While Captain America is typically the leader of the Avengers, there have been times when Hawkeye has given the super soldier a run for his money. Steve Rogers is an undeniably natural leader, but when it comes to a superhero team, it takes more than just heart to make the best plans for success. The Avengers' leader also needs to be aware of each members' strengths - and more importantly - their shortcomings.
In 1996, Marvel threw its heroes into a pocket universe in Heroes Reborn. Then in 1998, it returned them back to the status quo in Marvel's Heroes Return - which was made up of several titles. Before being able to return, however, the Avengers had to escape from an alternate Medieval reality.
Avengers #2 (1998) had the creative team of Kurt Busiek, George Perez, Al Vey, Tom Smith, Comicraft, and Richard Starkings. It is part of the Heroes Return event and it opens with Captain America - here Yeoman America - confronting Hawkeye about this reality, reminding him who he is. In this reality, Hawkeye was going by the name of Longbow. After Captain America "wakes" him up, the two join forces to save the rest of the Avengers - but Cap makes a serious miscalculation that Hawkeye had already realized.
After waking Hawkeye first due to his dedication to being an Avenger, Cap decides to try and "wake up" Iron Man. Unfortunately, he hasn't factored in an important thing about Tony Stark - his ego. Hawkeye already knew that Tony would be one of the biggest challenges and selected alternate Avengers to address first. Naturally, however, he gets caught up in Captain America's mistake and doesn't hesitate to call him out on it. As Hawkeye says, Tony Stark is a "good guy, normally -- but he's waaay too into his whole nobleman/lord of the manor trip." This leads Captain America to mention asking his opinion "more often when it comes to team matters".
Hawkeye is a key member of the Avengers and has been for many decades. He's one of the most underrated members, being set aside by many fans due to his lack of superpowers. However, he's one of the most loyal Avengers and an unexpected leader. At times like this, he proves that he can even best Cap when it comes to knowing his teammates and strategizing based on that knowledge. Instead of realizing that the spell everyone is under would be extra effective on Tony, Captain America bet on Tony's heroism in the real world they're usually in. However, if Iron Man doesn't have knowledge of his experiences and is given a position of power, he isn't his usual self and cannot be approached the same way as other Avengers. Being the team leader of the Avengers requires not just faith in teammates or strength and super skillsets. The most effective leaders know the weaknesses of their teammates and can strategize accordingly in many situations - something Hawkeye proved to be better at than Captain America in this alternate reality.