What Pickleball Is Teaching Me About Sales

Three lessons from the court that will help you win more deals.

I’ll admit it… I’m hooked. Like, hook-line-and-sinker hooked.

Like so many people lately, I picked up a Pickleball paddle “just to try it” along with a group of friends a few months ago. I pretty quickly found myself playing it more and more.

Pickleball has a way of pulling you in, then increasing the doses of it you need, while also never letting go. At first, it feels like fun exercise. Then, as you play more, you realize there’s just sooo much depth to it… strategy, tactics, positioning, patience. You start to notice how small choices and changes change the outcome of a point.

And if you’re wired like me, you can’t help but draw parallels to sales.

The more I’ve learned about pickleball, the more I’ve realized it’s teaching me the same lessons that drive success in selling. Here are three of the biggest ones I’ve discovered so far.

1. Strategy Beats Power

When I first started playing, I thought winning was about who could hit the hardest. You think that smashing that neon-colored plastic ball would feel great… until it goes so far out of bounds that people two courts behind you start complaining.

The more I played, the more I realized that strategy wins points more than power ever does. The best players aren’t just swinging away… they’re thinking two or three shots ahead, always setting themselves up to win the point down the line.

Sales is the same. You can “hit hard” with volume-based outreach, but if you don’t have a strategy, you’ll burn out fast and send those shots way out of bounds… because no one will listen, and you may even damage your reputation in the process. A random string of dials, emails, or LinkedIn messages won’t create consistent wins.

Great sellers, like great pickleball players, start with a plan:

• Who is our ideal customer?

• Where are they active?

• What signals show they’re ready for a conversation?

On LinkedIn, that might mean building a Base Search in Sales Navigator to define your Ideal Customer Profile, then narrowing it into Saved Lists. You can then use Sales Navigator to keep you updated on job changes, company growth, funding, etc. …the exact signals that tell you when to “take the shot.”

Without strategy, sales feels like swinging at every ball that comes your way. With strategy, every move has purpose.

2. Positioning Decides the Point

If there’s one thing pickleball punishes (in my case, with annoying regularity), it’s poor positioning on the court. Standing in the wrong spot when the ball comes your way? That little sphere of annoyance goes behind you, and you’re either stumbling to get it or losing the point… and possibly your mind. Step into the proper position at the right time, and suddenly the game feels easier.

Sales is no different. Positioning yourself in front of the right people, at the right time, with the right message makes all the difference.

That might look like:

• Targeting: Using Account Filters in Sales Navigator to prioritize companies with leadership changes or department headcount growth.

• Engagement: Instead of swinging wildly, you play the “dink game” on LinkedIn: commenting thoughtfully on prospects’ posts, engaging with their content, and showing up consistently.

• Presence: Sharing value-driven posts that help prospects see you as a resource, so when you do send a connection request, it doesn’t feel cold.

In pickleball, if you’re stuck at the baseline while your opponent owns the net, you’re losing. In sales, if your competitor is positioned in your prospect’s feed because they’re present with liking, commenting, and posting while you’re silent, you’re losing out too.

In both sales and pickleball, positioning doesn’t guarantee the win. But poor positioning? Almost always guarantees the loss.

3. Mindset Makes the Difference

Here’s a humbling truth about pickleball: you’re not going to win every point. Even the best players miss shots. All. The. Time.

I’ve watched professional pickleball on streaming TV, and I’ve seen the pros miss all kinds of shots… even the ones I’ve missed.

The key isn’t perfection. It’s mindset.

If you’re focused only on winning every rally, you’ll press too hard, make mistakes, and lose more. But if you keep your head, trust your strategy, and hold your position, you’ll win the points that matter most.

Sales requires the same mindset. You’re not going to close every deal. Not every email gets a reply. Not every call goes your way. And that’s okay.

The goal isn’t 100% conversion. The goal is to stay in the game long enough, with the right mindset, to win more often. That means:

• Detaching from outcomes: Don’t measure success by one message or one call. Measure it by whether you’re moving more conversations forward.

• Playing the percentages: On LinkedIn, that looks like our 10:1 rule: writing 10 thoughtful comments on other people’s posts for every post you make. Enough consistent activity yields opportunities.

• Bouncing back quickly: A deal that goes dark isn’t the end of the game. You reset, check your Sales Navigator alerts, and move to the next prospect.

The sellers who stay calm, authentic, and consistent are the ones who convert. Just like the players who don’t melt down after a missed shot.

Where Pickleball and Sales Converge

When I step back, these three lessons -- strategy, positioning, and mindset -- form a simple truth: winning doesn’t come from doing everything perfectly. Because, guess what? You’re never going to do everything perfectly.

Winning comes from consistently setting yourself up to succeed.

Pickleball has taught me that you don’t need to crush every shot. In fact, you shouldn’t crush most of your shots. You just need the right plan, the right place, and the right perspective. Sales is no different.

Whether it’s through deliberate prospecting strategies, smart use of LinkedIn and Sales Navigator, or the mental resilience to keep showing up, the game is won over time. Point by point. Conversation by conversation.

From Court to Close: Bringing the Lessons Together

I’m still early in my pickleball journey, and I know I’ll keep learning more as I go. But already, the parallels to sales have been impossible to ignore.

If you’re leading a team, or even just managing your own pipeline, think about how these three lessons apply to your work:

• Strategy: Are you planning the rally, or just swinging?

• Positioning: Are you in the right place when the opportunity comes?

• Mindset: Are you focused on playing the long game, knowing you won’t win every point?

On the court or in sales, those are the elements that make the difference.

And just as I’m still learning about pickleball, I am also learning about sales. It’s a profession that’s never really static in nature; after all, sales nowadays is nothing like it was 30 years ago or even 10 years ago. As sales changes, we have to keep up!

I’d love to hear from you: what lessons from outside of work… whether pickleball, running, or any other passion… have shaped the way you approach sales?

Drop a comment or reply. Let’s compare notes, both on the court and in the sales world.

(NOTE: The base of this header/hero image of this article was AI-generated, but edited [with my terrible Canva skills] by me as ChatGPT doesn’t know things like the positioning of letters on a keyboard, how to actually spell “Sales Navigator”, etc.)