Technical Expert —
Chegg Skills (Thinkful)

Thinkful — acquired by Chegg — offered intensive bootcamp-style programs for adults changing careers into software engineering. As a Technical Expert, I supported students enrolled in the Prep Course for Engineering Immersion, meeting one-on-one via Zoom to review their project submissions and troubleshoot technical challenges in real time.

The prep phase is where many career-changers hit their first real wall — concepts like the box model, GitHub, and web deployment feel abstract until you're actually debugging a broken layout at 11pm. My job was to be the expert on the other side of that moment.

Sessions involved reviewing student-submitted GitHub repositories, walking through live code in the browser, writing structured graded feedback, and helping students understand not just what was wrong but why — so they could apply that thinking independently going forward.

The March 7 session is a good example of how unpredictable 1:1 support work actually is. Joshua came in needing help with Git — a foundational tool the curriculum assumed was already set up. It wasn't. Before any code review or assessment coaching could happen, the environment had to exist.

That's not a detour. That's the session. Getting the tooling right — git config, GitHub account, a cloned repository, a mental model of the terminal — is what makes everything else in the curriculum possible. Skipping it doesn't make a student more ready; it just defers the confusion.

The Chrome DevTools moment at the start was small but intentional. Switching to dark theme isn't a technical requirement — but taking a minute to show Joshua where the settings panel lives, and what else is configurable there, reinforced that DevTools is a workspace, not just a console. That framing pays off later.

By the end of the session Joshua had a working Git setup, a cloned repository on his machine, and enough terminal fluency to navigate to it. From there, the actual project work could begin.

The second half of each session often shifted into JavaScript — working through coding challenges on Qualified.io, a browser-based assessment platform used by Thinkful to evaluate students' readiness for the full engineering program.

In the session recorded here, the student was working through a campsiteCount challenge: iterate through an array of campground objects and sum the partySize for any campground where isReserved is true.

The student had the loop structure right but hadn't yet connected the conditional. My role was to ask the right questions — "what property tells you whether a site is reserved?" — rather than just typing the answer, so the student arrived at the solution through their own reasoning.

The Technical Expert role refined something I'd been developing across years of bootcamp and online instruction: the ability to write feedback that teaches, not just evaluates.

Good feedback tells a student what to fix. Great feedback explains the principle behind the fix — so the next time they encounter a similar problem, they have a framework for solving it themselves. That's what I tried to deliver in every written evaluation and every live session.

It's the same principle that drives good instructional design: the goal isn't to answer the question in front of you, it's to build the learner's capacity to answer the next one on their own.

Technical Expert, Chegg Skills (Thinkful), 2022.