Part II: The art of workplace finesse

Knowing 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.

1. Identify when to ask for forgiveness vs permission

2. Acknowledge that perception matters

3. Know what you can get away with

4. Don’t be too literal

5. Know when to be discreet

6. Never bet against incentives

Read time: 7 minutes

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This is Part II of a series on finesse:

• The unspoken skill of finesse

• Part I: What finesse looks like when reading people and situations.

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.

⛑️ If you’re looking to dramatically improve your communication and leadership, I typically work with tech leaders on: managing up to a CEO/SVP, strengthening your executive communication, and delegating to a team of ICs while raising the bar. If you’re interested in how I can support you, learn more about 1:1 coaching.

2. Acknowledge that perception matters

People 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 with

What 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:

I try to avoid bending down to pick up heavy things (like cases of water bottles) from the bottom of a shopping cart because it hurts my back.

A lot of coworkers were having issues with this, so during a team huddle, I shared what I came up with to deliver good customer service while still protecting my lower back: I would use a peppy voice, smile brightly, and lightly pat the counter shelf while asking customers to lift items from the bottom of the cart while I started scanning items that were within my reach.

I advised my coworkers with the disclaimer that they needed to find a version of what to say to customers that works for them. My script/act works for me because I'm a 5 ft tall, cheerful person, but my coworker DJ (who hates interacting with customers and has a dead look in their eyes when working the cash register) is not going to be able to pull off that act with the same effect.

4. Don’t be too literal

I’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 discreet

I 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 incentives

There’s a fable called the Scorpion and the Frog:

A scorpion wants to cross a river but cannot swim, so it asks a frog to carry it across.

The frog hesitates, afraid that the scorpion might sting it, but the scorpion promises not to, pointing out that it would drown if it killed the frog in the middle of the river. The frog considers this argument sensible and agrees to transport the scorpion. 

Midway across the river, the scorpion stings the frog anyway, dooming them both. The dying frog asks the scorpion why it stung despite knowing the consequence, to which the scorpion replies: ‘I am sorry, but I couldn't help myself. It's my character.’

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.

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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

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