Prompting 7 min read

The Hate List: Find Your First AI Win in 2 Minutes

RW
Ryan Wanner

AI Systems Instructor • Real Estate Technologist

Everyone asks "What should I use AI for?" Wrong question. The right question: what do you hate doing?

Everyone Asks 'What Should I Use AI For?' Wrong Question.

I hear this every week. Agents come to the AI Acceleration workshop and their first question is: "Where do I start?"

They've read the articles. They know 68% of Realtors have used AI tools. They've seen the demos. They've downloaded ChatGPT. And then they sit there staring at a blank prompt box with no idea what to type.

The problem isn't AI. The problem is the question. "What should I use AI for?" has a thousand answers. That's why it paralyzes you.

Better question: what do you hate doing?

That question has three answers. Maybe five. And one of them is your first AI win.

The Hate List Exercise

McKinsey found that generative AI can automate 60-70% of the work activities that absorb employees' time. Sixty to seventy percent. But you don't need to automate 60% of your work. You need to automate one thing.

Here's the exercise. Takes two minutes.

Write down three tasks you did this week that you hated doing. Tasks that required zero emotional intelligence. The kind of work that makes you wonder why you got into this business.

Updating CRM notes after showings. Writing the same follow-up email for the fifth time. Pulling comp data into a spreadsheet. Formatting a market report. Cleaning up transaction files.

Now circle the one that took the most time.

That's your first AI pilot.

Not your whole AI strategy. Not a transformation roadmap. One task. One pilot. 66% of Realtors say they adopt new technology primarily to save time. Start with the task that wastes the most of it.

Try It Right Now

Prompt
THE HATE LIST EXERCISE — 2 MINUTES

Grab a pen. Or open your notes app. Do this now.

1. Write 3 tasks you did this week that you hated doing
   and that required ZERO emotional intelligence.

   Task 1: ____________________
   Task 2: ____________________
   Task 3: ____________________

2. Circle the one that took the most time.

3. Run it through the Pilot Selection Filter:
   [ ] High Frequency — Does this happen every day or every week?
   [ ] Low Risk — If AI messes it up, does anyone get sued?
   [ ] Measurable Win — Can you prove it saved time?

   If all three boxes are checked, that's your pilot.

4. Commit: "For the next 30 days, I will use AI for
   __________________ every time it comes up."

That's it. You now have an AI strategy.

The Pilot Selection Filter

Not every hated task makes a good first AI project. The filter matters.

High Frequency. Your pilot should happen every day or every week. Not once a quarter. Frequency is how you build the habit. If you only do the task twice a month, you'll forget to use AI by the third time.

Low Risk. Your first AI project should not be something where a mistake has legal consequences. Don't start with contract language or disclosure statements. Start with CRM notes, follow-up emails, social media captions. If AI produces something mediocre, you edit it and move on. Nobody gets hurt.

Measurable Win. You need to prove this works — to yourself, not your broker. Time the task before AI. Time it after. If you can't measure the difference, you can't sustain the habit. 85% of agents using AI report time savings. But reporting time savings and measuring time savings are different things. Measure it.

All three boxes checked? That's your pilot. If it fails one filter, pick the next task on your Hate List.

Pilot Selection: Good vs Bad First Projects

TaskFrequencyRiskMeasurableVerdict
Post-showing CRM notesDailyLowYes (time per entry)Good pilot
Writing listing descriptionsWeeklyLowYes (time per listing)Good pilot
Follow-up emails after open houseWeeklyLowYes (time + response rate)Good pilot
Contract clause draftingWeeklyHighYesBad pilot — legal risk
Quarterly business planningQuarterlyLowHard to measureBad pilot — too infrequent
Social media contentDailyLowYes (time per post)Good pilot

If your task passes all three filters, you have your pilot. If it fails one, move to the next task on your Hate List.

Replace vs Augment: The Decision Framework

Once you've picked your pilot, one more decision. Are you replacing the task or augmenting it?

Replace means AI does the entire task. You review the output and hit send. CRM note summaries, social media first drafts, market data compilation. If you can write a manual for it — step-by-step, no judgment calls — AI can probably do it.

Augment means AI gives you the raw material, and you deliver the final product. AI drafts the listing description, you edit it with local knowledge. AI pulls the comp data, you interpret it for the client. AI writes the negotiation talking points, you deliver them in the room.

Most tasks start as augment and graduate to replace over time. That's fine. The point is to start.

Real estate operations teams report saving 10-20 hours per transaction using AI tools. They didn't get there on day one. They started with one pilot task, proved it worked, then expanded. The 5 Essentials framework calls this the OODA Loop approach — observe the result of your pilot, orient toward what's working, decide on the next task to add, act on it.

Your AI Pilot Launchpad

  • Complete the Hate List exercise — write 3 tasks, circle the biggest time sink
  • Run it through the filter: High Frequency + Low Risk + Measurable Win
  • Decide: replace or augment? Can you write a manual for it, or does it need your judgment?
  • Time the task today without AI — write down the number
  • Open ChatGPT, Claude, or Gemini and do the task with AI — time it again
  • Commit to 30 days — use AI for this one task every single time it comes up
  • After 30 days, pick the next task from your Hate List and repeat

Sources

  1. McKinsey — The Economic Potential of Generative AI (60-70% automation potential)
  2. NAR — Realtors Embrace AI Digital Tools Survey (68% adoption, 66% for time savings)
  3. All About AI — Real Estate AI Statistics (85% report time savings)
  4. ListedKit — Real Estate Technology Trends 2025 (10-20 hours saved per transaction)
  5. AI Acceleration Course — Section 6: The Hate List Exercise

Frequently Asked Questions

What is the Hate List method for AI?
The Hate List is a 2-minute exercise from the AI Acceleration course. Write down 3 tasks you did this week that you hated doing and required zero emotional intelligence. Circle the one that took the most time. That's your first AI pilot. The exercise cuts through decision paralysis by starting with what you already know — the work you dread.
How do I choose my first AI automation?
Use the Pilot Selection Filter. Your first AI task should be High Frequency (happens daily or weekly), Low Risk (if AI messes up, nobody gets sued), and produce a Measurable Win (you can prove it saved time). If a task passes all three filters, it's a good pilot. If it fails one, pick the next task on your Hate List.
What makes a good AI pilot project?
Good first AI projects are repetitive, low-stakes, and easy to measure. CRM note summaries, follow-up email drafts, social media captions, listing description first drafts, and market data compilation all pass the filter. Bad first projects involve legal documents, infrequent tasks, or anything where a mistake has serious consequences.
Should I automate marketing or operations first?
Start with whatever you hate most. But in general, operations tasks like CRM updates, transaction file cleanup, and email follow-ups make better first pilots because they're more repetitive and lower risk. Marketing tasks like listing descriptions and social content are strong second pilots once you've built the AI habit.
How long should I test an AI pilot before expanding?
30 days. Use AI for your one pilot task every single time it comes up for 30 days. This builds the habit and gives you enough data to measure the time savings. After 30 days, pick the next task from your Hate List. Don't try to add multiple AI tasks at once — that's how people quit.
What is the difference between replacing and augmenting a task with AI?
Replace means AI does the entire task and you review the output. Augment means AI provides the raw material and you add your expertise to deliver the final product. If you can write a step-by-step manual for the task with no judgment calls, AI can replace it. If the task needs your local knowledge, relationships, or professional judgment, AI augments it. Most tasks start as augment and graduate to replace over time.

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