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In this week’s post, we’ll cover principles of what finesse looks like when reading people and situations.

1. Share bad news effectively

2. Understand power dynamics

3. Know when to call someone out

4. Understand intention vs impact

5. Recognize the question behind the question

6. Consider what’s advantageous for both parties

7. Realize popular adages aren’t fully accurate

Read time: 6 minutes

Earlier this year, I wrote about the unspoken skill of finesse.

It’s such a nuanced and situational topic, with so much tacit knowledge baked in. Not many people have dissected what finesse is and what it means, even though companies want to hire and promote operators with this quality.

It can be hard to put your finger on what finesse (or lack thereof) looks like, so I thought I’d compile some non-exhaustive principles.

Here’s what finesse can look/feel like, focusing on the areas of how to read people and situations:

1. Finesse is sharing bad news in a way where your recipient doesn’t hate you afterward.

The first step is realizing that the way you share information actually matters and can influence how your recipient receives the news.

In my experience, when people are too “blunt,” it’s often because they weren’t the person responsible for the outcome—someone else was. They had the luxury of being blunt because someone else was cleaning up the mess. 

If you were responsible for the fall-out, all of a sudden, you’re highly incentivized to make sure your audience doesn’t freak out. This is as much about skill as it is about motivation. When you’re motivated, you can think of many ways to share the news in a better way.

More on how to deliver bad news when it’s not your fault.

⛑️ Welcome and thanks for being here! 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 my coaching approach.

2. Finesse means understanding the power dynamics at play. 

This means not asking someone much more powerful than you to pick a time from your Calendly—that’s making them fit around your schedule.

Since you are less powerful AND the one asking for a favor, you should pick from their calendar. 

You might say, “Well, Wes, technically picking from my Calendly is faster/easier and I’m offering it to be thoughtful.”

Finesse is realizing you might intend to be thoughtful, but you actually look obnoxious. 

You can insist on being right on principle, or you can acknowledge that your recipient’s perspective is legitimate too, and therefore adjust your behavior to avoid a misunderstanding.

(Also, you actually can ask powerful people to pick from your Calendly, but you need to execute well. It’s playing on hard mode. If you want to do it, here are examples of scripts to use so you come across as sincere, not entitled.)

3. Finesse is knowing when to call someone out. 

Let’s say someone is trying to impress you by casually name-dropping. Or a salesperson is trying to use reciprocity by offering a favor in a DM, but clearly will sell you something the instant you reply. 

You could say, “I see what you’re doing here” and proceed to call them out. Does this benefit you? Is it worth the effort? What’s the point?

Finesse means realizing there’s no need to call someone out if there’s no upside to doing so. This fits under the general principle of picking your battles. When in doubt, ask yourself, “What’s my goal here?”

4. Finesse is realizing people kind of (but don’t really) care about your intentions.

It’s better to have good intentions than bad intentions. But so often, people use good intentions as an excuse to absolve themselves of responsibility. Like, “Oh I had good intentions, therefore you can’t judge me based on my poor execution.”

Actually, I can, and I will. I will take into account your intentions, but I am very much still going to judge your execution and the impact of what you did.

There’s skill involved in translating your intentions into reality. Many posts in my newsletter are about this.

5. Finesse is recognizing when there’s a question behind the question.

It’s not always advisable to ask a question directly. Sometimes you have to read between the lines.

Keep your antenna up about what the QBQ might be. This allows you to think about the bigger picture in every conversation, and let that inform your actions.

More on identifying the question behind the question.

6. Finesse is considering: “What is advantageous for me AND for the other person?” 

If you only think of what’s good for you, it’s short-sighted and you won’t get away with a good deal for long. 

The market corrects itself, people catch on, and they don’t like being duped. If you don’t also think of what’s good for others, you may not survive for long enough to continue making a difference.

This could mean thinking a few steps ahead and playing out different scenarios.

For example, let’s say a startup CEO insists on sharing their failures publicly because they want others to learn from their mistakes. This is noble. But being too open about failures might mean potential hires and investors think the business is a dumpster fire because you’re constantly talking about how it’s a dumpster fire.

A better approach may be to share selective failures, while keeping in mind you need to come across as competent enough for people to still want to engage with you.

Optimize for win-win solutions that make sense over time. Anything else isn’t sustainable.

7. Finesse is realizing that certain popular adages are not fully accurate, so you must use your common sense.

This might be more about using good judgment than finesse, but they’re related so I’m including it.

For example, a common saying is, “Just ask! The worst thing that can happen is they say no.”

I disagree. If your recipient believes you overstepped, the worst thing is NOT that they say no and things go back to the way they were. That’s actually the best thing that can happen.

The worst that can happen is they say no (again, not that bad) and think less of you or have less trust in you because they felt insulted and your ask showed a lack of judgment.

Think about when someone asked for or said something you thought was a bit out of line. It was uncomfortable. You were surprised. It made you question your relationship.

Now, “just ask” might make sense for transactional interactions where you never have to see the person again, so you might as well go for it. But it doesn’t work that well when you’re playing an infinite game, or if the content of the ask is legitimately questionable. Basically, I’m all for shooting your shot. But do some critical thinking first.

This is just one of many, many business sayings that sound good on the surface, but should probably be applied in a narrower context than you might assume. Always use your judgment. Reason from first principles to decide whether the advice makes sense for you and your specific situation.

To recap:

1. Share bad news effectively

2. Understand power dynamics

3. Know when to call someone out

4. Understand intention vs impact

5. Recognize the question behind the question

6. Consider what’s advantageous for both parties

7. Realize popular adages aren’t fully accurate

This was not an exhaustive list, but merely some examples illustrating the hard-to-put-your-finger-on nature of finesse.

Do you have other examples of finesse when reading people and situations? Hit reply because I’d love to hear from you. Next week, I’ll cover finesse when managing your image and impact.

Thanks for being here, and I’ll see you next Wednesday at 8am ET.

Wes

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