The single most difficult decision in pickleball is when to move from the baseline to the kitchen line. That decision becomes doubly hard when playing with a partner. A basic rule of thumb in doubles is that players should move together (Let's Stay Together). Therefore, the decision to move forward must be shared by two minds.
First, we must acknowledge that getting to the kitchen is a worthwhile goal. A previous post - written by Prem Carnot and titled You. Must. Get. To. The. (No-Volley) Line - detailed the reasons why getting to the line is important so I will not revisit that issue.
It is easy for one player to advance to the kitchen. He can almost walk to the line when a ball is hit to his partner. So, why not have that Player A advance and then allow his partner to work his way to join Player A at the line? The answer is simple - the gaps created are huge and both players are put into hard-to-defend positions. Let's revisit the 3 lanes available to opponents as shown in Figure 1.
Figure 1
In this case, Player A advanced to the kitchen line and left Player B behind. If a ball goes to the opponent in the lower court, the entire middle, the easiest hitting lane, is wide open with about a 15 foot gap between players. If a ball goes to the opponent in the upper court, the middle is not quite as open but still available, plus he has the angle to Player B's sideline. Players A and B are in big trouble in this position. They must move forward together in order to avoid this.
The decision to advance is dependent on the set-up shot, generally a third-shot drop. But advancing on a bad drop shot can end the point quickly. A drop shot that is either too high or too deep will be smashed back at players' feet when caught in no-man's land between the baseline and kitchen line. Players should stay back in that circumstance.
The key to successfully moving forward is a good set-up shot. Unfortunately, the shot is rarely known to be good until it actually bounces. Players need to use every clue available to make their decision. The first clue should come from the player hitting the shot. He should immediately warn his partner if he knows the shot is not good enough. The second clue is the reaction of the opponents. They will shows signs of their forthcoming shot by raising or lowering their eyes and paddle, for example. When all signs are good to go, then move forward together. Move until the opponent is ready to hit the ball, then stop, using the Split Step, regardless of how far forward the team has gotten. Teams should continue to earn their way to line through the same tactics.
A Mark Renneson video called When to Move Forward in Doubles and When to Stay Back below details some of the decision-making process.
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