2026-05-13 20:01:58
👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer. To level up faster, check out my intensive course on Executive Communication & Influence. You’ll learn alongside mid-career operators from orgs like Netflix, Stripe, OpenAI, Meta, Anthropic, etc. → Save your spot
⛑️ If you’re looking to dramatically improve your communication and leadership, learn more about my coaching approach.
Read time: 4 minutes
I once had a direct report, we’ll call him Matt, who kept submitting work with errors, typos, weird formatting, and bad writing that increased cognitive load for customers.
I would repeatedly remind him to use the clear text feature in Google Docs/Gmail, which, if this is the first time you’re hearing about it, is a game-changer. That little Tx button has saved me from sending emails where the “Hi First Name” looks obviously copied/pasted because the font was size 14 in Verdana when the rest of the email was size 12 in Arial. This isn’t even the point of the story, but I think more people would benefit from cleaning up their email formatting, so here’s how you do it:
One day, I sat him down and said,
“Matt, I need you to pretend like your reputation is on the line when you send work to me. I am judging you for this work. I know this isn’t your best. Even though you are signing these emails under our organization’s name, I need you to pretend you’re signing it as Matt, and sending this email to 50,000 of your friends and the public."
Your work is the average of what you ship. If you’re not proud of it, consider investing in improving your craft, finding a function that’s a better fit, or whatever else you think will allow you to show how good you really are.
A tiny percentage of you might say, “Wes, I would publish work with typos and bad grammar under my own name. I don’t mind.”
First of all, this:
Second, you might not mind, but your organization does. Sloppiness reflects poorly on your brand, distracts from your message, and erodes trust. If you’re going to do 90% of the work, you might as well do the last 10% to give it another read and put your stamp of approval on it.
Ask yourself:
If I were signing off with my name, would I make this better?
Is there sloppiness that might reflect poorly on me or my company?
Am I passing the burden to others to fix my errors?
Does the work I’m shipping represent my ability?
If you’re saying, “I just can’t be detail oriented and don’t want to try,” I will say, “Cool, I will hire someone who is or can be, because the details matter in this job.”
For most knowledge worker roles, being able to produce work that’s error-free most of the time is a prerequisite. I’m not saying you need to be in the 95th percentile of detail orientation.
You may be surprised to find that I’m not even that bothered by typos, and think they’re the least egregious type of error. I’m saying if you want to be trusted with more responsibility, you need to be able to produce work that is generally error-free because your manager can’t always be your safety net.
Back to the story of my direct report Matt. Matt admitted that he felt like I’d always catch his errors, so he felt more lax about it. I get that.
You might say, “Wes, you enabled him to be less detailed.”
Perhaps I did. But this quip is not as clever as you think. Because what’s the alternative? Let him send an email to 50,000 customers and make them suffer?
Andy Grove, co-founder and former CEO of Intel, said it well:
“The responsibility for teaching the subordinate must be assumed by his supervisor, and not paid for by the customers of his organization, internal or external.”
The idea of “let the person fail and they’ll learn” makes sense in theory, but in reality, it’s not worth sacrificing brand credibility and taxing your customers for an employee to learn a lesson. Don’t make your manager or customers pay for your weaknesses. You don’t and probably can’t turn weaknesses into strengths, but you can and should reflect on which weaknesses you want to improve on enough so they aren’t a blocker for you.
I’ll end with a story that should gives you hope:
Most people assume I was always good with details. The truth, is I used to be super disorganized.
For example, in junior high school, I missed assignments because I forgot about them, or jotted it in one of many notebooks, then forgot which one.
In my sophomore year of college, I did an internship at a tech PR firm. One of the senior leaders chewed me out because he asked me to organize an Excel spreadsheet, and when I turned in my finished work, he rightfully pointed out all the ways the spreadsheet was messy with random font sizes, centered vs left justified text, etc. I didn’t see it until he pointed it out. But from that day on, I knew what to look for and trained my eye to notice formatting.
Even to this day, I have myriad systems in place (checklists, calendaring, alarms before meetings, and yes, still using the clear formatting Tx button in Gmail) to make sure I don’t let a lack of detail orientation screw me over.
Most skills are learnable and you can make many mistakes, but don’t get stuck in a loop repeating the same mistakes over and over. Ideally, you graduate to making better, smarter mistakes, and you improve enough so your weaknesses don’t become prohibitive.
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
The May cohort is now sold out, but I opened a new July cohort with the dates of July 16th and 17th. The cohort opened last week and there are already operators from Figma, Amazon, Mozilla, Grammarly, Stripe, OpenAI, etc signed up.
In my private coaching practice, about 1/3 of my clients are technical. My clients include eng managers, staff engineers, startup CTOs, technical founders, VPs of data science, etc. And engineers make up the second largest function in my course:
Technical people can be hard to please. They’re usually hyper rational, logical, and have a low tolerance for hand-waviness.
This is probably why engineers like my course so much.
I built this course because I was frustrated that most communication resources were too basic or too vague. My course treats communication as a skill, one where there are underlying principles and a bell curve for the quality of your execution. My goal is to help you see differently, so you notice what you can improve in your own speaking and writing. Then you can build intuition over time, so communicating well becomes faster and more instinctive.
The question you might be asking is, “Is the course worth it?”
Here’s what engineers are saying:
“[Wes’ course] provides a great foundation to level-up your comms, and practical tools which you can use in nearly any scenario.” - Samuel Kramer, Forward Deployed Software Engineer, OpenAI
“I wish I had taken this course earlier. Wes shared some incredibly practical tools that, if applied, can meaningfully uplevel the way you work and communicate.” - Manohar Sripada, Engineering Manager, Meta
“The course shows what great communication looks like and bar that you can aim for. The exercises were very useful in determining your current level and reading through answers from different students gives a lot of different perspectives. I will be coming back again and again to review the content as I gradually build up by communication skills.” - Srihari Venkatesan, Engineering Manager, Apple
“Great course that summarizes foundational wisdom, principles, and actionable steps for effective communication.” - Alexei Koulikov, Engineering Manager, Shopify
“I got a ton of value out of this course, you move fast, cover a lot. Written communication, presentation to execs, informal / verbal, etc... The exercises are where the real learning is at, easy to be an armchair expert but these helped me feel where my deficiencies are” - David Illing, Senior Data Engineer, Credit Karma
“Great course overall. Lots of great actionable advice and insight into what it means to execute at the next level.” - Oscar Funes, Senior Staff Engineer, PayPal
“Lots of communication and influence is super abstract. This course was a really great way to structure things tangibly. I am excited to try out these ideas and convey them to peers/reports.” - Suvir Jain, Engineering Manager, Stripe
I hope to see you in class. If you’ve been thinking about joining, check out course details.
Is this your first time here? Subscribe (it’s free)
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Learn more about 1:1 coaching to sharpen your executive presence
✨ Course: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 2,000 tech operators have taken this course, and every cohort so far has sold out. → Join the July cohort
2026-04-29 20:02:59
👋 Hey, it’s Wes. Welcome to my newsletter on managing up, leading teams, and standing out as a high performer. To level up faster, check out my 2-day course on Executive Communication & Influence. You’ll learn alongside mid-career operators from orgs like Netflix, Stripe, Figma, Anthropic, etc. → Save your spot in the July cohort
I originally published a version of this essay in September 2015, and have since expanded it. Enjoy.
Read time: 4 minutes
It’s to your benefit to be as clear as possible when you speak or write, because clear communication helps you get what you need.
One way to do this is to speak in the affirmative, rather than the negative.
If you speak in negatives, your recipient has to take an extra mental step.
To understand “Don’t do that”.... you have to think about “that,” then reverse it to do the opposite.
A better way is to say, “Do this.”
If you can save your recipient a mental step, you’re doing a kind thing. Most people have too much they need to mentally process, so avoid adding more friction than you have to. Reducing cognitive load applies in UX design, marketing call-to-actions, or requests to your coworkers.
A diving coach might say, “Don’t flex your feet,” which can be confusing when you’re mid-air doing a reverse double-somersault tuck into the water.
If they phrased in the affirmative, they would say, “Point your toes.”
Saying don’t can sound reprimanding with a finger-wagging undertone. This makes you seem unnecessarily negative, even if you're justified in what you’re saying.
This is a practical issue. If the person you’re giving feedback to starts to get defensive, they’ll stop hearing what you’re trying to say.
Yes, the person receiving feedback should stay open-minded and remember to listen. But as the person giving feedback, it’s also your responsibility to think about how you’re sharing the information. This is a much larger topic, but stating things in the affirmative is a simple way to improve both the clarity of what you’re saying and the emotional tone.
Let’s say you’re giving a junior team member feedback on how to present to your CEO.
🚫 “For a 30 minute call, don’t spend 25 minutes on backstory. Don’t delay getting to the meat of what you want to discuss.”
✅ “For a 30 minute call, spend 2-3 minutes on backstory. Then focus on the meat of what you want to discuss.”
In the “before” example, the focus is on spending the majority of time on backstory, which is not what you want your recipient to think about. The focus is also on what they’re doing wrong.
You want your team member to visualize themselves doing things right. We’re applying the power of visualization to workplace scenarios. Encourage people to imagine going in the direction you want them to go in.
Remember: what you give airtime to will expand in your recipient’s mind.
There may be times when you have to address the negatives. Don’t do mental gymnastics to avoid saying the negative thing.
Instead, say what you don’t want the person to do, then say what you want them to do.
🚫 “Don’t disappear for three weeks then show the final product.”
✅ “Don’t disappear for three weeks then show the final product. Share what you have in a few days, so we can make sure we’re aligned.”
If you only say what not to do, you end up leaving a void. A void begs to be filled, and your recipient might fill it with an idea you disagree with. Always fill the void with what you want your recipient to think.
Speaking in the affirmative applies to stating what you’re able to do.
Let's deconstruct these two statements:
🚫 “I can only meet between 11-3pm.”
✅ “I can meet between 11-3pm.”
When you say “I can only...” it sounds like you THINK you should be more available. Or that your counterpart has a right to want you to be more available.
This puts you in an unnecessarily weak position. If you can meet between 11-2pm, own it. If the person pushes back, you can explain further, but there’s no need to start off with insecure vibes.
Notice the next time you start phrasing an idea using a negating sentence structure of “Don’t do X” or “I can’t do X.” Spend an extra few seconds to see if you can flip it around to say the same thing in the affirmative.
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
PS For further reading, check out how to avoid incepting negative ideas.
The May cohort is sold out, but good news: A new July cohort is now open for enrollment. The course dates are July 16 -17, 2026.
If you’re wondering “Is this for me?” check out these student reviews from last month’s cohort:
“Extremely worthwhile course. The opportunity to see other students’ responses and spawn new ideas on framings / variations from one’s own typical communication style made the difference.”
- Alice Rhee, Sr. Staff UX Researcher @ Mozilla
“I knew this course would be valuable for my day-to-day work and for how I want to grow in my career, and it did not disappoint. The frameworks around executive communication and influence immediately changed how I think about structuring ideas and driving alignment. The additional material provided is a gold mine. I can already see myself coming back to it for years to come.”
- Denny Beeler, Software Engineer @ Progressive
“Excellently structured, detailed, and thoughtful course with a wealth of actionable insights. I enjoyed the hands-on approach: deliver exercises quickly then review each other’s, and learn from each other’s strengths and weaknesses together. The course was energizing and I feel confident in taking action on what I learned.”
- Daniella Latham, Principal Product Marketing Manager @ Atlassian
“This course was a fantastic use of my time as a cross-functional communicator and leader. Not only was it packed full of extremely useful takeaways, but it was also very efficiently run. Wes is a fantastic communicator and her application of best practices was digestible and relatable to my day to day. I look forward to putting the many things I learned here into practice.”
- Anna Mumford, Director, PMO @ Hims & Hers
“This course was rammed with useful and practical content for all facets of work within an organization with others. How to explain yourself more effectively, be more succinct, and generally start to move with more ease through work.”
- Charlotte Hilton, Sales Account Executive @ Harvey AI
If you’ve been thinking about joining, I hope to see you in class. Learn more about the course.
Is this your first time here? Subscribe (it’s free)
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Learn more about 1:1 coaching to sharpen your executive presence
✨ Intensive course: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 2,000+ tech operators have taken this course, and every cohort so far has sold out. → Save your spot in the July 2026 cohort
2026-04-15 20:02:49
👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer. Check out my intensive course on Executive Communication & Influence. You’ll learn alongside mid-career operators from Netflix, Stripe, Meta, Figma, Anthropic, etc. → Join the May 2026 cohort
⛑️ If you’re looking to dramatically improve your communication and leadership, learn more about 1:1 coaching.
Read time: 3 minutes
Fundamentals is a new series that highlights my core concepts in communication that I personally keep coming back to.
This week’s fundamental principle:
Since writing this, I’ve realized that starting a sentence with a signposting phrase is even more useful than I thought. I didn’t realize how I had trained myself to speak and write this way because it’s become my default. Basically, when you start with a signposting phrase, you’re giving your reader a preview of what’s to come.
^ This is why kicking off a sentence with “The most important part to keep in mind is [this piece of info]” is infinitely easier to skim, than “[This piece of info] is the most important part to keep in mind.” If you start with “this piece of info,” your reader doesn’t know what to focus on until the back half of your sentence.
I wrote signposting with written communication in mind, but it’s just as effective for verbal communication. It might actually be even MORE useful with verbal communication because your listener can’t read ahead. They have to listen to you reveal one word at a time.
^ For example, I love when I’m in a meeting and hear the speaker say, “The surprising thing is…” or “The biggest takeaway was…” My attention might have drifted, but hearing them say that signposting phrase allows me to snap back into focus and listen to what they have to say next.
One common misunderstanding or misapplication of signposting, is readers thinking that simply adding headers is good enough. Headers, subheaders, toggles, paragraphs, etc are a type of signposting, but these formatting elements alone are not enough. I’ve read MANY docs that looked well-organized in Notion or Google Docs, but the content itself was weak, poorly argued, or generic. See this related post on how good design (or formatting) can hide poor logic.
I posted about signposting on LinkedIn. Here are some highlights on which signposting phrases folks found most helpful:
After you read the article, reflect on these prompts:
Look at the last long-ish memo you wrote. What signposting words could you use to make the flow better?
Think about a recent presentation where your audience seemed confused or asked lots of clarifying questions. How could you have used verbal signposting (“First... Second... The reason this matters is...”) to guide your audience?
Pick a meeting where you’ll need to communicate complex information. What signposting phrases could you use to help add structure to what you’re saying?
Thanks for being here, and I'll see you in two weeks on Wednesday at 8am ET.
Wes
The upcoming May cohort is currently 75% full. In the past week alone, operators Etsy, Amazon, Rakuten, PayPal, GoFundMe, Clay, DoorDash, etc have signed up.
Here are reviews from students who took the course last month:
“Wes discusses several issues which come up in work situations where you can improve your chances of getting what you want. Very clear tips on how you might be sabotaging yourself, how to communicate at the right level and how to be focused on the recipient, have logic and reduce cognitive load.”
- Rajesh Shenoy, Senior Staff Software Engineer/Engineering Manager (L7) @ Meta
“A masterclass in high-leverage communication. Wes provides incredibly tactical frameworks that teach you how to stop asking for permission and start driving outcomes. Essential for anyone operating in a fast-paced, asynchronous tech environment. 10/10.”
- Galit Alon, Engineering Manager @ GitLab
“Great sessions. I really appreciate Wes walking us through each topic and sharing clear examples to drive each home. I love the approach of making most of the exercises written, especially with a time limit. Helped train me to quickly comprehend and execute within minutes.”
- MD, Senior Manager, Technical Program Management @ Squarespace
“A course that is well-paced, engaging, and filled with thoughtfully-designed concepts and frameworks that are easy to immediately action upon. I walked away with several new communication tools in my toolbelt. Thank you, Wes!”
- Ruth Corson, Director of Global Digital Marketing, Basketball @ Nike
“This course is packed with valuable and actionable information. The flow and the quality of the information and the way that Wes presented the material kept my mind engaged the entire time. I am very energized by this course and can’t wait to start implementing my learnings. Must-do for everyone.”
- Anoush Kabalyan, Director of Growth Analytics @ Salesforce
If you’ve been thinking about joining, I hope to see you in class. Learn more about the course.
Is this your first time here? Subscribe (it’s free)
Follow me on LinkedIn for more insights
Learn more about 1:1 coaching to sharpen your executive presence
✨ Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,500 tech operators have taken this course, and every cohort so far has sold out. NOTE: The May cohort is 75% full and will fill up in the next few weeks. → Save your spot
2026-04-01 20:01:21
👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer. Check out my intensive course on Executive Communication & Influence. You’ll learn alongside mid-career operators from Netflix, Stripe, Meta, Figma, Anthropic, etc. → Join the May 2026 cohort
⛑️ If you’re looking to dramatically improve your communication and leadership, learn more about 1:1 coaching.
Read time: 6 minutes
I often get readers who ask, “Wes, if I’m not naturally loud, how do I speak up or talk about my accomplishments? How do I gain more visibility, either internally in my company or externally online?”
As a fellow introvert, I can relate.
No joke, in elementary school, I was so shy I used to not raise my hand to use the bathroom during class because I didn’t want 30 of my classmates to look up when I came back into the classroom.
That’s right, I chose physical discomfort to avoid drawing attention to myself.
So I’ve come a long way over the years, as a founder who’s been on ~50 podcasts (including Lenny’s Podcast), spoken at SXSW twice, taught as a guest lecturer at top 10 MBA programs, in addition to leading countless internal team meetings, speaking at all-hands, sharing business updates, etc.
Here are a few ways I get myself to speak up and share more.
Tell me if this sounds familiar:
You: “Hmm I don’t know if I agree with what Joe just said. Should I say something? I’m not sure. What if I don’t explain myself well? What if people disagree with me? Okay, I should speak. No I shouldn’t. Okay yes, I should. Oh no, the group has already moved on.”
Is this you? This was me too.
If you try to decide during the meeting, you’re going to miss your window. Decide BEFOREHAND that you’ll share your point of view and speak at least once during the meeting.
This way, you’re not debating whether to speak, you’re looking for an opening of when to do it.
I’ve worked with many coworkers who were naturally extroverted. They didn’t overthink, and they felt comfortable speaking up when they were 60% confident they were right. It’s hard to compete with colleagues who don’t rehearse what to say in their mind before saying it.
This is why I try to speak first in big meetings. I try to get it out of the way and prevent someone else from saying what I wanted to say.
Is this at odds with the advice of “leaders should speak last”? I would say no.
The variable here is power dynamics. If you are nervous about not being able to speak up, presumably it’s because you’re not the most senior person in the room. Many managers are confident speaking to their direct reports or folks more junior, but get self-conscious when presenting to senior leadership, peers, or the entire company. This is very normal.
So when you are among peers and higher ups, it’s fine if you speak first, especially if waiting to speak means you might end up not speaking at all.
Not all “speaking up” has to happen verbally. Another way to speak up more is to share more in writing. A well-written doc can get circulated in your organization and get shared in rooms you’re not in, with leaders much more senior than you. Some docs even outlive the person who wrote them.
If you have an idea that’s hard to describe in 45 seconds to an impatient audience, I recommend drafting a doc that’s easy to read and pitches your idea. In your doc, you can describe the problem, cost of inaction, potential solutions, etc.
When you make a business case and share an evidence-backed point of view, you show good judgment. If you show that X problem is costing your company money, you may get senior leaders’ ears to perk up.
When you write, you create an artifact. You create a concrete record of yourself contributing useful solutions, which builds your credibility.
In terms of sharing ideas externally, writing a newsletter/blog or sharing on LinkedIn is great too. I started my blog in 2010, where I shared teardowns of ad campaigns (like my analysis of this Airbnb ad), marketing insights, etc. Writing regularly helped sharpen my thinking back then, and still does every week. It shows you’re passionate about your craft and actively thinking about the world around you.
More on how to speak up, even if you’re afraid of being wrong.
When you're armed with a few go-to phrases, you’ll be able to jump in before the moment passes. So get ready to unmute yourself on Zoom and say:
“Yes, to add some color on that...”
“That's a great point. My POV on this is...”
“I love that you brought that up. The thing we need to remember is…”
The other benefit of having go-to phrases: you buy yourself time. Even an extra second can help give yourself a beat to think of how you want to articulate your idea.
I find it a lot easier to chime in on Zoom than in IRL meetings. If you work remotely, use this to your advantage.
Sit higher in your chair so you don’t look short on camera. Get a $50 box light on Amazon so you’re well lit. Try to have a good “shoulder line” so your shoulders look defined against your background. When you fill the frame and look good, you'll feel powerful and remind yourself you have a lot to share.
I actually think Zoom meetings are amazing for introverts. In an IRL meeting, it’s easy to get nervous if you see 10 or 15 or 20 people sitting around a table. But in Zoom, everyone is in a one inch box on your screen--this can help reduce anxiety from a public speaking perspective.
More on how to prevent insecure vibes.
One of my direct reports wanted to practice speaking up more in meetings.
I asked how I could best support her, and here’s what we agreed on: If we were in meetings together, I would send her a Zoom chat DM saying, “Hey I think you could share something on this. No pressure.”
Then she would often unmute herself to chime in.
If you aren’t in a position to ask your manager for help, do this with a trusted colleague. Give each other a gentle nudge and help boost each other up.
To recap, here are the tactics you can try:
Decide to speak before the meeting starts.
Try to speak first, or early on.
Share more in writing.
Prepare go-to phrases to insert yourself in meetings.
Look more authoritative on Zoom.
Ask a colleague to keep you accountable.
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
I just wrapped up an incredible March cohort two weeks ago. Every time I run the course, I’m humbled by the talented operators who join and learn together.
Of the 1,700+ tech operators who have taken the course so far, there’s a wide range of functions represented, with the largest groups from product, engineering, and marketing:
New student reviews from this month’s cohort are rolling in. Here’s what folks are saying:
“At the risk of being hyperbolic, spending these 6 hours in the course may have been some of the most insightful and impactful hours of my career. The course was concise and extremely tactical, and illuminated countless improvements I can make to communicate more effectively with leaders, and be seen as a leader myself.”
- Cadence Greenberg, Senior Research Manager @ The New York Times
“I was skeptical with the value the training can bring in such a short time, but Wes managed to change my perspective on multiple concepts in minutes. The bonus material also gives me things to read and implement in the coming weeks and months.”
- Barbara Bihari, Senior Integration Manager, Strategic Partnerships @ Kayak
“This course is packed with frameworks and insights, and delivered in a way that is digestible and immediately actionable. I feel equipped with the right tools to out into the world and put this new information into practice. Wes is an engaging presenter and makes a large Zoom feel very communal. It’s also really well-paced for the amount of content we move through. Highly recommend.”
- Kaela Chandrasekaran, Staff User Researcher @ Asana
“This course is a gold mine and worth every penny. I’ve struggled with communicating my ideas, being concise, and ensuring I’m giving the right amount of context depending on my audience. Everything in this course was super actionable and I’ve already put some of these learnings into practice.”
- Beth Saunders, Senior Community Manager @ Amplitude
“I wish I had taken this course earlier. Wes shared some incredibly practical tools that, if applied, can meaningfully uplevel the way you work and communicate.”
- Manohar Sripada, Engineering Manager @ Meta
The upcoming May cohort is already 55% full. So far, the cohort includes operators from Adobe, Experian, OpenTable, Webflow, Visa, Google, Robinhood, Discord, Hims & Hers, Zendesk, Yelp, 1Password, Shopify, etc.
If you’ve been thinking about joining, I hope to see you in class. Learn more about the course.
Is this your first time here? Subscribe (it’s free)
Follow me on LinkedIn for more insights
Learn more about 1:1 coaching to sharpen your executive presence
Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,700 tech operators have taken this course, and every cohort so far has sold out. → Save your spot
2026-03-18 20:03:48
👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer. For more, check out my 2-day course on Executive Communication & Influence → The May cohort is now open
⛑️ If you’re looking to dramatically improve your communication and leadership, learn more about my coaching approach.
I originally published a version of this essay in September 2018, and have since expanded on the topic. Enjoy.
Read time: 5 minutes
I give a talk called “Storytelling for Technical Leaders,” where I share how technical founders and operators can tell better stories and be more compelling to their audiences.
About 1/3 of my private coaching clients are technical (eng managers, staff engineers, startup CTOs, VPs of data science, etc).
From working with dozens of technical leaders, here are the most common storytelling mistakes I see:
Real-life is non-linear, but stories are linear. Therefore, stories are always a simplification.
Read that again. Stories are always a simplification. In order to simplify, you as the presenter will need to decide which details to include and exclude.
Many technical folks are afraid their audience will call them out for not being comprehensive enough. The paranoia is real and I’ve felt it myself. But the solution is not to be extremely comprehensive all the time, and to treat all details as weighted equally.
Your audience doesn’t want a story weighed down by caveats and technicalities in every other sentence. Your audience wants to be wooed, entertained, and taken on a journey — in addition to learning about your project and vision. If you lose your audience because they’re asleep, they won’t appreciate all the context and details you’re sharing anyway.
What about fellow technical folks or subject matter experts who have questions about specific details? They’ll ask. And you’ll be ready to answer and impress them with your depth.
Anytime you feel the urge to say, “Well, technically…,” you’re about to kill a good story.
Remember: What gets someone in the door isn’t necessarily what gets them to stay.
For example, think about J.Crew. The front of the store has tables with a rainbow assortment of t-shirts in fun patterns and neon yellow.
Nine times out of ten, I walk in…and buy a neutral color (white, black, navy, grey). Most customers do this , which is why retailers plan the inventory accordingly and have stockrooms full of basic SKUs.
But if they put only the most basic stuff on display, you would keep walking and never enter the store.
Hook your audience so you get them in the door. If your audience is eager to hear more, you’ll earn the opportunity to share details.
Ask yourself:
Can I simplify my story to make it even more powerful?
Can I remove tangential comments, so I can focus on my main point?
Am I spending precious time describing context of secondary importance that I could share later?
More on the importance of sales, then logistics.
When you are in the moment, don’t try to remember a list of storytelling tips and strategies. This is more likely to make you anxious and worsen your performance.
By all means, practice your pitch. But once you’re out in the wild (in front of a room of colleagues, prospective customers, or at a networking event), let go of the laundry list of things you learned in preparation for telling your story. Don’t feel pressure to stick with word-for-word scripts.
Instead, stay present and focus on eliciting emotion: “How can I make this person’s eyes light up?”
I call it “ELU” for short.
ELU is the moment when your audience gets emotionally invested. We all know when people are listening to us to be polite. And you can tell when someone suddenly wakes up during the conversation and wants to hear more.
It’s hard to anticipate what will resonate with your audiences, so experiment with what you say and look for that spark.
Ask yourself:
How can I stay present, enjoy telling this story, and look for moments when my audience leans in with excitement?
More on Eyes Light Up.
If you’re telling a story about your camping trip, don’t start when you were brainstorming options for tents and carpooling. Start right before you almost get eaten by a bear on a 13 mile hike.
I constantly remind myself to cut backstory, and am usually glad for it. Backstory can easily take up the majority of the time you have during an introductory call or meeting, so be mindful to avoid backstory scope creep.
Ask yourself:
Can I cut out more of the backstory?
Does my audience really need to know this part?
What’s the bare minimum I need to set the context, so I can spend time on the juicy stuff?
Your colleagues do not have time to listen to a full hero’s journey story in a quarterly business review meeting.
Seriously, do not attempt to do a 12 step (some say 17 step!) hero’s journey type of story. Your business or project does not warrant this, and everyone will be catatonic by the time you finish.
Am I against long stories? No. Am I against boring, pointless, wtf are we talking about stories? Yes.
Long stories can be good IF you are a good storyteller. Most of us (technical or not) aren’t in this bucket. In order for storytelling to work, the story needs to hit a certain threshold of quality, and that bad is higher than people realize.
Therefore, storytelling is not as practical of a tool for most people who don’t have time to invest in getting good at it. It’s like tango. I’ve heard it takes a minimum of ten years for one to look even remotely passable doing tango. Compare that to lindy hop: it’s a forgiving dance. There are obviously professionals who are next level, but amateurs don’t look terrible and they still have fun.
Most founders and leaders should tell short stories where the narrative arc is a few minutes long at most. I might not even call them stories. I’d call this using evocative vocabulary or sharing a quick anecdote, where you use visual language to paint a picture for your audience.
This, you can easily do in as little 5-15 seconds. I did this often on Maven sales calls and internally when coaching my direct reports, and it led to the same positive outcome of telling stories but was much faster and easier to do well.
—
As usual, it’s not complicated . It’s just hard. There are hundreds of permutations and combinations of ways to tell your story, so it’s part art and part science. If it feels unnatural for you at first, it’s totally normal. Developing your muscle memory with storytelling is part of the process.
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
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2026-03-04 21:03:34
👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer.
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Read time: 6 minutes
In my early twenties, I wished I had a manager who would “coach” and “mentor” me. I wanted this so badly.
One day, I realized, my manager taking the time to rip my work into shreds AND patiently share actionable feedback…
This WAS coaching me.
This WAS mentoring me.
This WAS investing in me.
I was too busy whining to realize, in fact, I was getting what I wanted all along.
You may have an idealized version of the perfect manager in your mind, but your manager won’t able to live up to that ideal.
“Coaching” and “mentoring” and “investing in your growth” don’t only show up in formal career conversations, or look a certain way.
If your manager cares enough to say, “Hey, this kinda sucks, but here’s how to make it better,” they are investing in you.
Who would you rather have?
A manager who talks about your career during performance reviews, but doesn’t give you detailed feedback on a weekly basis.
A manager who talks about your career path when you initiate, but gives you consistent, actionable, detailed feedback regularly.
Of course, you’d want both.
But if I were to choose, I’d say the latter is more important.
You might be thinking, “Alright Wes, my manager is already giving me some feedback. But how do I get more coaching from them?”
Read on, my friend.
Yes, it’s part of your manager’s job to give you feedback. No, this doesn’t mean they feel obliged to do it, mainly because giving good feedback takes effort and your manager is probably swamped.
You’re more likely to get feedback if you sell them on the upside of doing so. For example:
If your manager were to engage with you on this topic, how will it save money or make money for the company?
How will it allow you to add more value?
How will feedback now improve everything that comes after?
If your response is, “Getting an answer to my question doesn’t really impact my ability to add value to the business,” your question might not be worth the time to discuss.
Most senior leaders are ruthlessly focused on driving value for the firm. If addressing your question doesn’t contribute to that, it makes sense why they’d deprioritize it.
At the end of the day, managers invest in people they believe are worth investing in. It’s a bit circular, but it’s worth saying because there are a few implications.
Generally, you want to behave like someone who learns quickly, is going places, and is a strong performer. You want to act like an owner and do what’s best for the business. When you have a history of good judgment and continuous improvement, this makes your manager want to give you more feedback.
Try to react positively when managers give you any type of coaching. This matters because many managers have learned the hard way that they need to carefully phrase their feedback using words that will be more acceptable for their direct reports.
Otherwise, they risk being seen as an insensitive asshole.
If you’re a direct report, you do not want your manager to feel the need to “translate” too much because it reduces the chances they’ll give you feedback at all.
You benefit when your manager can speak freely with you. For example, you can say,
“Feel free to be super direct. If this sucks, tell me and share why/how I can improve because I want to learn. Feel free to rip it apart.”
It’s usually much easier for your manager to react to something specific, soon after it happened, than it is to ask about vague ways you can improve.
🚫 “What can I do get to the next level?”
✅ “What do you think I did well in the presentation to our SVP just now? What could I have done differently to be more effective?”
In the “before,” questions like this are hard for your manager to answer. They require your manager to think about everything you do, don’t do, where you fit in the org…then create a curriculum to teach you.
In the “after,” this is a much more manageable question that feels less loaded. Your manager can give you feedback about the meeting you were both in just now, which you can apply to future presentations.
Another example:
🚫 “Can you teach me about strategy?”
This is hard. Your manager has to think of how to teach you this intimidating, complex, large topic of strategy.
✅ “I drafted a strategy doc. Could you tear this apart? What are you skeptical about? No need to hold back. I want to make a strong argument and address any potential risks.”
Here we go. This ask minimizes cognitive load and is less intimidating to tackle, so it invites your manager to teach you about strategy on the job.
Other questions you can ask:
“What would you do differently? What’s missing?”
“What grade would you give this? What would make this an A+ in your eyes?”
“What is the most interesting 20% of this? Most boring 20%?”
“Could you mark which parts of this memo are confusing?”
“What would you do if you were in this situation?”
“Do you see any risks or logical gaps that I missed?”
Notice how these questions are designed to draw out insights from your manager.
When your manager is actively giving you their insights on how you can improve, this is coaching. This is mentorship. Don’t let it go to waste.
If you’re a manager (or want to be one), here’s how to coach your direct reports:
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
I rarely do free workshops, so if you’ve been curious about my course or if you found my Lenny podcast episode valuable, this is for you…
I’m excited to be featured in Lenny Rachitsky’s “The AI-Native Product Manager” series. As part of this series, I’ll be teaching a free workshop on the topic “How to Get Executive Buy-in as a PM.”
Product managers are one of the biggest groups represented in each cohort, and about 1/3 of my private coaching clients are product leaders. I believe the bar for product is getting higher each quarter, so if you are a self-aware and thoughtful product person, I want to help you stand out.
In this session, I’ll cover how to:
Present to impatient executives: Be prepared to move fast, speak directly, etc.
Manage up to senior leaders: Most PMs suck at managing up. We'll cover principles that will serve you now and throughout your career.
Anticipate questions and prevent skepticism: How to anticipate questions to avoid endless back-and-forth.
You will be able to apply these principles to stakeholders upwards, downwards, and laterally.
The free workshop will be on Friday, March 13 at 12:00 - 12:30pm ET.
There are already 4,584 people signed up, which is pretty nuts.
If you’re interested, click here to RSVP.
Is this your first time here? Subscribe (it’s free)
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Learn more about 1:1 coaching to sharpen your executive presence
✨ Course: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,500 tech operators have taken this course, and every cohort so far has sold out. → Save your spot in the May 2026 cohort