The Chicago Blackhawks were far from a dynasty 17 years ago when Ken Holland called the club's then-general manager Bob Murray to inquire about a trade for future Hall of Famer Chris Chelios.

Holland was two years into what's become an unparalleled run of success as the Detroit Red Wings GM. He wanted to know if the Blackhawks, one of the worst teams in the NHL, would move their three-time Norris Trophy-winning defenceman.

Chelios wasn't available, Murray told Holland.

"If things change, give me a call," was Holland's reply.

The phone rang two days before the March 23 trade deadline.

"We're trading Chris Chelios," Murray said, according to Holland's recollection of the conversation. "Do you still want to be in?"

Trades at the deadline rarely pay off like the Chelios deal – the star defenceman went on to help the Wings win two Stanley Cups -- because, as Holland says, there is simply no blueprint for success.

"It's not like there's a manual, that you become the manager of a team, I give you a manual and [it says] 'This is the way trades are made,"' Holland said as he prepared for Monday's 3 p.m. ET trade deadline. "There is no process to getting a deal done. It's a whole bunch of balls flying around the air and they're moving in different directions."

It can be an exhilarating, nerve-racking and anxious time for GMs. The preparation begins in January when teams bring their staffs together for two days of scouting meetings, both on the amateur and professional sides. Teams compile lists of players that interest them while also identifying their priorities.

But Dallas Stars GM Jim Nill says "90 per cent of the time" teams never get the players at the top of their lists, often settling for secondary players instead.

"A lot of things that you work on don't work out, but you know what, maybe it's three months later on July 1st, something happens with that same player," said Devils GM Ray Shero.

That can be one of the frustrating aspects of the deadline experience, according to some GMs.

"You've got a list of guys and first guy on your list sometimes he's gone," Shero said. "Next guy on your list he's gone. Third guy on your list, team says 'We're not going to trade him, we just signed him'. It's fast-moving. It's exhilarating. It's disappointing at times."

Preparation can't be discounted. Knowing the players, knowing who's available, knowing which teams are in the hunt and which teams are out, it's all part of the juggling act.

'It might not be a big trade ... but that trade could be the one that helps you get through two games in Game 6 and 7 [of a playoff series].' - Stars GM Jim Nill on filling the seemingly unimportant holes of a team before the NHL trade deadline

Nill points to Holland, his former boss, and Scotty Bowman as masters of preparation. Their expertise was (and is in the case of Holland) making sure that every hole in the organization was filled, even those that may seem unimportant.

"It might not be a big trade, it might be the littlest trade out there, but that trade could be the one that helps you get through two games in Game 6 and 7," Nill says. "We always tell our staffs, 'We know who the top guys are', but it's knowing that secondary guy."

Holland says the first order of business for any GM is self-determination. Teams need to decide if they're buying, selling or sitting on the bubble and doing nothing.

It's also about understanding the market and knowing which teams are likely to move assets. What complicates the process sometimes, Holland said, are teams that hope to sign their impending unrestricted free agents to new contracts. Negotiations can keep those players in limbo a little while longer.

When the Pittsburgh Penguins traded for Marian Hossa in 2008, Shero, then the Penguins GM, had to wait it out as the Atlanta Thrashers determined whether they could sign their star forward.

Squeezing the market

Increased parity and a points system that awards teams for losing in overtime and the shootout also has more teams in the playoff hunt later in the season, further squeezing the market. Sellers don't arrive at that designation until late in the process, if at all, which raises the price and competition for assets.

"It's not like other people aren't trying to get Marian Hossa or aren't trying to get Jarome Iginla, or aren't trying to get anybody," Shero said, recalling past trade deadline commodities. "You're in competition with teams usually and it's not like 'Oh, we got that guy' because we're the only team bidding on him."

There's a danger of getting dragged into the frenzy, which has now become an annual obsession among fans and media.

"If you don't get what you want every GM has to go to the media that afternoon and say 'We really like our team'. What are you going to say? And sometimes that is the best thing," Shero said.

There's a fine line to walk, too.

"You can make all the trades in the world, but if they come in that dressing room and it just isn't a fit you get yourself in trouble," Nill said. "You have guys that have battled through 60 games for you already. Are you knocking somebody out of the saddle that's been there all year? That's a fine line. You've got to be careful."

"You don't know when you do it," Shero added. "No one makes a trade thinking 'Oh, that's a crappy trade'. Everybody makes a trade thinking that's going to help your hockey team."