From Stuck to Skilled: Jorge Capestany Shares Pickleball Drills That Actually Work
Game Changers Interview – Episode 2 with Jorge Capestany
We’re back with another episode of Game Changers, and this one is special — it’s the first time we’ve had a returning guest! Jorge Capestany, a world-renowned tennis coach and now a leader in the pickleball world, joins us again alongside Kalindi Dinoffer, CMO of OnCourt OffCourt, to dive deep into how players can break through plateaus and level up their pickleball game.
If you missed Jorge’s first episode, go check it out — it covers his inspiring story, from sweeping tennis courts to building the largest tennis drills website in the world. In this episode, we focus on pickleball drills — and it’s packed with practical, actionable tools.
Why Drills Matter More Than Just Playing
Jorge starts by calling out the most common frustration in both tennis and pickleball: players feeling stuck. Whether you’re trying to break out of the 3.5 level or just get your returns more consistent, the key might not be more games — it might be more purposeful drilling.
Here’s the kicker: the average pickleball point lasts only 9 shots, and even in a full hour of play, players only hit the ball for about 26 minutes. Compare that to structured drilling, where you can be getting 45+ minutes of quality reps, and it’s clear why many players don’t improve as fast as they’d like.
As Jorge puts it: “Ball count matters.”
The 5 Play Situations Every Player Should Train
Jorge breaks down pickleball into five key play situations:
- Serve
- Return
- Baseline Play (Groundstrokes)
- Transition Zone / Volleys
- Dinking
Every drill he shares ties directly into improving one of these areas. And it’s not about overloading yourself with all of them at once — Jorge’s advice is to identify your weakest link and start there.
A Preview of Game-Changing Drills
Here are a few of the creative and competitive drills Jorge shared:
- Serve Tic-Tac-Toe – Turn serving into a target game with fun pressure and competition.
- Serve Horse – Like the classic basketball game, but with pickleball serves.
- Depth Returner & Dice Returner – Practice placing your returns in specific zones for max effectiveness.
- Third Shot Dropper – Rapid reps to master one of the most critical shots in the game.
- Drives & Drops – Alternate groundstrokes to train strategy and control.
- Crash & 7-Eleven – Transition zone drills that teach how to defend and attack midcourt.
- Tug-of-War – One of Jorge’s favorites for volley practice and game pressure simulation.
- Romanian Dinks & Carpadingham – Dynamic dinking drills that train movement, accuracy, and reactions.
Most of these drills are two-person friendly, so you don’t need a group to start improving. And for those coaching or running clinics, Jorge also includes scalable versions for 4+ players.
Free Resources + The Ultimate Drill Library
You can try out many of these drills for free at PickleballDrillsHQ.com, Jorge’s go-to hub for all things pickleball training. No email or credit card required — just click and go.
And if you want full access to his 430+ pickleball drills, 12 online courses, and video playlists that work seamlessly on mobile, the site offers a $1 trial for 10 days. It’s a serious resource for anyone who’s committed to getting better.
Final Thoughts
Jorge’s message is simple but powerful: If you want to improve, you need more touches on the ball. Playing alone won’t get you there.
Whether you’re a 3.0 trying to move up or a seasoned player chasing more consistency, Jorge’s structured drills and “ball count matters” philosophy are a game changer — pun intended.
Kalindi Dinoffer is trained in multiple aspects of mindfulness in life and in sports, sharing on her blog MindfulKalindi.com. She is also certified to teach yoga, fitness, reiki, and MFR. Kalindi also serves as CMO at OnCourtOffCourt.com, a leading supplier of tennis, pickleball, fitness and yoga training aids and equipment and has been published in Tennis industry Magazine and Pickleball Magazine, and has conducted workshops at conferences around the world. In her spare time, Kalindi plays tennis, pickleball and table tennis and enjoys outdoor activities such as hiking and biking and cross country skiing in the winter.
