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.
To level up faster, 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 for 1:1 coaching to dramatically improve your communication and leadership, learn more about my coaching approach.
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.
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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
2026-02-18 21:03:14
👋 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 intensive course on Executive Communication & Influence for Senior ICs and Managers. Over 1,500 operators from Netflix, Anthropic, OpenAI, Figma, etc have taken the course.
✨ UPDATE: The March cohort is sold out, but the new May 2026 cohort is now open. → Save your spot
Read time: 4 minutes
Fundamentals is a new series that highlights my core concepts in communication, leadership, and influence. Even as my newsletter has grown to 75,000+ subscribers, I often find myself referencing these principles with clients and in my own work. Whether you’re new here or a longtime reader, this concept deserves a spot in your toolbox.
This week’s fundamental principle: Question behind the question
Before you launch into an answer that is overly tactical or too in the weeds, consider the QBQ. This will help you answer at the right altitude. (Practicing how to answer at the right altitude is a concept I teach in my live course.)
Thinking about the question-behind-the-question might feel like an extra step, but once it becomes part of your muscle memory, it only takes a few extra seconds. It becomes second nature. Many times, I don’t even actively think about the QBQ because my brain naturally goes there.
Some readers ask, “Can we just straight up ask ‘what’s the question behind the question?’” Personally, I don’t like doing this because it can sound a bit aggressive. I don’t want to risk insinuating that my recipient is being coy. Instead, I like probing to get a bit more context, or even better: asserting my interpretation and asking them to correct me if I’m wrong. Most people are very happy to tell you if you’re wrong.
Iff a journalist asks me a question, their underlying QBQ might be: “What is newsworthy and quotable here?” So I try to answer questions in punchy sound-bites that highlight what’s new/interesting. This gives the journalist what they want and is win-win.
If a senior exec asks you a question, the underlying QBQ might be, “How does this impact the business?” Execs are further removed from your work, and they usually care about driving revenue or saving on costs. Avoid diving straight into logistics.
If a prospect/customer asks you a question, they might not be able to articulate what’s really gnawing at them. I’ve noticed the best salespeople answer my tactical surface question AND go deeper to get at the root of the issue.
Here are a few reader comments I want to highlight:
“Earlier in my career, my instinct was to answer as fast as possible to show I was on top of it. Taking a moment to consider the question behind the question was something I had to learn and practice. Not an easy skill but important to learn.
I have found that taking a quick pause before answering gives me a chance to gather my thoughts and decide what approach to take.” - Josh
“I’m familiar with the QBQ and I’ve [been] practicing a lot… especially this part: ‘Your question-asker might not know why they feel skeptical, so you're trying to hit a moving target,’ made me realize that I too often take for granted that people know and have clear what they want to ask.
Which is rarely the case. This will definitely help me not get stuck in never-ending back-and-forth as I often do, moved by my goodwill.” - Concetta Cucchiarelli
After you read the article, reflect on these prompts:
Think about a recent situation where you felt like you kept repeating yourself or getting random follow-up questions. What signs did you notice that suggested there was a deeper question you weren’t addressing?
Consider the colleagues you interact with regularly. What are their typical underlying concerns or priorities? How can you proactively address these issues?
Watch out for the next time someone asks you a question you don’t feel like you have enough context to answer. Use this script to uncover their true concern:“Great question. If you could share a bit of context on what's top of mind for you, it’ll help me get a sense of what’s most relevant to share.”
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
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Learn more about 1:1 coaching to sharpen your executive presence
✨ Course: The March cohort has sold out. The new May 2026 cohort is now open. 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. → Save your spot
2026-02-04 21:02:47
👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer.
⛑️ If you’re looking for 1:1 coaching, I work with tech leaders on managing up, advocating for your ideas, and strengthening your executive presence. Clients include operators at Amazon, Meta, DoorDash, Atlassian, OpenAI, etc. Learn more about my coaching approach.
Read time: 4 minutes
I once knew a CEO who had a habit of telling people, “I know you better than you know yourself.”
Their reaction was, “You don’t know me. GTFO.”
The thing is, the CEO often had good insights about his team. But folks were too busy feeling unfairly labeled to listen.
If you try to tell people how they are, their natural reaction will be to push back.
The solution: Avoid overly broad claims. Stick to facts of what you are able to observe. And frame your ideas as what they are: observations.
For example:
🚫 “You are X.”
✅ “You come across as X.”
✅ “You might come across as X.”
✅ “You seem X.”
This language is intentional because I don’t want to trigger people to argue with me.
It is harder to argue with me if I say, “You come across as X” vs proposing that I somehow have special insight into who you are deep down.
As a manager, I only see a slice of who you are. I don’t presume to know who you are at your core—I only know how you show up at work, and how you come across based on how you behave and what you say. So my feedback will be rooted in that.
Sometimes a debate is healthy and exactly what you’re looking for.
Other times, a debate is a distraction. You have a point, but your recipient is too hung up on some other comment you made, that they can’t focus on your main point.
I’m hyper-rational, and many of my coaching clients are tech operators who are hyper-rational too. If they sense BS, they will call you out on it. They will want to debate you. They will want to show how you are making a logical leap, and how you don’t actually have the grounds to be making such a sweeping claim.
This is not productive. I do not want to trigger someone to debate me, especially if I’m pretty sure about my point and I want them to focus on my point.
Therefore, it’s to your benefit NOT to over-reach. Don’t give your counterpart anything to get distracted by.
Many problems can be avoided if you simply speak accurately. For example, see these two statements:
“X will Y.”
“X tends to Y.”
These two statements are not the same. The first implies complete certainty. The second implies that X generally does Y, but not always.
[Note: Don’t be too literal here. I’m not saying to never say “X will Y.” The context matters. If you are writing a strategy doc, you might say: “Investing in this channel will lead to more users.” The context itself implies that this is an assertion. Your reader likely knows that you can’t guarantee that this channel will lead to more users. In this case, the sentence structure is a reflection of your high conviction that this is the right path.]
Here’s an example of an overly-broad claim vs a narrower, more right-sized claim:
🚫 “You lack emotional regulation.”
^ This is a broad sweeping statement that assumes the person always lacks emotional regulation. Even if this is true, they are likely to feel threatened by this and want to prove how I’m wrong.
✅ “When you do X specific thing, you seem like you lack emotional regulation.”
^ This is a narrower claim. It’s more accurate and more objective. I point to the specific thing that leads me to believe the person could lack emotional regulation.
There is a difference in positioning, and it impacts whether your recipient hears you. It’s not only semantics.
If I say you lack emotional regulation, you might say, “Well Wes, I regulate myself plenty well in 90% of situations” and start debating me on this point.
If I say you SEEM like you lack emotional regulation, well, there’s not much you can debate there. I’m sharing how I’m interpreting your actions, and I’m clear that this is my interpretation, which might be how others see you, too. Most people are glad to hear how they might be viewed by other people. More on the importance of speaking accurately.
By phrasing your feedback more thoughtfully (which takes two seconds, as shown in the examples above), you can increase the chances your team actually listens without getting defensive.
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
PS Related reading for managers:
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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
2026-01-21 21:01:45
👋 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 intensive course on Executive Communication & Influence for Senior ICs and Managers. NOTE: The upcoming March cohort is 90% full. If you’re interested, I’d love to see you in class.
⛑️ If you’re looking for 1:1 coaching, I work with leaders at companies like Amazon, Meta, Atlassian, DoorDash, Anthropic, etc. Learn more about my coaching approach.
Read time: 4 minutes
Let’s say I send you a Slack DM that says, “Hey, this is a priority.”
What do you think I mean?
You should prioritize this over all other projects for the rest of Q1.
Focus on this over other projects if you’re on the fence.
This must be done by end of week.
This must be done by end of day.
Drop everything and do this in the next hour.
Trick question, because there’s no way to know.
To be clear, I like the word “priority” and use it myself. There’s nothing inherently wrong with the word, and I am not saying you should never use it. What I am saying is:
Vague language can have a large (negative) blast radius when used haphazardly. It can create anything from avoidable anxiety to hours spent going in the wrong direction due to miscommunication. Yet, it’s surprisingly common in the workplace. Most of us have used vague language at work, and have been on the receiving end of it.
Over time, I’ve realized it’s not helpful to say “ASAP” (and similar phrases like “time-sensitive” or “priority”) without additional context.
So how do you convey time-sensitivity in a more productive way?
Instead of talking about urgency in a vague sense, do these two things:
Talk about the sequence
Clearly define the timeline
By doing this, we move from an abstract sense of “yikes this is important and time-sensitive” to a concrete sense of what to do about it.
Here’s are scripts of what this looks like in action:
I’ve used this with more junior team members, and they’ve shared feedback that being so clear and explicit was helpful.
The benefit here is you show the stack rank of priorities. You reiterate the hierarchy of what to do, which is particularly useful if you have multiple tasks on the docket.
For example:
“By tomorrow…”
“By Thursday EOD…”
I always say that “over-communicating” is usually the right amount of communication. This is especially applicable when working with new team members, junior staff, external vendors, contractors, etc.
It’s even helpful with mid-level and senior folks:
🚫 “This strategy doc is a priority so we should review it soon.”
✅ “Let’s plan to review an initial draft of your strategy doc at our 1:1 on Thursday.”
This approach is helpful when delegating too. (Here’s more on how to delegate while maintaining high standards).
“If you only have time to do one of these tasks--do this one.”
“If you were to prioritize one goal this week, make it this one.”
This helps elevate one project/task over all others. This is useful if you want to emphasize one thing and really get your point across.
“I’m going to leave this here for you. You don’t have to do it immediately, but can you handle it by today at 3pm?”
“I need X by EOW. Items 2, 3, 4 can wait until next month.”
There are many things that aren’t hugely urgent, but still have to get done. It’s good to be clear on what can wait. Above, I show two different styles of communicating what doesn’t have to get done right away. The first is a bit more collaborative and the latter is more concise. I’ve used both styles depending on the person and project.
For related reading, here’s more on how to be concise.
“Here’s what I’m going to do if I don’t hear from you by 5pm …”
You should use this approach with judgment and finesse because it can be easy to overstep.
Use this approach for lower-risk items, like smaller/tactical decisions, tasks your manager has approved before, or ideas where you’re already generally aligned.
🚫 “Hey manager, if you don’t approve my proposal by EOW, I’m going to assume you’re on board with shutting down our current operations and launching this new business unit and having me lead it.”
✅ “Hey manager, if you don’t approve my email reply to our vendor by 5pm, I’m going to assume you’re good with it.”
You may think, “Am I at risk of being too specific? Is this being too detailed?”
Maybe.
But I think both managers and direct reports can generally benefit from being more specific.
As a direct report, you often to need to “assign” tasks to your manager as part of managing up. I loved when my direct reports were clear in sharing exactly what they needed from me, by when, and why. I could get back to them much sooner and remove myself from their critical path. I might say “I can’t do that,” but I at least knew what they needed from me without a doubt.
As a direct report, I appreciated when my managers understood that I can’t read their mind. Being more concrete allowed us to have more productive conversations and allowed me to allocate my bandwidth accordingly.
In closing: You can use words like ASAP, time-sensitive, and priority. But don’t ONLY say that and expect your recipient to read your mind. Make sure to add more context by using the scripts above.
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
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
✨ 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 upcoming March cohort is 90% full. → Save your spot
2025-12-17 21:03:17
👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, executive communication, and standing out as a high performer. For more, check out my intensive course on Executive Communication & Influence for Senior ICs and Managers.
⛑️ If you’re looking for 1:1 coaching, I typically work with director-level and above at companies like Amazon, Meta, DoorDash, Amplitude, etc. Learn more about my coaching approach.
Read time: 3 minutes
First, a few announcements:
1. As part of my yearly tradition, I’ll be taking a 4-week break from my newsletter for the holidays.
As usual, I’ll be taking the holidays to spend time with family, reflect on what I want to do more/less of, and set my intentions for the new year. I hope you have a wonderful holiday, and I’ll be back in your inbox on Wednesday, January 21, 2026.
2. Announcing: New March 2026 course cohort
I’ve opened a new cohort for March 2026. The course dates are Thursday, March 19 and Friday, March 20.
This year, I ran six cohorts and I’m humbled that every cohort has sold out. Over 1,700 operators have taken the course with a 4.6/5 star rating from 500+ student reviews.
Students and alumni are from companies like Uber, Amazon, Grammarly, Netflix, Workday, Meta, Google, Pinterest, Sephora, Twilio, Roblox, Shopify, Airbnb, Vimeo, Waymo, Figma, Unilever, HelloFresh, Cisco, Buffer, Peloton, 1Password, OpenTable, Microsoft, Lyft, Autodesk, Credit Karma, Stitch Fix, DailyPay, Lockheed Martin, Klaviyo, Hubspot, U.S. Bank, Novo Nordisk, Walmart, Plaid, Intercom, Coinbase, Coda, SoundCloud, Instacart, Samsung, Salesforce, Apple, Spotify, Anthropic, GitHub, Zillow, PayPal, Atlassian, Square, Stripe, etc.
If you’ve been wanting to invest in yourself and level up your executive communication, I hope you’ll join us. See the course details.
Here are my most popular posts from 2025. I’ve divided these posts into four categories. Feel free to start with the ones that jump out at you.
Happy binge-reading!
Why high performers make assertions: The difference between insights, suggestions, and assertions - An insight is just a starting point. The rare, courageous thing to do is to develop an assertion, i.e. a hypothesis and point of view that answers “so what?”
Stop apologizing for reasonable business decisions - Why saying sorry might unintentionally shift the power dynamics.
No, I don’t want to hop on a call - I do not want to hop on a call because you are too lazy to write a cogent message.
Take 3 minutes to delete these words and improve your writing forever - Before you hit “send,” delete these words from your writing. Your message will be stronger for it.
Use “but” strategically - “But” is a negating word. Here’s how to use this intentionally, so you sound direct and positive.
To sound more sincere, do this - If you aren’t careful, you may come across as less sincere because your writing doesn’t translate your intent.
Stop trying to change your manager - Because you don’t have the leverage to turn your manager into a different person. Here’s what to do instead.
Everything takes longer than you think - The problem isn’t that you’re not working fast enough. It’s that your expectations were never realistic to begin with.
What you give airtime to will expand - Successful operators intentionally direct their recipients’ attention. Focus less on what you can’t do, and more on what you can do.
How to delegate while maintaining high standards - This is for managers who want to delegate AND maintain a high bar for quality of work. Here are tactics I learned over time that made delegating easier.
7 Phrases I use to make giving feedback easier for myself - Here are practical phrases I use when sharing feedback because it allows me to speak freely.
Which of these are you most excited to read? Hit reply because I’d love to hear from you.
Thanks for being here, as always. Happy holidays, and I’ll see you in 2026.
Wes
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