Olli can help you prep for meetings, analyze deal progress, and get insights from your pipeline. Here are some tips to get the best results and what to do if something goes wrong.
Be specific about what you want
Olli works best when you give him a clear, focused question.
A good Olli prompt includes:
A deal, meeting, or person to focus on
A timeframe (today, this week, since last meeting)
A clear question (summarize, compare, find objections, check progress)
"How did the Acme deal progress since our last meeting?"
"What objections came up in my call with Sarah yesterday?"
"Summarize the key takeaways from my Lenovo intro call"
Avoid asking Olli to do too much at once
Broad requests that touch many deals or team members at the same time can overwhelm the conversation.
Instead of: "Analyze all of my team's deals and tell me how to coach them individually."
Try: "Look at Jake's recent Acme meetings — did his discovery approach change?" then follow up with the next rep in a new chat.
Start fresh when switching topics
If you've been going deep on one deal and want to ask about something unrelated, open a new chat. Long conversations with lots of context are more likely to run into issues.
What Olli has access to
Olli can pull from your deals, meeting transcripts, and pipeline data, and more. He works best when your question maps to data he can look up: names, deal names, meeting dates, and specific topics. Olli can pull from your deals, meeting transcripts, documents, accounts, and pipeline data. Use the @ button when typing a message to tag a specific deal, transcript, document, account, or framework; this helps Olli find exactly the right context instead of searching broadly, which takes time and tokens.
If you see an error
Occasionally Olli will run into a problem he can't recover from. Here's what the messages mean:
Error message | What it means | What to do |
"We've talked about so much. Please start a new chat with a focused question." | The conversation has too much context for Olli to process. | Start a new chat with a more focused question — try narrowing to a specific deal or meeting. |
"I'm going back and forth too much. Want to try a different approach or should I keep going?" | Olli got stuck in a loop trying to answer your question. | Try rephrasing your question, or tell Olli to keep going if you want it to try again. |
"I'm temporarily unavailable due to high demand. Try again in a moment." | Olli's servers are experiencing high traffic. | Wait a minute and try again. |
"My response was interrupted. Try sending your message again." | The connection dropped mid-response. | Resend your message. |
"I wasn't able to read that PDF. The file may be too large, corrupted or in an unsupported format. Try re-exporting it and uploading again." | The uploaded PDF couldn't be processed. | Re-export the PDF and upload again. If the file is very large, try a shorter document. |
"This conversation hit a snag I can't recover from. Please start a new chat." | The conversation state got corrupted. | Start a new chat — retrying in the same thread won't help. |
"I ran into an issue. Try sending your message again, or start a new conversation with me." | Something unexpected went wrong. This is the non-specific error message for a variety of less common situations. | Resend your message. If it keeps happening, start a new chat. |