Watch Me AI: GPT-5 prompting tips + LinkedIn agent building + trivia use case

Practical GPT-5 prompting lessons, a recap of building a LinkedIn content agent, and a fun trivia-game prompt for killing time with family.

By Mollie Amkraut Mueller · August 21, 2025 · 2 min read

GPT-5 prompting learnings + tips

I've been experimenting with GPT-5 and it's definitely a different world of prompting than before. Here are a few tips:

Give longer, more detailed prompts. Pre-GPT5, short prompts worked. Now, the more detail the better. I like to ask it to give me the full prompt.
- Example: "I want to create a how-to guide for LinkedIn content agent building based on the recording from my live session and other stuff I've done. What's a good prompt to get you to create a really great guide?"
Literally tell it to "think harder." (Write those two words in your prompt). This has been surprisingly effective.
I'm loving its Next Steps. One thing that's been consistently excellent is the Next Steps GPT-5 recommends at the bottom of its response. I find myself often saying "yes" to those.
It's amazing with tools ("connectors"). I needed an updated list of prior Crew coaches. The info lived across a few old Google Sheets + emails. I asked GPT-5 for an updated list, and it pulled the Sheets + recent emails together into one clean list I could copy into my outreach email. Here are my exact prompts:
- First ask: "I'm looking for a full list of all former Crew coaches. These are people I would have emailed as a group several times in 2024 and a few times in early 2025. Are you able to find that list for me from my Gmail?"
- Follow up: "Great start. There should also be a longer list of coaches, maybe in my Google Drive, including coaches who had applied to Crew but didn't end up coaching with us. See that anywhere?"
- Note: You'll need to connect your ChatGPT to your email and G-drive (or other file storage system). You can do this in Settings, Connectors.

Recap: build a LinkedIn content agent with me

Last week's live session focused on LinkedIn content creation (that thing we all hate but know we need to do). We covered how to:

Automate your LinkedIn content pipeline
Use AI agents to research, write, and schedule posts
Build workflows that still keep your authentic voice

AI tip of the week: trivia games on demand

A fun use case: I was with my extended family the other day, waiting for food at a restaurant. We were hangry and in need of a distraction, so I asked ChatGPT for a trivia game. It came back with a list of questions. I skimmed them, decided they were too easy, told it to make them harder, and ended up with a perfect game that killed the hungry wait time.

My lazy prompt: "Give me a trivia game for my family while we wait for food."

Try it next time you need a quick group activity. It works great across generations.

My deep thoughts this week

Lots of deep thoughts but no new essays this week, I've been on vacation.