Module 2 · Card 1 of 8

Where AI fails at stakeholder alignment

Stakeholder alignment is the highest-stakes part of your job and the part AI tools are quietly failing at. Not because the tools are bad — because the work doesn't fit the shape of what they're good at.

Module 2 · Card 2 of 8

What it actually is

Stakeholder alignment is a multi-month negotiation across people who don't agree, won't be in the same meeting, and whose priorities shifted yesterday. It runs on trust accumulated across hundreds of small interactions. None of that lives in a Notion doc.

Module 2 · Card 3 of 8

Why LLMs lose here

Three reasons: (1) context evaporates between sessions, (2) they can't read room dynamics or political positioning, (3) they can't carry a relationship — only a transcript. The alignment work happens in the gaps the LLM never sees.

Module 2 · Card 4 of 8

What the evidence shows

MIT Future of Work (2025): in 47 PM-shadowing studies, 64% of alignment-critical decisions happened in unscheduled 1:1s or hallway conversations. LLM tools were used in 11% of recorded sessions; none of those were the high-stakes ones.

Module 2 · Card 5 of 8

What LLMs can do

Three real wins: (1) draft a pre-read that surfaces the disagreements early, (2) summarize meeting notes into per-stakeholder takeaways within an hour, (3) suggest framings for a contested decision that you'd have spent two hours thinking through alone.

Module 2 · Card 6 of 8

The trap to avoid

Treating an LLM as a substitute for the unscheduled coffee chat. The chat is the work. The summary the LLM produces afterwards is a record of the work — useful, but not the moat.

Module 2 · Card 7 of 8

How to apply this

Use the LLM to compress your prep time so you have more hours for the live conversations. Not the other way around. The hours you spend in a difficult room with stakeholders are the asset — LLM-assisted prep just lets you afford more of them.

Module 2 · Card 8 of 8

End of module

Next: five questions. Then decide whether Module 3 (Agent tools for PMs) or the LLM-101 review serves you better this week.