Why Your Pickleball Drilling Isn’t Working (And the 2-Step Fix)

If you’ve been putting in practice time and still feel like your game isn’t moving forward, you’re not alone. Most pickleball players drill regularly and still plateau. The frustrating part is that it’s usually not a lack of effort causing the problem. It’s the way the drilling itself is structured — or more accurately, what’s missing from it.

There are two specific things that almost every recreational player leaves out of their practice sessions. Once you add them, the gap between what you can do in a drill and what you can actually execute in a real game gets much smaller, much faster. This breakdown is based on the methods used by Richard Livornese on YouTube, who has spent thousands of hours refining his drilling process alongside his training partner Zach.

First, Let’s Explain This for Anyone New to Pickleball Drilling

If you’re newer to pickleball or haven’t thought much about how you practice, here’s the basic idea. Drilling in pickleball means practicing specific shots repeatedly with a partner, rather than just playing out full games. Most people do this by standing in one spot while their partner feeds them the same ball over and over. That’s called stagnant drilling, and while it has a place, it becomes a problem when it’s the only thing you do.

The issue is that real pickleball doesn’t look anything like that. In a real point, the ball comes from different angles, your feet are always moving, and the bounce changes every single time. If you only practice by standing still and hitting a predictable ball, you’re essentially training for a version of pickleball that doesn’t exist. The two things missing from most practice sessions are structured progression and live ball drilling. Both of these bridge the gap between repetitive practice and actual game performance. Once you understand how they work, your court time becomes dramatically more productive.

The Core Problem: Stagnant Drilling Has a Very Limited Role

Stagnant drilling — standing still and hitting the same ball from the same spot — has exactly one legitimate use. It helps you learn a brand new shot from scratch. If you’ve never attempted a two-handed backhand volley before, then yes, standing still and making contact repeatedly makes sense. You need to build basic coordination before you can add complexity.

But the moment you can make the shot with some consistency, staying in that stationary setup is actively holding you back. You’re not training your feet. You’re not reading different ball trajectories. You’re not learning how to execute when you’re slightly out of position, which is most of the time in a real match. According to pickleball drilling guides, the players who improve fastest are the ones who push out of that stationary comfort zone deliberately and systematically. The fix for this comes in two parts: drill progression and live ball drilling. You need both. One without the other still leaves a gap between practice and real play.

What Drill Progression Actually Means and How to Use It

Progression means taking a shot you already know and deliberately making the drill harder in a structured sequence, step by step, until you’re practicing it under conditions that closely resemble a real game. The key word is structured. You’re not just randomly making things harder. You’re adding one variable at a time so your technique can absorb each layer before you add the next one.

Here’s how Richard applies this to the reset, which is one of the most important and most poorly practiced shots in pickleball. The pickleball reset is a defensive shot that takes a hard ball and softens it back into the kitchen to neutralize the rally. Here’s the four-step sequence he runs through with his training partner every day.

Step one: Stationary reps at one court position. Start at mid-court. Your partner feeds speed-ups at you. You reset with one hand, then two hands. This builds the basic feel for the shot — the grip pressure, the angle, the soft hands needed to absorb pace. You’re not thinking about footwork yet. You’re just building the fundamental contact.

Step two: Change your court position. Move up toward the kitchen line, then back toward the baseline. The ball feels completely different from different depths on the court. A ball coming at you when you’re deep requires a different adjustment than one coming at you when you’re near the net. Deep court balls often require more short-hopping. Shallow balls require faster hand reactions. By practicing from multiple positions, you’re no longer conditioning yourself to one specific scenario.

Step three: Roaming. Now you’re moving continuously — forward and backward — while your partner keeps feeding. This is where the footwork component enters the picture. You have to read the ball off the bounce and out of the air while your feet are active. This step is the one most players skip entirely, and it’s also the one that has the biggest payoff. Almost every reset you hit in a real match will happen while your feet are moving. Practicing it while standing still is only telling you half the story.

Step four: Focused live play. Your partner plays out real points with you but intentionally feeds roughly seventy percent of balls into the zone you’ve been working on. You’re no longer in a controlled drill, but you’re also not just playing randomly. There’s still an intentional structure keeping you focused on the specific skill you’re developing. This last step is where most players never arrive. They do step one for thirty minutes, call it a session, and wonder why nothing transfers to their games.

Applying Progression to Dinking at the Kitchen Line

The same four-step structure applies directly to dinking practice. Richard uses the forehand middle ball as his specific example, and it maps perfectly onto this framework. Dink placement is one of the most nuanced skills in pickleball, and it requires deliberate, layered practice to truly develop.

Step one: Feed and repeat. Your partner feeds from a bucket. You hit the middle ball over and over from a stationary position at the kitchen. Pure repetition to groove the contact point and paddle angle. At this stage you’re building the muscle memory for where the ball needs to land.

Step two: Move to create the ball. Your partner still targets the middle ball, but now you’re moving around the kitchen line before each rep. You have to set your feet and create the right body position before hitting. The footwork now has to match the shot. This sounds simple but it changes everything about how the shot feels and how repeatable it is.

Step three: Partner can attack. Your partner is now allowed to grab any ball that sits up above the net. This is where you immediately get honest feedback on whether your middle ball is actually landing where it should. If your partner is attacking frequently, your dinks aren’t tight enough. If your partner rarely has an opportunity to attack, your placement is solid. This instant accountability is something stationary drilling can never give you.

Step four: Focused live dinking. Full points are played, but your partner keeps directing the majority of balls toward the middle. You’re adding speed-ups, working your shot selection, and reading defense, all while staying focused on that one area of the court. This is what real, transfer-ready dinking practice looks like.

What “Live Ball Drilling” Actually Means

Live ball drilling means starting every rep from a realistic game situation rather than a hand-fed, perfectly predictable setup. The ball you start with in a live drill should look like something you’d actually see in a match. This distinction sounds small but the practical impact is enormous.

Here’s how it works with the reset drill. Your partner drops and feeds a ball. You hit a float that sits up — a bad ball, the kind you’ll hit constantly in a real game. Now you have to work your way into the kitchen off that bad ball, exactly like you would in a real point. That one simple change teaches you three things that stagnant drilling cannot.

Ball recognition. You’re watching your partner’s paddle and feet while you’re recovering from your own previous shot. You’re reading whether the incoming ball will be attackable or neutral before it even crosses the net. This kind of anticipation is what separates players who always seem one step ahead from players who are constantly reacting too late.

Positioning under pressure. When should you close hard on the ball and when should you hang back and let it come to you? Richard describes closing on a low ball because he knows it won’t come back above his waist, while a higher ball tells him to wait and short-hop it. That read only comes from doing it live, repeatedly, until the decision becomes instinctive. No amount of stationary drilling builds this skill.

Movement efficiency. Getting from the baseline to the kitchen isn’t just about running fast. It’s about knowing exactly where to be based on the quality of the ball you just hit. If you hit a great third shot drop, you can close aggressively. If you hit a floater, you need to be more conservative. That court movement awareness is built in practice through realistic reps, not figured out on the fly during a match.

The Third Shot Drop Drill That Finally Looks Like Real Pickleball

The third shot drop is one of the most drilled shots in pickleball and also one of the most poorly drilled. The reason is that most players practice it in a way that bears almost no resemblance to how it actually happens in a game.

The old version: your partner stands at the kitchen and hand-feeds you a ball. You hit thirds over and over. It feels productive. You’re hitting the shot. But a hand-fed ball from a stationary partner looks nothing like a real return of serve. The ball speed, trajectory, spin, and timing are all completely different. You’re training for a situation that will never happen in a match.

The live version: your partner drops a ball and simulates a return, feeding it in live from the baseline. You hit a third shot drop off a real moving ball, then follow the shot forward. Your partner applies pressure immediately. That one adjustment changes everything about what you’re actually practicing. You’re working on third shot drop placement while also developing your transition movement, your read of an incoming attack, and your ability to recover to the kitchen under pressure — all from the same rep.

Richard and Zach also vary where the simulated return comes from. Sometimes middle, sometimes wide left, sometimes hugging the sideline. Because in a real match, you don’t get to pick where the return lands. Your forehand and backhand both need exposure to different angles and different court positions. Drilling from only one spot gives you a skill that only works from one spot.

How to Know When to Move to the Next Progression Step

The rule is simple. Move to the next step when you can make the shot consistently and your feet are no longer a problem at the current level. If you’re still shanking the ball or losing your balance when you try to add movement, you’re not ready to move on yet. Stay where you are and get clean before you add complexity.

The goal isn’t to rush to live play. The goal is to make sure every rep you take is as close to a real game rep as your current ability allows. Pushing to the next step before you’re ready just means you’re grooving bad habits under more chaotic conditions, which is worse than standing still. Rotating through different progressions across different shots across different sessions is also important. When you build a variety of drills into your practice week, you develop a more complete game faster than players who just rally or play open points with no specific focus. Focused work compounds. Random repetition doesn’t.

What a Full Drilling Session Should Actually Look Like

Here’s a realistic practice structure you can use starting with your next court session. This isn’t a rigid template — it’s a framework built around the principles above.

Pick one or two shots to focus on per session. Don’t try to work on everything at once. Resets and thirds one day. Dinking and counter-attacks the next. Spreading your attention across every shot in a single session means none of them get enough quality reps to actually develop.

Start with stationary reps only if necessary. If you’re working on a technique change you made recently or you’re genuinely rusty on a shot, a short block of stationary reps makes sense to rebuild contact feel. Otherwise, skip straight to movement. Stationary drilling should be the smallest portion of your session time, not the largest.

Add roaming or movement for at least half your reps. Your feet should be active for the majority of your practice. If you’re standing still most of the time, your drilling will feel productive but won’t transfer. Movement is where the real training happens.

End every session with focused live play. Play out real points with your partner intentionally skewing toward the shot or zone you’ve been working on. Don’t just open play freely. Keep the focus. This is what bridges structured drilling and actual match play.

Vary the feed position every single session. Wide, middle, near the sideline. Your partner should never give you the same ball from the same spot repeatedly during live phases. Predictability is the enemy of real game preparation.

If you want to go deeper on how advanced players think about structuring their training week, the principles here apply at every level above 3.5. The players who improve the fastest are consistently honest about what their drills are actually training. If your drill wouldn’t look anything like a real game situation, it’s time to redesign it. You don’t need more court time. You need better reps.

Frequently Asked Questions

What is the difference between stagnant drilling and live ball drilling in pickleball?

Stagnant drilling means standing in one spot and hitting the same ball repeatedly, which is only useful when you’re learning a brand new shot. Live ball drilling means starting each rep from a realistic game situation — like a simulated return or a recovery from a bad ball you just hit — so your footwork, ball reading, and decision-making are all trained at the same time. Most players spend the majority of their practice time in stagnant drilling and never make the switch to live ball work, which is why their game stops improving despite regular court time.

How do you progress a pickleball drill from basic to game-like?

Start with stationary reps at one court position, then change your court depth, then add continuous roaming movement, and finally move into focused live play where your partner plays real points but targets your practice zone more frequently than anywhere else. Each step adds one layer of complexity that brings the drill closer to game conditions. The critical rule is not rushing to the next step before your technique is stable at the current level.

Why doesn’t just playing more pickleball improve your game as fast as drilling?

Open play exposes you to every situation randomly, which means you might go an entire session without facing your weakest shot in a meaningful way. Structured drilling lets you get twenty or thirty quality reps on a specific shot in the same time it