What Time Is It? How to Discern Your Leadership Season

2025-01-30

We often hear about "awareness" and "seasons" in leadership, but what if the key to making better decisions isn't about setting the right goals—but recognizing the season you're actually in? In this episode, Jonathan and Alan dive deep into the overlooked yet powerful concept of leadership seasons. They discuss how understanding the phase you're in—whether it's one of pruning, growth, acceleration, or transition—can bring clarity, reduce overwhelm, and lead to more effective actions. Key Takeaways Your goals aren’t the problem—...

We often hear about "awareness" and "seasons" in leadership, but what if the key to making better decisions isn't about setting the right goals—but recognizing the season you're actually in?

In this episode, Jonathan and Alan dive deep into the overlooked yet powerful concept of leadership seasons. They discuss how understanding the phase you're in—whether it's one of pruning, growth, acceleration, or transition—can bring clarity, reduce overwhelm, and lead to more effective actions.

Key Takeaways

Your goals aren’t the problem—your season might be. Are you in a time of expansion or a period where slowing down is wiser?
Seasons change, and so should your leadership strategy. You can’t hustle the same way at 40 as you did at 25.
Naming your season brings clarity. Learn two powerful methods for identifying where you are.
Leadership isn’t always about acceleration. Organizations, teams, and individuals go through rhythms of pruning and growth.
Action follows awareness. Once you know your season, what courageous steps will you take?

Reflection Questions

Hit pause, grab a journal, and reflect on these:
What season have you just come from?
When did (or will) that season end?
What season are you currently in?
What should you say yes to in this season?
What should you say no to?
What’s scary about this season change?

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