tone doesn’t mean sugarcoating serious issues; it means you’re framing the conversation around improvement, not punishment. For example, “I know you have it in you to deliver on time, because I’ve seen you do it. Let’s figure out how to make sure you’re set up for success on the next project.” This sort of language frames the problem as solvable and conveys that you’re on their side. Wes Kao notes we are “more motivated and committed when we’re excited to do something, not when we’re being punished.” . So even if the feedback is hard, position it as “I believe you can get even better and I want to help you get there,” rather than “You really let me down.”
Use the 10% Rule in Conversation: During the actual talk, continually apply the litmus test: “Is what I’m about to say strategy or self-expression?” . Stick to the crucial 10% that drives your point home. For instance, if you catch yourself piling on examples or repeating the complaint, pause and ask if it’s really needed or if you’re just venting. It might feel like you didn’t fully express your side, but remember, the conversation’s success is measured by their behavior change, not by how much you got off your chest.
Emphasize Benefits of Changing: Clearly outline how the new behavior or change will benefit them, the team, or the company. For example: “If you delegate more to your team (which I’m urging you to do), you’ll free yourself up for higher-level work and also empower your team members to grow. It’s a win-win for you and them.” This way, feedback isn’t just “stop doing X,” it’s “do Y because it will lead to positive outcome Z.” People are more receptive when they see an upside.
Invite their perspective: After sharing feedback, let it be a dialogue. Ask something like, “I’d love to hear your thoughts on this. How does it land with you?” or “What do you think about these observations?” . This gives them a chance to process and respond rather than silently stewing. Often, if you’ve kept the conversation respectful, the person might acknowledge the issue or at least share what’s challenging them. As Wes suggests, you can even ask: “What parts are resonating most with you?” . This does two things: it forces them to articulate their understanding (so you can confirm they got the message) and it creates a bit of commitment (if they say “I agree I need to manage my time better,” they’re more likely to follow through). It also surfaces any misinterpretation – maybe they thought you meant one thing, but you clarify another. Engaging them in the solution (e.g., “How do you think we can improve this going forward?”) increases buy-in.
Avoid Triggering Defensiveness: Some phrases can unintentionally provoke defensiveness. Steer clear of absolute language like “You always…” or attacks on personality (“You’re just careless”). Also, be mindful of your tone – a condescending or angry tone will sabotage your message. The moment the person feels attacked, their mind shifts to protecting ego and the constructive part is lost. If you sense defensiveness (body language or tone changes), you might say, “I’m not attacking you; I’m discussing the behavior. I know you want to do well and I want to help you succeed.” Bringing it back to a mutual positive intention can defuse tension.

By focusing on strategic feedback aimed at results, you transform these tough talks into something much more productive. Instead of dreading feedback conversations (or causing others to dread them), you’ll build a reputation for being fair, motivating, and effective in how you coach others. As a leader, that’s gold. People will listen to your feedback because they know it’s coming from a place of helping them win, not just telling them what they did wrong.

Finally, remember to follow up after feedback. If you see improvement, acknowledge it. Positive reinforcement when someone makes progress will lock in the new behavior and shows that you notice their efforts. If the behavior hasn’t changed, don’t wait too long to revisit it – sometimes one conversation isn’t magic and that’s okay. Reinforce the key points (again focusing on the future). Over time, by consistently using this strategy-over-venting approach, you’ll cultivate a team culture where feedback is seen as a helpful tuning process rather than an ordeal.

Delegating and Explaining: The CEDAF Framework

As an entrepreneur or team leader, effective delegation is essential – you can’t (and shouldn’t) do everything yourself. But delegation isn’t just about handing off tasks; it’s about setting your team up for success when they take on responsibility. Wes Kao observed that many managers “suck at explaining things, then complain that other people don’t understand” . Her solution is the CEDAF framework, which ensures you give enough context and clarity when delegating so that your delegatee can excel. CEDAF stands for Comprehension, Excitement, De-risk, Alignment, Feedback .

Think of CEDAF as a checklist whenever you’re assigning a project or task. Hitting these five points greatly increases the chances of a good outcome:

Comprehension – Ensure they understand what success looks like. Do they fully grasp the assignment and your expectations? Ask yourself: “Am I explaining this in a way that’s easy to understand?” . Share the necessary background: why it’s important, what the end goal is, and any non-obvious nuances. Don’t assume they know everything you know. For example, if you’re delegating a market research task to a new hire, outline the key questions you’re trying to answer and how this research will be used. Provide any relevant documents, examples, or standards (“Here’s a report from last year that we liked.”). Check their understanding by asking them to recap or by prompting, “What do you think will be your first steps?” – this can reveal if they’re on the right track or if clarification is needed. Essentially, set context so they aren’t guessing. As Wes notes, even a 5-10 minute upfront explanation can save countless hours of confusion later .
Excitement (Buy-in) – Get them motivated about the task. This is the “sales” part of delegation. Ask: “Am I getting the person excited about doing this?” . People perform best when they want to do something, not just because it’s assigned. So, sell the vision or the “why” behind the task. For instance, “This project will expose you to our key clients, which is a great opportunity,” or “Solving this will really unlock our team’s productivity – you’ll be the hero who figured it out.” Tailor the pitch to what motivates that individual: learning, visibility, impact, creativity, etc. Even if a task is mundane, you can frame it in terms of the bigger picture (e.g., data entry might be boring, but if it helps launch a feature that changes the business, emphasize that outcome). Showing enthusiasm yourself also helps; if you present the task as drudgery, they’ll feel that. Instead, transfer your enthusiasm for the end result to them. This builds buy-in so they tackle the task with energy, not just obligation .
De-risk – Address potential pitfalls upfront. Consider what could go wrong or what challenges they might encounter, and guide them on those. Ask: “Am I addressing obvious risks or areas where they might get stuck?” . For example, if a project has a tight deadline, warn them about that and perhaps suggest ways to speed up (like using an existing template). If the person is less experienced, point out tricky parts: “Be careful when you do X, because if Y isn’t handled, it could derail the process.” Also encourage them to think ahead: “What risks do you foresee, or is there any part you feel unsure about?” By discussing risks early, you save them from potential missteps and show that you’re a supportive safety net. It’s similar to telling a hiker about a slippery bridge on the trail ahead – better they know now than find out the hard way. This doesn’t mean hand-holding through every step; it means equipping them with foresight. They will appreciate that you prepared them rather than setting them up to stumble.
Align – Ensure mutual understanding and agreement. Delegation is a two-way street. After explaining, confirm that you and they are on the same page. Ask for their input: “Does this approach make sense to you?” “Do you have any ideas or suggestions before you start?” People are more committed when they’ve had a chance to contribute or at least agree on the plan. Alignment also means making sure they feel comfortable with the scope. Maybe they have too much on their plate already – if you delegate without aligning on priority, they might secretly deprioritize your task. So you could say, “I know you’re also working on Project Z; let’s talk about how to balance these, or if we need to adjust timelines.” By doing this, you’re respecting their workload and showing flexibility. Wes’s framework suggests asking yourself: “Am I giving them a chance to speak up?” . That’s crucial – it surfaces concerns now rather than after weeks of silent struggle. Alignment might also involve other stakeholders: ensure the person knows who else needs to be kept in loop or if their approach should align with another team’s processes. Basically, you’re verifying that all minds are synced on goals, approach, and context before they charge off.
Feedback Loop – Set up check-ins to provide feedback and support. Don’t just delegate and disappear. The “F” in CEDAF reminds you to create a short feedback loop . This could be as simple as, “Let’s touch base after you’ve done the first prototype,” or scheduling a midpoint check-in date. By doing so, you ensure two things: (a) the person stays on track (and you catch any divergence early), and (b) they don’t feel abandoned. It provides psychological safety because they know they’ll have a chance to show progress and ask questions soon, rather than fearing messing up the final deliverable. It also implies accountability – they know you’ll review it, so quality likely stays higher. Importantly, when you do get together for the check-in, focus on coaching, not controlling. Ask how it’s going, review their output or approach, and give constructive feedback. If everything looks good, give praise and green light them to finish. If there are issues, course-correct together. This iterative approach is much more efficient than only reviewing at the end when it might be too late to fix major issues.

Using CEDAF, you essentially delegate with clarity and care. Here’s a quick scenario tying it together: Imagine delegating the organization of a small customer event to a team member.

You explain the purpose (comprehension: “This event is to build loyalty with our top 5 clients, so quality interaction is more important than having a huge turnout”),
share why it’s exciting (excitement: “It’s a chance for you to network with our biggest customers directly and show off your project management skills”),
warn about risks (de-risk: “Heads up, the budget is tight and the CEO will likely want to see the guest list, so we need to manage those carefully”),
ask for their thoughts (align: they might say “Given the timeline, can I involve another teammate for help?” – which you discuss and agree on),
and set a check-in (feedback loop: “Let’s meet next Friday to go over the plan outline before you finalize invites.”).

After that delegation conversation, your team member would likely feel clear on what to do, excited to do it, mindful of pitfalls, on the same page with you, and supported by an upcoming check-in. That’s empowering delegation.

Finally, keep in mind that the level of detail in CEDAF can be adjusted based on the person’s experience. Senior folks might not need as much context or frequent check-ins; junior folks might need more. But as Wes notes, even senior people appreciate when someone concisely covers these bases . It saves time in the long run.

By delegating with CEDAF, you not only get better results on the tasks you hand off, but you also grow your team’s capabilities. People learn more because you gave them context (the why), they stay motivated, and they feel you have their back. Over time, you’ll trust your team more (because they deliver), and they’ll trust you as a competent, supportive leader. That’s a win for everyone.

Write Emails and Slack Messages that Get Results

In startup environments, much of your communication happens via email or Slack (or other messaging apps). Writing clearly in these mediums is a superpower – it can mean the difference between a swift consensus vs. a long thread of confusion, or a decision made vs. an email ignored. Wes Kao points out that “the blast radius of a poorly written memo is way bigger than most people think” . A confusing Slack message to 15 coworkers can trigger a flurry of follow-up questions, wasted time, and misalignment. Conversely, a well-crafted message can convey exactly what’s needed and prompt timely action with minimal fuss.

Here’s how to sharpen your written communication in emails and chats:

Use a Clear Subject or Lead: For emails, always use a descriptive subject line that signals the purpose (and urgency if applicable). E.g., “Proposal – New Pricing Strategy (Need Feedback by 5/10)” is much better than “Quick thought” or an empty subject. For Slack or chat, lead with a concise summary if your message is longer than a sentence or two. You might start a Slack message with “TL;DR: proposed timeline change – seeking approval by EOD” and then provide details. Busy readers often scan the first line or subject – make it informative.
Bottom Line Up Front (BLUF): Just as we discussed in conciseness, start with the main point or ask. In an email, your first sentence should usually answer: Why am I writing and what do I need from the reader? For example: “Can we move our launch to Feb 15? Here’s why I recommend this change:” then go into context. This respects your reader’s time. If they read nothing else, they’d still know what you wanted. Wes Kao calls this “main point above, context below” – a very useful rule for written comms. Executives and colleagues will appreciate you for it, since they can grasp your point immediately and decide how to allocate their attention.
Be Brief but Complete: Aim for the shortest message that fully conveys what’s needed. Don’t write an essay if a few sentences will do. However, include all necessary info that the recipients need to understand and act. If you’re scheduling a meeting, for instance: specify the purpose, duration, and who will attend – don’t make them hunt for details or ask follow-ups like “what’s this about?” or “who’s joining?”. Being thorough upfront prevents back-and-forth. A helpful practice is after drafting, read it from the receiver’s perspective: Would I have any obvious questions after reading this? If yes, answer them now in the message. As one of Wes’s principles says, “Do not force other people to do the heavy lifting to draw basic information out of you… When you cover the basics, you’re setting them up to ask better, more advanced questions.” .
Structure for Readability: Large blocks of text are daunting. Use line breaks and bullet points to organize information. If you have several questions or points, list them out (- or 1. in emails; in Slack, you can use line breaks or even Slack’s formatting for bullets). For example, an email to the team might say: “Key updates: 1) Hiring freeze lifted; we can proceed with filling the UX role. 2) Project Phoenix timeline moved up to Q3; please adjust your plans accordingly. 3) Office Wi-Fi will be upgraded this weekend.” Each point on its own line is far easier to scan than a chunky paragraph. Bold or highlight crucial phrases or dates if needed (but don’t overdo it). Good formatting is essentially another form of signposting – it guides the reader’s eyes.
Use Signposting Phrases: Apply the signposting words from the earlier section in your writing. Preface supporting details with “for context,” use “as next steps” to clearly denote action items, etc. For example: “Our Q4 sales dipped by 5%. Because two major clients delayed orders, we ended slightly below target. As a next step, I’ll focus on re-engaging those clients to close the deals in Q1.” This kind of wording makes your email feel well-structured and logical. It’s especially useful in longer messages or documents – signposting phrases act like headers in prose, making sure the busy reader doesn’t miss the logic.
Call out the Ask/Action Needed: Make it crystal clear if you need the recipient(s) to do something. Too many emails end without a clear indication of what the sender expects, leading to confusion or inaction. If you need a decision, state “__Decision needed: Should we do X or Y by Friday?” If you need a reply by a certain date, say “Please send me your feedback by EOD Thursday.” If it’s just an FYI, you can say “FYI – no action needed from you at this time.” This way, each reader can quickly identify their responsibility. Use @mentions in tools like Slack to ensure the right person sees their name attached to a task or question.
One Topic per Message (when possible): If you overcrowd an email with multiple unrelated requests, there’s a risk some will get overlooked. It can be better to send separate shorter emails/slacks for separate topics, unless they’re intimately related. This also allows people to respond in-line to each topic or forward just the relevant email to someone else. If you must include multiple topics (like a weekly update), use numbered sections or bullet points with clear headings (e.g., “Update 1: Hiring – …”, “Update 2: Product Launch – …”).
End with Next Steps or Summary: Especially for longer emails, it can be nice to conclude with a brief summary or reiteration of next steps. E.g., “In summary, I propose we delay the launch to Feb 15 to ensure quality (as outlined above). Next steps: If I don’t hear any objections by Wednesday, I’ll consider this plan approved and proceed accordingly.” This reinforces the key point and sets a default action, which often helps avoid drawn-out indecision.
Proofread and Edit: This seems obvious, but in the rush of startup life, it’s easy to fire off messages full of typos, incomplete thoughts, or unintended tone issues. Take one minute to re-read your important Slack message or email before sending. Check for clarity and courtesy. Ask yourself: Is there any ambiguity here? and Is the tone right? (It’s easy to sound curt or harsh in writing without realizing it – adding a “thanks” or a short greeting can soften when needed). Also ensure attachments or links are properly included if you referenced them (few things are more frustrating than “see attached” with nothing attached). That brief polish can save everyone time. As Wes Kao highlights, a little extra time upfront can prevent hours of confusion later .
Use Templates for Recurring Communications: If you often send similar emails (like monthly reports, onboarding instructions, etc.), create a template or swipe file entry for them. For instance, your team status update email can follow a consistent format: “Achievements, Challenges, Next Month’s Focus, Needs/Asks”. Using a template ensures you don’t forget important elements and keeps communications consistent and professional. Just be careful to update all placeholder info each time to avoid embarrassments (e.g., don’t leave last month’s numbers in this month’s report!).
Mind the Medium: Recognize when to take something out of Slack/email and into a call or doc. If a Slack thread is exceeding, say, 10-15 back-and-forth messages and still not resolved, that’s a sign it might be too complex for chat – someone should propose a quick call or meeting. Similarly, long-form discussions (like brainstorming a strategy) might belong in a shared document or live discussion rather than an endless email chain. Wes Kao mentioned an anti-pattern of “using a medium that doesn’t match the complexity of the topic”, resulting in protracted Slack or Jira threads . So pick the right channel: quick updates = Slack; detailed proposal = email or doc; sensitive or very complex issue = face-to-face or video call. That is part of good communication – knowing where to have the conversation.

Example – Effective Slack Message: Instead of posting “Hey team, I think we might need to change the design a bit. Thoughts?” (which is vague and will lead to a dozen clarifying questions), a well-crafted message would be:

“@design-team FYI: User testing showed confusion with the signup flow. Proposal: Change the order of steps in the onboarding. Why: 30% of users dropped at step 2 (profile setup) – I suspect moving that later will improve completion. Next steps: I’ll draft a revised flow and share by tomorrow for your feedback. Let me know if you have initial concerns. Thanks!*”

This message is longer but it’s clear. It tags the right people, states the issue, makes a proposal with reason, and outlines what will happen next. A team member reading this knows exactly what’s going on and what’s expected (review the draft tomorrow). It pre-empts questions like “why are we doing this?” or “what do you need from me?”.

Remember, writing in a startup context often persists – people search their email or Slack history for info. If your messages are clear, they become useful documentation. If they’re sloppy, they won’t age well. By writing emails and Slack posts with clarity, brevity, and structure, you’ll facilitate faster decision-making and reduce miscommunication within your team.

Develop Career-Boosting Communication Habits (Swipe Files, Small Tweaks, and AI Assistants)

Improving communication is not a one-and-done task; it’s a continuous journey. The good news is that small improvements compound over time , and there are simple habits you can adopt to keep leveling up. Here are some habits and tools to sustain and accelerate your growth as a communicator:

Create a “Swipe File” for Inspiration: In the copywriting and marketing world, a swipe file is a collection of great material to draw inspiration from. Wes Kao suggests creating one for communication – “Collect examples of effective communication that you can reference later. Even the act of noting these examples trains you to recognize effective patterns.” . This could include: emails from leaders that you found exceptionally clear, newsletter or blog snippets that explain a concept really well, templates for proposals, or even phrasing of tough messages (like a superb way someone declined an offer or gave tough feedback gracefully). Whenever you come across an example of communication that strikes you as excellent, save it (e.g., in a notebook, document, or note-taking app). Over time, you’ll have a personal library of proven ways to say things. When you’re stuck writing your own, you can refer to your swipe file for a nudge. Importantly, building this file trains your eye: you become more attentive to how good communication is crafted, which subtly influences your own style.
Practice Micro-Improvements: Pick one aspect of your communication to focus on each week or month. It could be something like “this week, I will practice using signposting in every meeting update” or “I’ll try to pause for 2 seconds before responding to questions (to avoid rambling).” These might seem minor, but as Wes notes, such tweaks “might seem minor, but (a) it compounds, and (b) all the ‘big things,’ everyone else is already doing. So there’s not a lot of alpha in that.” . In other words, the small things can set you apart because big things (like basic professionalism) are table stakes. Over a year, 10% improvement in several micro-skills can make you unrecognizably better at communication. For instance, you could cycle through practicing concise writing, then active listening, then storytelling technique, etc., and come back around, each time at a higher level than before.
Invest Time Up Front: Make it a habit to spend a bit more time planning and editing key communications. It’s tempting in a startup’s hectic pace to shoot from the hip. But remember the adage: “If I had more time, I would have written a shorter letter.” A little extra preparation goes a long way. “Spending a few extra minutes crafting clear communications saves hours of back-and-forth clarification later,” Wes reminds us . Before an important meeting, jot an outline of your main points (30 seconds of effort, huge payoff in clarity). Before sending that important email, re-read and tweak it (2 minutes could save 10 emails later). Think of it as an investment with high ROI – it’s literally trading minutes now to save hours collectively for you and your team. Eventually, you’ll internalize structures and do this “prep” much faster, but even then it’s worth it.
Solicit Feedback on Your Communication: Yes, meta-feedback! Just as you’d get feedback on a project deliverable, ask trusted colleagues or mentors how you’re coming across in communication. You could ask in one-on-ones: “Hey, I’m working on being more concise – how am I doing in our meetings? Any suggestions?” Or if a presentation didn’t land as well, ask a friend on the team: “What parts were unclear? How could I improve?” This does two things: it gives you valuable input to improve, and it signals to others that you care about improving (which already frames you as a thoughtful communicator). Some companies do 360-reviews on soft skills – take those seriously if available. If not, simply being open to input will help you catch blind spots. Perhaps you overuse certain phrases, or maybe when you think you sound confident you actually come off as aggressive – better to know and calibrate.
Leverage AI Tools like ChatGPT to Refine Your Messaging: In the modern era, AI language models can be your personal communication coach or assistant. Wes Kao herself encourages using tools (she references Claude and ChatGPT ) to aid in better communication. Here are a few ways to use AI:
- Brainstorming and Outlining: If you’re stuck on how to structure a message or presentation, you can prompt ChatGPT with a summary of what you need to convey and ask for an outline or the main points to include. For example, “I need to announce a delay in our project to the team, emphasizing why and what we’re doing about it. What key points should I cover?” The AI might give you a sensible structure (e.g., apologize for delay, state reasons, reassure about plan, end on positive note) which you can then flesh out.
- Draft Refinement: You can paste a draft of your email or proposal and ask the AI, “Please make this more concise and clear.” Often, it will tighten the language and suggest clearer wording. Of course, you must review the output to ensure it retains the correct meaning and tone – don’t blindly send AI-edited text without reading it. But it’s a great way to do a first pass edit, especially if you struggle with wordiness. The AI can also catch when you’ve been too abstract and add clarifying details (or vice versa).
- Tone and Style Checks: Worried that your message might sound too harsh or too timid? Ask the AI to adjust the tone: “Make this sound more friendly and motivating.” or “Make this more formal/professional.” It can infuse a bit of warmth or formality as needed. Again, treat it as suggestions – you decide what fits best, but the AI can provide options.
- Anticipating Objections or Questions: Similar to MOO, you can use AI to sanity-check your communication. For instance, “Here’s my plan summary. As a skeptical investor, what questions might you ask after reading this?” The AI can simulate a reader and generate possible questions or doubts. If it surfaces something you hadn’t thought of, you can then address that in your next draft. This is like having a practice audience to test on.
- Grammar and Clarity: At a basic level, tools like Grammarly (not AI like ChatGPT but worth mentioning) or the AI itself can correct grammar and suggest clearer phrasing. If English isn’t your first language, this is extremely helpful to polish your writing.

Using AI as a helper can speed up your writing process and also teach you over time. By seeing how it rephrases your sentences, you might learn new ways to write. It’s like having an editor on call. That said, be cautious to review everything – AI might sometimes change nuance or add incorrect info. Use it as an assistant, not an autopilot.

Keep Communicating (Don’t Shy Away): Finally, the habit that truly builds communication skill is actually doing (love this!) it, repeatedly. It can be tempting for a less-confident communicator to avoid opportunities – e.g., not speaking up in a meeting because you fear rambling, or not sending a team newsletter because you’re not proud of your writing. Fight that instinct. Volunteer to present, write, and speak whenever it makes sense. The more reps you get, the better. Treat each meeting or email as practice. If something goes poorly, don’t retreat – analyze it (maybe ask for feedback as above) and try again with improvements. Over time, what once took great effort (like crafting a persuasive proposal) will become second nature.

As you implement these habits, remember that everyone starts somewhere. Even renowned speakers and writers improved by continuously honing their craft. Communication is very much a learnable skill. By being intentional with habits like keeping a swipe file, iterating on small improvements, and using new tools, you’ll keep climbing to new levels of mastery.

To wrap up, let’s echo a key mindset from Wes Kao: Communication is the bedrock skill that amplifies all other skills. You can have the best ideas or work ethic, but if you can’t communicate effectively, your impact will be limited. Conversely, if you communicate sharply and compellingly, you multiply the effect of your ideas, rally people to your cause, and fast-track your career or business. It’s worth every bit of effort to improve this craft.

In conclusion, becoming a better communicator is a journey of continuous learning and practice. Use the frameworks like “Sales, then Logistics” to structure your messaging, anticipate objections with MOO, practice concise and signposted delivery, manage up with solutions, give feedback that inspires change, delegate with clarity (CEDAF), and polish your writing. Keep examples of greatness to learn from, and don’t hesitate to get a little help from AI tools for the grunt work of editing. By following this guide and embracing these techniques, you’ll find that over time you’re getting the buy-in you seek, aligning teams with ease, and making a stronger impact as a leader.

Remember: if you’re not getting the reaction you want, focus on improving how you communicate – this guide gives you the playbook to do exactly that. Now it’s up to you to put it into action. Happy communicating!

Sources:

Wes Kao on Lenny’s Podcast – “Become a better communicator: Specific frameworks to improve your clarity, influence, and impact” (Key frameworks and tips summarized from podcast transcript and Lenny’s Newsletter) - linkedin - amazing podcast - you should listen to it! 🚀
Wes Kao’s newsletter article
The podcast of Lenny