👋 Hey, it’s Wes. Welcome to my weekly advice column on managing up, driving growth, and standing out as a high performer.

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Today, we’re going to talk about the leadership trait of finesse.

• Part I: What is finesse?

• Part II: Same question, three different levels of finesse

• Part III: The best ways to develop finesse

Read time: 10 minutes

Many successful operators and leaders have what others would call “finesse.” It’s an important skill, especially for senior leaders and operators who want to continue to advance.

When people talk about finesse, there’s an air of je ne sais quoi, an abstract sense of “you know it when you see it.” There’s this innate feeling that some people have finesse while others don’t.

As you progress in your career, finesse becomes increasingly important. If you lack it, your CEO can’t put you in front of your most important customers. They can’t trust that you’ll be able to handle delicate, high-stakes issues. This stalls your growth and impacts your ability to add value.

Given how important finesse is, there’s shockingly little written about it.

I believe if we can dissect it, we can have more objective conversations about who has finesse, who gets rewarded for having it, and how to develop it in yourself and others.

But first, we need to understand what it is.

Part I: What is finesse?

For years, I’ve been fascinated with the topic of good judgment. You could give 10 operators the same primary data, and they’d potentially come up with 10 different recommendations of varying quality.

This is because deciding what to do and what to say requires judgment. And folks have varying degrees of judgment depending on their task-relevant maturity.

I see finesse and judgment are cousins. I’m still shaping how I’d define finesse, but for now I’ll say:

• Finesse is the skill of interacting with other humans in a way that gets the outcome you’re looking for, despite situations that have grey area and a range of potential outcomes.

• Finesse is the ability to notice what’s unsaid and handle sensitive dynamics.

• Finesse is good judgment applied to delicate scenarios, usually involving communicating with other humans.

I’m sure others might define it differently, and I welcome building on what I have here. For the purpose of this essay, I’m mainly looking at finesse through the lens of interacting with customers, i.e. one the most important stakeholders.

Finesse requires good judgment because you need to:

1. Read a situation

2. Understand your levers

3. Identify risks

4. Determine what to do or say

5. Determine how to do it or say it

6. Execute your strategy to get the outcome you’re looking for

You might look at this list and think, How could anyone possibly do all this, especially in near real-time, while staying present with whoever they’re with?

Finesse might come more naturally to some, like a personality trait—just like some people are more attuned to picking up clues and micro-expressions, or seem to always know what to say to make someone feel seen.

But luckily, it can be learned. As with anything that seems like magic from afar, I believe it’s a skill that can be intentionally dissected, honed, and practiced.

So let’s go to an example of finesse I’m excited to show you.

Part II: Same question, three different levels of finesse

One of the harder parts of my newsletter is showing you redacted examples, where after I redact, the point still shows through. After redacting, many things no longer make enough sense to be valuable.

Which is why I was straight-up giddy when I came upon this example for you.

Check out this Slack thread with three team members and how they each replied to a customer question. The customer asked:

“How many users can your platform serve at any one time?”

On the surface, this seems like a simple question with a simple answer. There’s only one way to reply, right?

Wrong.

Here are three people—a mid-career operator, senior leader, and C-level executive—answering the same question in different ways.

All three answers are pretty good, but they get progressively better:

Here’s how I would dissect and rate their responses:

• Person A’s response is too direct for a situation that isn’t as straightforward as they assumed. They simply say “500 users.” There’s no framing to help contextualize this information. It’s a missed opportunity to guide the reader on how to feel about this fact. To be clear, I love being direct and concise, but this is actually missing important context that should have been included. Rating: ⭐️⭐️

• Person B’s response is better, but introduces a new unexpected issue of negative framing. There are a lot of negative phrases: Don’t have hard limits, without major issues, run into some performance issues, but. The reader leaves thinking using your product might be tenuous. This is common: You notice and solve for X in your messaging, but your solution ends up introducing a new problem Y that you didn’t realize. Rating: ⭐️⭐️⭐️

• Person C’s response is the positive, strong version of Person B’s response. Person C shares the information, the right level of framing, and frames it positively so the user can interpret the information the way you want them to interpret it. After this reply, the user thinks more highly of your brand because you gave an answer that’s both customer-centric and direct. Rating: ⭐️⭐️⭐️⭐️⭐️

One of the things I like to do is dissect what seems simple on the surface, but upon a further look, offers more levers than you originally thought. More levers equals more opportunity to drive value.

As you can see, Person C noticed levers that Person A and Person B missed.

A bell curve of finesse

The range of finesse in the replies is a microcosm of the difference in skill and judgment that could be happening throughout your organization, in minor and not-so-minor ways.

The example above wouldn’t be that interesting if it were an isolated incident. But I’ve seen examples like this countless times, and it illustrates the varying levels of savvy among team members. Your team members are executing in hundreds of micro-interactions with coworkers, partners, leads, and customers on a weekly basis. This is slack in the system that, if removed, is all upside.

You’ve likely seen examples like this in your own team, but it’s hard to pinpoint. For example, a more skilled (often more senior, but not always) operator shares their point of view and it just makes sense. It’s just… better than what other people said. But it’s hard to put your finger on what made their input more insightful and more right.

Every leader should actively look for opportunities to teach their team judgment. If you’re not doing this, you’re barely scratching the surface on what “learning on the job” means for your team.

You need to teach them to “see” how you see, and notice what you notice. Explain the “why” behind what you said or did, or the “why” behind your feedback. When someone on the team displays finesse, point it out. Let everyone learn from it.

Over time, your team will improve their ability to pick up on what you pick up on, and eventually, to make the judgment calls you would have made.

I believe doing this, regularly and with gusto, is how you create a culture of high standards and dramatically improve your team’s chances of winning.

Part III: The best ways to develop finesse

1. Learn from your actual day-to-day work

I believe it’s almost impossible to learn finesse purely in theory. The way to learn finesse is by thinking more deeply about the specific, real-world examples you encounter day-to-day.

Trying to learn finesse in human interactions, without actually interacting with other humans, is like trying to be an Olympic water polo player from your desk. You learn when you get in the water, flail around, and start to realize what you don’t know you don’t know. Then gradually, you keep at it and you fill in the blanks, and you get better.

For example, let’s say you want to have more finesse when interacting with customers. There are times when you might want to ignore your customer’s question altogether, and instead, answer the question you think they should be asking.

This sounds extreme, but good salespeople and founders do this all the time. Marc Randolph, co-founder of Netflix, talks about the skill of answering whichever question you want to answer. He said,

You don’t have to answer the question. It’s perfectly appropriate to simply acknowledge how good of a question it is, but then go on to tell them something completely different. The skill is figuring how to establish a plausible linkage between the two.

This isn’t only about projecting confidence and knowing this tactic exists. It takes judgment to know when to do this, and finesse to execute well in real-time.

I can’t tell you whether you should use this tactic without getting more information. Why? Because I don’t know enough about you, your personality, your skill level to pull it off, who the other person is, whether they’d balk or appreciate you doing this, and other important context.

There are too many variables to think about finesse in abstract terms. Focus on learning from real-life scenarios you’re encountering at work.

2. Pay attention to your self-awareness and situational awareness

One of the first things you can do is to become more aware of times that could benefit from finesse. At first, you might see opportunities as black-and-white, when often they are not. So simply acknowledging the range of outcomes, and your ability to influence those outcomes, is helpful. For example:

• When should you err on being more matter-of-fact?

• Where’s the line between an appropriate amount of framing vs turning your answer into meaningless marketing-speak?

• What’s considered “too on-the-nose”?

• What’s the right amount of backstory to share? How much is too much?

• How do you take power dynamics into account?

• How do you decide whether to play high or low, but not too high and not too low?

• What’s the right tone to use and why?

• When should you be more conservative vs aggrandize a bit within reason?

• When you can be a bit cheeky and what you’re able to “get away with”?

This is why I find it so rewarding to work with my 1:1 executive coaching clients. We get to work on a real situation, and strategize how to best add value to and appeal to real individuals (their CEO, direct reports) who have different personalities, worldviews, motivations, etc.

You can practice this with a trusted friend, as long as you believe they would notice things you might miss and you trust their judgment.

3. Become a keen observer of what’s around you

Here are other ways to improve your finesse, most of which are small steps you can start doing today:

• Reflect on your "personality-message-delivery fit. Certain personalities can “get away with” different things. I used to say to my co-founder, “I can’t believe you said that—and it worked!” But there was something about his vibe, who he was, and delivery that all came together and felt authentic when he said something a bit cheeky, and people could pick up on that. Similar to product-market fit, I call this personality-message-delivery fit. It takes self-awareness to know what works for you. So observe others for inspiration, but know thyself.

  ^ By the way, I’m sure you can think of a friend or coworker who says things you could never see yourself saying, but somehow it works. If you think of examples, tell me because I’d love to hear about it.

• Study people who have finesse. When you think of finesse, there is likely someone who comes to mind. Think about when they’ve displayed finesse. What do you think they were aiming to do? What insight allowed them to react the way they did? What did they say? What could they have said that wouldn’t have landed as well?

• Strategy, not self-expression. Always have a goal in mind of what you want your audience to do. If you’re not sure, figure it out, then have the conversation.

• Study psychology. Both in books about applied psychology topics, like sales, negotiation, behavioral economics, influence, persuasion, conflict resolution, etc. But also, study psychology by studying the people around you.

• Improve your vocabulary. Words shape perception and meaning, so studying this will increase the chances of getting the outcome you’re aiming for. Often the difference between finesse vs hitting a problem with a blunt instrument is word choice.

• Consider the question behind the question. Try to understand where the person is coming from and why. Practice playing out how someone might (mis)interpret what you’re saying, and how to frame to increase comprehension and enthusiastic buy-in. Think about where there are opportunities to sell your ideas in the general direction you want to go in.

4. Don’t let your ego get in the way

Don’t let your ego prevent you from getting input that will help you improve your finesse. Let others give you feedback, preferably in public channels where your coworkers can learn too.

If Person A hadn’t shared their initial proposed answer in a public channel, the rest of the company wouldn’t have seen the improved versions of the response. The end result was better because of collaboration and iteration—it would have been a shame for everyone to miss out on that learning.

We can all improve our finesse in various situations, so let your manager and peers be honest and direct. You’ll be able to add more value, and take this newfound level of finesse with you wherever you go next.

There are different types of finesse, and different occasions that benefit from finesse. Keep an eye out for them in your daily work—they are all free opportunities to learn as an individual and as a team.

Give yourself and your team the gift of learning from specific examples you can all look at in front of you. As coworkers, you have intense amounts of shared context that you’ll never have from a book, course, coach, or anything outside your company.

Take full advantage of this opportunity to learn from each other.

If my approach resonates with you, here are three more ways I can help:

1. Follow me on Twitter or LinkedIn for bite-sized tips throughout the week (free).

2. Book me as a keynote speaker to inspire and level up your team at your next event.

3. Work with me for 1:1 executive coaching. Hit reply or fill out this form.

Thanks for being here,

Wes

PS If you’re as excited about the topic of finesse as I am, here are posts on how to improve your judgment for common workplace situations:

When to disagree and commit Wes Kao · Apr 3 Read full story

The unspoken power dynamics of Calendly Wes Kao · December 13, 2023 Read full story

How to interrupt (and be interrupted) respectfully in the workplace Wes Kao · Mar 6 Read full story