Leadership & Circumstance

In response to last week's post, my wife said, “That was different; you usually stick to business.” 

That's true, but it was hard to really focus on leadership lessons when I was spending the whole week feeling like I was living through the Lend-Lease chapter of a book on World War III. 

Here, with a bit more space from the start of a war, I’ve been reflecting on just how important circumstance is to leadership. 

It’s hard not to see Ukrainian President Volodymyr Zelensky being lauded across the media for his leadership through the current crisis. Indeed, he seems to have mastered the communication and symbolic elements of leadership as he leads the Ukrainian resistance.

Yet before the war started, his approval rating was as low as 24%. And just two weeks ago, Olga Rudenko, the editor of The Kyiv Independent, wrote an opinion essay in The New York Times that ran with the title: “The Comedian-Turned-President Is Seriously in Over His Head.” In that piece, she called Zelensky “dispiritingly mediocre.”

Zelensky has valiantly called on citizen resistance to the invasion. However, his pre-war position that war wasn’t imminent likely caused innocent civilians to delay escaping to safety. And in calling on citizen resistance in the cities, it may make some of these areas legitimate combat zones. (That's not to rid the Russians of ultimate responsibility for the results of their egregious and indiscriminate military actions thus far.)

So which interpretation of Zelensky is the right one? Is he a good leader?

Who knows?

The stories about Zelensky made me reflect on just how many leaders’ reputations are affected by events outside of their control and how murky it is to assess their leadership quality. 

Three weeks ago, UK Prime Minister Boris Johnson was being scolded in Parliament and seemingly on the way to getting sacked over the 10 Downing Street parties he attended during COVID lockdowns. But if one watches Prime Minister’s Questions over the last two weeks, Johnson looks like a leader in command. 

Then again, if we really are in the Lend-Lease period ahead of a wider escalation, Johnson and Western leaders’ decisions in this time period won’t be remembered fondly in the historical account. 

Another UK Prime Minister, Winston Churchill, also provides a case study in the difficulty of assessing leadership quality. In fact, Churchill enjoyed an up-and-down career as a junior government minister. For example, he was forced out of his position as head of the Royal Navy in WWI, partly due to a failed campaign in the Dardanelles.  

Before WWII, Churchill had the judgment to spot the emerging German threat and advocate for British rearmament, And during the war, his powerful communication was widely credited for rallying the British people. Still, his judgments also included prosecuting the indiscriminate “strategic bombing” of German cities, including of non-military targets, that was meant to break the will of the German people. That was a controversial decision then, and likely considered a war crime by today’s standards. 

Given this uneven record, was Churchill a good leader? 

Finally, one of the greatest examples of this conundrum is George Washington. Here's a man whose upward trajectory was driven by having inherited fortunes from his father, brother, and his wife. Yet despite those inheritances Washington struggled mightily to keep his “business” afloat. Indeed, Washington talked about freeing his slaves for years, but never accomplished this because he could never afford to do so. Finally, Washington’s record as a military commander is objectively mediocre. He was inexperienced at tactics and slow in decision making. If you judged him solely on those leadership experiences, it wouldn’t be a good record.  

But Washington was great at the performative elements of leadership. Helped by his height and athleticism, he looked the part. He led from the front, putting himself in harm’s way. And his political skill helped him successfully hold together his insurgent Army and manage the sometimes wavering support of the nascent Congress. 

Washington never decisively “won” the war, but held on long enough for the Brits to decide after Yorktown that further fighting wasn’t worth it. And for that, he’s rightly considered the father of the United States.     

That all leads me to two points. 

First, we often have a bias toward those who are great at the performative elements of leadership—e.g., the great speech, leading from the front in dangerous situations. We latch on to those actions because we can see them. 

However, we often have far less visibility into their private leadership actions and judgments, especially in real time, which leaves uncertainty about their true skill. It’s almost impossible to assess the quality of this part of leadership without the distance of time. 

Second, those perceived as great leaders are rarely great (or even good) across the board. Instead, they are often those who find themselves—through no fault of their own—in situations that call on their particular strengths. I’ve cited examples here of leaders whose records fit that pattern. 

I also think of this skill-situation challenge whenever I see news about a CEO getting fired. Often the portrayal is negative, as if the person wasn’t good at business. But that’s like saying someone released from an NBA team isn’t good at basketball. The person wouldn’t have been in the role in the first place if they did not possess a tremendous amount of skill. 

The problem, then, is usually that these leaders ran into circumstances in which it’d be hard for anyone to succeed, or circumstances in which there was a mismatch between the leadership skill needed and what they could provide.

In that sense, there’s an element of chance in whether leaders even have an opportunity to demonstrate their capabilities and in how they are judged when they do.