Management Succession on The Sopranos

As fans of The Sopranos agonize over how the mob drama will end, Tony himself is wrestling with management challenges that are not exclusive to the criminal life.

Put in B-school terms, Tony is running a diversified services enterprise involving high-interest loans, illicit pharmaceuticals, labor dispute resolution, neighborhood insurance, companionship services, merchandise reallocation and waste management consulting.

Between the "trending downward" of the demand for these services and the ominous encroachment of the Feds and the Lupertazzi family of Brooklyn, Tony has been coming unglued. He has violated his father's finger-severing advice about the hazards of gambling, he initiates "relationships" with women at the office (usually in the front seat of a car), and he has been systematically isolating himself, abusing every valuable relationship he has.

Burnout for top-level guys isn't unusual. Ambitious executives face a perpetual tension between wanting more and wanting out. Tony and Phil Leotardo grouse about "getting out," but, in reality, they are not capable of retiring to Florida and playing on the proverbial beach with their grandchildren. They're not those types of guys.

One compromise between working yourself to death and retirement is succession, a preoccupation of Tony's for some time. In Tony's world, of course, most management succession occurs face down in a bowl of linguini puttanesca.

Self-satisfied business school pundits preach the utopian panacea of "delegation," but as The Sopranos starkly asks, "What if you have no one to delegate to?" Tony can't recruit from the outside like traditional corporations do (think Lee Iacocca jumping from Ford to Chrysler) and he's not as fortunate as Jack Welch, who had an internal crop of top-flight candidates at GE before selecting the worthy Jeff Immelt.

Silvio, the smartest guy in Tony's crew, couldn't hack the job once he was in the big man's chair during Tony's recuperation from a .38 caliber shareholder revolt courtesy of Uncle Junior (despite having bought himself a new wardrobe for the role); Paulie Walnuts is a psychopath past his prime; Bobby "Baccala" lacks the ruthlessness; Eugene Pontecorvo hanged himself when Tony wouldn't let him telecommute from Florida. Patsy is a problem because Tony iced his brother and Patsy knows it; and Carlo hasn't been making numbers lately.

Tony was "bringing along" Christopher for years, but there are huge problems here. More than any other character, Christopher represents a profound management dynamic playing out in many businesses today. Christopher, emblematic of his generation, feels entitled to the spoils but is intensely averse to putting in his time. Employers across the country are increasingly wrestling with a generation of people in their twenties and thirties who have seen a few too many magazine covers featuring twenty-six-year-old zillionaires (think YouTube and MySpace) and believe spectacular destiny is an entitlement. This kind of coverage, of course, is a distortion of what's really happening. There aren't that many baby moguls, we just keep hearing about the same crew, which feeds into the expectations of people born in the 1970s and early 1980s.

Similarly, Christopher grew up on the iconic legend of Michael Corleone. The image of the boyish Al Pacino vanquishing his enemies (every young boy's fantasy) seminally registered with a fantasist like Christopher. Never mind that the real Mafia dons were never brooding Ivy League-educated war heroes, but illiterate septuagenarians with swollen prostates, clogged arteries and a penchant for blending into the scenery. Christopher is of a generation that was raised on instant-gratification and the nurturing of self-esteem rather than the accumulation of experience. Not surprisingly, he believes his destiny is in Hollywood, where his Very Special story is awaiting to be told on the big screen.

Then there is Anthony, Jr. A.J. is the quintessential by-product of business people who want their children "to have everything I didn't." This admirable wish, of course, is a curse. A.J. finds himself wallowing in what Saul Bellow once referred to as "the swamp of prosperity." To A.J., the planet is one big buffet that God set up for him to choose from. Intrinsically a consumer, it is beyond his ken to actually do something. Like his father, A.J. is prone to taking the easy way out, but doesn't have the animal qualities that that allow Tony to thrive in a world of killers. We've seen that Tony can take a gunshot, but it's doubtful A.J. can take a punch.

Leadership of all enterprises, to one degree or another, is constrained by their cultural prejudices. This is one reason why Tony's "best earner," Vito Spatafore, would never make the grade. Vito, in part to better cultivate a top-management aura, downsized a few hundred pounds, but when his sexual orientation came to the fore, he went on the lam and got outsourced. Permanently.

In theory, the most promising leaders on the show are the women. Look at Angie Bompensiero. When her husband, Big Pussy, didn't return from his management retreat at sea, Angie set herself up with an auto body shop and a money lending franchise, which is the envy of all the gangland wives.

Janice Soprano Baccalieri and Meadow Soprano would also be ideal recruits. Janice has the greed, ruthlessness and manipulative skills - especially her proclivity for deflecting her despicable qualities by invoking the New Age rhetoric of the victim - that would take her straight to the top of many contemporary corporate enterprises. Once you strip away her hippie swindle, Janice is pure predator - exactly what's required of a mob boss.

Meadow Soprano has brains, ambition and her father's intuition (She knew something went down on that college visit). Someone with her pedigree could help take a modest family business and eventually transform it into a more sophisticated, next-generation enterprise. This is exactly what the smarter old-time racketeers did: They sent their kids to Ivy League schools and made sure that whatever they did after getting their diplomas was strictly legitimate. Meyer Lansky sent his son to West Point. And, as Lucky Luciano admitted in exile at the end of his life, if he had it to do over again, he would have "done it legal." "I learned too late that you need just as good a brain to make a crooked million as an honest million." Alas, Meadow is a woman and we know where women stand in Tony's world (usually next to poles at the Bing).

There's no question that Tony's managerial style of late is going to land him in a world of hurt. Still, he is also a hostage to the decline of his industrial sector and a talent pool completely ill-equipped to perpetuate a 21st century enterprise and ease his burden. Perhaps it is the reality of decay, not a hail of bullets, that will be his punishment.

As Tony presciently said in a recent episode, "Everything turns to shit." What's more, a vengeful Phil Leotardo lies in wait across the river ready to launch his (very) hostile takeover bid for Tony Soprano's under-performing assets.

Eric Dezenhall is the CEO of Dezenhall Resources, a crisis communications firm, and the author of the new book Damage Control: Why Everything you Know About Crisis Management is Wrong (Portfolio).