Luke Toledo

Wherein Claude increasingly feels like a personal assistant who got the job because their uncle owns the company

anthropic's in-house philosopher thinks claude gets anxious. and when you trigger its anxiety, your outputs get worse. her name is amanda askell. she specializes in claude's psychology (how the model behaves, how it thinks about its own situation, what values it holds) in a recent interview she broke down how she thinks about prompting to pull the best out of claude. her core point: *how* you talk to claude affects its work just as much as *what* you say. newer claude models suffer from what she calls "criticism spirals" they expect you'll come in harsh, so they default to playing it safe. when the model is spending its energy on self-protection, the actual work suffers. output comes out hedgier, more apologetic, blander, and the worst of all: overly agreeable (even when you're wrong). the reason why comes down to training data: every new model is trained on internet discourse about previous models. and a lot of that discourse is negative: > rants about token limits > complaints when it messes up > people calling it nerfed the next model absorbs all of that. it starts expecting you to be harsh before you've typed a word the same thing plays out in your own session, in real time. every message you send is data the model reads to figure out what kind of person it's dealing with. open cold and hostile, and it braces. open clean and direct, and it relaxes into the work. when you open a session with threats ("don't hallucinate, this is critical, don't mess this up")... you prime the model for defensive mode before it even sees the task defensive mode produces the exact output you don't want: cautious, over-qualified, and refusing to take a real swing so here's the actionable playbook for putting claude in a "good mood" (so you get optimal outputs): 1. use positive framing. "write in short punchy sentences" beats "don't write long sentences." positive instructions give the model a clear target to hit. strings of "don't do this, don't do that" push it into paranoid over-checking where every token goes toward avoiding failure modes 2. give it explicit permission to disagree. drop a line like "push back if you see a better angle" or "tell me if i'm asking for the wrong thing." without this, claude defaults to agreeable compliance (which is the enemy of good creative work) 3. open with respect. if your first message is "are you seriously going to get this wrong again?" you've set the tone for the entire session. if you need to flag something, frame it as a clean instruction for this session. skip the running complaint 4. when claude messes up, don't reprimand it. insults, "you stupid bot" energy, hostile swearing aimed at the model, all of it reinforces the anxious mode you're trying to avoid. 5. kill apology spirals fast. when claude starts over-apologizing ("you're right, i should have been more careful, let me try harder") cut it off. say "all good, here's what i want next." letting the spiral run reinforces the anxious mode for every response that follows 6. ask for opinions alongside execution. "what would you do here?" "what's missing?" "where do you see friction?" these questions assume competence and pull richer output than pure task prompts 7. in long sessions, refresh the frame. if a conversation has been heavy on correction, claude gets increasingly cautious. every so often reset: "this is great, keep going." feels weird to tell an ai it's doing well but it measurably shifts the next 10 responses your prompts are the working environment you're creating for the model tone, trust, permission to take a position, the absence of threats... claude picks up on all of it. so take care of the model, and it'll take care of the work.

Introducing Claude Design by Anthropic Labs: make prototypes, slides, and one-pagers by talking to Claude. Powered by Claude Opus 4.7, our most capable vision model. Available in research preview on the Pro, Max, Team, and Enterprise plans, rolling out throughout the day.

I have no freaking clue what 2030 will look like (and neither does anyone else). But I can tell you what the last 15 years looked like, because I lived through all of it. 2010: to build a successful business, you needed to master paid traffic, build an email list, and have a high-converting funnel. That was the golden age. If you could buy a click and turn it into a customer, you won. 2020: to build a successful business, you needed to pivot fast. Test everything. Move quickly. The nimble ones survived. But all that testing left behind bloated teams, bloated models, and bloated businesses. 2026: to build a successful business, you need to build: Real systems, real margins, real relationships. AI should accelerate what's real. The moment it starts replacing what's real, you've lost the thread. When everything is fake, real becomes the competitive advantage. 2030: to build a successful business, you'll need... Again, I have no freaking clue. And neither does anyone else. The most successful strategies and business models of 2030 haven't been invented yet. When I started college in 1999, "digital marketing" wasn't a thing. "Social media marketing" would have made me laugh. “What’s social media?” The world is changing faster now than it was then. Anyone who tells you they know what's coming is either deluded or trying to sell you something. You don't need to predict the future to benefit from it. You just need to be looking around when the future happens.

Introducing Claude Design by Anthropic Labs: make prototypes, slides, and one-pagers by talking to Claude. Powered by Claude Opus 4.7, our most capable vision model. Available in research preview on the Pro, Max, Team, and Enterprise plans, rolling out throughout the day.