Just because a task can be automated, should it be?

Gus Waite sorts business tasks into black, white and gray: work AI should always do, work a person should always do, and the middle where you decide.

Not always. Some tasks should go to AI every time, because a mistake costs almost nothing. Some should stay with a person every time, because the moment needs a human being in it. My partner Gus Waite calls those black and white. Most of a small business lives in the gray between them, and in the gray the fact that a machine can do something doesn't decide whether it should.

Gus opened Season 2 with me. He ran a team of a hundred agents as a managing broker in New York City for twenty years, and before that he owned an acting school and did stand-up. He came to Cape Cod to retire and found out you can only play so much pickleball. He dug into AI about four years ago. I came to it much later and I came to it resisting. I'm a writer and a speaker. I love people, and my first picture of AI was some agent taking their jobs. So the first thing I wanted from him on tape was the line: what goes to the machine and what doesn't.

What should AI always handle?

Anything where a wrong answer is cheap to fix. Gus's example is the text from his doctor's office confirming an appointment tomorrow at two. If it gets something wrong, he calls and says he doesn't have an appointment, and that's the end of it. Nobody gets hurt. Confirmations, reminders and scheduling belong in this black column.

What should always stay with a person?

Anything where the person on the other end needs to feel another person. Gus used the same doctor. When he's sitting in the office and the doctor is reading back his blood results and telling him whether the news is good or bad, that is never a job for a machine, however accurate the machine is.

That should always be a human being.

Gus Waite

Every business has its own version of the blood test conversation. For a dentist it's the treatment plan with a big number on it. For a contractor it's the call when the job is running late. For a broker it's telling a seller the offer came in low. Those moments are where trust gets built or lost, and they stay human.

How do you find the gray area in your own business?

You stop looking at jobs and start looking at tasks. Gus put it in one sentence that changed how I read my own org chart:

Every job is a series of tasks.

Gus Waite

His suggestion is practical. Take a job description, give it to an AI model, and ask it to list every task in that job that could be done agentically. Agentic is the word that trips people up, so Gus spelled it out. A chatbot is something you talk to and get answers from, like asking it to write a listing description. An agent takes actions on your behalf. Once you have the task list, you sort it. Black goes to the agent. White stays with the person. The gray gets a conversation, and usually a person checking the agent's work before anything leaves the building.

What did I see that changed my mind?

It happened in the shed where Gus and I work. Before I met him, I was paying a social media coach to teach me how to rise above the noise. I was shooting B-roll by the beehives and walking around New York holding a stick for the camera. I felt like a poser. I was promoting instead of attracting, and I hated it.

Then Gus interrupted our conversation because he had a client call. I asked who it was. He didn't know. He was doing ten to twelve podcasts a week at that point and, by his count, had about twenty clients. On his screen came up every message that had gone back and forth with this person, written on his behalf in his voice. A person on his side had reviewed the exchange, booked the call on his calendar and handed him the notes. He opened with her name, picked up exactly where the messages left off, and within minutes he was helping her. No funnel, no B-roll, no posting schedule. One agent and one human in the loop. My jaw was on the floor of that shed.

That day is also where our first agreement came from. I told Gus I would never do this work unless we held one line, and he agreed:

We never replace people.

Gary Kadi

The gray area is where that line gets tested. The point of sorting tasks is to take what your people hate off their plate, the repetitive work they drift toward that never moves the business, so they can spend their day on the white column.

What does the gray area look like in sales?

Here's one I lived. When I wanted to raise sales in my old business, I closed the doors for two days and did no revenue. I hired a sales trainer at $10,000 a day and brought the whole team in on a Thursday and Friday. They went home for the weekend, came back Monday and had forgotten most of it.

Now we have an agent plugged into Zoom and into my sales system that works alongside the conversation while it's happening. It suggests the next question and when to ask for the close. That's gray on purpose. The agent coaches in real time and the person still does the selling, because the relationship is theirs.

How much time does an owner have to sort this out?

Less than most think, in Gus's view. He compared it to QuickBooks. For twenty years you learned it once, used four features out of thousands and got a small update every so often. He says the AI models change every three months, so the owner can't learn it once and coast. His read is that there's an eighteen to thirty-six month window to start understanding what's possible, and that firms growing without adding headcount will pull away from the ones standing still. That's his forecast, and he said it as one.

I'd add the part owners skip. The minute a founder announces the company is going AI forward, the team pushes back. People get nervous, and they should hear from you where the line is before an agent touches their work. Team resistance is one of the things I know best, and we'll come back to it this season.

Where do you start this week?

Pick one role in your business, your own included. Write down every task in it. Put each task in one of three columns: the machine always does it, a person always does it, or it's gray. For every gray task, write down who checks the agent's work and what happens when it gets something wrong. You'll find the black column is longer than you expected, and the white column is where you and your people actually want to spend the day.

Gus closed the episode with a challenge, and I'll leave it with you. If you own a business and you aren't taking this opportunity for yourself, your family and the people around you, look inside and ask yourself why.

Cut from How to Build a Business That Stops Costing You Your Life.