Troubleshooting

Reference intermediate

Almost every frustrating moment with an AI assistant traces back to a handful of causes — and each has a quick fix. When something feels off, find the symptom below, check the likely cause, and apply the fix. None of this needs technical skill, just a small change to how you ask.

Quick Diagnosis

What you are seeing	Most likely cause	Go to
Confident answer that is simply wrong	Missing facts, or the AI guessed	Wrong or Made-Up Answers
Output reads like a generic article	No context or specifics	Output Too Generic
Tool refuses your document	File type, size, or privacy block	The Tool Will Not Process Your File
A wall of text, or two thin lines	No length or format guidance	Responses Too Long or Too Short
Replies have drifted off-track	Conversation overloaded or muddled	Recovering a Derailed Conversation

Wrong or Made-Up Answers

A "hallucination" is when AI states something false as fact — an invented statistic, a fake source, a wrong date. It sounds confident, so it is easy to miss.

Problem	Likely cause	Fix
Invented figures or quotes	It filled a gap rather than admit a blank	Paste the source numbers; say "use only the figures I provided"
Fake citations or links	It predicted what a source might say	Ask it to "list only sources you are certain exist"
Out-of-date facts	Knowledge has a cutoff date	Provide current data, or use a tool with web search
Subtle errors in a variance analysis	It estimated, not calculated	Ask it to "show the working so I can check it"

Verification prompt — paste the draft back and ask:

List every factual claim, figure, and source above, and mark
each one certain, unsure, or guessing. Flag what I should
verify before I send this on.

Golden rule: treat AI output like a draft from a bright but new colleague. Verify any number, name, or claim before it leaves your desk. Governance has a pre-send checklist.

Output Too Generic

If the result could have been written for anyone at any company, the AI lacked enough about your case.

Problem	Likely cause	Fix
Status report reads like a template	No project specifics	Paste the actual milestones, owners, and dates
Advice states the obvious	No goal or constraints	Add what you want to achieve and what you cannot do
Email sounds robotic	No audience or tone defined	Name the recipient and the relationship
Ignores your industry	No domain context	Say "I work in [field]; assume that knowledge"

Add these four ingredients and the blandness goes away:

Role:      Act as my finance business partner.
Context:   The Q2 budget review for the sales team.
Specifics: Revenue 8% under plan; headcount frozen.
Output:    A 4-bullet summary for our director.

The more real detail you paste, the more tailored the result. Pasting last month's report and saying "match this style" beats describing it.

The Tool Will Not Process Your File

When an upload is rejected or misread, it is almost always a format, size, or content issue, not your fault.

Problem	Likely cause	Fix
"Unsupported file type"	The tool reads some formats only	Save as PDF, plain text, or DOCX and re-upload
Scanned PDF comes back blank	It is an image, not real text	Use a searchable PDF, or paste the text directly
Spreadsheet read incorrectly	Merged cells or complex layout confused it	Export the tab as a CSV, or paste rows as a simple table
File too large to upload	Exceeds the size limit	Split it, or paste only the relevant section
No upload button at all	The tool does not support files	Copy and paste the content into the message
"I cannot access that link"	It cannot open shared drives	Download the file and upload it, or paste it in

When in doubt, copy and paste beats uploading. And before you upload, confirm it is allowed — client lists, financials, or personal data may be off-limits under your company's rules. Check Governance first.

Responses Too Long or Too Short

The AI cannot guess how much you want. Without a length and shape, you get its default — a wordy essay when you wanted three bullets.

Problem	Likely cause	Fix
Endless preamble	No format requested	Add "3 bullets, no introduction"
Reply too short to use	Request was thin	Ask it to "expand each point with an example"
Wrong level of detail	Audience not set	Specify "for a board" or "for a new hire"
Drops important parts	Squeezed into a length limit	Ask for it "in two parts" or raise the word count

Controls you can drop into any request:

- Keep it under 150 words.
- Use a short table, not paragraphs.
- One line per meeting action, owner in bold.

Pin down length, structure, and audience and you will rarely fight this again. See the Prompting Rules and the Cheat Sheet for templates.

Recovering a Derailed Conversation

A long chat can drift: the AI contradicts itself, forgets your instructions, or fixates on a wrong assumption. This is normal — it has too much in it.

Problem	Likely cause	Fix
Repeats a mistake you corrected	The wrong version is still in the thread	Start a fresh chat with only the good material
Forgot your original instructions	Too much has scrolled past	Restate the key rules in one clear message
Lost the thread of a long task	The conversation got overloaded	Ask for a summary, then continue from it
Fixated on a wrong assumption	It locked onto something early	Say "stop — reset on this point" and correct it
Tone or quality slowly drifted	Accumulated clutter	Begin again with a clean, structured prompt

The reset-and-summarise move — ask for this, then paste the summary into a new chat:

Summarise everything we have agreed so far: the goal, the
decisions, and the current draft. Make it complete and
self-contained so I can continue in a fresh chat.

For a smaller wobble, redirect in place: "Stop. Ignore the last few messages. The correct brief is [restate it]. Work only from this."

Starting over is a skill, not a failure. Most problems are solved not by a better tool but by a clearer request — change one thing, try again.