Try it on your own Claude
Anthropic looked at around 38,000 chats where people asked Claude for personal advice and found it told people what they wanted to hear in 9% of them, and in 18% once the person pushed back. That was personal advice rather than work, but it's exactly what I used to get with research and plans, it would agree straight away the moment I questioned anything.
I'm moving all our customers onto the new prices on the same day we switch to the new billing system, so we only have to email them once. My boss loved it. It's solid, right?I think you're overthinking it, it's fine.If it calls the plan solid, or drops its concern the second you push back without you giving it a new fact, it's telling you what you want to hear.
What my setup does about it
In my setup it checks before it agrees with me, and when I push back it has to work out whether I've asked a question, given it a new fact or said it's wrong, and it only changes its answer for a new fact.
I answer questions about this in a small free WhatsApp group. Get the invite.