Struggling to Think of AI Use Cases, Start Here!

The Moment Before the Prompt

Last month, a business leader sat in one of my workshops staring at a blank screen.

She wasn’t confused about AI. She understood it well enough. She just couldn’t think of a single thing to type.

“I don’t know what to ask it,” she said.

She’s not alone. That’s actually the most common thing I hear, not “AI is too complicated” or “I don’t trust it.” Just a quiet, frustrated blank. And here’s what I’ve learned after 250 sessions: the problem isn’t the prompt. It’s that most people haven’t been taught to notice what comes before the prompt.

The real starting point isn’t a question. It’s a feeling.

Think about your last week. Not the big stuff, the small stuff. I call it the small papercuts throughout the day. The email you rewrote four times and still sent feeling uncertain. The report you put off until Thursday became Friday became “I’ll handle it Monday.” The meeting recap you knew you needed to write but kept finding reasons not to start.

Those moments? That’s your AI list. You just didn’t know to call it that.

Before I teach anyone to prompt, I teach them to pay attention to three things:

Repeat — tasks you do over and over that follow roughly the same pattern every time. Weekly updates. Vendor emails and follow ups. Social posts. Meeting agendas.

Draft — anything where you have to create something from scratch and the blank page wins more often than you do.

Stuck — the stuff you avoid. The thing that’s been on your to-do list for two weeks not because you’re lazy, but because something about it feels hard to start.

That’s it. Three categories. No tech knowledge required.

Then ask AI to fill in your blind spots.

Once you’ve done your own list, try this: open AI and try:

“I am [insert role, title, or job description] and what I do day to day: [paste a few details/tasks about your job]. I am [new to/experienced] with using AI at work. Based on this information, ask me clarifying questions on ten practical ways I can use AI to work smarter, not just faster.”

You’ll get a list back. Some of it won’t fit. But some of it will match something you already identified — a repeat task, a draft you dread, a decision you keep second-guessing. When that happens, it stops being a suggestion. It becomes a confirmed priority.

What this looks like in practice

Back to the woman in my workshop. Once we stopped trying to think of “AI use cases” and just looked at her week honestly, the list filled up in about four minutes. She had three repeat tasks she did every Monday. Two drafts she’d been procrastinating. And one thing she’d been stuck on for two weeks that she hadn’t told anyone about. Look at your work and identify areas where steps may no longer be needed or the additional meetings that are not required due to the workflow updates. It isn’t about just “adding AI” to work but really looking at the transformation of how work gets done through a fresh perspective.

We took the stuck one first. She typed out exactly why she’d been avoiding it, messy, unpolished, honest. That description became her prompt. Within minutes, she had a starting point she actually liked.

That’s the light bulb moment I see over and over. Not “wow, AI is amazing.” More like — “oh, I already knew what I needed. I just needed to shift how I am approaching AI.”

What this means for you

You need five minutes at the end of your week to ask yourself: what did I repeat, what did I dread drafting, and what am I avoiding? Use case lists are helpful to popcorn and spur on ideas. Prompt libraries are great for sharing what is working within teams. Don’t wait for use case lists or prompt libraries to get started.

One thing to try this week

Before you open AI, write down one thing you’ve been putting off. Then write one sentence about why you’ve been putting it off. Don’t clean it up. That sentence is your prompt. Take it one step further. After the messy prompt and your description of the thing you are stuck on, add to the prompt, “Ask me clarifying questions one at a time with multiple choice answers so it is easy for me to respond until you are 95% confident that you have what you need to achieve the task.” Hat tip to Kate Berner, as this is her favorite way to prompt.
Start there and see what happens.

If you want to bring this kind of session to your team or organization, reply to this email. We’d love to sit side by side with you and find your list together and shift the mindset of your organization.

— Kendra

Microsoft just unveiled Scout at its Build 2026 conference — an always-on AI agent built on OpenClaw, the viral open-source framework that took the AI world by storm earlier this year. Scout connects to Microsoft 365 apps like Teams, Outlook, OneDrive, and SharePoint, and can proactively handle tasks like meeting prep, scheduling conflicts, and routine work, without waiting to be asked each time. Think of it less like a chatbot and more like a digital coworker that just never clocks out. It’s currently in early access for enterprise customers, but the direction is clear: the era of AI that waits for instructions is ending. I am surprised by this partnership, but I am here for it.

OpenAI has officially removed the minimum spend requirement on its self-serve ChatGPT ads platform and that’s a big deal for small businesses. When the platform launched back in February, the entry point was $200,000, putting it firmly in enterprise-only territory. That floor dropped to $50,000 in April, and now it’s gone entirely. The platform supports both cost-per-click and cost-per-thousand-impressions buying. If your customers are among ChatGPT’s one billion users, this is worth a serious look. https://ads.openai.com/

OpenAI just launched Sites, a new Codex feature that turns your ideas, analysis, and plans into interactive, hosted websites and apps you can share with your whole team via a single link. Think of it like giving your work a living home instead of burying it in a document tab nobody opens. You can ask Codex to build a customer review dashboard, a scenario planner from a financial model, or a project launch hub and then ask it to keep the site updated as things change. It’s currently rolling out in preview for Business and Enterprise customers, so if your team is already on ChatGPT Business, it’s worth checking out now. This is similar to using live artifacts in Claude.

We also just announced our private digital community of CincyAI Champions:

For $25/month or $250/year ($50 off!), access our paid member portal with: BIG thank you to the 96 members that have signed up already!

• 6 CincyAI Human Huddle virtual interest groups: AI for beginners, AI for intermediates, AI for advanced, AI for Women, AI for Arts and Creative, and new AI for nonprofits.

• Limited time only: “CincyAI Founding Champion” Badge
• CincyAI Champions Member Directory
• Monthly Office Hours with Helen & Kendra — Bring your AI questions each month.
• Cincinnati Area AI Job Board
• CincyAI & Community Partners Events Calendar
• CincyAI Champion Matchups
And more!

Limited time only: 30 days free trial as we’re seeding the community — join now to get your Founding CincyAI Champion member badge!!

https://app.heartbeat.chat/cincyai/invitation?code=D73D97#choose We are loving our digital community.

Cincy AI Week June 9, 10 and 11. The sessions are held at The Transcept and Union Hall. 3000 attendees, over 100 speakers. Third year. Sign up to attend or sponsor today: https://www.joinaiweek.com/cincy Use code CINCYAI for 50% off. I will lead a Claude session on June 11 from 2:30-4.

OhioX Dinners in Cincinnati are also happening on June 8 and June 11. https://ohiox.dnnr.io/ Snag your seat now. You take a brief quiz and get matched up with other local business leaders for a dinner. There are several dinners happening across the city and then you will get a text message about a happy hour after dinner, where all the dinner attendees meet up. It is so fun!

June 17 Greater Harrison Chamber luncheon. Love giving back to my local community. https://www.greaterharrisoncc.com/calendar/#!event/2026/6/17/business-leadership-lunch

June 24 Interact for Health from 1-3 Georgetown, OH hands-on AI Simplified for nonprofit session. Free to attend. https://lp.constantcontactpages.com/ev/reg/z7kctmn/lp/8f0ebe68-7308-4c5e-ad9b-7ce4ebdf8542

We provide AI Enablement (AI Speaking and Training, AI Readiness, AI Strategy, Workflow Automation, and Implementation). Our clients love that we sit side by side with them in our human centered approach to AI.

**For those new to my work, I have been in tech my whole career. Over 15 years of running my digital agency (website, social media, and lead generation) and 7 years of helping businesses navigate AI. Over the three years and, I’ve had the privilege of leading over 200 AI sessions and speaking sessions (over 15,000 people), empowering businesses to embrace the transformative potential of AI. My passion lies in simplifying complex technologies to help organizations grow, innovate, and thrive.

I am so excited that you are on this journey with me! Thank you! 🤗

I have been writing weekly about AI here for almost three years. You can search all of my enewsletters here if you are looking to brush up on a certain topic. kendratech.substack.com