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June 10, 2026

Issue 23: Smarter by Thursday

Smarter by Thursday — Issue 23

Issue 23 · week of June 08, 2026

Smarter by Thursday

One practical AI win, every week. No jargon required.

By Dr. Rowan Hayes · Estimated read time: 6 minutes

This week we’re using AI for two things that look small on paper but quietly change how your days feel: **spring cleaning with a custom checklist** and **giving thoughtful feedback to a team member**. One makes your physical space calmer and more manageable. The other keeps your working relationships from quietly decaying under unspoken frustration. Both are places where a little structure - the kind AI is good at - goes a long way.

Try at least one before Sunday. That is the whole assignment.

Use Case 1 of 2

Use Case 1: Spring cleaning using a checklist AI creates

On a rainy Saturday morning in late May, Denise, 57, was standing in the doorway of her spare bedroom, coffee in hand, just staring. The room had become the family storage unit: old tax files, her son’s college boxes, two half-broken lamps, and a treadmill that mostly held laundry.

She wanted to “do a spring clean” before her daughter visited in June, but every time she tried to start, her brain served up vague orders: “Declutter house” and “Deep clean everything.” Fifteen minutes later she would be doing something completely different - refilling the bird feeder or scrolling recipes - because the task in front of her felt too big, and too undefined.

Her knees weren’t great, she worked full-time, and she had maybe 30 minutes on weeknights and an hour or two on Sundays. A “perfect” checklist she found online just made her feel worse. It assumed she had endless weekends and a 25-year-old back. She didn’t need perfection. She needed someone to look at her real life and say: “On Tuesday, do these three things. Here is exactly where to start, and here’s how you’ll know you’re done.” That “someone” can be an AI, if you tell it what you actually need.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

I want you to act as a personal household project planner and create a realistic, room‑by‑room spring‑cleaning checklist for my home.

Ask me 5 - 8 clarifying questions first about: - how many rooms I have (kitchen, bathrooms, bedrooms, living areas, storage areas) - whether I live in a house, condo, or apartment - how much time I realistically have per day (in minutes) - any physical limitations (e.g., bad knees, can’t lift heavy things) - whether I will have help from other people - my priorities (for example: kitchen and bathrooms must be spotless; I don’t care about the garage)

After I answer, create: 1) A 7‑day schedule with specific tasks for each day, grouped by room. 2) A single master checklist I can print, with checkboxes and simple, concrete actions (for example: “wipe baseboards in living room” rather than “deep clean living room”). 3) A SHORT “start here” list of no more than 5 tasks I can do in 30 - 45 minutes if I get overwhelmed.

Make sure the tasks are: - realistic for my time and energy - in a logical order (declutter before deep cleaning, top‑to‑bottom in each room) - specific enough that I don’t have to think about what each one means.

At the end, ask: “Would you like me to break any day into smaller 15‑minute chunks?” and, if I say yes, create that as well.

Why this prompt works:

You’re not asking for “a spring cleaning checklist,” which usually produces a generic, guilt-inducing list. You’re telling the AI to play a specific role (household project planner), forcing it to ask you clarifying questions about your space, time, limitations, and priorities first. Then you specify *format* (7‑day schedule, printable checklist, short “start here” list) and *rules* (realistic, logical order, concrete actions). This moves the output from “Pinterest inspiration board” into “planner you can actually follow.”

One thing to watch out for

AI has no idea how your body feels at 7 p.m. after a long day. It will often overestimate how much you can do in 30 minutes, or forget small realities like “trash pickup is Thursday” or “I don’t own a step ladder.” Read the plan and adjust ruthlessly: cut tasks in half, move heavy or ladder work to days when you have help, and ignore anything that feels like it belongs in a magazine photo shoot, not your real life. If you feel a wave of “this is too much,” ask the AI to halve the workload and simplify.


Use Case 2 of 2

Use Case 2: Giving feedback to a team member

On a Tuesday afternoon, Malik, 49, was staring at an email draft to one of his project coordinators, Ana. She’d been with the team for about six months. Smart, enthusiastic, good with clients - but chronically late with documentation and light on details. The last three reports had missing figures, vague timelines, and no clear next steps.

He’d already “hinted” twice: a comment in a meeting, a note in the margin of a shared doc. Nothing changed. His frustration was building, but he hated conflict. The last time he gave blunt feedback, five years ago, the person cried, he felt awful, and he’d been pulling his punches ever since.

Now he had a different problem: he was either too vague (“let’s tighten this up”) or too sharp (“this can’t keep happening”). He wanted to be kind and clear at the same time, and he wanted something he could use both as talking points in their 1:1 and as a follow-up email so Ana wouldn’t leave the conversation guessing. He didn’t need AI to decide what was wrong - he already knew. He needed help turning a knot of thoughts into a short, honest, human-sounding message.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

I want you to act as a communication coach to help me give clear, kind feedback to a team member about their work.

First, ask me these questions and wait for my answers before drafting anything: - What is the team member’s role and how long have they been in it? - What specifically is not working in their recent work (with 1 - 2 concrete examples)? - What is working well that I genuinely appreciate? - What outcome do I want from this feedback in the next 4 - 6 weeks? - Do I plan to give this feedback by email, in a meeting, or both? - What is my natural tone (for example: straightforward, diplomatic, warm, etc.)?

After I answer, do the following: 1) Draft a brief feedback message I can use as a script or email.

Use this structure: - one sentence acknowledging something they are doing well - 2 - 3 sentences describing the specific issues, in plain language, with examples - 1 - 2 sentences explaining the impact on clients/the team - 2 - 3 sentences being clear about what “better” looks like in the next 4 - 6 weeks - one sentence expressing confidence in their ability to improve

2) Suggest 3 - 4 open‑ended questions I can ask them in conversation to invite their perspective (for example: “How does this land for you?” or “What would help you make this change?”).

3) Offer 2 - 3 alternative phrasings for the “tough” sentences so I can choose the one that sounds most like me.

Keep the tone: - respectful but honest - specific, not vague - focused on behaviors and outcomes, not personality.

At the end, ask: “Would you like this to sound more direct, more gentle, or stay as is?” and be prepared to revise the wording based on my answer.

Why this prompt works:

You’re not asking the AI to judge your colleague or invent the problem. You’re telling it to ask for your facts first, then apply a clear structure: appreciation, specific behavior, impact, expectations, confidence. That structure matches how good managers naturally give feedback, but most of us struggle to hold it all in our heads when emotions are involved. You also insist on multiple versions of the “hard” sentences so you can pick what sounds like *you*, and you give it instructions on tone so it doesn’t default to robotic corporate-speak.

One thing to watch out for

AI is very good at sounding “reasonable” and can accidentally sand off all the edges. That can leave you with feedback that is pleasant but too vague to be useful - the email equivalent of “keep up the good work, but please also somehow change.” Before you send anything, read it out loud and check: is it completely clear what needs to be different in the next month? If not, ask the AI to make the expectations more concrete, and then add one sentence of your own so your voice is in there. Also, never paste in confidential performance details with real names if you’re using a work account that might be logged or monitored; anonymize or generalize where needed.


Know someone who spends too long on things AI could do in two minutes?

Forward Smarter by Thursday to three people who subscribe and I will send you my free AI Prompt Starter Pack: 20 ready-to-use prompts for everyday life.

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Smarter by Thursday · By Dr. Rowan Hayes · drrowanhayes.com
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