With the loss of Pascal Dupuis to a knee injury, the questions surrounding Tomas Vokoun and Jeff Zatkoff in net, the need for more grit up front and the spector of free agency for five current Pens, Shero and his staff will have a lot to consider between now and March 5.
As reports surface of scouts crossing the country to assess potential trade targets and as the rumor mill starts to crank up, let's look at the five realistic trade targets for the Penguins.
History has shown that, in order to be successful playing alongside Sidney Crosby, players have to have two things; speed and a willingness to go to the high-traffic areas on the ice.
Mike Cammalleri of the Calgary Flames has both of those attributes in abundance and, considering he is a point-per-game playoff performer during his career and in the final year of his contract, he figures to be a prime trade candidate for the Pens.
While even the pro-rated portion of his $6 million annual salary might be cost-prohibitive, the Flames are in rebuilding mode and might be willing to take on some of the remaining salary for the right return as the Carolina Hurricanes did last season in the Jussi Jokinen trade.
Having made the biggest splash of last year's trade deadline with the Flames by acquiring Jarome Iginla, Shero wouldn't have to cough up nearly as much for a 31-year-old winger who was on his way out of town anyway.
Known for both his feisty style of play and his legendary goals in the seventh game of the 2009 Stanley Cup Finals, Max Talbot was a fan favorite in Pittsburgh.
That was until he signed a five-year, $8.75 million contract with the cross-state rival Phildelphia Flyers in the summer of 2011.
Having been traded to the Colorado Avalanche earlier this season, Talbot has the grit and tenacity that the Pens have been lacking at times and his return would go a long way to shoring up the Pens' bottom-two lines which have struggled at times.
With the Avalanche reportedly in the market for a top-four defenseman, something the Pens have in great supply, a trade for Max Talbot, whose cap hit is only $1.75 million for the next two seasons, seems like a good move for both sides.
If speed and goal-scoring ability at a manageable cost are what the Penguins are looking for to replace Pascal Dupuis, Ray Whitney may be the perfect candidate.
Since Whitney's name has been connected to the Pens in trade rumors for years, most might dismiss the possibility as old news but the situation is different this year.
Whereas Whitney had been an integral part of playoff-bound teams in Carolina and Phoenix who each wanted a top-pick in return, the Dallas Stars are tied for tenth place in the Western Conference and are looking to rebuild.
In addition, he had demanded a contract extension as a condition to waiving his no-trade clause in previous years and that, coupled with a high asking price took him off the table for the Pens.
However, Whitney is now 41 and maybe looking for one last postseason ride. Playing alongside Sidney Crosby wouldn't be a bad way to ride off into the sunset.
It's rare to find a former 40-goal scorer on a one-year deal at age 31, yet that's the case with Brad Boyes of the Florida Panthers.
Despite leading the Panthers in both goals and points, Boyes figures to be on the way out of Sunrise, Fla. as the Panthers sit in 15th place in the Eastern Conference entering February and are in the midst of a rebuilding.
Able to contribute on both the power play and penalty kill units in addition to being a scoring threat in five-on-five play, Boyes' speed and skill would be a good fit in the Pens' up-tempo system.
With the Panthers in need of both younger two-way defensemen and goaltending, the Pens are well equipped to make a strong offer for Boyes and, considering his low $1 million per year salary, would be able to afford him beyond this season as well.
With 10 impending unrestricted free agents and four restricted free agents, the Buffalo Sabres figure to be one of the NHL's biggest sellers at the trade deadline.
Therefore, it should come as no surprise that one of their free-agents-to-be, Matt Moulson, has been repeatedly linked to the Penguins.
A three-time 30-goal scorer with the New York Islanders, Moulson, who was originally drafted by the Pens in 2003, has a lot of the same qualities as Pascal Dupuis and has proven to be a good fit in up-tempo systems like the Pens employ.
With the uncertainty of when Beau Bennett will return from injury, the Pens have tried to fill Dupuis' spot with speed in Brian Gibbons and skill with Brandon Sutter.
Matt Moulson would bring both elements to the table and would be a natural fit on the Pens' top line.