Steve Jobs was in pretty rough shape in 2009, even as Apple was celebrating some amazing triumphs.  

He'd been battling pancreatic cancer for at least five years, and he knew that his time was likely running out. In fact, he was about to take a six month leave of absence to focus on his health issues, and appoint Tim Cook as acting CEO.

But at the same time, Apple was enjoying a renaissance. The iPhone was less than two years old, and the App Store had been going gangbusters. The company's stock price was at the start of a climb that would continue almost uninterrupted for nine years.

Then, a team led by an Apple employee named Phillip Shoemaker made a big mistake.

Baby Shaker 

Shoemaker was in charge of the app approval process. He'd only been on the job for three weeks in fact, and the volume of submissions was skyrocketing. The whole process for approving apps was a work in progress, and it was inevitable there would be some mistakes,

And as he explained this week in a podcast, approving an app called "Baby Shaker" was a mistake indeed.

The app was innocuous enough (and anachronistic enough, given what apps are like now) to begin with. It showed a drawing of a baby, and when the baby cried, the user was supposed to rock the iPhone back and forth gently.

But if the user shook the iPhone, the baby photo would get giant red X's over its eyes, as if it were dead, and the app would display a message: "Never shake a baby!"

'You're stupid and you hire stupid people.'

Shoemaker explained the result this week on the Decrypted podcast:

"We had Shaken Baby Syndrome folks picketing outside of Infinite Loop. ... It should never have got approved. It got approved on a Monday or a Tuesday, and we announced record earnings ... [We] announced something like the billionth download from the App Store. All these amazing numbers, and the stock went down."

Then, Shoemaker continued, he got a call. The ID on his phone indicated it was Steve Jobs's office:

"I picked up, reticent, and I got his admin who said, 'Steve would like to talk to you.' And Steve just had simple words for me: 'You're stupid and you hire stupid people.'"

Then Jobs simply hung up the phone.

'The best conversation'

You might imagine this would have been the end of Shoemaker working for Apple. But he had the opposite reaction, even though the truth was that he'd inherited the people who made the mistake on his team.

"That was one of the best conversations I had with Steve," Shoemaker said. "It was just so succinct and to the point. ... I understood his gist. I didn't hire the people that reviewed it. I didn't review it myself. But I got it."

I don't think most of us would react so well to our boss calling and saying something like this and hanging up. And I don't think most of us as bosses could get away with it.

But in Jobs's unique situation, I think it was a brilliant demonstration of leadership. Here's why:

1.    He knew the audience.

I don't know how well Shoemaker knew Jobs before this; as he says he'd only been aboard with Apple in this job for three weeks or so. But a decade later, Shoemaker himself describes the conversation "one of the best." We'll explain more about why that's the case, but so much of this kind of dressing down depends on the recipient's reaction. Here, it seems like 

2.    The context was key.

By this time, everybody knew that Jobs was sick, and that the disease he was fighting was usually fatal. It was also clear that Jobs's legacy was Apple: not his kids, not his pronouncements, not his wealth. It was, "how many people's lives could he change with this company?" 

3.    It was harsh but mostly accurate.

Shoemaker didn't actually hire the people on his team at this time, but he was responsible for them. And as he freely admits now, it was a big mistake to have approved the app. I get the sense that Shoemaker knew his team had screwed up, but that he also knew that Jobs had to say something. Silence would have suggested it wasn't that big a deal -- something Shoemaker himself didn't believe.

4.    It worked.

Or at least, it didn't hurt. Jobs passed away in 2011, but Shoemaker stayed aboard as the head of the office approving apps in the App Store for another seven years. During that time, the App Store ballooned into a massive revenue source: $11.5 billion in the last quarter alone.

I've written before about some of the off-hand comments that Jobs made during his life that wound up living much longer than he did. The last five words he said to his daughter might be the most interesting.

But his succinct statement to Shoemaker showed a special breed of leadership. It's not always nice to hear, but it it necessary. 

However, Shoemaker said it wasn't the only memorable conversation he had that day.

"The next phone call I got was from the office of Al Gore," who was a member of Apple's board of directors. "That just blew my mind.He just wanted to know what the review process was and how this mistake [happened]. He was just very pleasant. Unlike Steve."