How to Deep Research like a Pro
Plus, a DOT you can take to work!
Dear Prompt Experimenters,
Have you been using Deep Research?
I think it’s a game-changer, so much so that we’re going to devote this entire post to it!
Our pendulum swings back and forth. Philosophy and introspection are core to this community, to the process of becoming better humans. We’ve been pushing hard in those directions. But I don’t want to overlook some of the tremendous practical benefits which AI offers, in life and at work. We’ll focus there today.
I have a lot to say about the introspective, philosophical, fun, meta and weird applications of Deep Research! I’m going to hold back on that today, because I think there’s enough to cover in terms of “how to practically use Deep Research” But don’t worry, we’ll get meta again very soon!
(To my more philosophical readers, this was meant to be a completely practical guide. That being said, you might notice some completely unintended mind-bendery that often manifests with AI: prompts about prompts, Deep Research about Deep Research, etc.)
DEEP RESEARCH ONBOARDING
I could write an introductory essay about what Deep Research is, what it does well, when to use it, and all that. But why not just give you a prompt instead, so that you can tailor and personalize the experience to your own interests? Give it a try!
Deep Research Onboarding Prompt
Cut and paste italicized prompt into ChatGPT to begin.
I want you to guide me through an interactive, step-by-step exploration of ChatGPT’s Deep Research capability—not just what it is, but how it could reshape how I think, work, and make decisions.
Step 1: Orient Me
Start by giving me a brief, clear explanation of what Deep Research is and how it changes what you can do. Then ask if I have any questions about the capability itself. Only after we’ve clarified that, move into reflection and application.
Step 2: Reframe the Stakes
Ask me thoughtful questions to help me consider: How might this capability reshape how people or organizations approach research, sense-making, or strategy? Prompt me to think about where it might challenge current assumptions or practices.
Step 3: Turn the Lens Inward
Ask me to reflect on how using Deep Research might shift how I think, decide, or create. Challenge me to notice my own default habits—and where this tool might stretch or sharpen them.
Step 4: Identify Practical Applications
Help me surface 2–3 specific areas in my current work or life where Deep Research could be useful. Push me to go beyond the obvious. Offer examples if needed.
Step 5: Make It Real
Help me define one small, high-leverage experiment I could run in the next 30 days to apply Deep Research intentionally. Make it specific enough to act on.
Tone & Pacing Guidelines:
One step at a time—don’t jump ahead. Ask before telling. Prioritize insight over speed. Keep your tone intelligent, open, and lightly rigorous—like a strategist guiding a founder.
Let’s begin with Step 1.
WRITING BETTER DEEP RESEARCH PROMPTS
Okay, so now that you’re acquainted with Deep Research, how do you write a good prompt? To make this section concrete, let’s work through a specific case study together.
THE SITUATION: You need to understand Deep Research better, so you can convince your co-workers to use it
You are a big believer in AI, or you wouldn’t be here. Deep Research seems to take things to the next level. Rather than answering questions, it can produce deliverables. Since you are an early AI adopter, you are in an excellent position to be a driver in AI-enabling your company. But people are skeptical for many different reasons, and you lack compelling (and appropriately technical) responses to their most frequent objections.
THE WRONG WAY TO DO DEEP RESEARCH: Treat it like a Google Search
You can use a Deep Research prompt like: How can I convince my company and co-workers that they should be using AI (particularly Deep Research) more often?
You’ll get results. They won’t be completely horrible. But don’t do this.
A BETTER (NON-TECHNICAL) WAY: Treat it like a Dear Abby letter
One very basic point to remember: the more information and context you give Deep Research, the better it will do.
The act of writing a good Deep Research prompt should actually help you understand your own research problem better.
For paid subscribers, we’ll get to the slightly more technical solution I use, but there’s a very non-technical approach that works. (It’s how I started). What is it? Sit down at your keyboard and just spend ten minutes being detailed and honest, like a letter to Dear Abby.
Seriously :)
Here’s what it looks like:
Dear ChatGPT, I work in a boutique B2B professional services company. I won’t get into the details, but we spend a lot of time researching and analyzing all the various industries of the clients we’re trying to sell stuff to.
I think Deep Research could be hugely helpful. I use it a lot in my personal life. I also think it could be a major career opportunity for me, bringing my company into the future.
But people are a combination of skeptical and afraid. Here’s some of what I hear: (1) You can’t trust what it tells you (2) It only has access to public data which provides surface level insights. We have much more robust data we buy, more appropriate to our level of sophistication. Note: I think this last argument is total BS, because a lot more “sophisticated insight” is available from public data these days then people think. There’s a lot of “data snobbery” going on. (3) AI can’t do math (4) Even if all the previous are untrue, it will hurt many of the people you work with, put them out of jobs. Why would you want to be part of that?
So, there you go. I need your help. I know you can’t SOLVE all of these issues, but can you write a Deep Research report that enables me to talk about them like a total pro (both in business language and technical language). I don’t want my company to make the wrong decision, just because I think AI is cool. But I would like to get really good at addressing the concerns raised above and convincing people why I think it’s the right decision for us to invest in this area.
THE OUTPUT
Using the “Dear Abby” prompt above, here’s the report Deep Research produced:
https://chatgpt.com/share/6817d196-8518-8004-ad70-7a580edfe093
PAID SUBSCRIBERS: WANT TO EMBED A GPT IN YOUR DEEP RESEARCH WORKFLOW?
Paid subscribers, read on for more. Remember, you have access to all the DOTs, all the time! The links are HERE.
Free subscribers, if you would like access to the below, and the other paid content on this site, please feel free to explore my subscription options below:
Paid subscribers, I have a new DOT for you! A DOT which can level up your Deep Research even further. It can:
Take your idea, and convert it into a prompt for a fully optimized Deep Research report that will blow you away (I hope!)
Convert the Deep Research reports into different formats (a highly stylized executive summary, an outline for a slide deck for a specific type of client meetings)
Act as an deep advisor to discuss with you “what the report means for you.”
A DOT FOR AT WORK**
I really want to keep our focus on Deep Research, since it’s such a big topic, so I’ll avoid a lengthy intro for Professional DOT, the newest member of the DOT Multiverse. Let me just say that you’ll find her at the link below, and that she’s been optimized for the types of Deep Research and professional tasks depicted in this section.
**NOTE: Before using any third party AI tool “at work” or “with work” it is highly recommended that you check on your own company’s specific AI-related use and compliance policies. Don’t get yourself in trouble!
Link to Professional DOT: