Newsletter · Issue 01

The Human in the Loop

Practical AI for work, family, and everything happening in between.

Issue 01 August 31, 2026 About a 6-minute read

Hey everybody, I'm Michelle Hamilton.

Many of you have attended the AI × CRE AI 101 session, and on September 18 we're going one step further with a "Build Your Own Chief of Staff" workshop.

But here's really why I wanted to start this.

Every week, somebody calls me with some version of:

And those are honestly some of my favorite conversations. Because most of the time my answer is: "Oh my gosh. I've got an idea for you."

That's what I want this newsletter to feel like. Not more AI noise. Not a list of 47 tools you now feel guilty for not knowing. Just the few things I think are actually worth your attention, something useful you can try right away, and occasionally something completely ridiculous because life is too short for every AI conversation to sound like a board meeting.

CREW is full of extraordinary women (and a few men) who are leaders, professionals, mothers, partners, daughters, friends, mentors, caregivers, adventurers, and CREW sisters. We have very full lives. AI should help with that. Not replace us, but assist us. Because when women in CREW win, we all win.

Read more about the global AI work that takes me on so many adventures.


This week

Okay, these two are actually worth knowing

If it feels like your AI changes every time you open your laptop, you are not imagining it. I'll keep watching all of that and share some insight. Here are the two things this week that made me stop and think: okay, people are actually going to use this.

Tool · OpenAI

ChatGPT can finally see more of the week you're actually trying to manage

Anyone else managing one calendar for work, another for life, several email accounts, and some mysterious third system that appears to exist solely to destroy Tuesday? This one is for us.

OpenAI now lets supported ChatGPT users connect multiple Gmail, Google Calendar, and Google Contacts accounts in the same ChatGPT experience. So your work calendar can be here. Your personal calendar can be there. And you no longer have to be the exhausted human integration system attempting to remember both.

You could ask things like:

  • "What does next week actually look like when you put both calendars together?"
  • "Do I really have time to take that 3:00 meeting?"
  • "Find the email about that dinner I know someone sent me."

This is available on supported Plus, Pro, Business, and Enterprise plans. Want the details? Read OpenAI's announcement about connecting multiple Google accounts.

Why do I care? Because AI becomes dramatically more useful when it understands the situation you are actually trying to manage instead of one tiny piece of it.

Tool · Anthropic

Claude works directly with you inside Chrome and can actually help (but know the risks)

This one made me stop. Claude in Chrome is now generally available on paid Claude plans. That means Claude can work with you on the webpages you already use. It can read what is there and, when you allow it, click, type, navigate, fill out forms, and move between tabs.

Think:

  • Vendor portals.
  • Research sites.
  • Registration pages.
  • Travel sites.
  • Association websites.
  • And so much more.

All of those systems that may not have an AI button built into them. I already used mine to find and book a hotel near an upcoming convention in NYC, in my budget, with the amenities I prefer, on my Expedia account, then made dinner reservations, and set up a watch for sales at some of my favorite NYC businesses. I watched it work while I worked on a proposal, and thought: "I know some other people that don't have the time to get this granular."

Important rules: I never let it see my credit card information or account logins (all the same things I don't put on social media), and anything governed by an NDA, internal governance, or HR rules. Start with things like reading, researching, comparing, organizing, or filling out low-risk information while you get comfortable with it. Then decide where you trust it.

Want to see what Anthropic released? Read the Claude in Chrome announcement.


If Copilot is what your team uses at work

Make Copilot deal with the meeting logistics

I know a lot of you live in Microsoft 365 all day. So every issue, I'm going to try to find one Copilot thing I think is genuinely useful. Here's this week's.

If you use Microsoft 365 Copilot in classic Outlook for Windows, Microsoft is rolling out the ability to schedule meetings directly through Copilot chat.

  • You can ask it to schedule a meeting with colleagues.
  • It can look for available times.
  • Book a room.
  • Draft the agenda.
  • And send the invitation.

That is my kind of AI. Not because scheduling a meeting requires tremendous intellectual horsepower, but because somehow finding 45 minutes when six adults can all attend has become an Olympic sport. If your organization gives you Microsoft 365 Copilot, this is exactly the kind of little task I would start handing off.

Microsoft has the details here: scheduling with Copilot in Outlook.


Try this week

Stop carrying your entire week in your head

If your life is currently being held together by Outlook, text messages, sticky notes, caffeine, and optimism, I have an idea for you.

Take whichever AI chat you already use. ChatGPT. Claude. Copilot. Gemini. Whatever you actually have or use, give it the information you are comfortable giving it about the next seven days.

Maybe your AI can already see your calendar, email, and messaging (Teams or Slack). Paste in your schedule, commitments, notes, or anything else it needs. (Hint: a screen capture works too.) Then copy this:

Prompt · Weekly brief
Help me get control of the next seven days.

Review my schedule, commitments, messages, and notes I give you and create a one-page weekly brief. Let me know if you have access to my email, calendar, and IM system like (Slack or Teams).

Include:
1. Meetings or appointments I should prepare for.
2. Deadlines or commitments I have made.
3. Decisions I need to make.
4. People I owe a response or follow-up.
5. Personal commitments that may affect my work schedule.
6. The three things I should protect time for this week.

Separate confirmed information from anything you are assuming. Let me know if you need access to or copies of any details/accounts.

Do not make, send, cancel, or change anything for me.

Finish by telling me what I may be forgetting or how I can work smarter, faster. Give me three more ideas of how we can work together to improve my day.

That last question is one of my favorites. What am I forgetting? We spend a lot of time asking AI to create things. Sometimes its most useful job is helping us notice something before it becomes a problem.

And once you know that move, use exactly the same idea on:

Give it the mess. Ask it to create structure. Then use your judgment. That pattern works almost everywhere.


Before you go

Something unnecessary, useful, weird, or delightful

I promised this would not turn into one more serious AI newsletter that makes you feel like you need a certification before breakfast. So every issue gets a little room for something unnecessary, useful, weird, delightful, or all four.

This week's experiment: I often feel like I run on caffeine as my OS. I ran this prompt and here is what I got. What "fuels" you? Send me your results and I'll post my favorite in our next issue.

Prompt · Image · What fuels you
Create a photorealistic construction-site scene with three professional women, ages 35-60, gathered around architectural drawings. Each wears a bright hard hat with a playful job title. Their torsos have transparent x-ray cutaways showing coffee-powered internal systems physically built into their bodies, with no bones or organs visible.

Left: green industrial drip-coffee system with carafe, filters, tanks, gauges, and pipes. Center: copper/brass espresso system with grinder, pressure gauge, tamp, extraction chamber, and espresso cup. Right: teal/copper retail coffee-counter system with cups, menu, supply, prep, and serve stations.

Make the machinery dimensional, believable, and fully integrated into their bodies. Keep the women relaxed, capable, and warmly interacting. The center woman points to an unrolled blueprint; the right woman holds a paper to-go coffee cup. Add subtle coffee/construction humor. Active commercial construction site, cranes and equipment, cinematic natural light, polished architectural-advertising photography, realistic skin and clothing, sophisticated but playful.

One thing I'd tell a friend

Please do not make keeping up with AI another job

We all have so many. You do not need to master ChatGPT, Claude, Copilot, Gemini, and whatever drops next Tuesday while you are trying to get through lunch.

Use the AI you have. Bring it a problem you actually want solved. Give it enough context to help. Question what it gives you. Keep your judgment. And learn the moves that travel from one AI tool to another. That is where the real advantage is.

I'll keep sorting through the rest with you.

Michelle Hamilton
AI Adoption & Change Management Practice Lead · AnswerRocket
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