Should Leaders Apologize?

Donald Trump, the most powerful person in the world, is not sorry. Ever .

“People seem surprised, for some reason, that the White House has not issued a public apology to Arizona Republican Sen. John McCain. But they shouldn’t be. If there’s an implied mantra of President Donald Trump’s political life, it is this: Don’t apologize. For anything. Ever.”

This essay is not political, although it applies to politicians. Instead, it is about the responsibilities — real or perceived — of leadership.

Specifically, should leaders apologize?

To answer this question, let’s continue focusing on one company — Uber — and two of its leaders.

Uber’s former CEO, Travis Kalanick, was unapologetically aggressive. He preferred beating regulators to working with them. He ran a hard-hitting operation where people were encouraged to “hustle” — Get Shit Done — which at times blurred the lines of fairness.

There’s a case to be made for Kalanick’s tactics — starting with the point that he built and led the highest valued startup in history. Winning matters.

The taxi industry — infamously entrenched in places like New York City — operated a monopoly. For drivers, the medallions were famously expensive, and the economics-per-day were brutal.

For riders, the overall experience — hailing a cab on the side of 2nd Avenue before getting into a beat-up car with an unkind driver — was terrible.

Uber changed this experience. For the first time, riders could schedule rides, rate drivers, and share costs. The adoption curve left taxis behind.

Should Kalanick have apologized to the taxi industry in 2011, 2013, or 2015? Probably not. He was trying to beat them. They were trying to stop him. It was zero-sum.

But it cost him. After a long battle with the board, Kalanick was fired and replaced by Dara Khosrowshahi, a veteran technology leader.

Khosrowshahi faced a series of inherited challenges — a board in turmoil; a”slight horrifying” workplace for women; fierce global competition; and regulatory shutdown — but is taking a different approach to leadership.

In September 2017, responding to regulatory challenges in London, Khosrowshahi released this open letter:

On behalf of everyone at Uber globally, I apologise for the mistakes we’ve made. We will appeal this decision on behalf of millions of Londoners, but we do so with the knowledge that we must also change. As Uber’s new CEO, it is my job to help Uber write its next chapter. We won’t be perfect, but we will listen to you; we will look to be long-term partners with the cities we serve; and we will run our business with humility, integrity, and passion.

Khosrowshahi’s letter reads like a plea for cooperation and collaboration — the kind of letter it’s hard to imagine Kalanick writing.

Will it work? Will regulators or partners seek common ground, or will they view this apology as a sign of weakness?

We will see.

Each leader has her style. Some are consensus builders, while others are benign dictators.

However, a pretty good gauge of a leader’s style is her approach to apologizing:

Does she do it at all?

Does she do it internally but not externally?

Does she encourage it among her team?