In 1985, an Apple middle manager named Donna Dubinsky faced a decision that would define her career: challenge Steve Jobs or stay quiet. Jobs, then chairman of the board, had proposed eliminating Apple's six U.S. warehouses and shifting to a just-in-time production system. Computers would be assembled on demand and shipped overnight via FedEx.
On paper, the idea seemed innovative. Reduce inventory costs. Streamline operations. Cut expenses. The kind of efficiency Silicon Valley celebrates. But Dubinsky, who managed Apple's distribution, saw a fatal flaw. She understood something Jobs missed: the actual day-to-day reality of how Apple's business worked.
"In my mind, Apple being successful depended on distribution being successful.”
The company wasn't shipping integrated products. The Apple II, which generated the most revenue, required components from multiple sources. Computers arrived from one facility, monitors from another, disk drives from somewhere else. These parts came together at distribution centers before reaching small, undercapitalized retailers who couldn't afford to maintain inventory themselves. Jobs's plan ignored this reality. It wasn't just a minor oversight. It threatened the entire business.
What Dubinsky did next deserves our attention. Rather than bow down to the powerful founder, she delivered an ultimatum: give her 30 days to develop a counterproposal, or she would resign. Donna had done her homework. She had savings to fall back on. She knew the business deeply. And most importantly, she cared more about doing what was right for Apple than protecting her position. The result? Her proposal was right. Rather than getting fired, she earned a promotion to run an Apple software subsidiary. Later, she would go on to become CEO of Palm Computing and co-found Handspring, creating some of the first smartphones.
Having the conviction to stand behind your expertise when it matters most is a superpower.
Organizations fail because smart people stay silent. What made Donna exceptional was her willingness to risk her position to protect the company she served. She understood that true loyalty sometimes means challenging leadership, not blindly following it. My friend Brook Cupps has a core value on his basketball team of being unified. He defines that as speaking and acting with urgency. When I asked him what “unified” actually looks like in practice, he gave a great example: “Seeing a teammate not touch a line during sprints and not speaking up is a selfish act. If a teammate is not upholding the standard, and you don’t say something, you are being selfish. You are choosing your comfort over the standards of the team. Don’t be selfish.”
In our careers, we'll all face moments when we must choose between comfortable silence and uncomfortable truth. Most choose silence. The path to exceptional outcomes requires truth. The next time you see something wrong in your organization, think of Donna Dubinsky. Consider that your decision to speak up might end your career… Or it could elevate it. This is growth in its most practical form. Every time you choose difficult honesty over easy silence, you build the muscle that separates good careers from great ones. You're proving to yourself and others that you can handle the bigger problems that come with bigger opportunities. The conviction to stand behind your expertise when it matters most is surprisingly rare. Most people want to work with someone who will tell them when they're about to make a serious mistake. Be that person.