Wes Kao - Part II: The art of workplace finesse
Part II: The art of workplace finesseKnowing when to ask for forgiveness vs permission, what you can get away with, and more👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, career growth, and standing out as a high-performer. For more, check out my course on Executive Communication & Influence. In this week’s post, we’ll cover examples of finesse in the workplace.
Read time: 7 minutes This is Part II of a series on finesse: Today we’re going to dive deeper into examples of what finesse looks like, especially when working with others, managing your perception, and increasing your impact. Let’s dive in. 1. Identify when to ask for forgiveness vs permission“Don’t ask for permission, ask for forgiveness.” This falls under the category of catchphrases I generally agree with, but I see people misapply all the time. The biggest mistake is assuming this is a blanket rule. Obviously, you don’t want to be overly supplicant. Being too conservative and asking for approval for every tiny thing—this puts the burden on your manager, when you should be the one taking ownership. At the same time, it’s equally bad to take advantage when you shouldn’t have. There are times when you actually do want to ask for permission because it’s not worth your recipient feeling miffed. You don’t want them to think you were too aggressive and exploiting them. There is a cost to over-playing your hand. The cost is losing trust. Here’s a happy middle ground: Inform your manager what you’re planning to do. This gives them a chance to stop you and/or to align. I hate surprises. Your manager probably hates surprises too. Don’t surprise them by saying: “Surprise! I did this thing, and if you’re upset, please forgive me.” You can skip that entire song and dance by simply giving your manager a heads up. More on how to plan before you ask.
2. Acknowledge that perception mattersPeople judge you based on subtle signals. If your hair is greasy and you have a stain on your shirt, this makes you look like you don’t have your shit together. People judge books by their cover. You can be annoyed by this (I am) but if you pretend it’s not true, you still suffer the consequences. If you do video calls often, get a ring light, don’t eat sloppy food on video calls, make sure there’s nothing in your background that creates a visual line cutting into your head, and get a good mic. Don’t walk around your house doing chores on calls. It’s giving people vertigo with your shaky camera and it makes you look like you don’t take work seriously. Your manager likely won’t tell you this because they don’t want to look like an asshole, so I’m telling you out of love. 3. Know what you can get away withWhat works for your colleague might not work for you because you have different personalities, vibes, and archetypes. You have different assets that work to your advantage. I call this personality-message fit. Personality-message fit is why you can’t just copy and paste what other people are doing and saying. You must tailor it to fit you, so you sound authentic. A friend who worked at Trader Joe’s said:
4. Don’t be too literalI’m shocked at how literal people can be--that they need things extremely spelled out, step by step, in detail, for the exact situation they are dealing with, in order to understand what’s happening. You will be leaps ahead of other operators if you can do something that seems relatively simple: Think flexibly, pattern match, and adjust advice to fit your situation. If you say, “But how do I adjust advice to fit my situation?” This is exactly the type of question where you can practice reasoning from first principles. If you can reason and adjust principles to fit your situation, you will be so much more empowered than if you ONLY know what to do when people give you clear explicit directions for your exact situation. Many operators have access to similar resources. So why do some people create work that makes their audience’s eyes light up, but others create work that’s middling and mediocre? You have paint. You have brushes. You have a canvas. Try to turn a yellow spot into the sun. 5. Know when to be discreetI know people who talk loudly in public places and use the name of their company, manager, coworkers, etc when talking about problems. “No one in the cafe knows us.” “No one here is listening.” “The Uber driver doesn’t care. You’re being paranoid.” That’s not the point. The point is: Talking loudly about sensitive information has very little upside. If it exposed you to risk WITH potential upside, that would be a different mental calculus. But there is rarely any upside to having your Uber driver or the passengers behind you on a plane hear you talk about potentially confidential work details. And the “cost” is simply lowering your voice a bit, which honestly most people would appreciate if you’re in a public space anyway. People who lack finesse do not understand this. Again, this is something your manager probably wants to tell you, but doesn’t want to risk having you freak out and say, “This is just the natural volume of my voice” or “We’re not doing anything bad, I don’t see why I have to lower my voice.” If you can’t be discreet when you should be, and think people are “paranoid” when they want you to be… Why should your manager and senior leaders trust you with sensitive information? 6. Never bet against incentivesThere’s a fable called the Scorpion and the Frog:
You can’t blame the scorpion for stinging the frog. Similarly, you shouldn’t be surprised when people act according to their incentives. Remember: Incentives override how much someone likes you, how great they think you are, and how much they want to do the right thing. This is why you can’t blame your HR person for caring more about the company than they care about you as an individual. It’s their role and incentive to protect the company, and that sometimes means going against individual employees who can be a threat. This isn’t personal. This is the HR person acting according to their incentives. Another example: A few years ago, I met a successful founder who had a large exit and was now working on a new product. It was an app that allowed employees to send short off-the-cuff videos to their managers to build camaraderie and save time from meeting synchronously. Basically, it was Snapchat with your manager. You can’t force direct reports to all of a sudden feel casual about sending their managers material that their manager may use to judge them later. Direct reports are incentivized to seem competent in front of their managers. Something like Snapchat-with-your-boss was betting against incentives. Despite the founder getting their successful CEO friends to use the app at their companies, the product didn’t work and the company shut down soon after. Remember: Never bet against incentives. ___ Finesse isn't about following rigid rules. It's about developing the judgment to read situations, think flexibly, and respond well. The most effective operators aren't only competent at their core work—they're also able to navigate unspoken dynamics and unwritten rules. Do you have an example when you showed finesse, or lacked it in hindsight? 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 Executive Communication & Influence for Senior ICs and Managers courseIf you’re looking for hands-on practice on any of the topics in this newsletter, I created a 2-day intensive course called Executive Communication & Influence for Senior ICs and Managers. The course is for ambitious operators who want to continue improving for themselves and their organizations. You’ll learn alongside fellow tech operators from organizations like Uber, TikTok, Grammarly, Workday, CVS, Google, Wealthsimple, Pinterest, Expedia, Sephora, Twilio, Spotify, GitHub, Zillow, PayPal, Netflix, Square, and more. If you’re interested, learn more. Here’s what students are saying: And if you want to hear what the course was like from a student who took the October cohort, check out the post below from Jordan Cutler, a senior software engineer at Pinterest:
Thanks Jordan for sharing your reflection and takeaways. Full post here: Connect with Wes
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