courageous & critical conversations
Building Transformative Internal Dialogues for Engaging Communities Sharing Leadership in Evaluation
by: Karen T. Jackson and Angelicque Tucker Blackmon
November 21, 2025
Courageous and Critical Conversations are more than just asking questions or collecting and analyzing data—they are about using what we learn to look for opportunities to make intentional connections that lead to shared purpose. We have these Courageous and Critical conversations hoping we can create real, substantive, and positive change in the lived experiences of the communities we engage. These conversations are the beginning of our process and center the voices and experiences of marginalized communities to help evaluators understand and challenge power imbalances, and connect new insights directly to action rather than just words.
What do courageous and critical conversations look like in practice? These conversations start with honest, sometimes difficult discussions that go beyond surface-level issues. These conversations invite everyone to critical and conscious reflection on both their own internal beliefs, assumptions, and mental models, as well as on the external systems and structures in which they work.
Key elements of courageous and critical conversations that transform practice include:
- Action-oriented reflection: We don't just think; we act with intention. We translate what we learn into meaningful steps toward improvement.
- Critical and conscious analytical process: Every decision and change is informed by a deep, honest look at what is really happening, who is affected, and why.
- Intentional Praxis: This means ongoing cycles of reflecting, critiquing, and then deliberately applying those lessons to create change.
Courageous and Critical conversations invite questions like:
● How do we determine our belonging and value as evaluators?
● How do we evaluate to acknowledge the humanity of all?
● How can we better evaluate human kind in our society?
● What do you see when we rise above the situation?
● Who needs to be part of the interpretation process?
● How can leadership be shared or shifted to those most impacted?
Still these conversations require plain, everyday language to connect personal identities and lived experiences with evaluators’ professional practices. Understanding who we are and how our backgrounds and biases shape our work, our analysis, what we focus on and what we don’t focus on is paramount. For example, some evaluators notice important cultural or contextual factors in community-based stories that others may overlook. Such critical reflection, grounded in lived experience, is a powerful tool that can shift power dynamics and advance evaluation methods, especially in fields like education, leadership, technology and public health.
Courageous and Critical conversations complement culturally responsive evaluation methods. It supports evaluators in doing the "internal work"—examining their own mental models and identities—while also analyzing and challenging broader systems that perpetuate structural imbalances, whether intentional or not.
Ultimately, integrating courageous and Critical conversations helps evaluators go beyond chronicling problems; it centers value in learning and unlearning while creating space for inspiration and preparation for the new…. whatever comes next. This approach is about both knowing and changing evaluators’ internal worlds (status) that are then reflected and operationalized outward.
Resources
https://www.eval.org/Publications/Newsletters/Newsletter-Archive/Article/aea-newsletter-october-2025
https://aea365.org/blog/reflective-evaluation-in-a-time-of-political-disruption-by-karen-t-jackson/
Coming in 2026 - Jackson, K.T. & Watzeig, E. Z. (Eds.). (2026). Community Engaged Leaders: Sharing Leadership with and through the Complexities of Social Change. Emerald Publishing.
Scott, Susan (2004). Fierce Conversations: Achieving Success and Work in Life One Conversation at a Time. Berkley Books.
