Cultivating Self-Awareness in Professional Development

In this episode, Dave and Jamison answer these questions:

1. Can you coach self-awareness? I manage someone who seems to believe their skill set is on par with their teammates, regardless of their constant PR feedback regarding the same issues over and over, the extra attention they are regularly given to help them overcome coding challenges, and the PIP they are currently on to address these issues (and others). What are some approaches I could take to help steer them to better understand their areas for growth when explicit measures don’t seem to get through?

2. I work at a small 10-person startup. The company has absolutely nothing to do with AI, but one of the founders has gone full evangelist. He genuinely believes AGI is arriving this year and that there isn’t a single job, task, or process where an LLM isn’t the obvious tool.

   Day in, day out, he’s posting links to random AI products with captions like “looks interesting 👀”. It’s like Clippy got a16z funding, moved to Shoreditch, and now spends his days flogging us apps we didn’t ask for. He also insists we “use AI more in development,” despite not understanding development in the slightest.

   The routine is always the same:

   1. He asks the engineering team how to achieve some goal (always involving an LLM).
   2. We give a sensible answer, weighing complexity, cost, feasibility.
   3. He comes back with a massive pasted transcript: “here’s what ChatGPT thinks.”
   4. We pick out what’s actually useful, quietly bin the nonsense.
   5. He takes our response, shoves it straight back into ChatGPT, and returns with another transcript: “here’s what ChatGPT thinks.”

   This has been going on for months. At this point, he’s basically a human middleware layer for ChatGPT — no analysis, no original thought, just endless copy-paste recursion. I’m genuinely worried he’s outsourcing his entire thinking process to a chatbot and slowly losing the ability to engage with ideas on his own.

   How do I tell him — politely but firmly — that this is both rude and a bit tragic? And, half-serious: is there a prompt injection I can use to jailbreak my founder back into being an actual founder rather than a ChatGPT relay bot?