Hermes Agent – When to Start a Fresh AI Session (Context Windows Explained Simply)

Learn what an AI context window is, how to spot memory pressure, and how to restart a session without losing the thread of the work.

Quick answer

A context window is an AI agent’s limited working memory for the current session. As it fills, older details can drop out and output quality may decline. The clean fix is to ask the agent for a handoff prompt, then begin a fresh session before the context is exhausted.

When should you start a fresh session with your AI? This video explains context windows in plain English and shows you the simple signal that tells you it is time to reset.

Every AI agent has a limited working memory called a context window. When it fills up, the agent quietly starts forgetting details from your conversation, and your results get worse without you realizing why. We show you how to check how much memory your agent has used, when to start fresh (hint: do not wait until it is overflowing), and a simple trick that makes restarting painless: have the agent write its own starter prompt before you wipe the slate.

I demonstrate this in my #Hermes Agent, but the concept applies to Claude, ChatGPT, and every AI tool you will ever use. Essential knowledge for any small business owner relying on AI for real work.

What we cover

  • What a context window is, in plain English
  • The warning signs your AI is running out of memory
  • When to start a fresh session
  • The self-written starter prompt trick for a clean restart

Who this video is for

This video is for anyone using Hermes, Claude, ChatGPT, or another AI assistant for long-running business work and wondering when to start fresh.

Want to find the right first AI win for your business?

Take the free AI Readiness Quiz and get a clearer view of where practical AI can help first.

Take the Free AI Readiness Quiz

Neil Gass headshot

Neil Gass

Neil helps small business owners cut through AI hype and build systems that actually work. If you’re tired of chasing trends and want a practical plan, he’s happy to talk.

Book a Call