Coaching Real Leaders How Do I Handle So Much Organizational Uncertainty?
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Nov 3, 2025 A seasoned leader faces uncertainty as her company shifts direction. She explores her value in a changing landscape, navigating the transition from generalist to specialist. Together with her coach, she identifies short-term goals to regain clarity and strategizes ways to leverage her institutional knowledge. With a focus on building networks and documenting her journey, she contemplates whether to lean into new challenges or step back. Ultimately, she’s equipped with actionable steps to tackle the unknown and define her future career path.
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Long Tenure Through Startup Growth
- Maggie spent most of her career at one company, growing through multiple phases from startup to scale.
- She rose five to six times and built numerous functions as the company evolved.
Scale Favors Specialization
- As companies scale, breadth of responsibility shifts toward specialization and defined roles.
- Long-time generalists must reconsider how they define value in increasingly structured organizations.
Measure Success In Short Windows
- Define short-term success measures (daily/weekly) you control to stay grounded on the precipice.
- Track 30/60-day wins as your north star instead of waiting for new leadership to define success.
