Your AI is a yes-machine. Here's how to fix that Last week I kicked off the column talking about Projects—dedicated workspaces that give your AI the context it needs. Since then, several of you have written in with some version of the question: "Why is AI so cloyingly sycophantic?" (Read: It basically agrees with everything you say.) The short answer: AI tools are trained to produce responses that feel satisfying, which means they default toward telling you what you want to hear rather than what you need to know. Here's what you can do to avoid this as much as possible: Start with "critical but supportive." At the start of any chat where you want honest feedback—a draft, a plan, a decision you're weighing—add this to your prompt: "Please be critical but supportive. I want balanced feedback, not validation." That one phrase can shift the tone of everything that follows. I use it in almost every chat. Give it the full picture upfront. AI will work with whatever you give it, even if that's not enough. The more specific you are from the start, the more useful the response. If I'm asking about a health question, I include relevant history and what I've already tried. For career coaching, I give it my actual situation—not just the sanitized version. Then add: "Do you have any questions before we get started? Feel free to ask for more information as we go." Use a second chat as a reality check. For higher-stakes situations (like health, mental health, or a big career decision), ask the AI to save everything in the chat into a markdown file (your prompts and its responses both). Then drop that into a fresh chat and ask: "Assess this conversation. Point out any inconsistencies, gaps in reasoning, or perspectives that weren't considered." A second chat reviewing the first's work will often catch angles the original one didn’t. This is how I get something closer to a genuinely different perspective. One other tip: If you're not sure what a tool can actually do, ask it upfront—then ask it to confirm before you get started. It won't always volunteer its limitations, but it'll usually tell you if you ask. —SM |