People struggle with AI prompts because the model lacks background on their goals and progress. The solution is 'Context Engineering': creating an environment where the AI continuously accumulates user-specific information, materials, and intent, reducing the need for constant prompt tweaking.

An AI product's job is never done because user behavior evolves. As users become more comfortable with an AI system, they naturally start pushing its boundaries with more complex queries. This requires product teams to continuously go back and recalibrate the system to meet these new, unanticipated demands.

The evolution of AI assistants is a continuum, much like autonomous driving levels. The critical shift from a 'co-pilot' to a true 'agent' occurs when the human can walk away and trust the system to perform multi-step tasks without direct supervision. The agent transitions from a helpful suggester to an autonomous actor.

Superhuman designs its AI to avoid "agent laziness," where the AI asks the user for clarification on simple tasks (e.g., "Which time slot do you prefer?"). A truly helpful agent should operate like a human executive assistant, making reasonable decisions autonomously to save the user time.

User workflows rarely exist in a single application; they span tools like Slack, calendars, and documents. A truly helpful AI must operate across these tools, creating a unified "desired path" that reflects how people actually work, rather than being confined by app boundaries.

Most users re-explain their role and situation in every new AI conversation. A more advanced approach is to build a dedicated professional context document and a system for capturing prompts and notes. This turns AI from a stateless tool into a stateful partner that understands your specific needs.

The primary interface for AI is shifting from a prompt box to a proactive system. Future applications will observe user behavior, anticipate needs, and suggest actions for approval, mirroring the initiative of a high-agency employee rather than waiting for commands.

The current chatbot model of asking a question and getting an answer is a transitional phase. The next evolution is proactive AI assistants that understand your environment and goals, anticipating needs and taking action without explicit commands, like reminding you of a task at the opportune moment.

Instead of manually maintaining your AI's custom instructions, end work sessions by asking it, "What did you learn about working with me?" This turns the AI into a partner in its own optimization, creating a self-improving system.