Brad Keywell

What Baseball & Politics Can Teach Us About Leadership: 4 Lessons from Political Strategist David Axelrod

On October 27, 1960 in New York City, five-year-old David Axelrod went to see John F. Kennedy  on the campaign trail in Stuyvesant Town at the corner of 21st and 1st. As he sat on top of a mailbox and watched the young presidential candidate speak to the crowd, he had a sense that something big was happening.

At that moment, he was bitten by the politics bug. By the age of 9, he was passing out leaflets for Bobby Kennedy and devouring the daily news, the beginning of his lifelong career in government and journalism.

Today, “Axe” is well-known in the world of politics, having worked on more than 150 campaigns, most famously as a key strategist and architect of President Obama’s three victories: his 2004 Senate race, the historical 2008 Presidential election and the 2012 re-election.

Given the time David has spent working alongside some of the world’s greatest political minds, he is uniquely suited to answer: “What does great leadership look like?” He shared a number of stories with me when he joined me on The Upside, and below are four of his lessons and opinions on leadership. To hear the entire episode and others, subscribe to The Upside on iTunes, SoundCloud, Stitcher, TuneIn, or your other favorite podcast player.

And I’m going to borrow a good idea from a friend, Reid Hoffman, who has his own incredible podcast called Masters of Scale (by the way, if you haven’t read Austin Kleon’s Steal Like an Artist, you should). Reid asks people to write short reactions to his podcast episodes on their LinkedIn newsfeeds and share their opinions with a wider community. 

So with that, I’d like to hear your thoughts and reactions to this podcast episode with David Axelrod. Tag your post on your LinkedIn newsfeed with #theupside so I can find it, or tweet at me (@BradKeywell).  What actions do you think represent good leadership? How important is storytelling to galvanizing action?  

Lesson #1:

“You measure leaders, to me, not on their best day but on their worst day.  Not on your organization's best day, but on its worst day.”

This resonates with me. I have been CEO at Uptake for almost 4 years, and am the co-founder of over a dozen companies. There are days that I look back on and think, “Yes, I could have handled that better.” David’s words reminded me that every leader goes through the same thing. Now I do my best to recognize that every decision, every action I take has implications, not just for the business but also for the morale and focus of my team.

Axe told a great story about the Obama team losing the Texas and Ohio primaries in the 2008 election. Instead of yelling or getting angry or pointing fingers, Obama acknowledged that everyone in the room probably felt like there were things they could have done better, himself included. He infused a little humor into the situation before sitting down with his yellow legal pad and encouraging a few hours of honest conversation about what they can do to improve the next time.

Lesson #2:

“I liken a baseball season, particularly when you have championship aspirations, to a presidential race, in that it is long. It is, by definition, going to be marked by ups and downs, and it's all conducted under the watchful eye of millions of people who think they can do it better than you. And don't know shit. But his [Maddon’s] brilliance is that he focuses his guys on the task. ...He says, I never talk about winning and losing. Because everybody wants to win. But that just gets you tight. He says process is fearless. Just do the things that you need to do. Just field the ball properly. Take the right base. Do those things. And he said, the rest will take care of itself.”

There is beauty in doing the little things right. It can be unhelpful and unproductive to focus on the outcome; often times you can do everything right and still lose, because no matter what, luck always plays a part. It is important to take 100% responsibility for what you can control.

Lesson #3:

“I think that part of what makes someone a successful disruptor is that oftentimes... they tend not to follow sort of the standard rules and norms.”

Axe made this observation based on an interaction he had with the late, great Steve Jobs - a hilarious story that perfectly fits with the myth of Steve Jobs’ persona. But it got me thinking: A few of my latest podcast guests have pointed out this same trend about disruptors and innovators. Is it a rule that you must follow your own rules to successfully create? Does anyone have an example in which the opposite is true?

Lesson #4:

“What John F. Kennedy said, when I saw him in 1960, was, ‘...Being an American citizen in the 20th century is a hazardous duty. Filled with peril, and also hope. But we'll decide which path we take.’ In other words, we can grab the wheel of history and steer. And that's a beautiful thing, that ability to determine our future. So I continue to be a believer.”

Politicians aren’t the only leaders we need in the future. To reach our highest potential as a society, we will need leadership and participation from everyone. A worthwhile reminder from David Axelrod, an authentic optimist.

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© Brad Keywell 2021