Career Contessa Mid-Career and Losing Steam? Let’s Fix That
Feb 17, 2026
Carolyn Dewar, senior partner at McKinsey and coauthor of A CEO for All Seasons, shares leadership research from interviews with top CEOs. She explores why mid-career plateaus happen and how outsider thinking and anonymous feedback can reignite momentum. Carolyn discusses quiet ambition, using AI as a challenger, protected thinking time, and practical resets to reinvent impact within your role.
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Play The Competitor To Reimagine Strategy
- Act like a future attacker: imagine you're the competitor and redesign the business from their viewpoint.
- Use devil's-advocate or red-team exercises to invite challenge and surface blind spots.
Michael Dell's 'Be The Attacker' Exercise
- Michael Dell warned his team about a future attacker and then asked them to role-play as that competitor.
- That provoked reinvention and helped Dell's team rethink the business proactively.
Watermelon Dashboard And Anonymous Survey
- A team used an anonymous 1–10 confidence survey and found a spread from 1 to 9 despite public optimism.
- The anonymous responses uncovered real concerns and changed their plan.
