Strategic Disappointment: Leadership Lessons from Apple, Netflix & Microsoft [Fast Company Feature]

Leadership often requires making unpopular decisions that disappoint stakeholders in the short term. In my latest Fast Company article, I examine how strategic disappointment has become a crucial leadership skill for driving innovation at companies like Apple, Netflix, and Microsoft.

The article introduces the Strategic Disappointment Matrix, a decision-making framework that helps leaders navigate uncertainty. This matrix categorizes decisions into four quadrants based on certainty and potential disappointment levels, offering guidance for when to proceed with potentially unpopular choices.

Real-World Examples of Strategic Disappointment

Key examples from the article include:

• Apple’s removal of the headphone jack in 2016 – initially criticized but later proved prescient
• Netflix’s pivot from DVD delivery to streaming in 2011 – lost 800,000 subscribers initially but secured the company’s future
• Microsoft’s shift from Windows to cloud computing under Satya Nadella – transformed the company into a cloud and AI leader

The article emphasizes that tomorrow’s most valuable leaders won’t be those who pleased everyone today, but those who had the courage to disappoint purposefully when necessary.

The full article dives deeper into how leaders can apply the model to their own decision-making processes, including specific tactics for timing and communication.

Read it here:
https://www.fastcompany.com/91337119/why-the-best-leaders-embrace-strategic-disappointment

About the Author

Kate O’Neill is a strategic advisor and keynote speaker known as “The Tech Humanist.” She helps leaders align technology with human needs and is the author of several books including “Tech Humanist” and her latest, “What Matters Next: A Leader’s Guide to Making Human-Friendly Tech Decisions in a World That’s Moving Too Fast.” Her insights on strategic decision-making have been featured in Fast Company, European Business Review, and Wired.