Several months ago, I found myself wrestling with a simple but challenging question: How can I better engage my student staff? A mentor offered me guidance that shifted the way I think about supervision. They encouraged me to approach my employees with curiosity, to see them not just as people I care about, but as supervisees on their own professional journeys. They explained how our paths intersect for a time, but rarely forever. When we stay curious about who our staff are becoming, we help them grow in the direction they’re meant to go, even when that direction eventually leads them away from us.
My mentor shared an exercise that’s been transformative for me, and I’m excited to pass it along. It centers on three simple, themed questions, each designed to help us explore someone’s path. Whether we’re reflecting personally or supporting those we lead.
1. Where have you been?
This first question invites reflection on our past experiences and motivations. What used to get us out of bed in the morning? What kept us awake at night? What career paths once felt possible or appealing? Looking several years into the past helps us identify the values, activities, and interests that shaped us. Understanding this starting point gives context to how far we’ve come, and what has stayed constant.
2. Where are you now?
Asking “Where are you now?” lets us compare our current lives with the vision we once had. Which values have shifted? What new responsibilities or opportunities have emerged that weren’t part of the original plan? This reflection isn’t about judging where we’ve fallen short. Instead, it helps us notice how simply walking our path opens doors we couldn’t have predicted and closes ones we once imagined taking. This stage also reveals patterns where we naturally thrive, where we struggle, and what our present experiences are teaching us.
3. Where do you want to go?
The final question focuses on the future we hope to build. It encourages us to explore not only our dream roles, but also the realistic range of paths that would still bring fulfillment. We can examine the kind of impact we want to make and the work environments that would allow us to do so. Thanks to the earlier reflections, we can now ask two especially meaningful questions: How are my current experiences helping me get where I want to go? And How do I get in my own way? The answers often reveal practical steps we can take (and habits we may need to change) to move toward our vision.
Closing
Throughout our careers, we will lead many different people, each with their own hopes and trajectories. It’s important to recognize that our vision for the organization may not align perfectly with theirs, and that’s okay. Effective leaders create space for others to grow in the direction they want to go. When people feel seen, supported, and valued for their aspirations, engagement and trust follow naturally.
We all hope to retain our top performers. But ultimately, the most caring act of leadership is to help people grow while they’re with us and to let them go, confidently and proudly, when the next opportunity calls.
