AI investing prompts: 30 questions to ask about your own portfolio

The most useful AI investing prompts ask the assistant to explain, summarise and argue both sides, not to predict or pick. Good examples: "What's the news on my holdings this week, and which stories actually matter?", "Which of my holdings report earnings in the next two weeks?" and "Give me the bull and bear case on my biggest position, with sources and dates." Below are 30 prompts you can copy, grouped by what you're trying to do.

They work in ChatGPT, Claude, Gemini and other assistants. Prompts that mention "my holdings" need the assistant to know what you own, which is covered at the end.

How to get better answers from any prompt

A few habits improve almost every answer:

• Ask for sources and dates. It makes claims checkable and exposes stale information.
• Name the time window. "This week" or "the last 30 days" beats "recently."
• Ask for both sides. The bear case is where assistants add the most value.
• Ask it to explain, not decide. "What are the considerations?" gets a better answer than "Should I?"
• Use the ticker and the company name. It avoids mix-ups, especially between Canadian and US listings.

Staying on top of news

• "What's the news on my holdings from the past week? Group it by company, newest first, with sources and dates."
• "From this week's news on my holdings, which stories could change the long-term picture and which are noise?"
• "Summarise the news on this ticker from the last 30 days in five bullet points."
• "Is there anything in today's news that affects more than one of my holdings?"
• "This stock moved sharply today. What news came out, and when?"

Earnings

• "Which of my holdings report earnings in the next 14 days?"
• "What reports in the next two weeks across my holdings and my watchlist?"
• "Walk me through the last earnings report for my largest position. Beat or miss on revenue and EPS, and what did guidance say?"
• "Show me the last four quarters of results against estimates for this company. Is there a pattern?"
• "Have any of my holdings beaten estimates recently but still dropped? Why might that be?"
• "Remind me the day before anything I own reports earnings."

If you have a holding like that, Why did my stock drop on good earnings? explains the usual reasons.

Understanding your portfolio

• "Show me my holdings with portfolio weights, largest first."
• "How concentrated is my portfolio by position and by sector?"
• "Which of my holdings are ETFs and which are single companies?"
• "Show me my holdings grouped by account."
• "Do any of my ETFs already hold large positions in the individual stocks I own?"
• "What's my gain or loss on each position based on my average cost? Which currency are you using?"

Researching a company

• "Explain how this company makes money, in plain English."
• "Pull the fundamentals for this stock: market cap, P/E, EPS, dividend yield, 52-week range and beta. Explain each in one line."
• "Compare this company's fundamentals to a close peer. What might explain the differences?"
• "Give me the strongest bull case and the strongest bear case for this company, with sources and dates."
• "What would a sceptical analyst say about the bull case you just gave me?"

For a full method, see How to research a stock with AI.

Checking your own thinking

• "Help me write a one-paragraph thesis for my largest position, including what would break it."
• "Here's why I bought this stock. Based on the latest news, does my reasoning still hold? Show both sides."
• "Give me the strongest argument against my most recent purchase."
• "Which of my holdings have had the biggest swings this year, and what drove them?"
• "Help me think through the time horizon for each of my accounts."

Learning as you go

• "Explain EPS using one of my holdings as the example."
• "What does guidance mean, and why can it matter more than the results?"
• "What's the difference between a P/E of 10 and a P/E of 40? Use companies I own as examples if possible."

Prompts to avoid, and what to ask instead

The first column invites either a refusal or a confident guess. The second gets you information you can use.

This is general information, not investment advice.

Following up: the prompts after the prompt

The first answer is rarely the most useful one. Short follow-ups often get more out of the same conversation:

• "What's the source for that, and what's the date?"
• "What would change that conclusion?"
• "Explain that like I'm new to investing."
• "Now argue the other side."
• "Which part of that are you least sure about?"

The last one is underused. Assistants are often more candid about uncertainty when you ask directly, and it tells you which claims to check yourself.

Making "my holdings" prompts work

About half of these prompts need the assistant to know what you own and to have current market data. You can paste your holdings in each time, but it goes stale quickly.

A read-only connector does it for you. Bywell links your brokerage, such as Wealthsimple, Questrade, TD Direct Investing or Interactive Brokers, through SnapTrade and gives your assistant tools for holdings, news, fundamentals, earnings, watchlists and reminders. Many of the prompts above come straight from Bywell's own learning path, where each short lesson ends with something to try in your assistant.

To set it up, see How to connect your brokerage account to ChatGPT or Claude, or start here.