Sure, he should get tricked every now and then. Nobody is perfect. He should get tricked about as much as Steve Rogers (the leader all the Avengers traditionally defer to) does, or as much as Batman (the leader the Justice League defers to) does. Because a legion of superheroes with rosters about as big as those routinely decide to let him play boss man.
I think you're giving Cyclops way too much credit. You're also lumping Batman and Cap into the same group when they're really not.
Batman is the metaphorical a chess player, playing multiple moves ahead of everyone else, a long-term planner with excellent tactical abilities based on dictating the terms of engagements, and then improvising in-battle as necessary. Plus, is Batman really the leader of the JLA? I'd say, more often than not, the JLA is led by Superman.
Cap is an amazing field tactician and general, a guy who is able to feel out his opposition and defeat them by finding their weaknesses and playing to his strengths.
If you pull the wool over Batman's eyes, you've done something incredible. Cap gets fooled all the time. He spends most of the time a move behind Red Skull, just managing to wiggle his way out of situations.
Even compared to that, it's rare that I've ever seen Cyclops do anything but go on missions planned by Professor X, or respond to immediate threats.
Cyclops is like Superman. He's the team player, the guy who does the right thing, and who sets the example for and brings people together. He's not a dummy, but he's rarely painted as a master tactician. I don't think Havok was worried about living up to Cyclops' abilities as a planner and strategist, but as a leader of people.
