The new pope will almost certainly be the first to come of age in the post-Vatican II era. He could be the first with to use a smartphone. And he may be the first pope to come from outside Europe since the conclave began in 1276.
Unlike American elections, where the conversation often begins with potential candidates, papal elections begin with a conversation about priorities. The cardinals, in other words, are now asking themselves, "What is the situation of the church?"
This year, according to cardinals and Vatican insiders, they are looking for someone who can stabilize and sanitize a church bureaucracy mired in scandal and mismanagement. They're also looking for someone with charisma to break from Benedict's reserved nature and re-energize the faith.
The balance of those desires - as well as a power struggle between reform-minded cardinals and institutionalists - may become the story of this conclave.
Take back the Vatican
As the conclave kicks off, the biggest issue facing the cardinals is how to deal with the Curia, the church's Byzantine governing body that has been engulfed in controversy the past few years.
"We need someone who can take the Vatican back," one cardinal-elector said.
The unfolding of the "Vatileaks" scandal over the past 15 months has revealed alleged blackmailing of homosexual clergy, bribery in the highest levels of church bureaucracy and even details about the pope's personal finances.
The Vatican also has been accused of complicity or worse when it comes to the sex-abuse accusations that have rocked the church in America and Western Europe. (To be fair, Benedict quietly defrocked an unprecedented number of priests linked to those scandals.)
The Curia in particular is often described as a haven for patronage jobs, political favors and waste.
Although many of the cardinals are ready to pick someone who will overhaul the bureaucracy, getting their guy might not be so simple.
Electing a pope requires a two-thirds majority, so it takes only 39 of the 115 voting cardinals to derail a candidate's chances. A bloc of largely Italian pro-Curia cardinals might be emerging, setting the stage for a possible "Curia vs. The World" showdown.
Overcoming an obstructionist minority would require finding a candidate who can assuage the preferences and peeves of a vast majority of the remaining cardinals - someone who would cause the least concern for the fewest constituencies in the conclave.
One past comment on a theological issue or lack of experience in a particular field could cause 10 or 15 votes to defect and torpedo a candidate's chances of overcoming the pro-Curia minority.
This dynamic is partly why so much uncertainty surrounds this papal election. Unlike many past conclaves, there is no ideological issue driving the agenda and no front-runner with a large, undisputed base of support.
The next pope could be Peter Appiah Turkson, of Ghana; Sean O'Malley, of Boston; Odilo Scherer, of Sao Paulo, Brazil; Gianfranco Ravasi, of Italy; or Marc Ouellet, of Quebec.
Or it could be none of the above.
After the death of the enormously popular Pope John Paul II in 2005, the conclave sought a lower-profile pontiff, an older man who would have a relatively short papacy and not feel the need to live up to his predecessor's rock-star status.
Joseph Ratzinger, a conservative German who was in his late 70s and confidante of his predecessor, was the man for the job. Now, after eight years of Benedict's understated ways and the growing sense that the church is losing touch with its traditional base, many in the conclave appear ready for another great communicator - someone who can attract a new generation of Catholics.
Enter the e-pope.
Although Benedict launched the barque of Peter into the Twitterverse in December with a public tap on an iPad, the now-retired @Pontifex penned his drafts in longhand and left his cellphone to his secretary's keeping.
The next guy will likely be more adapted to the digital world - or at least used to the sight of a computer on his desk.
Beyond tech-savviness, the next pope will need charisma if he is to connect with Catholics.
Some cardinals said they want someone who can compellingly and convincingly present the faith - in word and through the media, both at home and on the road.
Even more than a desired style of governance, this is where the electoral calculus gets tricky: It's a question of personalities, where one elector's champagne can be another's vinegar.
Scherer, of Brazil, has been praised by some and scorned by others for his prolific use of social media. Ravasi, of Italy, is admired for his ability to converse in English, Hebrew, Arabic and Italian. But he also has been cast as too bookish to be the church's ambassador to the world.
One new factor that could smooth the balloting is that the cardinals do not appear to be concerned with ideology as much as they have in the last two elections.
The pontiff-to-be will almost certainly be the first who wasn't present at the Second Vatican Council in the 1960s - the church's last dogmatic overhaul and the source of theological fault lines for decades.
There's a good chance that he, like most of his red-capped peers, wasn't even a priest yet during Vatican II, meaning the dust may finally be settling on one of the greatest debates in Catholic history.
Rocco Palmo authors the blog Whispers in the Loggia. Portions of this story appeared on that blog.
On Twitter: @SeanWalshDN