Garth Snow faces the first of those two challenges in two weeks, and all eyes will be watching to see how the backup goalie-turned-GM reacts under the pressure on trade deadline day. Some people around the league have been waiting for the chance to pounce on him from the very day the Islanders stunned the hockey world by making him GM last July 18.
If he's anxious, he wasn't showing it Tuesday. A calm and soft-spoken Snow mingled with the media at Air Canada Centre and appeared not the least bit concerned with the big decisions looming ahead.
"I think it's going to be exciting," Snow said of his first trade deadline day. "A lot of it is hype that's blown out of proportion but I think it's good for the game, it keeps the fans interested."
As a rookie GM, Snow can expect a few low-ball offers. But he says he hasn't felt like his veteran colleagues are outrightly trying to take advantage of his lack of experience as the trade deadline nears.
"Hey, I'll probably pick up the phone and ask for crazy things myself," said Snow. "Who knows? You never know unless you ask."
Either way, he likes it better on this side the fence. Players, whether they want to admit it or not, fret about the trade deadline. They worry about being dealt and having to transplant their families overnight. The rumour mill is going full throttle at this time of year, to the point where players go up to hockey writers and ask them what they've been hearing.
Snow, who was traded in March 1998 from Philadelphia to Vancouver, remembers being one of those concerned players every year at this time.
"Now that I'm on the other side of it, I realize there's no reason for it," he said. "Several rumours where we've been involved, it turns out I never even had a conversation regarding the player or the team. A lot of it is hype about nothing."
What drives players crazy at this time of year is not knowing what their GMs are thinking. Two players in the Leafs' dressing room Tuesday morning asked this reporter what he thought John Ferguson would do.
For the Islanders, all they have to do is ask their GM. After all, he was their teammate last season. Snow said if a player hears a trade rumour involving him, he can approach him about it.
"I have a good enough relationship with the guys in the room that if a situation like that does arise, they know they have access to me to find out whatever they want," said Snow, before adding the kicker, "as long as they buy me dinner."
Joking aside, Snow said he's maintained a strong relationship with his ex-teammates, which sets him apart from most other GMs in the league. Most GMs traditionally have an arms-length association with their players.
"I go to dinner with guys on the team, I try to have a cup of coffee with some of them in the morning, or lunch on the road," said Snow. "Because you really have to communicate with your players."
Still, leading scorer Jason Blake draws the line at asking Snow about possible trades. Just because they were teammates doesn't mean he'll cross that line between player and GM.
"One thing that you learn over the years is that coaches coach, players play and management manages," Blake said after Tuesday's pre-game skate. "If Garth asks the players for personal advice, then that's a different story. But he'll do what's best for the New York Islanders hockey club."
Blake is the most interesting test of that former teammate relationship. Right now Snow has a huge say in Blake's future. He's an unrestricted free agent July 1 and has yet to sign an extension. If the Islanders fall out of the playoff race over the next two weeks, other teams will surely come calling on Feb. 27 looking for a quality rental like Blake.
But Blake insists he hasn't personally brought up his delicate situation with Snow.
"I have not spoken to Garth," said Blake. "That's why I have an agent. It hasn't really been weighing on me. The last week and a half, there have been a lot of questions popping up and you have to answer them. But I think what it comes down to is that I like it on Long Island. My heart is in Long Island."
Snow, citing a team policy, wouldn't comment on Blake's situation. Blake's agent Neil Sheehy said the trade deadline was not acting as a huge barometer over contract talks, despite reports to the contrary.
"I don't think either side feels any real urgency to get it done by the 27th," Sheehy said Tuesday from his Minneapolis office. "To me that's kind of a false deadline. There's a perception out there that something needs to be done by that day but in my opinion it doesn't have to get done by then.
"And I don't feel Garth feels that way either. If we get something done, that'll be great."
The Islanders, meanwhile, are in a precarious situation. They began Tuesday three points out of a playoff spot in the Eastern Conference, too close to the promised land to be sellers at this point but not safe enough to add short-term help. That explains his answer when asked about his game plan approaching the trade deadline.
"We have a plan of what we're trying to achieve, not just this year but for years to come," said Snow. "We're not going to deviate from that and get caught up in the hype of making a deal that doesn't make sense for the organization."
Translation? The Islanders won't overpay for a rental player. But what will they do? Only the former backup goalie knows for sure.