Lead Like Leo: Lessons From ‘The West Wing’

Homebound by the Covid-19 pandemic, Americans are bingeing on TV shows like never before. New streaming service subscriptions are up more than 70%, and it seems like everyone is hooked on something. For me, it’s an old favorite, “The West Wing,” which originally ran nearly two decades ago but still gives me hope for the future. Watching a functional White House staffed by smart, compassionate, patriotic people—fictional though it may be—is not only chicken soup for my inside-the-beltway soul, it’s a master class in leadership I hope real-life West Wingers will take to heart.

I’ve been a senior executive in a federal agency and a major city and run a large county. This time through the series, I find myself less compelled by the policy debates and national security crises and more attuned to the internal dynamics of the White House team, a collection of idealistic, competitive overachievers who somehow work together to solve the biggest problems imaginable.

For me, the heart and soul of “The West Wing” team is not President Josiah Bartlet (played by Martin Sheen). It’s his chief of staff, Leo McGarry (the late John Spencer). At the center of a daily swirl of surprises, missteps, and lose-lose decisions, Leo was who everyone looked to for the way over, around or through. He could be grumpy and no-nonsense, but the twinkle in his eye and his purse-lipped smile betrayed his humanity. Other than his complete failure to model work-life balance – he told his wife that his job was more important than his marriage – Leo was everything a leader should be. Courageous, empathetic, loyal, and focused.

Here’s a viewer’s guide to the lessons he left us on what it means to lead.

Courage

Read The Gatekeepers, Chris Whipple’s insightful book about White House chiefs of staff, and you come to appreciate that what sets the good ones apart is their ability to tell the president what he doesn’t want to hear.  

One of the most pivotal conversations in “The West Wing’s” seven-year run is an Oval Office heart-to-heart between Leo and the president a year into the administration (Season 1, Episode 19, “Let Bartlet Be Bartlet”). The president’s approval ratings have dropped and the staff feels stifled by what it sees as Bartlet’s “play it safe” politics. Leo appeals to the president to stop dangling his feet in the water and take more chances, to be the kind of president he aspired to be. 

I’ve found in my career that the hard conversations become easier when you realize that a good leader is also a good follower. “Managing up” is the term of art for getting to know what your boss cares about, how they communicate, their decision-making process, their sense of identity.  

As budget director for the City of Baltimore during the Great Recession, bringing the mayor bad news became routine. I figured out quickly that she had little patience for numbers. She wanted to hear the stories behind the numbers – what they meant to real people – and solutions to make the most of scarce dollars. My stories moved the mayor to make tough calls that balanced budgets.

Knowing the boss prepares us to be persuasive, and preparation is scientifically proven to reduce fear.      

Empathy

Fans of “The West Wing” are sure to remember Leo’s “man in a hole” story (Season 2, Episode 10, “Noel”). A recovering alcoholic and drug addict, Leo understood better than most the demons we try our best to hide.  

When his deputy, Josh Lyman (Bradley Whitford), is showing signs of PTSD after recovering from a gunshot wound, Leo arranges for him to talk to a therapist and then offers him this parable: 

This guy’s walking down a street when he falls in a hole. The walls are so steep, he can’t get out. A doctor passes by, and the guy shouts up, “Hey you, can you help me out?” The doctor writes a prescription, throws it down in the hole and moves on. Then a priest comes along, and the guy shouts up “Father, I’m down in this hole, can you help me out?” The priest writes out a prayer, throws it down in the hole and moves on. Then a friend walks by. “Hey Joe, it’s me, can you help me out?” And the friend jumps in the hole. Our guy says, “Are you stupid? Now we’re both down here.” The friend says, “Yeah, but I’ve been down here before, and I know the way out.”

After a pause, Leo tells Josh, “Long as I got a job, you got a job, you understand?”

Josh’s trauma was no secret to his colleagues, but people can carry emotional loads that are harder to see. Leo’s lesson is that the best leaders get past “How are you doing?” to discover the needs of their people and give them help. Sharing your own vulnerabilities – fears, uncertainties, limitations – makes it safe for others to do the same.  

Loyalty

The most effective teams have an unbreakable bond of trust, friendship and loyalty to each other. That doesn’t mean they always get along; it means they can be brutally honest without fear of retribution, float off-the-wall ideas and have them taken seriously, and make mistakes – even big ones – that don’t get them fired.

Leo establishes this bond in the very first episode of the show, convincing the president to keep Josh when it seems like the whole world is calling for his head (Season 1, Episode 1, “Pilot”). At one point or another, Leo protects every member of his team from the worst consequences of a screw up, most more than once. He is a father figure, mentor and teacher, and his loyalty is returned in kind.   

I have lived the experience of making a mistake and finding myself sacrificed instead of shielded. Watching a team take a hit for one of its own literally brings tears to my eyes. 

Focus

All the emotional intelligence in the world won’t move a team in the right direction if the leader lacks strategic focus.  

In 1999, the year “The West Wing” premiered, I was working at the White House Office of Management and Budget. I’ll never forget how one of my colleagues described our work. “It’s like you’re a tennis player with a hundred different colored balls coming at you,” he said. “You’re only supposed to hit the yellow ones, but you’re color blind.”  

Leo saw his job as making sure the urgent didn’t crowd out the important, exhorting his team at the end of one especially hairy day, “We’re not going to stop, soften, detour, postpone, circumvent, obfuscate, or trade a single one of our goals to allow for whatever extracurricular nonsense is coming our way in the next days, weeks, or months.” (Season 2, Episode 21, “18th and Potomac”)

Staying focused on goals requires having them, being clear about your purpose. One of my early leadership lessons came from the powerful chair of the Michigan House Taxation Committee, who I interned for in high school. “Leadership is setting the agenda,” he told me simply. Leo knew this.

With a year to go in Bartlet’s second term, Leo senses that the team is content to coast to the finish line. So he gathers everyone around a white board and writes “365 days” at the top (Season 6, Episode 12, “365 Days”). “That’s how much time we have left,” he tells them. “What do you want to do with it?” The ideas start flying – “finally get serious about health care,” “a new approach to Latin America,” “it’s time to talk about race” – as the camera fades out.

To the thousands of men and women who will soon be asked to serve in leadership roles at the White House and Cabinet departments, not to mention statehouses and city halls: The secrets to your success won’t be found in any briefing book. The personal qualities you bring to the job, and the way you inspire and guide your team, will be your imprint. You could do a lot worse than to follow Leo McGarry’s example.  

Andrew Kleine is the author of City on the Line: How Baltimore Transformed Its Budget to Beat the Great Recession and Deliver Outcomes (Rowman & Littlefield). He has served as budget director for the City of Baltimore and Chief Administrative Officer for Montgomery County, Maryland.  His Twitter handle is @awkleine