Tommy Boy Needed the Right Succession Planning Model
To kick off the launching of my report, Succession Planning Simplified, I’m writing a series of blog posts this week with a study of the worst case of succession planning in history (and some might say, the worst film): Chris Farley’s low-brow comedy “Tommy Boy.”
This 1995-cult classic features the perennial pratfaller Chris Farley at his very best, although that’s entirely dependent on your taste in comedy. If you haven’t seen the film, I’ll leave it to you to consider its value, but let’s look beyond the laughs at the plot for Tommy Boy.
When you take a closer look, you’ll marvel not only at the character’s ability to squeeze into a pair of tiny underwear (not a scene for the children), but his ability to persevere through a case of botched succession planning.
This film is a story about horrible succession planning. Let’s find out what went wrong, how Tommy Boy miraculously came out on top, and what you can do to avoid similar mistakes.
How Big Tom Failed Little Tom
In the film, Thomas R. “Tommy” Callahan III (Chris Farley), graduates from college and returns to Sandusky, where a job as an executive in his father’s auto parts plant awaits.
Tommy is the typical child of privilege. Thanks to the successful family business, he’s been handed everything to him in life. This is definitely a good thing for Tommy Boy, because the guy is buffoon. He barely squeezes through college, and is woefully unprepared for his position at the parts plant.
Tommy Boy’s father, Big Tom, has big plans for his son. He’s also the key to the company’s success, but drops dead of a heart-attack during his wedding reception.
Here’s where the bad succession planning takes hold. Big Tom’s new wife is actually a con-artist. Her original plan was to marry Big Tom and then divorce him, suing for half of everything. But Big Tom’s sudden death results an unexpected payday: She inherits a controlling interest in the company.
Meanwhile, the auto parts company runs into another huge problem. Big Tom’s master strategy was to build a new brake pad division. However, without the astute leader in place, the bank reneges on its loan for the endeavor. Even worse, the bank seeks immediate payment of Callahan Auto’s debts.
The rest of the film chronicles Tommy Boy’s attempts to salvage the company and save its workers. Naturally, in the end he perseveres, though plenty of Farley’s trademark sophomoric humor. But while you’re laughing, you should also take note of what went wrong in terms of succession planning.
Five Reasons Why Tommy Boy Got the Succession Planning Shaft
Tommy Boy is a comedy, as if you hadn’t guessed by the presence of the late, great Chris Farley. But what happened to him is actually no joke – I see it time and time again. He’s a victim of poor succession planning, and here are the examples:
1. Big Tom thought he was invulnerable. The real culprit in Tommy Boy’s predicament is Big Tom. Like most CEOs, the last thing he wanted to think about was his potential demise, especially when he’s just married a younger woman.
However, Big Tom should have had a plan in place. In the absence of any kind of succession planning, there is a vacuum. In in a vacuum, evil power tends to flourish. That’s why Al Qaeda thrives in poor third world countries with little security. Or why Big Tom’s new wife, Beverly, gets an opportunity to cash in.
2. No one externally was aware of a plan. The bank chose to renege on Callahan Auto’s loan for a new brake pad division, as well as its current debts. Why? Fear, basically. Wouldn’t you be fearful to learn that Chris Farley was running the company you were loaning money to?
If there had been a well-communicated succession plan in place, the bank would have seen an established expert assume Big Tom’s position at Callahan Auto, ready to guide the company forward without a hitch. Instead, they panicked.
3. No one internally was encouraged to get on board with the transition.

Internally at Callahan Auto, the obtuse Tommy Boy garnered no respect. For example, smarmy Richard Hayden (portrayed by David Spade) is smarter and understands the business, but is bypassed for a promotion simply because of Tommy Boy’s bloodlines. He resents Tommy Boy, and grudgingly aids in the recovery effort.
The workforce also sees Tommy Boy as the buffoon he is, and has little belief in his abilities. Like the bank, they foresee a gloomy future.
Perhaps if a solid plan was in place and communicated effectively to the company, they would have understood and participated in the change. Instead, they resisted.
4. A training program was not established for Tommy.
Poor Tommy Boy. No training plan was in place for him to transition to a leadership position. Instead, he was left to his own devices, which included sticking his tongue in an oscillating fan, or admiring his new beer fridge. No one was there to show him the path he needs to take to keep the company afloat.
5. A thorough check of successors was not performed.
Tommy Boy: “We’re family. We’re going to be doing lots of dumb stuff together.”
Perhaps Big Tom’s most glaring mistake is that Beverly retains controlling ownership stake. In my opinion, choosing blood relatives or spouses to succeed you without consulting with any impartial experts is a sure-fire recipe for disaster.
What if a team of outside advisors had helped Big Tom create his succession plan? Might they have done some background checking on Beverly and discovered she was a notorious con artist with a criminal record? Without a doubt.
An external team might have also seen that Big Tom’s love for his son, however sincere, was not going to do the company any favors. They might have recommended a more seasoned professional assume the helm, and then provide Tommy Boy with a new position in the company, or a buy-out clause.
Why does Tommy Boy prevail?

You would think my answer would be, “This is just a movie. No one could possibly save the company, especially Tommy Boy.”
To tell you the truth, I think you’re wrong.
I think that Tommy Boy’s bizarre and crazy plan to save the company, one that ultimately works, could happen in the real world. Why?
It’s not because of the tactics, especially the part where Farley straps highway flares to his body, poses as a suicide bomber, and threatens to blow himself up unless his chief rival signs a sales deal. That might be a little outrageous.
But when businesses adapt, the unorthodox happens. You innovate. You struggle. You try. You fail. You learn. As Tommy Boy bumbles and stumbles, he discovers that he has sales ability and devises his plan.
Most importantly, Tommy Boy grows to possess the three Cs, which are perhaps the most critical aspects to any succession plan.
Tommy Boy and the 3 Cs
The 3 Cs are Competence, Commitment, and Character, and here’s how they worked for Tommy Boy:
Competence:
Tommy Boy: A lot of people go to college for seven years.
Richard: I know. They’re called doctors.
Obviously, Tommy Boy was woefully ill-prepared for his position, although he was brilliant at evading a drunken driving charge through his legendary “bees” technique.

However, he gains competence while on the road, engaging in difficult sales calls. Through repeated (and I do mean repeated) failures, Tommy Boy eventually sharpens his skills and gains the competence needed to succeed.
As I mention in my succession planning report, competence includes the necessary leadership and technical skills to succeed at a job. By the end of the film, Tommy Boy has them.
Commitment:
While many would argue that Tommy Boy should be committed, it’s hard to argue his commitment to the company or his family. He’s got a lot of heart (I’ll get to that in a second), and he battles time and time again for the company.
Is he overly committed? Does strapping roadside flares around your considerable girth and claiming you’re a suicide bomber count as pushing the line? Yes, but you know what? People appreciate someone who lives (and in Tommy Boy’s case, nearly dies) for the good of the company.
Conversely, Beverly has no commitment to the company. Her commitment is to herself and her partner-in-crime. That’s why she ultimately fails.
Character:
Tommy Boy is a character of epic proportions, but he does, deep down, possess character. He loves his dad, loves his company, and ultimately does what’s right. In fact, considering how sorely he lacks competence, its character that ultimately helps him prevail in the end.
Tommy Boy’s character is not just the stuff of Hollywood, either. I often cite Tom Brady’s success in the NFL (sixth-round draft choice) as an example of what happens when a person believes in himself and his abilities.
And don’t forget a strong sense of integrity and ethics. For any long-term success, you must adhere to a higher standard and do what’s right.
Am I out-of-line for using the farcical Farley as an example of succession planning?

Hollywood has the luxury of writing a script for life’s events. You don’t. You can’t hope that your successor will pull through it with the perseverance of Tommy Boy.
You need to do everything possible to ensure there will be a smooth transition. Any change is difficult, no matter how well prepared you may be. But for those who are prepared, a likelihood of success is much greater.
As for whether or not I’m out of line in terms of succession planning, let’s consider the benefit of comedy in this case. Sometimes comedy is the best way to deliver a serious message. Tommy Boy is sophomoric, sometimes vulgar, and often side-splittingly funny.
But for anyone in the succession planning business, it highlights commonplace mistakes the people make every day.
If you’re a Big Tom, and you’ve got a Tommy Boy waiting in the wings, don’t just laugh at this low-brow film. Learn from it.
Rock LaManna provides executive coaching for printing owners looking to grow their printing business, merge with a synergistic partner, make a strategic acquisition, or create a succession plan.