How the Na’aleh Team spent their Summer

At the Na’aleh Summer Staff Retreat, our team spent time exploring the risky, collaborative, and deeply meaningful work of leadership—and reflecting on what it means to support leaders every day.

One idea stayed with us: leadership is a journey, not a destination. It is rarely linear. There are questions, challenges, unexpected turns, moments of growth, and milestones along the way. And often, the most meaningful leadership happens in the moments when we don’t have all the answers.

As part of our retreat, we created a collaborative art piece representing the Leader’s Journey, capturing the twists, turns, questions, and milestones that shape us as leaders.

The experience also got us thinking about how teams can create more space for this kind of reflection in their own work. Here are a few ideas to try with your team:

Make space to reflect.
Leadership can easily become a cycle of doing, responding, and moving on to the next thing. Set aside time to ask: What have we learned? What has challenged us? What are we proud of? What do we want to do differently?

Embrace the questions.
We often think leadership is about having the answers. What if we made more room for curiosity instead? Invite your team to name the questions they are wrestling with and explore them together.

Map the journey.
Try creating a visual representation of your team’s journey—past milestones, challenges, turning points, and hopes for what comes next. A shared visual can spark conversations that might not happen around a conference table.

Celebrate the milestones.
Leadership growth isn’t always obvious. Take time to recognize the small wins, moments of courage, lessons learned, and progress that can easily get overlooked in the day-to-day.

Lead together.
The most meaningful leadership doesn’t happen in isolation. Create opportunities for your team to learn from one another, share perspectives, and recognize that everyone has something to contribute to the journey.

Take the Conversation Back to Your Team

Want to create more opportunities for your team to build trust, reflect, and grow together? Bring your team to Na’aleh’s Professional Playbook Deep Dive: Building a Culture of Trust on October 6th. It will be an opportunity to step out of the day-to-day, learn together, and explore practical ways to strengthen trust and connection within your team.

At Na’aleh, we are grateful for the privilege of learning alongside Baltimore’s leaders. As we begin another year, we look forward to continuing to ask questions, take risks, learn together, and strengthen the leaders and communities that make Baltimore’s Jewish community thrive.

*A huge thank you to Julie Wohl for guiding us in this process and to Baltimore Hebrew Congregation for hosting us.