Anna Bright: 3 Types of Pickleball Drilling Every Player Should Know

Most players show up to drill and have no idea where to start. These 3 types of pickleball drilling give your practice sessions real structure and purpose.

If you show up to drill and immediately wonder what to actually work on, pickleball drilling without a plan is almost as bad as not practicing at all.

Most players just start hitting balls and call it a session. They get touches, sure, but they don't get better in any measurable way.

This breakdown comes from Anna Bright on YouTube, who walked through exactly how she structures a practice session, from basic dinking all the way through competitive games with constraints.

Here's what that actually looks like and why it works.

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Why Most Drilling Sessions Waste Your Time

The problem isn't effort. Most players who drill are working hard.

The problem is that they run the same thing the whole session without any progression in pressure or context.

You can hit a thousand perfect dinks in isolation and still fall apart the moment someone speeds the ball up at you.

Pickleball drilling only works when it builds toward real game situations, which is the same logic behind the four key strategies shaping the modern game.

Anna breaks her sessions into three distinct types of work. Each one has a different purpose, and skipping any of them leaves a gap in your game.

Type 1: Isolated Skill Work with One Partner

This is where every session should start.

Two-person drilling lets you get clean, high-volume repetitions on a single skill without the chaos of game play interrupting your focus.

Anna started her session working on basic dinking with one partner, Juan.

That might sound boring for a pro, but there's a reason she still does it. The mechanics of a good dink have to be automatic before they can hold up under pressure.

If you want to build that kind of consistency, two-person pickleball drills are the best starting point.

You control the variables, you control the pace, and you get a ton of touches in a short window.

Here's what to focus on during isolated skill work:

• Pick one specific shot or pattern, not three.
• Keep the drill going long enough to feel actual fatigue in your arm and reset your mechanics.
• If the ball is going exactly where you want it, make the drill harder. Move the target. Add pace. Change the angle.
• Stay deliberate. Mindless repetition builds bad habits as fast as it builds good ones.

This phase is also where you address specific technical problems.

If your forehand dink keeps failing, two-person drilling is the only place you have enough reps to actually fix it.

Type 2: Three-Person Constraint Games

This is where things get interesting.

Once Anna's other drill partner Chase arrived, she shifted to three-person games with rules designed to force specific decisions.

Constraint-based pickleball drilling is one of the most underused tools in rec play.

You set a rule that forces the exact shot or situation you want to improve, even in a competitive context.

Anna's constraint was that only she could speed the ball up. Nobody else.

That means repeated offensive opportunities in a realistic setting, against players actively trying to neutralize her.

Very different from feeding yourself easy setups, and much closer to the kitchen line attacks you'll face in a real match.

The ball comes from a live rally. The situation isn't clean. She has to read, time, and execute under pressure.

If your drilling isn't translating to games, this is likely what you're missing. It bridges the gap between perfect reps and real competition, and it pairs well with drills disguised as games.

Here are constraint ideas you can run in your own sessions:

1. Only one player speeds up (the player focused on offense).
2. Dink-only until someone earns an attackable ball above the net tape.
3. One player must reset every ball hit at them before attacking.
4. All speed-ups must come from the backhand side only.
5. Play to 5, then rotate who has the offensive constraint.

The constraint keeps the drill honest. You can't just wait for a perfect ball. You have to create offense from the opportunities that actually show up in a real game.

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What Does "Off-Speed" Work Actually Mean?

Off-speed shots are attacks that use pace variation rather than raw power.

Instead of driving the ball as hard as possible, you change timing and tempo to catch your opponent mid-transition.

This is exactly what Anna focused on during the session.

Most players default to full speed or full soft, and there's a massive middle ground that gets ignored the same way the pros quietly abandoned the slice shot.

Off-speed works because your opponent's reaction time is calibrated to your previous speed.

When you change it, their hands reset late and the ball is already past them.

Practicing this inside a constraint game forces execution under realistic pressure.

You're finding the right moment in a live rally and pulling the trigger, which is also why most speed-ups fail.

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Does Attitude Actually Matter During Drilling?

Yes, and more than most players admit.

Anna specifically mentioned keeping a positive attitude when the constraint was lifted and the game opened up to anyone attacking.

That shift is a real mental test. You've been in control for the constraint portion. Now the pressure goes both directions.

It's easy to tighten up or get frustrated when you give up a point.

Your mindset during drilling directly affects what your brain retains.

Mindset shifts that you practice in low-stakes drilling become automatic in high-stakes matches.

If you reset emotionally fast in practice, you'll reset fast in tournaments too.

This is also why Anna plays for something. Push-ups for the losers, in her case. Small stakes make the games matter without making them stressful.

Your brain takes practice more seriously when there's a consequence attached.

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Type 3: Open Play With Real Stakes

The final phase is unrestricted competitive play. No constraints. Anyone can attack.

This is where you find out what's actually working.

Anna ran what she called "open sesame" games at the end. She won. Push-ups for the boys.

Open play at the end of a session serves a specific purpose. It's a test, not more practice.

You're checking whether the skill you just drilled holds up under full competitive pressure, including kitchen line hands battles.

If it's not holding, you know where to go back next session. If it is, you've moved the needle.

Order matters. Open play before you've grooved anything just reinforces whatever habits you already have, good or bad. Pros build the skill first, then test it, the same sequencing behind breaking 5.0.

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How Do You Know When to Move On Between Phases?

You don't need a stopwatch. Watch for consistency.

When the isolated skill feels automatic and boring, add pressure. When the constraint game feels too easy, open it up.

When open play exposes a new weakness, that becomes the focus of your next isolated phase.

It's a loop, not a ladder. You'll cycle back to isolation work constantly, even on skills you thought you'd mastered.

That's not regression. That's how good players maintain their edge, and it's the core idea behind the 70% rule for making practice skills stick.

Anna also took a break mid-session to eat cherries and reset.

Don't underestimate rest during a long drill block, and don't skip the warm-up that keeps your mechanics sharp as fatigue sets in.

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Putting It All Together for Your Next Session

Here's a simple framework you can use the next time you step on the court with a practice partner or two.

1. Phase 1 (15-20 min): Pick one skill. Dinking, resets, speed-ups, whatever you're working on. Two-person, high reps, deliberate focus.
2. Phase 2 (20-30 min): Add a third player and run constraint games. One player has the offensive or defensive constraint. Rotate every few points or games.
3. Phase 3 (15-20 min): That's it. You don't need a complicated system, just a reason for everything you're doing on court, the same way a 4-step system beats hitting balls at random.

That's it. You don't need a complicated system. You need a reason for everything you're doing on the court.

Improving at pickleball isn't about hitting more balls. It's about hitting the right balls at the right time with the right amount of pressure.

This three-phase structure gives you that every single session.

And if you want to track whether it's actually working, filming yourself during drilling is one of the fastest ways to spot what's breaking down under pressure that you can't feel in the moment.

The players who improve fastest aren't the ones with the most talent.

They're the ones who show up with a plan and adjust it honestly when something isn't working. Build that habit now.

Frequently Asked Questions

How long should a pickleball drilling session be?

Most productive drilling sessions run between 60 and 90 minutes. Beyond that, your mechanics start to break down from fatigue and you risk reinforcing sloppy habits rather than clean ones. Quality of focus matters more than total time on court.

Is three-person drilling better than two-person drilling?

They serve different purposes. Two-person drilling is better for isolated skill development with high repetition volume. Three-person drilling is better for practicing decisions and execution under mild competitive pressure.

You need both in your rotation.

What does it mean to use constraints in pickleball practice?

A constraint is a rule you add to a practice game that forces a specific skill or decision to come up repeatedly. For example, only one player is allowed to speed up the ball during a rally. Constraints let you practice a skill in a realistic context without waiting for it to happen randomly.

How do I know what skill to drill?

Look at where you're losing points in games. If you're giving up too many hands battles, drill resets and speed-up defense. If your attacks aren't converting, drill off-speed shots and timing. In-game mistakes are the clearest signal of where your practice time should go.

Should I play for something during practice games?

Yes, small stakes make a real difference. Push-ups, running lines, or even just keeping score publicly adds enough consequence to make your brain treat the game seriously. Practice under mild pressure produces results that transfer to real competition far better than pressure-free drilling.