2026-09-16 20:01:22
👋 Hey, it’s Wes. Welcome to my newsletter on managing up, leading teams, and standing out as a high performer. To level up faster, join my 2-day course on Executive Communication & Influence. → The November cohort is the last workshop of the year. Reserve your spot
An update about my newsletter:
I’m moving my newsletter from bi-weekly to an ad hoc publishing schedule. I recently started an exciting new project (will share more soon), and I only want to publish when I have insights worth sharing with you.
My full archive will continue to be free at newsletter.weskao.com. No action needed—if you’re on my email list, you’ll get a notification when I publish. If you’re not subscribed and want to be notified about new posts, click the orange button above.
In the meantime, I want to share some of my most popular posts. Feel free to bookmark so you can refer back to this page.
How to give a senior leader feedback (without getting fired)
Why high performers make assertions: The difference between insights, suggestions, and assertions
Thanks for being here,
Wes
PS If you enjoyed this post, here are ways to go deeper:
To get my next blog post, join my email list (it’s free)
Learn more about 1:1 executive coaching
Improve your ability to sell your ideas, gain buy-in, and increase your impact in my 2-day workshop. Learn alongside operators from Netflix, Stripe, Meta, Figma, Anthropic, etc. → Save your spot
The November cohort is the last cohort of the year. After this, the next cohort will likely be in mid-2027. If you’re interested and the November 19 & 20 dates work for you, I hope to see you in class.
To date, over 2,300 tech operators have taken this course with 942 reviews and 4.6 stars. Here’s what fellow operators are saying:
Are you wondering if the course is right for you? Check out course details
2026-09-02 20:02:13
👋 Hey, it’s Wes. Welcome to my newsletter on managing up, leading teams, and standing out as a high performer. To level up faster, join my course on Executive Communication & Influence. → UPDATE: The September cohort starts in two weeks and is 85% full. Reserve your seat
Read time: 4 minutes
I originally published a version of this essay in May 2020. With the rise of AI, the post is even more relevant today.
Employees used to swim in their own lane. That doesn’t work anymore.
At all types of organizations, I’m seeing more high-performers get rewarded when they can handle projects end-to-end. If a normal operator is an infantry soldier, these operators are Navy SEALs. They can parachute into unknown territory to quickly assess a situation. Then determine the best course of action.
They are strategic, flexible, disciplined, and tight in their execution.
End-to-end marketers have vision, can develop a strategy, and can execute to bring their idea to life.
Another way to think about this type of person: they have all the skills, resourcefulness, and savvy to be an entrepreneur. But they often prefer to work within organizations as intrapreneurs.
Let’s say a marketer wants to create a video series for their company. Imagine these two scenarios:
Marketer #1:
Has the idea, but doesn’t know what to do next. Expects their boss or subject matter experts to fill in the details.
Marketer #2:
Drafts the script copy themselves
Films a quick video on their iPhone themselves
Edits in iMovie themselves
Creates a mock LinkedIn account to post the video themselves
Shows the leadership team what it would look like
In our new world, marketer #2 will win. Because they’re able to bring their vision to life, they’re more likely to get a green light to move forward.
***
End-to-end operators don’t worry about who’s responsible for the “strategy”, “planning”, and “execution”. They just get the job done.
End-to-end operators take a little and turn it into a lot. What others see as weak signals, an end-to-end operator sees as clues to validate or invalidate their hypotheses. All with the goal of getting closer to the truth of what customers want and how to better serve them.
Learn to translate your vision into reality. End-to-end operators aren’t reliant on someone else to tell them what’s feasible. They know enough to say, “Here’s the part we’ve got under control. Here’s the hard part. I might not be able to build it all myself, but I know enough to write a spec.”
Practice switching between strategy and execution. Zoom out at the high-level 10,000-foot view to drive the strategy. Then zoom in 5 feet above ground to personally execute on those recommendations. Repeat.
Act like an owner. Do what it takes to get the job done. Work back channels and understand incentives. Proceed with discretion for delicate matters. Learn how to manage tension.
Turn chaos into order. When things get messy, be the person who sees a way through. Help the rest of the team feel safe. Get the job done without drama or fuss.
Think ahead. Think rigorously. Surface trade-offs so your team won’t be surprised. Don’t assume constraints are as fixed (or flexible) as they might seem at first glance. When everyone else is looking at what’s right in front of them, think ahead about second and third order consequences.
Make assertions—even if you’re working with imperfect information. Where can you raise the bar on what you’re doing and what’s next? What are weak signals worth exploring? It’s your mission to recognize opportunities and then fill in the blanks.
Assume you’re a team of one. This applies especially to the first marketing hire on a lean team. You might tap into designers and developers on the team, but you might not have your own dedicated team yet. You’ll be expected to identify what you need, why you need it, and to find the most collaborative way to get it done. This includes utilizing internal and external resources to help bring your vision to life.
Learn how to learn. You don’t have to be a channel specialist, but you can quickly learn enough about a subject to make smart decisions and execute. You’re comfortable reviewing data and turning it into actionable recommendations. At the same time, you’re deeply empathetic and view empathy as directly related to business success.
Cross train and develop skills in adjacent areas. MMA fighters don’t only know boxing. They know Muay Thai, Brazilian Jiu Jitsu, Taekwondo, Krav Maga, and more. This helps you attack a problem from different angles to find the best solution.
***
You likely have some elements of being an end-to-end operator already. Fill in the gaps that will let you operate even more independently.
When you can bring ideas to life with little outside help, you’ll become the most valuable operator in your company.
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
PS If you enjoyed this post, here are ways to go deeper:
To get my next blog post, join my email list (it’s free)
Learn more about 1:1 executive coaching
Improve your ability to sell your ideas, gain buy-in, and increase your impact in my 2-day workshop. Over 2,300 tech operators from Netflix, Stripe, Meta, Figma, Anthropic, etc have taken the course. → Save your spot
A few updates:
The September cohort starts in two weeks and is 85% full. If you’re interested in joining, sign up in the next few days.
The November cohort is the last cohort of the year. After this, the next cohort will likely be in summer 2027.
If you are a leader who wants to send your team, I offer $100 off for groups of 5+ people. Teams from Shopify, Meta, Atlassian, Canva, etc have taken the course together, and are benefitting from having shared shared language. Hit reply and I’ll send more info.
To date, over 2,300 tech operators have taken this course with 942 reviews and 4.6 stars. Here’s what fellow operators are saying:
Are you wondering if the course is right fit for you? Check out course details
2026-08-19 20:03:42
👋 Hey, it’s Wes. Welcome to my newsletter on managing up, leading teams, and standing out as a high performer. To level up faster, join my course on Executive Communication & Influence. → UPDATE: The Sept and Nov cohorts are the last cohorts of the year.
I originally published a version of this essay in May 2020. Enjoy.
Read time: 4 minutes
In an ideal situation, marketing and product teams talk to each other. What gets built is something people want because marketing is built into the DNA of the product.
But in reality, marketers are put in a tight spot. Your CEO comes to you and says, “We have a product launch coming up. Here it is. We need you to market it and make people want this.”
You’re thinking, “I wish you had looped me in earlier… If it had this feature, or that feature, it would be a lot easier to market.”
But it doesn’t have those things. And at this stage, you can’t change the product.
So what do you do? Turn bugs into features.
In software development, a bug is an error, problem, or unintended flaw. When you get an error message, or something won’t load like it should—those are bugs.
Bugs are negative. The running inside joke is engineers will claim a bug is actually a feature.
That’s not necessarily true with software… But luckily in marketing and positioning, we actually can turn bugs into features. The best marketers and brands do this regularly.
When you turn bugs into features, the things you thought you were errors, constraints, liabilities about your product, could actually become selling points.
Turning bugs into features is a frame shift.
The goal is to see your own product with fresh eyes. Features that you thought were initially bad might end up being what you emphasize. Those features might be perfect for a different kind of customer or in a specific scenario.
Instead of having a knee-jerk reaction and prematurely rushing to change your product, you can save hundreds of hours by working with what you already have.
You can show customers (and realize yourself) that X feature is actually exactly what certain customers needed all along. By doing this, you increase perceived value and become more prized in your customers’ mind.
Here are three examples:
In the 1960s, Avis was the #2 car rental brand and Hertz, their competitor, was #1. Back then, it was blasphemy to market anything but being #1 in your category.
But Avis turned the fact that they were #2 from a bug into a feature. They messaged that #1 brands don’t try as hard. But because Avis was #2, they’d go the extra mile for you. This caught customers’ attention and built trust in Avis.
One-fifth of all fruit and vegetables are thrown out because of small imperfections. This causes a lot of waste. So a French supermarket turned a bug into a feature:
They marketed ugly fruit as quirky, irreverent, interesting. This gave customers a story to tell when their friends came over and saw this weird looking apple or funky looking banana.
They repositioned a bug as a feature. It turns out, the ugly fruit was such a hit that it sold out faster than normal fruit.
If you think your category is boring, think about trying to market a trash can. Except Simplehuman, the high-end trash can company, turned a category that was completely utilitarian, into a design-driven, luxury experience. Some of their trash cans sell for over $300 and they have a cult following.
NOTE: When I first wrote this in 2020, the trash cans were $150. I just went on their website and the two items I clicked on were both $300. Inflation is real.
Turning bugs into features is one of the easiest and most powerful ways to create a frame shift. Whatever you do, make it intentional.
If you’re going to do something anyway, frame it as an intentional choice. Frame it as a selling point, a prize the customer gets to have, a thoughtful decision, a thing you’re proud of that benefits your customer. There are tons of opportunities to turn bugs into features in your daily work and life.
Bug 🚫: “This sucks because there are major quality control issues...”
Feature ✅: “These ceramics are hand-made, so each piece is unique and will have minor differences.”
Bug 🚫: “I don’t want to do X. I don’t enjoy it.”
Feature ✅: “I could do X, but you mentioned wanting me to focus on Y because [why it’s more highly-leveraged].”
Bug 🚫: “This product is too basic. It doesn’t offer enough features.”
Feature ✅: “We do one thing and one thing only: X. This lightweight solution is for folks who don’t want bells and whistles.
When you feel frustrated by the product you have to market, think about how you can turn a bug into a feature.
Is your product “too simple” compared to competitors? Maybe simplicity is exactly the value proposition that a specific type of customer is looking for.
Or vice versa. If your product is “too complicated” compared to your competitors, maybe there are customers who want a comprehensive, heavy duty product.
Ask yourself:
What’s the thing you think you have to hide about your product? Is it something you can emphasize instead?
When you have a constraint, don’t automatically think, “We need to gloss over this or we need to downplay it.”
Turn bugs into features: The things you feel are a setback, could be the very things that makes your product stand out.
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
PS If you enjoyed this post, here are ways to go deeper:
To get my next blog post, join my email list here
Learn more about 1:1 coaching to sharpen your executive presence
Improve your ability to sell your ideas, gain buy-in, and increase your impact in my 2-day workshop. Over 2,300 tech operators have taken this course, and you’ll learn alongside mid-career operators from Netflix, Stripe, Meta, Figma, Anthropic, etc. → Save your spot
I’m excited to share that I just opened a new November cohort—this will be the last cohort of the year.
This is the first time I’ve had two cohorts open at once (Sept and Nov). Since the course is live, I often hear folks ask if there’s another option for workshop dates due to scheduling conflicts. Hopefully having more dates is helpful as you plan the back half of your year. (Also, how is it already mid-August?)
I’m planning to run significantly fewer cohorts in 2027 because of an exciting new project I’ll share more about soon that will take up most of my bandwidth. In the meantime, I’m tentatively thinking there will be two cohorts next year. This means there’s fewer opportunities to experience this intensive, condensed experience for yourself and your team.
Speaking of teams, the only discount available is $100 off for teams of 5+ people. In each cohort, there are multiple teams who take the course together, including folks from Shopify, Meta, Atlassian, Canva, etc. Hit reply and I can share more.
If you’ve heard great things about the workshop, I’m here to tell you those things are true. :] To date, over 2,300 tech operators have taken this course with 942 reviews and 4.6 stars.
Are you wondering if the course is right fit for you? Check out student reviews and course details here.
2026-08-05 20:03:57
👋 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, Google, Stripe, Anthropic, etc. → Save your spot in the September cohort
Read time: 6 minutes
“It will take too long to explain how to do to this.”
For years, I resisted delegating because it was faster to do the task myself. Intellectually, I understood the benefits of delegating, including the ability to scale myself, work through others, increase my impact, etc etc etc…
But carving out the time to explain all the nuances of a task felt like a lot of work. I was afraid I wouldn’t explain well and the person wouldn’t do a good job, which would lead to me redoing the work anyway.
One day, I realized that having a checklist might help me quickly identify what to tell someone outside my own head. I’ve since used checklists like the below on hundreds of requests for others. It works in a variety of situations where you need to establish shared context:
If you used to do the task, and are training someone else to do it going forward
If you’re not sure how to do a task, but you’re looping in a cross-functional partner to do their part in a project
If you want to use AI as a thought partner and you want it to give you advice that’s more relevant to your situation
Here are questions I ask myself so I can confidently share context when making a request:
1. What does this person know? What’s new for them?
Considering your colleague’s existing knowledge will help take yourself out of your own head and into theirs. From this question alone, you’ll remind yourself of what they already know (that you can explain more quickly or build on) and what’s new for them (that you probably wouldn’t remember was new for them until you consciously thought about it). This has the positive effect of making you more empathetic and patient.
Every situation, project, etc will be different, so use your judgment. For example, you’d share different context if your colleague is already working on a part of a project and you’re now bringing them into a different part of that project, vs if that same person were hearing about a project for the first time.
2. Why are we doing this?
If the task requires judgment, which almost all beyond the very basic tasks do, you want to help them make the right call when you’re not looking over their shoulder. Sharing the “why” behind the task means they won’t be overly reliant on following mechanical directions or step-by-step instructions.
Also, knowing how your part fits into a broader project makes any task feel more rewarding. You can see how your work is part of something bigger.
🚫: [Silence]
✅: “This matters because…”
✅: “Our goal is to vet which micro-influencers to reach out to for our upcoming campaign. We want to make sure they’re a good fit for the brand and this specific launch.”
✅: “Once you finish this, we’ll share it with X team and they’ll take it and…”
3. What do they need in order to do this task?
This includes access to tools, platforms, spreadsheets, docs, assets, budget, people, etc. Have this ready beforehand, or be ready to list this out verbally so the person can get these assets on their own. This is like mise en place in cooking. You want to gather everything the person might need.
4. What does great look like?
Try to “show, not tell” what great looks like. For example, share mock ups, examples, screenshots, docs, analogies, etc. You want to help them pattern match and viscerally understand what you’re saying. This is where an example can be worth a thousand words.
Even if you don’t have a one-for-one example because the thing you’re asking for is new, you can show examples and say “It’s like this, except…”
🚫: [Silence]
✅: “The final document should look similar to this.”
✅: “Here are a few examples of strategy docs. Yours doesn’t need to have the exact same sections, but notice how these docs cover the ‘why now?’ of a problem and [insert other things you want to point out].”
5. What’s the timeline and priority level?
You’ll want to note if this is a “do this in the next few hours” or a “sometime this week” or “sometime in the next two weeks” type of task. Avoid phrases like “ASAP,” “urgent,” and “priority” because they are too vague and can increase stress levels unnecessarily.
Re: how much time to spend on a task, it’s not always obvious what’s considered “good enough.” I’ve delegated tasks, but when the person delivered their work, I realized they were more detailed than I needed them to be. I didn’t properly set expectations.
I like asking my colleagues to give me a heads up if they’re partway through the project and realize my estimate is off. There’s no shame in this, so don’t blame them or assume they’re “working too slowly.” If you are delegating to junior team members, getting visibility into their process will allow you to help them be more efficient. In my experience, though, what seems like a speed issue is often actually a scope issue, so it’s not something that can be solved by simply trying to work faster.
6. What’s most likely to go wrong? What can I do to prevent this from happening?
These two questions pretty much cover 99% of derisking. If the stakes are low, spend less time on this. If the stakes are high, come up with a more comprehensive set of risks so you can assess the likelihood and impact of each issue. What do you not want the person to do?
🚫: [Silence]
✅: “I don’t need paragraphs of explanation or background about each customer. I only need the name of the customer and a few bullet points about why you picked them. From there, I’ll look up each customer you recommended and review their profile myself.”
To recap, here are the questions:
What does this person know? What’s new for them?
Why are we doing this?
What do they need in order to do this task?
What does great look like?
What’s the timeline and priority level?
What’s most likely to go wrong? What can I do to prevent this from happening?
These questions are a starting point, so there may be questions you want to swap out or add that are more specific to your situation. I encourage you to create your own go-to questions.
The next time you delegate or make a request for help on a project, give these questions a try. I’d love to hear how it goes.
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
The cohort next month will be the second to last cohort of the year. If you’ve been thinking about joining, check out the course details.
Here are new student reviews from the cohort a few weeks ago.
“Just the right amount of time to get the tools and exercises to feel equipped. Wes Kao’s principles, tools are fantastic. Loved how course was structured around exercises and realistic scenarios.”
- Lilly Chen, Product Manager II @ Google
“I left with concrete actions to improve my communication, and a feeling that this is a lifelong exercise and skill well worth investing in.”
- Anita Lillie, Senior Principal Product Designer @ Amplitude
“Really helpful. Wes went beyond theory and gave practical examples and tips. Love the cues that Wes gave to start addressing some of the issues that I find myself frequently dealing with (self sabotaging, indirect communications, rambling).”
- David Li, Lead Product Manager @ Yelp
“This course was phenomenal. Effective communication is hard, and even when you think you’re good, you realize you have a long ways to go. If you are looking to improve what you bring to the table in conversations you’re having with clients, peers, leaders and more, I highly recommend taking this course with Wes.”
- Cooper Armstrong, Enterprise Account Executive @ Chainguard
If you’re interested in joining, the upcoming September cohort already has students from Google, Figma, Toast, Amazon, Perplexity, OpenAI, Netflix, etc. Join us.
→ Reserve your spot in the September cohort
2026-07-22 20:03:05
👋 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 intensive course on Executive Communication & Influence. → Save your spot
⛑️ If you’re looking for 1:1 coaching to dramatically improve your communication and leadership, learn more about my coaching approach.
Read time: 3 minutes
There is a difference between work that seems useful vs work that’s actually useful.
Your work can be:
Defensible
Meet all stated requirements
Look fine at first glance
Be wrapped in professional polish
...and yet still fundamentally miss the mark on adding actual value.
It’s a natural human tendency to optimize for “not getting into trouble” rather than “figuring out the truth.” Even environments that pride themselves on rejecting mediocrity can fall into this trap of surface-level adequacy.
I care a lot about quality, which is a tough topic that often feels subjective. But one question I’ve started asking myself and my clients who care about quality is:
“This is defensible. But is it good?”
***
Do we need to see a spike in abandonment rates to make our product flow better?
Do we need to wait until customers riot before we improve our service?
Do we need to wait until users start deleting our app en masse to make things better?
Many of us wait for dramatic, obvious clues that things are going south, assuming anything before that is fine.
I believe it provides a false sense of security to wait for obvious signs that something is wrong before you wonder if something is wrong.
One of my coaching clients is a COO. Their team keeps using the excuse of wanting more data before making an improvement to the product.
They say, “The unsubscribe rate of X email is in line with the average. We don’t need to improve our emails.”
Folks, we can use our eyes here.
The emails are confusing, ugly, and adds no value. We don’t need to gather data to tell us this. We are allowed to use our judgment. We MUST use our judgment.”
They are a small startup, they are not in a position to A/B test everything in order to make decisions. They have to use their creativity and taste.
Another client has gotten feedback for not being vocal enough and not having enough of a perspective. He’s a talented engineering manager, and his response was, “I feel like if the idea is decent, I’m good to go with it.”
If you work with decently competent people, there are many ideas that are decent. Is “decent” good enough? It depends on the situation, and of course you shouldn’t try to maximize everything.
But many times, “decent” doesn’t meet the bar for allocating finite budget and finite headcount on an initiative. If you only get a limited number of bets per quarter, you should have conviction that this is the bet you want to make.
There are many ideas that are okay. It doesn’t mean you should drop what you’re doing and do those ideas.
You can run around doing busy work, following “processes,” and doing defensible stuff like setting up customer calls, but still not make real progress.
It requires intellectual honesty to make sure you’d stand behind the decision you’re making. Don’t hide behind doing things that are defensible, but don’t actually move the needle.
Last week, we wrapped up another amazing cohort. The latest student reviews are rolling in. Here’s what your fellow operators are saying:
“This course was very valuable to me. I wish I had taken this course sooner. As an experienced designer, I am very comfortable with explaining the rationale behind decisions, but I struggled with the dynamics of communicating ideas to different stakeholders at different altitudes. This course was exactly what I needed to sharpen my skills. Thank you so much.”
- Taís Lessa, UX Design Lead @ Wikipedia
“The course was extremely well thought out, felt applicable in my every day work, and provided clear actionable tips I can use immediately. Highly recommend and would love to do another course with Wes again.”
- Grace Dawson Beatty, Head of Product Marketing @ Plaid
“This was a GREAT course. I don’t know where else I would have gotten such quality content, packaged well, and taught by a world-class person that’s been-there-done-that. The hardest part isn’t attended this class (which you should ABSOLUTELY do) but incrementally applying the tips, tricks, and tactics learned. Thanks, Wes!”
- Chris Viglietta, Workshop Instructor @ Clay
“The value from this course was evident the moment I returned to work. I feel like I can see under the hood of all my incoming and outgoing Slack messages now.”
- Evan Hart, Motion Designer @ Figma
“Dense, actionable, well-structured, and paced to keep you engaged. Even if you think you’re quite good at written (and spoken) communication, you’ll leave with fresh insights and stronger skills. I joined as a long-time subscriber to Wes Kao’s newsletter, and I’m glad I did. I still learned a ton of new stuff!”
- Kalina Tyrkiel-Szymańska, Senior Content Designer @ Zendesk
If you’re interested in joining, the upcoming September cohort already has students from Amazon, Capital One, Figma, Perplexity, GitHub, Netflix, OpenAI, etc.
→ Reserve your spot in the upcoming cohort
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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 has sold out. → Save your spot
2026-07-08 20:03:27
👋 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. UPDATE: The July cohort is 95% sold out, but a new September cohort is now open. This will be the second to last cohort of the year.
Read time: 4 minutes
I remember one of the last interviews I did before starting my own company. The interviewer asked, “Could you tell me about a time when you solved a problem?”
What I wanted to say: “I solve problems all day. I wish there weren’t so many problems to solve. But I can’t think of one at this moment.”
I can’t remember what I ended up saying.
But what I can tell you, is that I have a deep distaste for behavioral interview questions.
I hated them as a candidate, and I hated them on the other side as a hiring manager. I believe this type of question doesn’t tell you much except whether the candidate prepared a set of stories beforehand.
But, alas, behavioral questions are still the default for many organizations. Recruiters and hiring managers will use how you answer these questions as a proxy for your effectiveness. So if you’re interviewing, it behooves you to learn how to answer them well.
For example, you’ve likely heard of the classic STAR (situation, task, action, results) framework. As a hiring manager, I often got lost in candidates’ answers because they told stories that were meandering and hard to follow.
I realized that candidates were using the STAR method, but accidentally spending too much time on the situation part of STAR. Backstory scope creep was happening.
Maybe it’s because you’re getting warmed up, or because you believe describing the situation is crucial for the rest of your story to make sense.
The problem is, when you spend too much time describing the situation (i.e. the context or background), you take time away from the other parts of STAR, all of which are more interesting and relevant. The situation should be a brief set up, so you can let the other parts of your STAR story really shine.
Most candidates speak for too long in their initial response. I’ve been guilty of this myself. I’ve seen my interviewer’s eyes glaze over. I’ve listened to myself talking in real time, and thought, “Why am I saying this? This is boring and kind of irrelevant.” If you are ever bored by what you’re saying, don’t ignore it. Wrap up your thought, and pivot.
When in doubt, aim to keep the situation part as short as possible. Aim for 2-3 sentences and 10-15 seconds, then move on to the task, action, and results. This allows you to allocate the bulk of time on what the problem was, why it mattered, what you did to solve it, and how much money you made for your company. Those are the juicy parts.
Zooming out, this doesn’t only apply to interviews. I realized I have a tendency to optimize for being comprehensive, when often, the actual better goal is to be interesting. If you are the same, then switching from “I need to tell it all” to “I need to tell what’s most useful and relevant” will take practice. A lot of continuing to improve is simply realizing your own tendencies, then catching yourself and consciously choosing a different approach.
In terms of getting to the root cause of where this tendency to be comprehensive comes from, I believe it’s partially because we’re afraid if we leave out a detail, we’ll be punished for it. And in the past, perhaps we were. So it feels safer to err on the side of sharing too much.
On the other hand, deciding what context to include requires you to have a point of view. It requires you to choose “this, not that.” Your choices might be wrong, and that feels a little stressful.
But NOT making a choice, and defaulting to sharing everything with equal weight, is not the solution. You will end up overwhelming your stakeholder, in this case, the hiring manager. They want to get an accurate sense of your abilities and experience, but won’t be able to, because they’re asleep.
It’s tempting to want to be thorough, even in times that don’t require it. You must fight this temptation. Keep the backstory short, so you save time for the good stuff.
We’re just one week away from the upcoming cohort of Executive Communication and Influence for Senior ICs and Managers. There are a few seats left. If you’re looking to get noticed by senior leadership, earn a promotion, or improve your ability to influence without authority, I would love to see you next Thursday and Friday. Grab one of the remaining seats here.
If you can’t make the July cohort, I’m opening the new September cohort today. This will be the second to last cohort of the year.
With AI reshaping the way every knowledge worker does their job, I believe skills like clear thinking, having a point of view, and strong communication are more important than ever.
In this latest cohort, I’ve added a new section on how I personally use AI to improve my communication. I won’t cover prompts. This is about using AI as a thought partner without turning off your own brain.
If you’re curious whether the course is for you, here’s what fellow operators are saying:
“Highly recommend this course for any seniority. Practical lessons and engaging exercises/homework. Ready to implement my learnings tomorrow.”
- Jenna Ochoa, Sr. Manager Partner Marketing, Strategic Alliances @ Zendesk
“I’ve learned a ton on this topic through intuition and experimentation, and now there’s Wes’s clear frameworks, rationale, and principles to pair it with. Along with practical exercises, I am exiting this course immediately better. This might be the first professional course I can internalize and actually apply on a daily basis.”
- Celeste Ridlen, Head of Research & Insights @ Robinhood
“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, easy to be an armchair expert but these helped me feel where my deficiencies are.”
- David Illing, Senior Data Engineer @ Credit Karma
“The course shows what great communication looks like and the bar 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 my communication skills.”
- Srihari Venkatesan, Engineering Manager @ Apple
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