For this milestone, I was pleasantly surprised by the capabilities of the AI. I used Gemini 3.6 flash and I found that it didn’t really catch something I missed, but it did use much clearer and concise terms to describe the exact insights I was thinking. For example, I categorized our affinity map into communication, responsibilities, work culture/expectations, current strategies, and streamlining work, but the AI broke it down into even nicher categories. I think it is good to help me look at quotes and then think of the broader idea that could be helpful, but the LLM I used was able to find patterns and make them quite specific. It used direct quotes, but I did add the guardrail of asking it to only use quotes and pull from the documents. I thought this was a great tool to help me see the details and also feel more confident in the details I picked up. I don’t think the AI was able to catch the nuance of the interviewee and their actions and what they say. As much as words describe a hectic schedule, when I saw the actual calendar and how the PM was describing a long work day, I could understand that the problem of multiple work streams and lack of clear prioritization is a much more impactful than other challenges such as a rude customer interaction.
In between my interviews, what changed was I used more of the idea of conducting a story based interview rather than a shorter question. It was important to understand the nuance and not just a solution. For example, instead of just asking what tools you use on a daily basis, I asked “Think of a project and tell me the tools and skills that you used to best support your product?”. This is the same question, but using a story in my round 2 script, like our reading of the week suggests, allows me to understand context and possibly digging deeper into insights about their fields.
AI Response (categories, left the quotes out)
- Lack of Clarity, Scope, & Direction
- Engineering Dependencies & Missed Deadlines
- Tooling Fragmentation & Manual Overhead
- Cross-Functional Alignment & Stakeholder Friction
- Pacing, Prioritization, & Shifting Context
- Accountability & Decision Ownership Without Authority
- Process Guardrails & Alignment Tactics
- Strategic Escalation & Partnering
- Personal Hacks & Automation Solutions
- Lack of Technical Depth / Domain Knowledge in Teammates
- Unfair Blame, Unproductive Dynamics, & Mandatory Quotas
- Boundary Misalignment & Responsibility Overload
