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Troubleshooting AI Assistants

  • Aug 6
  • 3 min read

A Practical Guide for Enterprise Teams

AI assistants are transforming how teams access knowledge, automate tasks, and collaborate—but they’re not without quirks. Whether you're using an enterprise AI assistant integrated into your workflows, a third-party platform like ChatGPT, Claude, or Gemini, or a custom-built tool, you’ll likely encounter challenges like inaccurate answers, permissions issues, or integration hiccups.


This guide breaks down troubleshooting into four key areas:

  1. Relevance and Accuracy

  2. Access and Permissions

  3. Unexpected Behaviors

  4. Integration and Configuration

Each section offers actionable steps to help you get the most out of your AI assistant.


1. Relevance and Accuracy


Problem: Search Results Are Inaccurate or Incomplete

Fix it with:

  • Better Queries: Use clear, specific prompts. Include project names, document titles, or teams.

  • Connected Data Checks: Ensure that the assistant is linked to all required systems (e.g., document repositories, ticketing systems).

  • Filters: Use content-type filters or restrict search scope to improve relevance.

  • Index Lag: Recently added content may not show up immediately—wait or trigger a re-sync if needed.


Problem: Chat or Assistant Responses Are Off

Fix it with:

  • More Context: Instead of “What are the risks?”, try “What are the open risks in our Q3 launch project?”

  • Rephrased Prompts: Break down complex queries into smaller questions.

  • Verify Sources: Click links or references provided and confirm the assistant's accuracy.

  • Understand Limits: AI may not access custom fields or freshly added info in real time. Use search as a backup.


For Custom AI Agents

  • Clarify the Agent's Purpose: Review and refine the prompt/instruction text.

  • Limit or Expand Knowledge Scope: Choose between “general” and “restricted” data sources depending on use case.

  • Test Iteratively: Use real prompts, gather feedback, and adjust.


2. Access and Permissions


Problem: “I Can’t Find That Document”

Fix it with:

  • Check Your Access: AI assistants can only show what you’re allowed to see.

  • Permission Sync Delays: Newly granted access may take time to appear—try refreshing or re-syncing.

  • Understand Boundaries: If an assistant says, “I can’t access that,” it likely means your user account lacks access.


Problem: Features Are Missing

Fix it with:

  • Check Admin Settings: Your organization may need to enable AI features for your environment.

  • Connector Authorization: Ensure third-party app connections haven’t expired or been revoked.

  • Share AI Agents Thoughtfully: If using a custom-built assistant, share the link or install details with others.


3. Unexpected Behaviors


Problem: Chat Freezes or Doesn’t Load

Fix it with:

  • Check Network or Platform Status: Could be a temporary issue. Refresh and try again.

  • Quota or Usage Limits: Some platforms enforce monthly limits. Heavy users may need expanded access.


Problem: Inconsistent or Vague Answers

Fix it with:

  • Add More Context or Examples

  • Use Structured Feedback Tools

  • Revisit Agent Prompt or Data Scope


Problem: Broken Formatting or Links

Fix it with:

  • Prompt Adjustments: Specify preferred output format (e.g., Markdown, plain text).

  • Avoid Overloading with Examples: Too much embedded markup may confuse generative outputs.


4. Integration and Configuration


Problem: Search or Chat Doesn’t Pull from Key Tools

Fix it with:

  • Connector Verification: Check admin panels or integration settings for apps like Google Drive, Slack, Teams, or SharePoint.

  • Reauthorize Expired Connections

  • Ensure Permissions Are Mirrored: Even if a connector is active, users must also have access in the external system.


For Developer Teams Using Custom Agents

  • Clarify Scope: Ensure your AI agent is installed across all relevant platforms if you’re using tools like APIs or SDKs.

  • Use Actions to Fetch Data: Implement custom actions to pull in context on-demand if not indexed by default.

  • Monitor Logs and Errors: Review logs to identify missing scopes or misconfigured data paths.

  • Stay Compliant: AI agents must comply with acceptable use policies—check for flagged content or behavior.

  • Test Before Deployment: Always try agents in a dev environment before rollout.


Troubleshooting Like a Pro

AI assistants are only as good as the configuration, access, and context they’re given. To improve performance:

  • Refine your prompts

  • Test and iterate

  • Align permissions

  • Monitor integrations

  • Give feedback

By applying the strategies in this guide, you'll transform frustrations into insights—and your AI assistant into a reliable teammate.


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