Guardrails & Evals | 7th Chicago Meetup

AI can generate an answer that looks right and still behave in ways a team did not intend. That makes testing AI-powered applications less about checking whether a response exists, and more about defining what acceptable behaviour looks like, where the boundaries are, and how consistently the system stays within them. At The Test Tribe’s 7th Chicago Meetup, Maneesh Maddala, Principal QA at Morningstar, will explore two core parts of testing AI systems: guardrails and evaluations (evals). Session Guardrails & Evals Speaker: Maneesh Maddala, Principal QA at Morningstar Maneesh will look at how teams can use guardrails and evals to make AI behaviour more testable and easier to reason about. The session will cover: What guardrails and evals are, and the different roles they play How guardrails can define boundaries around expected AI behaviour How evals can assess whether AI outputs meet defined expectations What to consider when writing guardrails and evaluation checks Why AI quality involves more than checking whether a response was produced successfully The focus is on giving QA teams a clearer way to think about expected behaviour, boundaries, and evaluation criteria when testing AI-powered applications. Event Details Date: 27 October 2026 Time: 06:00 PM – 08:00 PM CDT Venue: 10 S Riverside Plaza, Chicago, IL 60606 The final part of the evening is open for conversations, introductions, and comparing notes with QA professionals, testers, engineers, and technology practitioners from the Chicago community while the discussion continues over snacks. A look back We've done this before! Here's what our monthly meetups usually look like - expect more of this! About The Test Tribe The Test Tribe is the world's largest software testing community, empowering testers globally since 2018. With 700+ events and 150K+ members across 130+ countries, we bring testers together to learn, grow, and connect through meetups, conferences, cohorts, masterclasses, and more. Become a Speaker at The Test Tribe Events Wish to share your insights with the community at a future event? Submit your talk idea here, and our team will get back to you if the idea is a good fit for an upcoming event. By RSVPing, you agree to our Terms and Conditions and Privacy Policy and consent to be contacted by The Test Tribe and our event partners.