Business Lessons I Learned From The Sopranos

The Sopranos is one of my absolute favourite TV shows (The Simpsons is right up there). It is one of my favourite thought studies on change management, leadership and personal development.

Recently, I’ve been thinking about some of my personal takeaways from the show that impact my week-to-week work life as a small business owner and entrepreneur.

Here they are.

More is lost by indecision than wrong decision

“In any moment of decision, the best thing you can do is the right thing, the next best thing is the wrong thing, and the worst thing you can do is nothing.”

– Theodore Roosevelt

Originally attributed to Cicero, Carmela says this to persuade Tony into purchasing a new home.

Later in that episode, Tony says it to Johnny Sack, a New York underboss, with respect to a hit being carried out on Carmine Lupertazzi.

The quote’s context is an anecdote about leadership. Leaders in positions of authority oversee many departments, people and tasks. Right or wrong, they need to choose a lane. Indecision is not an option. Harvard Business Review’s research indicated that decisiveness was one of four critical qualities of successful CEOs, even in the presence of ambiguity. Decisive leaders were 12x more likely to be successful than higher-IQ but slow leaders.

Junior Soprano, Tony’s uncle and confidante, echoes this sentiment:

“Who says there is [a right answer]? That’s what being a boss is. You steer the ship the best way you know how. Sometimes it’s smooth. Sometimes you hit the rocks. In the meantime, you find your pleasures where you can.”

Some people are better consultants than employees

“This guy could fuck up a cup of coffee.”

— Joe Pesci, Casino

Some people were born to be consultants (me, for example).

There’s an ongoing joke in my Entrepreneurial Leaders Program (ELP) that I am “not an Ops guy.” This is because I often struggle with the operational realities of a theoretical plan.

Junior Soprano has a brief stint as boss of The Sopranos family. His tenure is riddled with authoritarian decisions that upset his capos (managers) and cost the family money. Tony has to frequently interject in order to steer a clear course.

However, Junior is certainly not “sharp as a cue ball,” to use one of his lines. He’s an advisor, the person Tony turns to for the most challenging decisions to be made, whether whacking an underboss or dealing with a disrespectful yet high-performing subordinate.

Advisors and consultants can make great strategists. When removed from the daily stress and emotional implications of management, they are better able to see the forest for the trees.

I, too, have experienced this personally. In 2023, I took stress leave from Good Robot Brewing, which I co-founded. The company was rapidly growing and I struggled to keep pace with the day-to-day operations of so many moving pieces, among other things.

My psychologist told me that many of his clients with ADHD find success in consulting rather than operations. Operations is a never-ending story, whereas consulting leverages novel and exciting chapters. Once a consulting project is done, the box is checked and the slate can be wiped clean. This “shedding” that consultants experience can be very helpful for people with ADHD.

Like me, Junior was, perhaps, a better consultant than an operator.

The cream rises until it sours

"In a hierarchy, every employee tends to rise to his level of incompetence… Work is accomplished by those employees who have not yet reached their level of incompetence."

— "The Peter Principle: Why Things Always Go Wrong"

Junior Soprano was a good capo and a less-than-capable boss.

Silvio Dante also fits this description. During Tony’s coma, Silvio’s brief stint as acting boss paints a picture of Silvio as indecisive and unable to manage the newly added stress he takes on.

Johnny Sacrimoni. Gigi Cestone. Paulie Walnuts.

The various crime families and crews in The Sopranos Universe are peppered with good tacticians who were promoted based on their ability as soldiers or second-in-commands. Once they get bumped up to a certain level, they flounder.

This is the essence of the Peter Principle, which suggests that people get promoted until they reach a role that they cannot handle.

I’ve certainly experienced this in workplaces: a really strong engineer gets promoted into a really weak manager. Morale takes a hit. HR issues arise. People leave. Output decreases.

Tony even knows he promoted the wrong man, poor Gigi, who ends up dying on a toilet from stress-induced constipation-induced heart failure. What’s the alternative, though? To demote a manager would cripple them. The other option is to fire the manager, which also rarely happens because firing people sucks.

Hence, we are left with a broken hierarchical system, one in which good leaders, like Bobby Baccalieri, are promoted far too late, if at all, and the sour cream continues to sit unperturbed.

Now, how does one finish a blog post about The Sopranos?

Oh, yeah.

Don't stop belieeeeevin'

Hold on to the feeeeeeelin'

Streetlights, peeeeople

Don't stop—