When Your Boss Is Dead Wrong: Boss-Management Tactics of Steve Job’s Direct Reports

Executive override by senior managers even where they lack expertise.

— Director Organizational Development

Three words: update your resume.


I wish it were that simple. On second thought, I don’t. Clashing with your boss is a serious problem. But running from it is not the best solution. At least, not until you’ve considered other possibilities.

An executive override can feel like someone has pulled the rug from under your feet. It stirs up a blizzard of bad feelings, from embarrassment to letdown to anger. Outside of direct sabotage, it’s just about the most disengaging thing anyone can do.

And why is that?

One, because it’s disempowering to have your boss ram his agenda down your throat. Two, it’s discouraging when management throws the full weight of its position and authority against you. And three, it’s humiliating when they show no respect for your knowledge and accomplishments. You feel two feet tall.

I’ve been in your shoes. I know the feeling. There were times when I’ve quit because of my bosses and times when I’ve stuck it out. On more than one occasion, I thought I had no choice but to put the whole stinking mess behind me. However, in my best moments, I’ve held on to my power, not because of, but despite the way I was treated. It is those times that helped me grow and prepared me for being my own boss.

Some of the brightest names in business have put up with catastrophic moves by their unruly bosses. And I’m not just talking about Dilbert. Anyone who has ever worked for Steve Jobs, for example, could make my case.

On top of being a boss from hell, for most of his life, Jobs was also a CEO from hell. He made more career-suicidal mistakes than any of his peers. I’ve heard an argument that his real genius was the astounding amount of trial and error he put himself through. And it wasn’t for lack of competent advice. Jobs was always masterful at surrounding himself with top talent.

Imagine what it was like to work for the most bull-headed boss on the planet. What kinds of skills could you gain from that? Here are a few possibilities.


What if you don’t take “no” for an answer? Your boss is only human. If you hold your ground long enough, you might catch him at a weak moment.

“One of [Jobs’s] biggest mistakes was opposing development of the Windows version of iTunes. When the iPod first came out in 2001, owners had to use a Mac to load music on it because iTunes ran only on Macs. Apple’s management team knew they had a hit with the iPod, and virtually everyone on the team wanted Apple to develop a Windows version of iTunes so that they could sell more iPods. Jobs resisted for months. And it’s not clear that he ever changed his mind. In the end, he just quit fighting his team over it, saying, “I’m sick of listening to you a**holes. Go do whatever the hell you want.”

??(Quora “What was Steve Jobs wrong about?” Answered by Windsor Smith, Apple enthusiast since 1980)

Consensus building.

Your boss may not know a good piece of advice if it walked into his office and knocked him on the head. But others in the company are more perceptive. Many great ideas initially rejected by CEOs have prevailed because they found other influential sponsors. Your boss can thank you later.

“I once read an article about how Steve Jobs was totally against making the iPod mini. He thought that because it held fewer songs and had a shorter battery life that no one would want it. He was wrong. What’s interesting is that the other executives at Apple went over Steve’s head and made the iPod mini anyway, even though he was totally against it. Shortly after launching, the iPod mini became the most popular portable music player on the planet.” ??

(Quora “What was Steve Jobs wrong about?” Answered by Sam Mallery, Startup marketer, writer, musician, tech podcast host at Mallercast.com)


If nothing can save your boss from himself, there’s always letting him fail. Bad business decisions are short-lived. Even Steve Jobs cannot argue with a dwindling bank account.

“He was wrong about trying to get Pixar to sell business computing platforms, similar to what he was trying to do with Next. They completely failed at this, were horrible at it, and didn’t want to do it anyway. If anything, it kept them from doing what they were all meant to be doing: making digital films.”

??(Quora “What was Steve Jobs wrong about?” Answered by Jonathan Brill, Steve Jobs amateur historian)

Getting the bigger picture.

Finally, although you can’t find fault with your own argument, there might be another perspective. This tragic conversation took place when Tim Cook offered to be the liver-transplant donor to dying Jobs.

“I said, ‘Steve, I’m perfectly healthy, I’ve been checked out. Here’s the medical report. I can do this, and I’m not putting myself at risk, I’ll be fine.’ And he doesn’t think about it. It was not, ‘Are you sure you want to do this?’ It was not, ‘I’ll think about it.’ It was not, ‘Oh, the condition I’m in…’ It was, ‘No, I’m not doing that!’ He kind of popped up in bed and said that. And this was during a time when things were just terrible. Steve only yelled at me four or five times during the 13 years I knew him, and this was one of them.”

??(Becoming Steve Jobs, Brent Schlender and Rick Tetzeli)

In the end, all of Steve Jobs’ mistakes were his to make. Nobody understood it better than people like Tim Cook, the current CEO of Apple, and Ed Catmull, the current president of Pixar and Walt Disney Animation Studios. Both men endured Jobs’ errors and triumphs alike and went on to become the greatest managers of their generation.


If you want your boss’s job, you might like my book, because it shows how to be a better boss.

8 surprising employee problems you can avoid with a modern intranet

Written by

Tim Eisenhauer is a co-founder of Axero Solutions, a leading intranet software vendor. He's also a bestselling author of Who the Hell Wants to Work for You? Mastering Employee Engagement. Tim’s been featured in Fortune, Forbes, TIME, Inc Magazine, Entrepreneur, CNBC, Today, and other leading publications.


Get the latest posts, promotions, and partnerships from Axero.

Girl Sitting
Unsubscribe anytime