Anecdotally, I've noticed that they tend to be more senior (so know what's possible / what they can get away with), less busy (so they're less frustrated and frazzled), and tend to deal with much more experienced travelers than a normal gate agent (so, again, they're less frustrated).
> Incarcerated Scholars, Qualitative Inquiry, and Subjugated Knowledge: The Value of Incarcerated and Post-Incarcerated Scholars in the Age of Mass Incarceration
http://www.jpp.org/documents/back%20issues/JPP%2025-2.pdf
It looks like it's mostly about the Indiana Women's Prison History Project which she participated in.