Randal Serr: My assumption, having never coached soccer, is that being head coach in MLS is very demanding and tries your patience. I can only imagine that after a two or three game streak of undesirable results that a coach starts to really get anxious. Wins mean everything and without them sports fans are the most impatient people in the world. It's like a social experiment. Just listen to a post-game RSL radio show after just one loss and you will hear at least one person will say that the front office should blow up the team. Cassar has to rise above all that chatter and know that the wins will come if he keeps working.
Kreg Asay: I think he's learned a lot from being Jason's #2 since Fraser left, so tactics and player management shouldn't be a big learning curve. What is likely to be though is handling the press. Jason had similar trouble the first few years and it took several fines and at least one suspension to figure out what coaches can and can't say.
Wes Brown: Managing the locker room. Especially if things don't go well in the opening weeks. Jeff's an excited guy, and his charisma bleeds through with everything he does. He's made it known that he's looking to conduct player relations in a more open fashion, and that's a good step. My concern is with him being stern with players that need a rough edge to motivate them. Don't get me wrong; Cassar's no pushover. Nor should it actually be that large of a problem. But he's still a first time head coach, and it's something he'll need to worry about. Luckily he has able-bodied assistants next to him that are capable of dealing with issues like this. And, honestly, Cassar should handle the challenges of the role extremely well.
Charles Barnard: I think Cassar will find that managing relationships might be the most difficult thing about being the head coach. As an assistant coach Cassar could play the buddy role with the players. As the main man he won't be able to have the same type of relationship with them. How he handles this will be key to the season.
Chad Loveland: Cassar will find the pressure from fans to be the most difficult part of the head coaching position. If things don't go super-smooth, a small part of this fan base might turn on him, and the nonstop comparisons to Kreis could weigh on him as well.
Matt Montgomery: Cassar seems plenty ready for the position - he's been training for it for several years now - but it won't be easy. The most difficult part of the job, to my mind, will be coping with strings of losses - we go through a few of those every year, and they must be trying for a coach expected to win. The weight of expectations on Cassar shouldn't be excessive, but managing those when we go through good spells and bad spells will be difficult.