Episode 478: Can you coach self-awareness and my boss is an llm

46 snips

Sep 15, 2025

Can self-awareness be coached effectively in a professional setting? The hosts unpack the challenges of guiding team members who struggle to grasp their growth areas despite persistent feedback. They also tackle the pitfalls of over-relying on AI in startups, humorously narrating the frustrations of an engineering team juggling unrealistic demands. With insights into the balance of enthusiasm for tech and practical decision-making, the conversation is as enlightening as it is entertaining.

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ADVICE

Give Direct, Compassionate Feedback

Ask permission and deliver blunt, compassionate feedback about repeated issues to break defensiveness.
Ask the engineer why they keep getting the same feedback and suggest specific process changes like peer review before PRs.

INSIGHT

Denial Often Meets An Unspoken Need

People who deny problems often use denial as a defense to protect unmet needs or avoid painful self-reflection.
Identifying what they gain by not acknowledging issues can reveal alternate ways to meet that need and enable change.

ADVICE

Fix The Process, Not Just The Output

Look for concrete process changes the person can adopt, like soliciting peer review before opening PRs.
Track those changes as manager-visible signals of improvement rather than waiting for vague self-awareness.

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In this episode, Dave and Jamison answer these questions:

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?
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?