Leading from the Naughty List: Leadership Lessons from Elf, Part 3 of 3

Zach Hughes
6 min readDec 23, 2021


Elf, 2003

The 2003 film, Elf, starring Will Ferrell and directed by Jon Favreau, is one of the most beloved Christmas films. My family makes a tradition of watching it every year. As with many of my favorite movies, I cannot help but notice the subtle leadership lessons sprinkled about like candy in spaghetti.

Elf is packed with too many leadership lessons for just one Zach on Leadership article, so I’ve thoroughly covered it over the past three weeks.

You may not realize it, but Buddy had three different work experiences and three different bosses, each of whom had their distinctive leadership style. We examined each of them to glean the lessons to be learned.

Two weeks ago: Santa’s Workshop and Ming Ming

Last week: The North Pole and the Gimbels Manager

This week: Greenway Press and Walter Hobbs

This article is about the Greenway Press, the workplace of Buddy’s father, Walter Hobbs. Buddy has already experienced manufacturing and retail. Now it’s time for a taste of corporate life. Let’s see how it goes and what we can learn.

Walter Hobbs is on the naughty list

When we are introduced to Walter Hobbs, we get an unflattering picture of his leadership style. Walter repossessed children’s books from a nun because she missed the payments. In the next scene, Walter made an executive decision to ship children’s books that were missing pages to avoid spending $30,000 on a reprint.

We need to be careful how we criticize Walter because he’s running a business, not a charity. It’s easy to judge him and say he should give away the books to the nun and spend the money on the reprint. I can’t judge him for being financially responsible, so what’s the real issue?

I believe Walter lost sight of his purpose. Why does Greenway Press exist? To turn a profit? No. Businesses do not exist to turn a profit. Businesses exist to serve some societal need. Profit is a means to that end, not the end itself.

While the film doesn’t explicitly tell us, the purpose of Greenway Press is presumably to enrich children’s lives by producing and distributing books that they love. I believe Walter lost sight of his purpose. Without purpose, all that’s left is profit.

Ironically, when companies focus on profit over purpose, they usually achieve neither. That point is validated in Greenway’s quarterly earnings report shared in a later scene.

Therefore, not only is Walter Hobbs a naughty person on Santa’s list, but he’s also an inadequate business leader. The best companies are driven by purpose over profit. If you’d like to read more on that topic, check out Inc.com, Financial Times, or Built to Last.

Bring in Miles Finch

Midway through the film, Walter was under extreme pressure to develop a new book for the first quarter. He assembled his two top writers, who pitched him the idea of hiring another writer, Miles Finch. While Walter was unwilling to spend the money on books for charity, or a reprint, he didn’t seem to have any problem shelling out top dollar for an arrogant consultant, who demanded to be received at the airport by a black S500 with the interior set to 71 degrees.

I don’t have a problem with hiring consultants. I hire consultants when I need some temporary help in an area where I don’t have expertise. However, it’s a bad sign when management hires a consultant for a core competency. To me, this signals that management isn’t confident or competent. Neither of those options are good.

Walter leads the creative writing function at Greenway Press. His top writers don’t have any good ideas. That’s an existential problem. We only see this moment in time, but clearly, Walter hasn’t invested adequately in the development of this critical capability. This may be a talent gap, a toxic culture, or some combination of the two.

When I ask my team if they have any ideas, they won’t stop talking.

Bad leaders have bad leaders

We’ve firmly established that Walter Hobbs’ leadership style leaves plenty to be desired. Why is that? What is the root cause? Why are some leaders bad and some leaders good? I firmly believe that leadership behavior (bad or good) is learned from what is modeled.

To better understand Walter’s shortcomings, we must look to the primary antagonist of the film, Mr. Greenway, Board Chair of Greenway Press, and Walter Hobbs’ direct boss.

Mr. Greenway was responsible for creating the conditions in which Walter performed poorly as a leader. In their first interaction, Mr. Greenway confronted Walter on the two missing pages from their latest book. Walter lied about it and blamed the printer. Mr. Greenway saw through the lie, but then changed the subject to the poor financial performance:

Have you seen the numbers for this quarter?

That frigging puppy and pigeon are tanking hard, Hobbs.

My people estimate we’re gonna post a minus eight for this quarter.

A minus eight! That does not happen!

Mr. Greenway was much more concerned about the financial performance than Walter’s ethical lapse, or his niece’s reading enjoyment of the puppy and pigeon book. His message couldn’t be clearer. He cared little about values or customers and cared most about profits.

As a result, Walter was crystal clear with where he stood with Mr. Greenway. He even shared this with his wife, Emily: “I am one bad pitch away from getting fired.”

This pressure made Walter Hobbs desperate to meet the demands of his boss. His desperation made him hire Miles Finch instead of investing in his team. When his son, Buddy, innocently torpedoed his plan, Walter snapped in a way that deeply broke his relationship and his integrity:

I don’t care where you go.

I don’t care that you’re an elf!

I don’t care that you’re nuts!

I don’t care that you’re my son!

Get out of my life now!

Shortly after that, Walter made his final attempt to please his boss. Even after all of this, Mr. Greenway sneered, “this better be good.”

As he was getting ready to pitch the new book idea, his second son, Michael, burst into the room, scared and worried about his brother, Buddy.

This is the climax of the film. In a long moment, Walter counted the cost of his career decisions. He violated his integrity. He neglected his team. He broke his relationship with his first son and was about to break his already-strained relationship with his second son.

This was a turning point for Walter. He made the right choice, left Mr. Greenway, and reconciled his relationships with his sons.

Here’s the point: Good leaders can’t work for bad leaders. You must leave or you will become bad. It’s that simple. Looking back at my 23-year career, I’ve been fortunate to work for good leaders. They made me who I am. I spent very little time working for bad leaders. When I did, I left as fast as I could. I knew I was susceptible to learning bad behavior and I couldn’t let that happen.

This is the end of my leadership analysis of Greenway Press, and the end of this blog series on Elf. I hope you’ve enjoyed it. I’ll end with one last observation: Not one of the three leaders I analyzed properly valued Buddy’s professional contribution. Not, Ming Ming, the Gimbels Manager, nor Walter Hobbs. But there is one that did: Santa. In classic Christmas movie tradition, Buddy saved Christmas by fixing Santa’s sleigh.

Read this article on my blog site or listen to it on my podcast🎙️



Zach Hughes

Technology Leader at CHS. Passionate about leadership and innovation. Posts are my own.