Turning Challenges into Wins by Leading with Curiosity
This holiday season, I’ve been reflecting on the power of curiosity and how it can transform even the most challenging situations. Last year, Jane, a brilliant leader at a big tech company who I coach, navigated a tough situation that became a powerful learning experience for both of us.
Jane was the manager of a high-performing product team and faced an unusual challenge leading up to Thanksgiving that year. Traditionally, her team takes time off during Thanksgiving week to recharge. It was a company holiday. But this time, Jane’s new manager, based in a different office out of state, insisted that she and her team remain available during the holiday.
Understandably, Jane was frustrated - her team was upset, and her manager seemed immovable on the issue. Unfortunately, this was not the first time this new manager seemed inflexible in the past few weeks. After multiple discussions that went nowhere, Jane came to me ready to either cancel her vacation plans or walk away—not just from the issue, but potentially from her role as she started to feel the manager was “difficult to work with”.
In our coaching session, I encouraged Jane to step back and approach the situation with curiosity. What if there was more to her manager’s stance than met the eye? As we explored the why behind the tension, three critical details emerged:
Her manager was facing intense pressure from the business’ busiest time of the year and was personally working through the holiday.
Senior leadership had requested a list of on-call team members
In her manager's office location, the day after Thanksgiving wasn't a holiday unlike where the rest of the team worked — a difference neither of them had realized.
Understanding these realities changed everything. With this new perspective, Jane shifted gears. She proposed a thoughtful rotation plan, ensuring her team could mostly enjoy their holiday while maintaining necessary coverage over the holidays. She also volunteered to be on standby herself.
The result? Jane diffused a highly charged situation, built trust with her new manager, and preserved her team’s morale—all by embracing curiosity and approaching the problem with empathy and collaboration.
As we move past another Thanksgiving season, this story reminds me how curiosity can transform even the most challenging workplace dynamics. Working with leaders like Jane continually shows us that when we pause to understand different perspectives, we often find solutions that work for everyone.
