2025-03-19 20:03:40
👋 Hey, it’s Wes. Welcome to my 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.
Read time: 5 minutes
Today’s newsletter is sponsored by Balsamiq. If your team is stuck debating specs, you’re not shipping—you’re stalling. Balsamiq helps you sketch rough ideas fast, so everyone’s aligned before work starts. No bloated tools. No waiting on a designer. No walls of text. Just clarity. Try Balsamiq free for 30 days.
One of the things that never fails to surprise me is how often you have to repeat information for people to really internalize it.
This applies pretty much at all levels, even when folks are earnest and trying their best to pay attention. It applies when you’re managing up, down, and laterally.
Today I want to share an example of why you have to repeat key information (especially potential trade-offs) and remind senior leaders of your strategy not once, not twice, but throughout the life of a project.
Tell me if this sounds familiar:
You: Hey senior leader, I want to give you a heads up about X risk. Do we feel comfortable with this?
Executive: Yes, that sounds like a reasonable risk. Thanks for surfacing. Let’s do it.
[One month later]
Executive: How did X risk happen? Did we know about this?? Why didn’t we prevent this???
This happens surprisingly often.
Every day, good operators get blamed for stuff that isn’t their fault because they haven’t set expectations properly.
Here’s how to ensure the enthusiastic yes you started with actually lasts throughout your project.
Why might your leader be surprised by something they already agreed to?
First, because they have a lot going on and might not remember the details of your project. Senior leaders typically oversee multiple direct reports, multiple teams, and multiple functions—each with projects, updates, decisions, risks, trade-offs, and evolving circumstances.
Second, because even if you mentioned a risk proactively, most humans secretly hope the downside situation won’t actually happen. Even if it’s an acceptable risk, we still hope for the best case scenario. Even if your leader admits you did mention that X issue might happen, they might still be surprised when it actually happens.
Both elements above—your leader being busy/having a lot going on in their world and understanding downside but hoping for upside—these are structural issues. These are big issues to fight against.
Which is why mentioning a risk once isn’t enough.
One of my coaching clients is a PM pitching their CEO on a new product launch. It took months of convincing, but eventually the CEO agreed. The PM was clear about the biggest risk: potential cannibalization.
PM: “If we launch this new product, our existing product will likely be cannibalized. We’re not sure for how long, but perhaps 6 months. I want to make sure we’re okay with this.”
CEO: “Okay, this makes sense. I agree with moving forward.”
Later that year, the product went live. The sales numbers started rolling in, and, lo and behold, the existing product took a hit:
CEO: “Wait, why is our existing product being cannibalized here?? This is really bad.”
PM: “Umm we discussed this when kicking off this initiative that our existing product would be cannibalized, at least for a bit until both business lines stabilized.”
CEO: “I don’t know why we didn’t prevent this more. I might have agreed, but didn’t realize our business would take this big of a hit. I’m not sure this new launch was worth it. Honestly I don’t even know why we decided to do it in the first place.”
Unfortunately, despite the work that went into the launch and its success in hitting targets, the project felt like a disappointment.
What could the PM have done to prevent this?
Most operators get buy-in at the beginning of a project—this is what allows you to move forward in the first place.
Some operators will close the loop with a recap at the end of a project.
But in my experience, very few operators reinforce expectations in the middle.
This is leaving a lot of proverbial money on the table because “the middle” is actually the MAJORITY of how the project exists.
If you don’t continue to “sell” during this phase, you risk losing the momentum you started with—or risk losing support for finishing the project at all.
Let’s continue with the PM and CEO example above.
The PM should have built alignment throughout the launch process.
You can do this by reminding your audience of your strategy at multiple touchpoints:
Beginning: Get initial buy-in for the strategy and trade-offs.
Middle: Remind the team of the strategy, including setting expectations about trade-offs, what you’re doing to minimize the impact of these trade-offs, and why the upside is worth pursuing.
End: Proactively share context as you share metrics. Instead of expecting the numbers to speak for themselves, add narrative to numbers. Contextualize what these numbers mean so your audience knows what’s “good” or “bad.”
“Selling” in the middle phase might look like sharing reminders for anything that might come as a surprise. For example, in a bi-weekly update, you could include a line like, “We’ve accounted for temporary cannibalization for the first 6 months of the new product. I’ve built this into our sales forecast and are aware this will likely happen.”
We must reduce cognitive load as much as possible for our recipients.
We cannot expect others to read our minds, connect dots, or keep our projects top of mind.
Remember: Buy-in is not binary. For projects with a longer time horizon, you need to get buy-in on a continual basis to remind your leaders and team about your strategy.
Have you ever had a leader act surprised by something they previously agreed to? What was your response? What’s one situation where you could reinforce buy-in throughout the project?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
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2025-03-12 20:02:11
👋 Hey, it’s Wes. Welcome to my 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.
✨ Course update: I opened the new May 2025 cohort a few weeks ago, and it’s already 40% full. This cohort will be the only opportunity to take the course this spring (the next time the course will be offered will be in the summer). To learn more, here are the course details.
Read time: 6 minutes
We all know comparison is the thief of joy, but for most of my life, I was very skilled at comparing myself to others. I could describe in great detail and specificity exactly where I was lacking, and why someone else was better than me.
I was proud of my intellectual honesty. Weaker operators might make themselves feel better, but not me. I was committed to staring my weaknesses in the eye.
Having an unvarnished view of myself was useful, to a point. On the one hand, the paranoia fueled me to work extremely hard. I wasn’t delusional about where I stood, and I was constantly learning from others around me.
On the other hand, most of the time, I felt shitty about not making enough progress vis-a-vis my peers.
When a friend would compliment me or be impressed at something I accomplished, I was quick to point out a bigger fish.
One day, I realized: The urge to put myself down is an invented obligation.
The good news was this was all in my own head.
The bad news was this was all in my own head.
If I wanted to stop being in a rat race, it dawned on me that I could…choose not to enter another race race. But I had to consciously choose to stop participating in this imaginary competition.
I wrote the below on LinkedIn in October 2023, when I had just left my startup, Maven. This was the first time popping my head up after three intense years of company building, and I spent that summer taking stock of where I was and reflecting on what I wanted to do more/less of. Could I be a more hospitable, friendly voice to myself? Yes, I realized.
Here’s the post below.
There’s always another rat race if you want to be a rat in a race. When I graduated from UC Berkeley, I thought, “Now I’m no longer in the Haas student rat race.”
When I left the fashion industry and joined a startup, I thought, “Now I’m no longer in the corporate retail rat race.”
When I moved from SF to New York and bootstrapped a company, I thought, “Now I'm no longer in the Silicon Valley tech operator rat race.”
When I started growing my audience as a creator, I thought, “Now I’m no longer in the FTE rat race.”
When I was a solopreneur in between my two companies, I thought, “Now I'm no longer in the CMO path rat race.”
When I started a VC-backed company with Tier 1 investors, I thought, “Now I’m no longer in the solopreneur rat race.”
When I left my startup and started working on my own, I thought, “Now I'm no longer in the tech founder rat race.”
Each time, I just joined a new race, with new rats.
I thought I was out of the race, until I looked up and found myself suspiciously comparing myself to others without realizing it was happening.
Now, I want to break the cycle. It's enough racing. I've raced since I was 16 years old, and I'm 37 now. I'm actively breaking the cycle, and it will take effort. It's moving a battleship in the opposite direction than the one it's been sailing in for years.
“Already” is the word for this spring.
I want to remind myself of what I already have, how I’m already achieving my goals, and how I’m already the person I want to be.
Flash forward to March 2025, and I’m proud to say I’ve made a lot of progress. I definitely still catch myself feeling jealous of others (that probably won’t ever go away), but most days, I feel motivated by my work and think less about what other people are doing.
If you are prone to beating yourself up for not being as “far along” as you should be, let this be a sign that you can change how you think too.
Obviously, I’m not saying you should stop improving or get complacent. Like many things, the answer is not one or the other: You can recognize how you’re already the person you want to be in some ways AND continue working towards being more of that person. You can acknowledge how you’re already doing some things right AND continue sharpening your skills.
If you are someone who is too hard on themselves, you may need to actively train your brain to see through a different, more positive lens.
No, you won’t lose your edge or get soft. You are probably too high strung to ever be so relaxed that you lose your edge.
The risk is actually that when you’re overly focused on the negative, you develop a warped view of your abilities. You become under-confident compared to your actual skills. This negatively impacts the way you communicate with others, the way you advocate for your ideas, and how willing you are to make bold moves.
It warps your ability to see clearly. For example, you might think your situation is futile when it’s not. You might see a bigger gap than what’s actually there, and give up when you didn’t need to.
Meanwhile, focusing on ways that you are already doing well, already winning, already doing great, is a way to have a more ACCURATE view of your situation. When you are overly anchored on the negative, you need to reset by swinging the pendulum to be overly positive to have a chance at landing someplace neutral.
I call this type of thought experiment a “rubber band exercise”: You stretch the rubber band so you when you release the tension, the rubber band is a bit looser.
So here’s a rubber band exercise for you. Ask yourself:
In what ways am I already the person I want to be?
How am I already achieving my goals?
How am I already becoming who I want to be?
Remember: You can choose to run your own race. You can choose to celebrate what you’re doing right, and how you’re already the person you want to be.
Do you tend to compare yourself to others to a point where it becomes counterproductive? More importantly, how are you already on your way to doing the things you want to do or being the leader you want to be?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
Since last fall, I’ve been focused on 1:1 executive coaching with a select group of clients, and on making my course the best communication and influence course for hands-on builders.
Every cohort, I meet the most interesting, sharp, thoughtful operators and I’m constantly in awe that I get to support leaders this like this.
We wrapped up the February cohort a few weeks ago, and I’m thrilled to share the latest student reviews:
“Wes’ course is a short, 2-day commitment that is packed with actionable advice and frameworks that you can put into practice immediately. This course changed the way I approach communication with my stakeholders.”
- Caro Galvin, Senior Product Manager @ GitHub
“I can't say enough good things about this course. Wes is so approachable and professional, and she offers an absolute treasure trove of resources, tips and frameworks that will change the way you approach your work and your life. If you're wondering if this course is worth the investment of time and money - the answer is a resounding yes.”
- Helen Jerman, Global Digital Content Manager @ ADI Global Distribution
“Great course! I appreciated Wes's actionable recommendations and the ability to practice tactical skills like rewriting communications of our own.”
- Cameron Langford, Founder & Principal Consultant @ First Principles Communications
“This was excellent. The course modules were cohesive and useful. The take-home materials we got have already been helpful to me in my day-to-day. Wes is a brilliant instructor and I particularly appreciated her feedback on the live exercises (rewrite this email, draft a script, etc.) for how targeted and direct it was.
It was also clear during the lessons that Wes was applying her own principles (signposting, right amount of context, etc.) to the course material itself. This made the lessons more effective, of course, but it was also a cool demonstration that ‘hey, this works’ that we could see for ourselves on the spot.”
- Tushar Chandra, Software Engineer @ Loop
“This course is a MUST, and one of the best learning experiences of my career. I can confidently say I would recommend this to anyone who is starting to interact more with leadership, or who wants to be prepared for when they do. (So…. Everyone.) I will probably never shut up about how much I loved this course and how immediately I am using the skills from it.”
- Desirae Odjick, Product Marketing Lead @ Shopify
The April cohort is full, but the May 2025 cohort is now open. The course dates are May 15 & 16 at 12:00 - 3:30pm ET with an optional Q&A afterward. If you’ve been thinking about joining, you’ll be in good company. I hope to see you in class.
→ Reserve your spot in the May 2025 cohort
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2025-03-05 21:01:58
👋 Hey, it’s Wes. Welcome to my 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.
Read time: 5 minutes
Today’s newsletter is sponsored by Balsamiq. Documents alone won’t sell your vision. But jumping straight to high-fidelity mock-ups slows you down. Balsamiq helps founders and PMs sketch and validate ideas fast. No fluff. No bottlenecks. No wasted time. Try Balsamiq free for 30 days.
There’s a scene in Civil War, where Kirsten Dunst is a war journalist mentoring an aspiring journalist.
There’s a shoot out, people are chopping each other up, and the 20-something-year old reporter says (paraphrased):
“Omg why aren’t we helping these people??”
Kirsten Dunst says (paraphrased): “We are journalists. It’s not our role to intervene. We document, so others can intervene.”
At that moment, I thought, “You know what, Kirsten Dunst, I respect that. That is some principled stuff right there.”
If you’re thinking the lesson of this post is “be objective, just show the facts,” you’d be wrong.
Because here’s the thing:
You are not a war photographer.
You are a product manager. You are a head of post-sales. You are a marketing lead. You are a GM. You are an engineering manager.
You actually ARE responsible for “intervening.” You are not simply documenting information for others to make decisions. When problems happen, YOU are the one who needs to solve them.
In my course, I bang on the drum of sharing your logic, being evidence-based, and explaining your rationale.
But I’ve noticed that some students, in an effort to be logical, swing the pendulum too far: They take “logical” to mean “facts only.”
“Facts only” is actually not as helpful in an organization as you might assume:
Asking others to interpret information adds cognitive load. If you only share information without a throughline, you’re forcing your recipients to do the heavy-lifting of interpreting what these facts mean. Humans are wired to conserve energy, i.e. they try not to think if they don’t have to. So if you’re relying on others to come to your same conclusion, they might never get there.
You have tacit knowledge your audience doesn’t have. “X fact obviously leads to Y conclusion” might feel true in your mind, but it’s often not obvious to others. Due to your proximity and lived experience with the issue, you have tacit knowledge you might not even realize you have. People living outside your head don’t have this context.
Facts can have multiple interpretations. This is why sharing the “so what?” is important. I can show the same data points to 10 different founders, and they could come up with 10 different interpretations of how they’d solve the problem—or whether they believe there even is a problem.
Being objective is good.
But when you are TOO neutral, you become detached—you withhold the emotional sentiment and your interpretation, which serves as important context.
Let’s say you share some not-great news with your executive.
Basically, when a leader hears a piece of information, they’re likely asking themselves: “How bad is this?”
If it’s not that bad, they don’t need to spend that much effort or attention on this. It’s low stakes enough that someone else can handle it, or it’ll handle itself, or even if things go wrong, it won’t do that much damage.
Leaders need to conserve their attention, so they are often assessing situations to be able to accurately diagnose how serious something is.
Acting too detached robs your audience of context clues about how serious an issue is.
When we have non-ideal news to share—the launch is delayed, a hiccup happened in production, there was an error that messed up the recent batch of X—we are afraid we’ll be blamed. This is a real concern.
But sometimes, this fear can manifest itself in overcorrecting and being too “facts only.”
Being overly matter-of-fact can make others think you’re spinning this news or hiding something: Does this person realize the gravity of what happened? Do they feel a little bad about it? Are they hiding something? They’re being so neutral it’s a little suspicious…
Luckily, you can strike a good balance:
🚫 Too groveling: “I’m so sorry. This is all my fault.”
🚫 Too detached: “An issue occurred and caused a delay. It affected X units over a one week period. It has since been corrected.”
✅ Just right: “An issue occurred, which caused us to need to toss half the units from the batch last week. This is pretty unfortunate, but luckily we caught it quickly and fixed it. We’ve also put fail-safes in place so it won’t happen again.”
In the “just right” example above, notice how I didn’t grovel or dwell for too long. I’m professional, concise, objective—and I still acknowledge that what happened wasn’t great.
Show that you understand the gravity of what happened because it shows you situational awareness and good judgment.
The next time you have negative news to share, be objective—but don’t be so matter-of-fact that you strip away emotional context that allows your recipient to understand the situation.
Acknowledge that what happened wasn’t ideal, then end on a positive note or redirect to mention what you’re doing going forward. Here’s what this looks like:
“This is not ideal, but [positive thing].”
“This was definitely disappointing, but [positive thing].”
“This was a miss because [impact]. Luckily, [positive thing].”
“This was a bummer and caused [impact]. Going forward…”
When you do this, you make it easy for your audience to understand the situation and therefore make a more informed decision as a team.
Have you ever been too matter-of-fact and detached? Or have you gotten information from a colleague who was like this? Hit reply because I’d love to hear from you.
Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
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2025-02-26 21:03:48
👋 Hey, it’s Wes. Welcome to my 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.
Read time: 5 minutes
Today’s newsletter is sponsored by Balsamiq. If your team doesn’t get it, they won’t build it. Specs get misread. Docs go ignored. Meetings drag. Balsamiq helps PMs, devs, and founders visually communicate requirements before work starts. No friction, bloated tools, or second-guessing. Try Balsamiq free for 30 days.
“If one says ‘red’ and there are 50 people listening, it can be expected that there will be 50 reds in their minds. And one can be sure that all these reds will be very different.” - Josef Albers, Interaction of Color, 1963
I read this quote from the German-American artist and educator, Josef Albers, and my first thought was:
Oh shit, this totally applies to operators.
If you say “good enough” and there are 50 operators listening, it can be expected that there will be 50 different ideas of what “good enough” means.
This is a problem (and opportunity) for you.
Most operators understand the concept of diminishing returns.
They might not use the term, but every time they say “it’s good enough,” they’re basically saying:
“I believe I’ve captured the value from spending time on this. If we spend more time, we might add minor gains, but those gains will be smaller and smaller. Therefore, it’s not worth my/our time to continue making this better.”
But the problem is, many people THINK they’ve hit diminishing returns, when they are actually nowhere close.
They stopped prematurely because it’s often not obvious if it’s worth the ROI to make your work product better. There is no hard and fast rule of “if this, then that” that applies to your situation. It’s highly context-dependent. You need to use your judgment.
Here’s an excerpt from my post called Are your standards too low? In defense of raising the bar:
For every team that says “This is as good as it’s going to get,” there’s a doppelgänger team out there who refuses to settle:
This team isn’t just ticking off boxes. They are innovating, challenging assumptions, and pushing the limits of their creativity.
They are always scanning for inspiration and keeping an ear to the ground for what customers want.
They realize they don’t have many levers, and can’t afford to cavalierly pull levers in a half-assed way.
They know there’s a spectrum of quality for any attempt. They know there’s no upper bound for how strong you can be at any skill where there’s craft and judgment involved, including writing, coding, design, sales, etc.
They acknowledge that aiming for a high bar can feel challenging in the moment, but being great at your job is rewarding and fun.
This team knows what excellence is and aims for it, sometimes hits it, and often acknowledges the gap between their vision vs their skill.
The second team doesn’t even realize they have low standards.
So the problem is… you might be the team that doesn’t realize they have low standards.
The opportunity is… you might be the team with high standards already, and if you aren’t, you can decide you want to raise those standards at any time.
I believe some assessments about “good enough” are more correct than others. In other words, not all 50 people are correct.
Example 1: Shipping a feature
The Navy SEALs say slow is smooth, and smooth is fast. This applies to knowledge work too: Shipping a careless attempt is actually slower net-net.
Let’s say you’re building a new feature.
“Good enough” means the feature adds value to the customer and you get an accurate sense of how useful it is. If this isn’t the case, then it’s not actually good enough.
“Good enough” does not mean, “My manager thought it was okay, so we shipped it and moved onto something else.”
People do the latter, then are surprised when no one is using the feature or customers are confused.
Yes, your customers are confused. Because the UX is confusing.
You do not get to act surprised about this.
The thing you shipped was not, in fact, “good enough.”
Example 2: Unconvincing email
Recently, I received a very annoying email that made me think, “Wow, I want to NOT do what this person is asking me to do, because they sound entitled and framed this ask so poorly.”
One of my pet peeves is when people think an email is “just” an email. No--email is a channel. Simply existing on a channel means nothing. “Good enough” does not mean “I sent out the email.”
What you put in the content of your email is the important part. And there is definitely a bell curve for how good the content is within a channel.
Whenever I post about improving quality, some people say,“But Wes, it’s not reasonable for me to spend 30 hours on every task to make it strong. That’s not sustainable.”
If this is your initial reaction, stop catastrophizing.
Like many things, improving quality is not binary. It’s a spectrum. A work memo could go from “barely decent” to “much clearer" with a few extra minutes of effort.
Instead of going to an extreme, you can move a few inches to the right on the quality spectrum. Pick the items that are most highly-leveraged, and go from there.
You might realize that the next level of “good enough” is quite doable and worth trying.
You might know something other operators don’t know, that leads you to believe that additional effort is worth it. For example, I believe the words we use shape our thinking, and we should be thoughtful with our language—I act accordingly, and have been able to capture value other people have left on the table.
Consider how you might develop an advantage from believing in (and therefore putting more thought into) something that other people think is extra.
Ask yourself:
Which tasks or work products tend to get the “good enough” reaction from you?
What would the next level of quality look like for these, and what impact might that have?
When have you pushed past what others would consider “good enough”? What was the result?
“Good enough” might seem completely subjective, but there’s usually some objectivity involved.
Reflect on where you might be claiming “good enough” too quickly—and whether you want to challenge some of those assumptions.
What’s an area where you set a higher bar for “good enough”—and how has this allowed you to capture value that others overlook? Hit reply because I’d love to hear from you.
Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
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2025-02-19 21:02:36
👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, leading teams, and standing out as a high performer.
✨ Course update: The April cohort of my executive communication & influence course is now full! I’ve opened a new cohort for May 2025. The course typically fills up quickly and will be the only opportunity to take the course this spring. If you’ve been thinking about joining, check out the course details and reserve your spot.
I originally published a version of this essay in February 2020. Enjoy.
Read time: 9 minutes
Today’s newsletter is sponsored by Balsamiq. If your team doesn’t get it, they won’t build it. Specs get misread. Docs go ignored. Meetings drag. Balsamiq helps PMs, devs, and founders visually communicate requirements before work starts. No friction, bloated tools, or second-guessing. Try Balsamiq free for 30 days.
The best marketers might call themselves marketers... But they are secretly strong in other disciplines.
Over the years, I’ve been asked, “How can I become a better marketer?”
My answer has changed over time. But one thing has stayed constant: only focusing on marketing is not enough.
By all means, study the fundamentals and latest trends in marketing. If you ONLY do that, though, you’ll back yourself into a corner. Your box will get smaller and smaller.
Instead, get good at adjacent disciplines. The adjacent disciplines will give you the je ne sais quois that expands your lateral thinking. They make you a sharper, savvier, more nuanced operator.
The best marketers have expertise in adjacent disciplines.
Under the hood, they are a salesperson.
Or a product person.
Or a designer.
Or all of the above (and then some).
These adjacent disciplines become a marketer’s special sauce. This allows you to create work with texture.
You’ll become a “marketer plus,” if you will.
Btw, I say marketer here, but this applies to operators in general.
If you want to level up, here’s a list of marketing-adjacent topics I recommend:
Negotiation is a dance and much of it is about what’s unsaid, reading between the lines, and taps into visceral, subconscious reactions. Your customer wants you to build value and not accidentally give up power/concessions. You want that too. So learn the negotiation basics, then go deep. You’ll start to see negotiations happening everywhere. It will help you sharpen your messaging, pricing, and everything in between.
Learn about this:
Power dynamics
Alternatives your customers have
Alternatives you have
Understanding incentives
Giving concessions
Building value
Not accidentally giving up power
You can’t nurture leads and build brand awareness forever. Eventually, you have to sell something. Sales teaches you to keep your eyes on the prize: closing sales. This helps you stand out as a marketer and will make you more influential within your organization. The closer you are to bringing in revenue, the more central you’ll be to important company decisions.
Learn about this:
How people make decisions
Buyer’s remorse
The role of fear in purchasing decisions
Psychology that shifts depending on low cost or expensive items
Deniability
Tension (when to resolve, when not to)
Rationalizing your decisions
Becoming impatient with BS and time-wasting
Ruthless focus on results and outcomes
Thinking flexibly
Choosing marketing tactics to support short-term vs long-term sales
You can work with data but not be analytical. You can be analytical without working with data.
Shockingly, I’ve worked with financial planners and paid acquisition managers who work with numbers all day, but did weird things like add percentages or celebrate raw numbers without checking the percentages.
I’m fortunate to have started my career as a business analyst at Gap Inc. I was part of a rotational program where they invested a ton into both formal training and on-the-job shadowing and mentorship. It’s made a lasting mark: The principles I learned there shaped how I think about numbers, interpreting data, and making defensible claims.
You can learn these concepts on your own, too. It’s not really about numbers. It’s about your ability to think clearly and interpret information. It’s about calling BS and developing a spidey sense for when numbers seem “off” and too good to be true.
Learn about this:
Levers (price vs volume)
Making inferences
Pointing out faulty logic or logical stretches
Raw numbers versus percentages
Percent contribution
Trend lines of change over time
Patterns and pattern breaks
Gut checking numbers
Healthy sense of paranoia
Using accurate language, i.e. using words that reflect your level of certainty
Stating assumptions explicitly
Making defensible claims
Creating “standalone” claims that don’t need your voiceover
Explaining your rationale
^ I wrote about much of the above in How to sharpen your analytical thinking—even if you’re not a numbers person.
Studying psychology and behavioral economics will help you better understand people, which is pure upside. When you master these concepts, you can mix and match to stack them.
Learn about this:
How people are irrational
What we say vs what we do
Common motivations
Unconscious biases and how they play out in daily life
Cognitive dissonance (one of my favorite unconscious biases)
Placebos (another favorite)
Recency bias (okay, lots of favorites)
Reciprocity
Loss aversion
Lies we tell ourselves
Practical ways to influence and persuade
Psychographics versus demographics
You will go far in your life if you can write well. You might have good intentions or a brilliant idea, but if you can’t express them… No one cares.
I find most people agree on high-level strategies, but things fall apart in execution. They can’t translate their strategy into customer-facing words and images that get the outcome they’re looking for. Strengthen your copywriting skills, and you’ll strengthen your execution.
Learn about this:
What makes you sound corporate versus human
When to break grammar rules intentionally
Using words with emotional resonance
Non-obvious things like the visual layout of text
How to edit your own writing
Basic UX principles of how people read/skim
Visceral reactions of certain words
Framing ideas
Sequence and priming your audience
Picking the right words/phrases to convey what you mean
Avoiding language that’s unintentionally dramatic, negative, or heavy
I studied the craft of writing fiction because it made me a better marketer for non-fiction copy. This is different from copywriting to sell. The craft of fiction will teach you about how to get people to FEEL something.
I have some friends who are the nicest people IRL. But when they send texts or emails, I think, “Do you hate me?? Are we even friends?” That’s because their warmth doesn’t translate in their writing.
Learn about this:
Believability
Motivations
Getting your audience to feel something
Show, not tell
Indirect ways to communicate
Whether a sequence of events make sense
Conjuring visual imagery
Highly-leveraged details and nouns
Word choice
Point of view (first-person “I,” second-person “you,” third-person)
Expanding or decreasing the psychological distance with your reader
Product and marketing are intertwined. The marketing should be built into the product itself. In other words, you can’t build a great product if you aren’t simultaneously thinking about how it will be marketed and why customers will tell their friends. And you can’t tap into the best ways to market your product if you don’t understand how the product is built, who it’s for, and what it’s for.
Especially in tech, there’s an idea that product people are rigorous, sharp, and analytical. But marketers don’t get that benefit of the doubt. Many people look at marketing as a fluffier discipline. This is ironic because the field of product management was inspired by brand management marketing to begin with.
My hope is marketers will one day get the recognition we deserve. I believe one way to accomplish that is to have a unified set of concepts/frameworks for talking about our ideas. This way, the outside world of non-marketers can understand our decision-making principles. The lists of sub-topics here are meant to be a start in this direction.
Learn about this:
How customers use the product
Unspoken needs
Looking at customer behavior, not words
User flow/user experience
Reading clues and making assertions
Product design
The construction of how things are made (yes, even for digital products)
Weighing cost/benefit of solving problems
Network effects
Getting people to do the thing you want them to do
Frequency/magnitude of a problem and how to solve
Whether to change the product or change the marketing
Design will heavily influence whatever you create. If you have great copy, but it’s paired with terrible design, no one will read the copy. They’ll be too distracted by the design.
“This doesn’t look like a product someone like me would use.”
“This doesn’t look legitimate.”
“This looks cheap.”
In the macro sense, design is the fastest and most visceral way to send a signal about who your product is for.
In the micro sense, if you have poor design in your everyday Google Docs, your manager and coworkers are judging you. Don’t send documents that are poorly formatted, with different font sizes, and hard to read. It’s distracting and makes you look sloppy, which undermines that good work you do.
Improving your design eye helps with both the macro and the micro.
Learn about this:
Visceral reactions from design
What do you want people to be reminded of when they see you
Using design to enhance your message
Semiotics and heuristics
Spotting common design flaws
Making sure design looks good enough not to be distracting
Not over-using formatting
Understanding why work looks messy
Creating work that looks clean
Marketers on lean teams are showrunners who produce campaigns, events, and more.
When you think like a showrunner, you think like a person who is accountable for making something happen. You own the big picture and every detail—because missing a detail could ruin everything. This ability to take complete ownership to ship a project is a valuable skill, whether you’re managing others or on a team of one.
Learn about this:
What it takes to get something done
How to herd cats
How to say no respectfully and warmly
How to create a good spec so you can delegate with confidence
How to follow up properly
Seeing big picture and individual component parts
Appreciation of airtight execution
Builder mentality of creating something that didn’t exist before
Finding low overhead solutions that are easy to implement and good enough
Read about these topics.
Practice them.
Take on projects that require these skills.
These marketing-adjacent topics will help you develop your sense of judgment. You’ll improve at making high quality, high velocity decisions—which will ultimately help you translate your intent into strong execution.
What is it all for? All of this helps you bring your ideas to fruition, so your audience will feel the same excitement you feel about your product.
Which of these disciplines is catching your eye? What concepts are you most curious to dive into?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
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2025-02-12 21:03:44
👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, leading teams, and standing out as a high performer.
⛑️ Update: It’s been incredible supporting senior managers/directors in big tech and startup executives via 1:1 executive coaching. I’ve noticed many conversations are about these four meaty topics: Managing up, sharpening your executive presence, building cross-functional influence, and delegating to a team of high-performing ICs. If you’re interested in how I can support you in these areas, hit reply or learn more about my coaching approach.
I originally published a version of this essay in August 2020, and have since expanded it. If you find it helpful, please share with friends and coworkers. Enjoy.
Read time: 4 minutes
Positioning and messaging is exciting because you’re picking your angle. Of all the ways you could talk about your product, which way should you talk about it?
Even if you’re feeling confident in your company’s spiky point of view, it’s important to test your story.
At this point, folks will usually ask,
“So how do we know if our story resonates?”
“How do we test our positioning and messaging?”
“How can we tell if customers are excited by this value prop?”
I want to share one of my favorite frameworks because it’s super easy and intuitive.
Here’s the deal:
You already know when people are excited to hear a story.
They perk up. Their energy level shifts. All of a sudden they look alive—and they want to hear what you have to say.
I call this the Eyes Light Up moment. Or ELU for short.
This is the moment when your audience is viscerally, undeniably excited about what you’re talking about.
That is the reaction you’re looking for. Whenever you tell a story, share your value proposition, or test your positioning/messaging…
Eyes lighting up is the reaction that matters.
If you ask a bunch of intellectual questions, you’ll get intellectual responses. These intellectual responses are usually not helpful. Hypothetical questions are even worse.
In the wise words of Ogilvy: “The problem with market research is that people don't think how they feel, they don't say what they think and they don't do what they say.”
It doesn’t matter if they say “Hmm interesting,” but meanwhile, they look dead in the eyes.
When your audience is ACTUALLY interested, their eyes light up. They might be interrupting you with questions, and you’d be having a lively conversation.
One of my former clients was going to SXSW.
I said, “This is a great chance to test your new positioning. Every time you talk to someone, describe your new product in a slightly different way. Notice what makes people’s eyes light up. Jot those down and let’s discuss when you’re back.”
They did this—and came back with pages of insights on what resonated in conversation. We emphasized and aggrandized certain elements. Then we trimmed parts people didn’t care as much about.
ELU will help you answer all these questions:
Which parts of your story are boring?
What parts do prospective customers actually care about?
What should you spend more time talking about?
Where are they confused?
What did they remember and repeat back to you?
What hot key words got them to perk up?
When you’re telling your story, the way to prepare is NOT to memorize a bunch of tactics. This is only going to make you nervous. You’ll be like an athlete trying to remember to keep your knees bent, but not too bent. Keep your back straight. Remember to follow through.
No. When you tell a story, the only thing you need to remember is this: Look for moments when your audience’s eyes light up.
Start becoming more alert to your audience’s reactions, whether your audience are customers, cross-functional team members, or your CEO.
Try this:
If your recipient’s eyes are glazing over, stop. Switch gears. If they are barely listening, you don’t have much to lose by changing up your approach. And you have a lot to gain, like their renewed interest in the rest of the conversation.
Acknowledge clues that are already in front of you. I believe humans are incredibly attuned to noticing subtle clues from other humans. But we ignore and “power through” because we’re excited by what we’re saying. When you notice someone isn’t into it, recognize this as a data point and take the reins.
When your recipient’s eyes light up and they want to talk, let them. This applies to 1:1 conversations, especially sales calls. I used to continue talking because I wanted to finish my thought. Now, I almost always stop—sometimes mid-sentence—and let the other person speak. If I’m trying to sell them, their excitement is a sign it’s working. And if they talk, they might sell themselves.
When was the last time you noticed your recipient’s eyes lighting up? When might you be ignoring subtle clues from your audience?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
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