AI Guardrails and Evals | 7th Chicago Meetup

​Most testers use AI coding tools in a familiar way: open the chat, ask for something, copy the result, and move on.
​That works, but it is only one way to use them.

​At The Test Tribe’s 7th Chicago Meetup, Maneesh Maddala will explore how Skills and plugins can make AI more repeatable by packaging instructions, context, and tooling around everyday testing tasks.

Session: Guardrails & Evals

​Speaker: Maneesh Maddala, Principal QA at Morningstar

​As AI becomes part of software products and engineering workflows, how do we make sure it behaves as expected?
​This session explores two important aspects of working with AI systems: guardrails and evaluations (evals). It looks at how teams can approach defining boundaries for AI behaviour, assessing outputs, and thinking about quality beyond whether an AI-generated response simply works.
​The discussion will also touch on writing guardrails and evaluations, and how these approaches fit into testing AI-powered applications.

​What you'll take away:

​Understanding guardrails and evals: Explore their roles in managing and assessing AI system behaviour.
​Defining expected AI behaviour: Understand how guardrails can help establish boundaries for AI-generated responses.
​Evaluating AI outputs: Explore how evaluations can be used to assess whether AI systems meet defined expectations.
​Writing guardrails and evals: Look at the considerations involved in developing checks for AI-powered applications.
​Thinking about AI quality: Examine why testing AI systems involves more than checking whether an output was generated successfully.

​Event Details

​Date: 27 October 2026
​Time: 06:00 PM – 08:00 PM CDT
​Venue: 10 S Riverside Plaza, Chicago, IL 60606

​Agenda

​6:00 PM – 6:15 PM: Welcome & Introductions
​6:15 PM – 7:15 PM: Session by Maneesh Maddala, Principal QA at Morningstat on “Everyday AI Coding: Skills & Plugins for Testers”, including Q&A
​7:15 PM – 8:00 PM: Networking over snacks
​8:00 PM: Event Wrap

​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.

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