The Question That Changes Everything: ‘What Else Should I Tell You?’

AI for Advisors newsletter

Quick take:

• Including questions in your prompt helps the AI explore alternatives, identify gaps, and refine tone or detail.
• One of the most effective tactics is asking the AI to ask you questions before completing the task.
• Answering the AI’s questions—even briefly—unlocks clearer, more tailored outputs.
• Great questions turn the AI from a content machine into a critical-thinking assistant.

In our advanced prompting framework, we’ve covered the foundational Role, Task, and Format (RTF) elements. The framework becomes “advanced” with the addition of three more elements: Context, Questions, Examples, which we shorthand as CQE.

Ask the AI

Now we’re turning to Questions—a deceptively simple technique that sharpens AI responses by prompting deeper thinking, follow-ups, and collaboration.

And one of the first and best ways to use this? Ask the AI to ask you questions before it proceeds.

You can completely change how the AI responds by adding a simple line like this to the end of your prompt:

“Before we go on and complete this task, please ask me any questions you have that will help us get the best results.”

Suddenly, instead of guessing what matters to you or your client, it pauses and asks what it needs to know. This makes the exchange feel less like typing into a search bar—and more like working with a smart, curious colleague.

Real example: Trust planning meeting

Prompt:
“Chatster*, I’m having a meeting tomorrow with some clients. They want to talk about setting up some trusts for their adult son who is autistic. Act as an expert in estate and trust planning. I want your help creating an agenda for our meeting.
Before we go on and complete this task, please ask me any questions you have that will help us get the best results.”

(*I refer to my AI models by personal names such as “Chatster” to personalize the interaction, making it feel more like a collaborative partnership than a tool-based transaction.)

The AI responds with questions like:

• What’s the nature of the son’s disability?
• What are the clients’ goals in creating the trust?
• Have they consulted an attorney or tax advisor?
• Do they have a preferred trustee?
• Are they familiar with special needs trusts?

Your answers (short and direct):

1. Low-functioning autism. Want to provide for his care after their death.
2. Yes, they want to include real estate and investment accounts.
3. They have a plan but need to update it.
4. Not yet—need education on trust types.
5. No trustee selected.
6. Haven’t spoken to a tax attorney yet.

From here, the AI can generate a far more thoughtful and practical meeting agenda—because it understands the full situation.

Real example: Tax planning after a move

Prompt:
“Chatster, I’m preparing a tax planning summary for a client who recently moved from California to Texas. He’s a high-income tech executive with stock options, RSUs, and deferred comp. Act as an expert tax planner and generate a short planning memo outlining key issues and opportunities. Before you complete the memo, please ask me any questions that will help you deliver the best results.”

The AI responds with questions like:

• Is the client still earning California-sourced income (e.g., through stock vesting or bonuses)?
• What’s the client’s expected timeline for exercising stock options?
• Has the client established Texas residency for tax purposes?
• Are there upcoming liquidity events we should factor in?
• Is he maxing out qualified plan contributions or using any charitable giving strategies?

Your responses:

1. Yes, still vesting RSUs that were granted in California.
2. Plans to exercise NQSOs next year.
3. Yes, official Texas residency started last month.
4. Big liquidity event in Q2 next year.
5. Uses a donor-advised fund annually.

Why it works:
Without these details, the AI might deliver a boilerplate memo. With them, it can focus on state tax implications, timing of income recognition, charitable planning, and strategic use of lower-tax jurisdictions.

Other ways advisors can use questions

Even when you don’t ask the AI to ask you, you can still use strategic questions to:

• Clarify intent (“What assumptions are you making in this summary?”)
• Request options (“What are three other ways I could say this?”)
• Identify blind spots (“What tax consequences might I be overlooking?”)
• Reframe tone or audience (“How would this sound if written for a cautious retiree?”)

These can be included directly in your prompt or used as follow-up prompts in a multi-turn conversation.

Example prompts using questions

For refining tone:
“Rewrite this post for a skeptical, investment-wary audience. What phrases might trigger distrust?”

For brainstorming options:
“Give me three different ways to explain Roth IRA conversions to someone new to tax planning.”

For simplifying complexity:
“How would you explain this concept in 90 seconds to a college student?”

Ask more. Get smarter.

In client work, the quality of your questions often defines the quality of the plan. The same holds true when working with AI.

Don’t settle for first drafts and obvious answers. Use questions—especially ones that let the AI ask you—to turn prompting into a smarter, more productive conversation. It’s not just about extracting content. It’s about shaping insight.

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