Your New Hire Needs Context. So Does Your AI.
You've been doing this with people for years. AI is no different.
You already know how to do this.
Last week, I sat in a room with 15 nonprofit leaders. Smart people. Mission-driven people. People who manage teams, write grant proposals, and navigate board meetings without blinking.
And when I asked them what their biggest struggle with AI was, every single one of them said the same thing.
“I don’t know what to ask it.”
That stopped me. Because these were not people who struggled to communicate. They brief volunteers. They report to boards. They make the case for funding to people who need convincing. Communicating is what they do.
The problem wasn’t the skill. It was the blank page.
Here’s what I told them:
You already know how to prompt AI. You’ve been doing it your whole career. You just called it something else: onboarding. Just like onboarding a new hire. You need to onboard your AI.
Think about the last time you brought someone new onto your team. You didn’t hand them a laptop and disappear. You told them what you were trying to accomplish. You explained who the audience was, what the tone should be, and what a great outcome looked like. When their first draft wasn’t quite right, you didn’t tell them to start over from scratch. You said “this part works, here’s what needs to change.” And you eventually got there and over time, you didn’t have to give as much refinement as the new hire learned how you like projects to flow.
That’s a prompt. You’ve been doing them for years.
The difference with AI is that it won’t tell you when your project brief was bad unless you tell it to push back or ask you questions. A new hire will ask the clarifying questions. They look confused enough that you know you need to say more. AI fills the gap, sounds confident, and hands you something polished, whether your brief was great or not. That’s the trap.
So the skill isn’t learning to prompt. It’s learning to brief the AI before you start.
The blank page problem has a simple fix: stop trying to write a perfect prompt. Just describe your situation. “I am [insert title or role]. I need to [insert task]. Audience is [insert who]. Goal is [insert goal of the task] and I’m not sure how to start” is a good start to a prompt. AI can work with messy. What it can’t work with is no context.
*Still struggling to identify use cases, I wrote about it here:
And when you’re not sure if you’ve given it enough? Ask it to ask you. Before you request the output, say “ask me the questions you need answered to do this task well, one at a time, and give me multiple choice answers.”
Your prompting starter kit
These eight moves will take you from intimidated to confident. You don’t need all of them every time. Pick the ones that fit.
Start with your problem, not a perfect prompt. Describe the situation. Let AI help you figure out the rest.
Brief it like a new hire. Who is this for? What’s the goal? What does done look like?
Give it a role to play. “Act as a communications director for a small nonprofit” changes the output immediately.
Show the AI what good looks like. Paste in an example, document, SOP, a tone you liked, a format that worked. AI matches patterns well when you give it one.
Ask it to ask you questions one at a time, with multiple choice answers. This is the move most people don’t know. It closes the gap between what you said and what you meant.
Tell it what you don’t want. “Keep it under 200 words” and “don’t make it sound too formal” are context. Give it constraints.
Refine, don’t restart. When the output isn’t right, build on what is. “This part works, now adjust the tone in the second paragraph” gets you further than starting over. Edit the original prompt. Ask it next time you run this task, what is a better way to prompt the scenario.
Plan first. Give the context and messy prompt and say let’s plan first before you do the task or build. This way you can easily refine things before having to go back and forth 20 times. Make sure the plan or approach to the task is in alignment between you and the AI. Once the plan is correct. Say build it or run it.
The blank page is the hardest part. Once you’re in the conversation, you’ll find it feels less like a test and more like a working session with someone who’s genuinely trying to help.
You’ve been briefing people your whole career. You’ve got this.
Resources
For the last three years, leaders have asked me for the assessments, templates, and planning guides we use in our AI sessions. So I pulled together the most requested resources and made them super affordable for small businesses and nonprofits because everyone deserves access to practical, approachable AI.
Inside you’ll find:
AI planning playbook for 2026, 11 pages
Policy templates (2 templates)
Adoption assessment reviewing 16 categories
AI leadership insights (lessons from 160+ sessions, 12 pages, including an Assessment)
ChatGPT modes, connectors and shortcuts
Claude Cowork 101- 8 page non technical guide. NEW
Or a bundle to get them all for only $99, a $250 value.
If you’ve been wanting a simple starting point or something to help your team move faster, this is for you.
Take a look: https://payhip.com/AISimplified
Would love your feedback on what to add next. Thank you all for your kind feedback. It makes me happy that you are finding them to be so helpful.
2026 AI Adventures
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 105 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 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.
August 26 Dayton AI Summit https://www.technologyfirst.org/DAID26 Leading a session with Kate Berner on Building a Living AI Workflow that adapts when AI models shift.
September 3 8-10 am hosted by Clermont Chamber. Our AI in Action session https://business.clermontchamber.com/eventcalendar/Details/2026-clermont-classroom-class-1-ai-in-action-stop-watching-start-doing-real-tools-real-results-1752414?sourceTypeId=Hub
September 8-10 MidwestCon https://midwestcon.live/
September 16 save the date for a special hands on workshop. Doors open at 8:30 and program is from 9-12 at 3z in Covington, KY. We will build your custom workflows together and give you a repeatable approach for additional workflows you want to map. Think of this as your work intelligence layer.
I love answering your AI questions. Feel free to message me.
Where AI and inspiration collide!
Kendra Ramirez
KendraRamirez.com
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 250 AI sessions and speaking sessions (over 20,000 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 three years. You can search all of my enewsletters here if you are looking to brush up on a certain topic. kendratech.substack.com