At the end of January, the Trepwise team gathered for our first semi-annual planning retreat of 2025. As usual, we had our agenda, discussion questions, and plenty of snacks ready to go. But this retreat felt different. So much uncertainty swirled around us, both at a professional level with recent Executive Orders disrupting and undermining the goals of our clients in the nonprofit landscape, and also at a personal level with fear around how new laws may impact our friends and families here in Louisiana. To put it lightly, it was hard to focus on planning for the future.
But before diving into our agenda, we paused. Our leadership team openly shared the challenges they were struggling with and invited others to do the same. The simple act of naming our emotions and embracing vulnerability transformed the room. It became a moment of mutual support, a reminder that none of us are facing this uncertainty alone. In times like these, practicing transparency is essential. Leaders who openly acknowledge challenges, share their thought processes, and invite input create a culture where team members feel valued and heard. Authentic conversations don’t just strengthen morale—they lay the groundwork for proactive problem-solving and resilience.
Tools for Building Connectivity in Uncertain Times
Name the Reality of the Situation: Leaders can reassure team members that they’re aware of the current challenges facing the team and committed to problem solving and alignment by saying, “I don’t have all the answers, but here’s what we do know and what we’re doing next.”
Create Space for Psychological Safety: Modeling vulnerability by sharing your own concerns first to normalize open conversations – as the Trepwise leaders did in the above example – can promote a sense of psychological safety in the workplace. In team check-ins and retrospectives, ask questions like, “what’s one thing you’re feeling uncertain about?”
Build External Partnerships: In challenging times, partnerships with like-minded organizations can provide new perspectives, helpful resources, and a sense of solidarity. Lead exercises on ecosystem mapping or partnership prioritization (e.g. a 2×2 grid based on impact and alignment) to discover new opportunities and ground the team in the work that’s already being done.
Strengthen Mission Alignment: As a mission-driven, community-centered organization, it’s easy to want to take on everything in order to fill increasing needs. However, focusing on decisions that align with core values will prevent mission drift and stretched capacity. Engage your team in a start/stop/continue exercise:
- What should we start doing to adapt to current challenges?
- What should we stop doing that’s no longer serving us?
- What should we continue doing that’s working?
Celebrate Small Wins: While it’s important to acknowledge the difficulties we face, maintaining a hopeful outlook is equally vital. Optimism doesn’t mean ignoring challenges, but rather believing in the possibility of positive outcomes even amidst adversity. Make a habit of celebrating small wins to sustain momentum and morale.
Reflecting on that retreat, the big takeaway wasn’t just the plan we laid for our future, but the sense of community we strengthened. Facing uncertainty isn’t about having all the answers. It’s about standing together, supporting one another, and moving forward with courage and compassion. When we embrace authenticity, form connections, and nurture hope, we don’t just survive uncertainty—we emerge stronger.
If you’re looking for support in building transparency and boosting team morale, Trepwise can help. Let’s start the conversation.
