Influencing Difficult Leaders

Summary

The article explores how determined and often difficult leaders, exemplified by Steve Jobs, can be persuaded to change their minds, highlighting the crucial role of those around them.
It discusses key psychological barriers—arrogance, stubbornness, narcissism, and disagreeableness—and shares research-backed strategies for overcoming each.
The piece uses notable anecdotes from Apple’s history to illustrate effective influence techniques that contributed to groundbreaking innovations like the iPhone and Apple TV.
The main conclusion is that cognitive flexibility—not just conviction—is essential for driving organizational success, and leaders must be challenged by those willing to question and persuade them.

(No explicit action items or owners stated in the article text.)

Directly confronting overconfident leaders rarely works; instead, creating situations where they recognize gaps in their understanding can reduce arrogance.
Example: Steve Jobs was persuaded to adopt Corning’s glass for the iPhone after being respectfully guided through his knowledge gaps by CEO Wendell Weeks.
The technique involves asking leaders to explain complex ideas, which reveals knowledge limitations and opens them to new information.

Stubborn people are often unmoved by direct, forceful persuasion and may even become more resistant.
Allowing them some ownership in the persuasion process, such as contributing to idea development, increases receptiveness.
Example: Mike Bell influenced Steve Jobs by asking questions and encouraging Jobs to engage with and refine ideas, eventually leading to the Apple TV project.
Research shows that inviting involvement and curiosity through open-ended questions fosters creativity and idea adoption.

Narcissistic leaders can demonstrate humility when their need for admiration is constructively met.
Criticism is best delivered after affirming their abilities in unrelated areas, helping them feel secure enough to acknowledge flaws.
Example: At an Apple developer conference, a critic prefaced negative feedback with praise for Jobs’s intelligence, prompting a humble and productive response from Jobs.
Compliments should focus on different strengths than those being critiqued to maximize openness.

Disagreeable leaders are often energized by argument and respect colleagues who stand up to them.
Persistent, evidence-based advocacy and willingness to refine and repeatedly present ideas are effective.
Example: Jobs’s team overcame his resistance to the iPhone by continually developing prototypes and reframing objections until he accepted the idea.
Research shows that those who challenge disagreeable bosses are more likely to earn respect and advance within organizations.

Leaders need to be challenged by trusted, courageous colleagues — This was essential to Apple’s success, as illustrated by Jobs’s openness to persuasion and the resulting innovations.

How can organizations systematically encourage more employees to respectfully challenge leadership for better decision-making?
What additional training or support might help individuals develop the skills to influence difficult leaders?