Onboarding Path Builder

Onboarding Path Builder solves a problem every engineering team knows well: new developers joining an unfamiliar codebase typically spend 2-3 days just exploring files and interrupting teammates with questions before becoming productive. This slows teams down and creates a rough first experience for new hires. Our solution uses IBM Bob to turn any repository into a personalized, structured onboarding roadmap. Instead of one generic prompt, Bob runs three targeted analyses on the codebase — architecture, the key data flow, and test coverage — and the results are organized into a clear, day-by-day learning path rather than a wall of text. A new developer can click into any step to ask focused follow-up questions about that specific part of the codebase, getting real answers grounded in the actual code. What makes this genuinely different from a generic AI coding chatbot is that it's a structured workflow, not a search box. Bob doesn't just answer isolated questions — it proactively analyzes the repository across multiple dimensions and builds a real learning path. Each roadmap step also includes a short comprehension quiz, generated live by Bob, so understanding is verified rather than assumed. This turns passive reading into active, confirmed learning — addressing not just "can they find the answer" but "did they actually understand it." The target users are new hires, interns, and any developer parachuting into an unfamiliar codebase — as well as engineering managers who want a scalable, repeatable onboarding process instead of relying on one senior developer's time for every new hire. Building this also meant genuinely wrestling with Bob's tooling, not just calling it once. We hit and diagnosed a real production-style bug where our automated Bob Shell calls hung indefinitely; using Bob IDE itself, we traced the issue to an unclosed input stream and fixed it. We also discovered Bob's raw CLI output included a full execution transcript rather than a clean answer, so we investigated Bob's actual CLI flags, and had Bob IDE read its own installed package's source code to learn its structured JSON output format, then rewrote our parsing logic to reliably extract clean responses. The result is a tool that effectively and efficiently addresses a real, everyday engineering pain point in a way judges likely haven't seen before: not a chatbot bolted onto a codebase, but a proactive, verified learning workflow built directly on Bob's multi-step analysis capabilities — turning what used to take days of onboarding into minutes.