Actual AI: Two Challenges to Kick Off a Year of Actual AI

Welcome to Actual AI.

Over the next year, this column will share real AI use cases that superintendents and district office leaders can put to work the same week they read about them. No vendor pitches, just workflows I actually use that buy me more time in schools, in conversations with our teachers and students!

For this first post, I am not going to share my most complex automation. Instead, I want to challenge you to take on two small tasks that will make every AI interaction you have this year dramatically better. Both take less than thirty minutes. One of them does not even require you to sit down! 

One important note before we start: My AI tool of choice for all of my professional tasks is Google Gemini as our district is a Google Workspace EDU environment. The following challenges can be done in any tool, so you won’t see any more brand names after this sentence. It is crucial however, that you use the enterprise tool your district environment lives in, as this allows you to give the tool rich context safely and in compliance!

Challenge One: Teach Your AI Who You Are

Here is the biggest reason most leaders get generic, forgettable output from AI. Every time they open a new chat, the tool knows nothing about them. You would never hire a chief of staff and then wipe their memory every morning, but that is exactly how most of us use these tools.

Every major AI tool now has a place to store standing context about you. The different tools name this place differently, but the trick is that you do not need to know where it lives, because your AI will tell you. Open your tool of choice and ask it something like this:

“I want you to help me build a short standing profile so future chats start out already knowing who I am. First, tell me where this kind of standing personal context should live in this specific product and how I open that setting. Then interview me, one question at a time, to learn my role, what I am focused on right now, how I like my outputs formatted, any hard constraints, and a handful of facts that would keep you from ever giving me generic advice. Then write it up as a set of instructions to a future assistant, walk me through saving it, and give me one test question I can ask in a brand new chat to prove it worked.”

For my advanced readers, yes, a fuller context portfolio with layered documents and knowledge bases is even more powerful, and I will walk you through building one in a future column. But do not skip this step. Fifteen minutes of answering questions, and every chat you open for the rest of the year starts out knowing about your district context, your state's laws, and your major projects. Bonus points if you complete this self-interview by talking, not typing, as your context will be much richer! More on that next:

Challenge Two: Take Your AI on an After Dinner Walk

This is my favorite challenge! I have even convinced one of my two daughters to do this with me! When we type to AI, we tidy up. We shorten, we self-censor, we leave out the messy context that actually matters. When we talk, we stay fluent. We include the history, the personalities, the thing we are worried about but would never bother typing.

So here is your second challenge: Pick one real problem you have been chewing on. A stalled negotiation, a facilities decision, a difficult personnel situation, a Board dynamic. Then put in your earbuds, open the voice mode or microphone button in your AI tool, and go for a walk after dinner. Before you start talking, give it instructions along these lines:

“I am about to brain dump everything on my mind about one specific problem. First, ask me what the problem is. Then tell me to keep talking until I have emptied out all the relevant context, and remind me I do not need to be organized or linear. When I say I am done, do not solve anything yet. Repeat back what you understood, including any contradictions you heard, and wait for me to confirm. Only then give me your best thinking, and be clear about what I actually said versus what you inferred.”

Then talk for ten minutes. Stay messy. Do not organize. When you get home, you will have a summary of your own thinking that is sharper than anything you would have produced at your desk, and a first draft of a plan waiting for you. 

Why These Two First

Everything else I will share this year builds on these two habits. Standing context is what turns a chatbot into a teammate. And the walk will make a big idea clear to you that a lot of people are behind on: if you give these tools rich context, you don’t need to be a “prompt engineer” that writes perfect prompts. 

Try both this week. Then email me at jeff.feucht@chsd117.org and tell me what happened!