Your AI will agree with you on most things. 3 ways to make it less sycophantic: 1. Stop asking just one agent. I hand the question to my /War-Council skill, a swarm of personalized subagents with different incentives 2. Give the AI something to lose. Mine incorporates game theory and bets $1,000 of imaginary money on the ideas it thinks will work (massively improve the answers) 3. Grade the plan in a brand new chat. I find the conversation that built the plan is usually too invested to judge it. This is a problem even at @Zapier. Run an idea through AI and it comes back sanded down, you lose a piece of it each time. There's a Ship of Theseus metaphor in there somewhere… Don't just ask your AI what it thinks, build it to argue.