Both the Sky Bet League One club's goals in Saturday's pre-season friendly at the Proact Stadium came from long balls as the Whites let a 1-0 lead slip before claiming a 2-2 draw late on.
Speaking on LUTV, Hockaday said: "I thought we started slowly, we then got into the game and by half time we were the better team.
"We were worth the lead when we went ahead and then we stopped, I don't know why because that is not in the game plan.
"I liken it to a fight. You get them on the floor but then you pick them up and allow them a free swing.
"We know that Chesterfield are a good passing team and they couldn't pass their way through us and score, so they bring on a big lad and start hitting long balls into him.
"It should be the easiest type of defending to deal with. If you cannot defend 50-60 yards balls then you have a problem and on the day, we couldn't handle it.
"To concede two goals from long balls to a passing team is just not good enough."
Jamaica international Rudy Austin put Leeds ahead a minute into the second half when converting a penalty after midfield partner Luke Murphy had been sent tumbling in the box.
Chesterfield equalised nine minutes later, with Sam Morsy slipping the ball under goalkeeper Marco Silvestri.
Morsy fired the Spireites into a 65th-minute lead when pouncing on a loose ball in the area before beating Silvestri for a second time.
But Austin converted his second penalty in the closing stages after Sam Byram had been brought down to deny the home side victory.