Imagine Chicago carried out three interrelated sets of assessments in its city-wide and community-based intergenerational interview pilots: 1) understanding the content of the conversations — the ideas, information, images and initiatives shared by interview participants; 2) determining the impact of the interactions — the experiences of the conversations, the kinds of relationships and feelings emerging from them; 3) evaluating the implications for future work. These assessments were ongoing, done at multiple stages, with a range of participants.

Our first level of assessment came out of the specific thoughts and experiences shared in the interviews. An adult mentor was present at each intergenerational conversation to take notes. Immediately following the interview, the mentor discussed with the interviewee highlights of the conversation and noteworthy perspectives. The interview transcript was typed up within a week. This provided the basis for the thank you note written by the young person, as well as an integrative learning opportunity. At several month intervals, groups of young interviewers gathered to discuss what stood out for them from multiple interviews and their current thoughts about Chicago and its future. They then compared responses across multiple interviewees and neighborhoods. It was in such a conversation that the "themes of the interviews" were named by the young interviewers. A further content assessment was done by a volunteer team of graduate students who read through and evaluated all the interview transcripts. They clustered the appreciative questions around the three main stages of Appreciative Inquiry: "valuing the present", "envisioning the future", and "co-creating the future". They interpreted the overarching themes to see what they told us about peoples’ experiences and their conceptions of Chicago’s future. A unique portrait of the city emerged, characterized by diversity and duality, with multiple layers of relationships, and many, many new possibilities.

Our second level of assessment approached the interview processes as a series of learning experiences. To gain an understanding of what the conversations meant for interviewers and interviewees, Imagine Chicago conducted a formal evaluation with several participants from all of the pilots. Three impacts were particularly noteworthy:

1. Shared Identity: The conversations brought people together, across boundaries of age, race, experience and geography, to reflect on their relationship to the city as a whole. They began to see commonalities among their visions for the city’s future and felt encouraged by their respective commitments.

2. Intergenerational Partnership and Accountability: The interview conversations opened up lines of communication between the generations. Both young people and adults commented that they gained an appreciative understanding of the other generation.

3. New Possibilities and Methods of Civic Conversation: Appreciative inquiry as a tool/perspective also made an impact on participants. Learning to ask and answer positive questions, and to actively listen, was a welcome shift for many participants. The conversations also infused public spaces with constructive and creative possibilities.