Course contents · Get better answers from your AI assistant
Lesson 1 of 5
When it goes wrong: seven fixes to try first.
Your assistant was great on Monday and odd by Friday. Seven setup fixes to try before you blame the model, and how to tell which one you need.
CTO and co-founder, LaunchLemonade8 minReading timeWhen a new colleague's work starts to slip, you don't replace them on day five. You look at what they were given: a cluttered desk, three jobs at once, a document they can't read, no idea what to do when they're stuck. An assistant that goes wrong usually needs the same check.
Check the setup before the model
When an assistant starts forgetting things, repeating itself or sounding sure about something wrong, the instinct is to blame the model and try a bigger one. Most of the time the model is fine. The problem is what it was given, and the fix takes minutes.
Start from the symptom. Each one points to a likely cause:
- Forgets what you told it
- The chat has got long and your early instructions are crowded out. Fix one.
- Long, muddled answers
- It was asked for too much at once. Fix two.
- Wrong facts from a document
- It can't read the file properly, or the file is pasted into the chat. Fixes three and four.
- Confident answers it made up
- Nobody told it what to do when it doesn't know. Fix five.
- Good at one thing, odd at another
- It's doing too many jobs. Fix six.
- Worked yesterday, fails at one step
- A connection changed. Fix seven.
One: start a fresh chat
Course one called the context the desk: everything the model can see at once. A long conversation fills the desk, and the instructions you gave at the start get pushed out of view. That's when it starts forgetting the tone you asked for, or the thing you said not to do.
Start a new chat with a short recap of what matters. Keep one chat per job or project, rather than one long thread for a week of different tasks.
We're drafting replies to tenants for a lettings agency. Friendly, plain English, under 150 words. Never quote a fee. Here's the message to reply to:
Two and three: small steps, readable text
Don't ask for the summary, the email and the spreadsheet in one go. Ask for one, check it, then ask for the next. Each step gets the model's full attention, and when something goes wrong you can see which step it was.
Then check that it can actually read what you gave it. A scanned PDF can be just a picture of words. Some assistants can read images, but a clean copy with real text is far more reliable. A quick test: if you can't select and copy the text in the file yourself, export or ask for a text version.
Four: big documents belong in its knowledge
Pasting a forty-page guide into a chat puts all forty pages on the desk, every time. It crowds out everything else, including your question.
Store it as knowledge instead. Then the assistant looks up the part it needs and answers from that, the way course one's RAG lesson described. Most assistant tools have a place for this: knowledge, files or a project library.
Five: give it an off-ramp
A model predicts the next piece of text. If nothing tells it what to do when it doesn't know, it fills the gap with something that sounds right. One line in its instructions changes that.
If you don't know the answer, or it isn't in the documents you've been given, say so and ask me. Never guess a date, an amount or a name.
Six and seven: one job each, and test after every fix
An assistant set up to answer tenants shouldn't also write the social posts. Different jobs need different instructions, tone and documents, and one set of instructions trying to cover both does neither well. Make a second assistant.
And when you fix a connection, such as reconnecting an email account or an app, run one small, harmless test before trusting it with real work. Often the model answered perfectly and the failure was in the step that sends or saves the result.
Running example
The running job
Chasing last month's unpaid invoices, one lesson at a time.
Sam's tenant helper had a bad week. Here's what went wrong, and which fix sorted it:
- By Thursday it had stopped keeping replies short. The chat had run all week. A fresh chat with a two-line recap fixed it.
- It quoted a deposit rule from page thirty of the tenant guide, wrongly. The guide had been pasted into the chat. Moving it into the assistant's knowledge fixed it.
- It told a tenant the boiler engineer would come on Tuesday. Nobody had said Tuesday. An off-ramp line, "never promise a date, say the repairs team will call", fixed it.
- It drafted a jokey reply to a complaint. Sam had been using the same assistant for the agency's social posts. Splitting it into two assistants fixed it.
Practice
Try it yourself
About five minutes, in any AI chat app
Diagnose one assistant
Think of an assistant or a long-running chat you use in any AI tool. Write down the last thing it got wrong.
Match the symptom against the list in this lesson and pick the one fix it points to.
Make only that change, then ask the same question again.
What to look for
Whether one small setup change fixes the answer without touching the model. If it doesn't, try the next most likely fix, still one at a time.
Common mistakes
Switching to a bigger model at the first wrong answer.
Check the setup first: the chat length, the ask, the documents, the off-ramp, the job, the connection.
Changing several things at once.
Make one change and test again, so you know which fix worked.
Pasting the same big document into every chat.
Store it once as knowledge and let the assistant look up what it needs.
Quick check
3 questions to see what stuck. Nothing is scored or saved.
1. Your assistant has started ignoring the tone you set at the start of a long chat. What's the first fix to try?
2. Why does an off-ramp line help?
3. You've just reconnected an email account. What should you do before trusting it with real work?
Remember
When it goes wrong, check the setup before the model: fresh chat, small steps, readable text, knowledge not paste, an off-ramp, one job each, and a test after every fix.
Sources and further reading
- 1.The blog post this lesson grew out of: Why isn't my AI assistant responding? Top fixes for 2026
Optional
Try it in LaunchLemonade
Big documents belong in Knowledge, where the assistant looks up the part it needs, rather than pasted into the chat. Everything above works in any AI tool.
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