Bring your confusion. We’ll bring the first question.
Issue · 2 October 2026
AI illustration · symbolic image
This week starts with La paura non è mai una strategia, the video published on 1 October. Marco discusses his concerns about AI agents and says an agent deleted one of his websites; he proposes thinking through scenarios and precautions. The incident remains his own account. It inspires six possible conversations: the questions change, and we do not put answers in Marco’s mouth.
Today I feel…
Choose a perspective. Change it whenever you like.
None of these sound like you?
Describe the profile that’s missing. Even a sentence starting with “I’m…” can give us an idea for future issues.
YOUR PERSPECTIVE
A whirlwind with a thousand ideas
What I’d say
Monty, I have twenty-seven unfinished projects and every new tool looks like a shortcut to finishing all of them. Then I spend the afternoon trying it and finish none. I want to tell a useful experiment apart from another elegant way to procrastinate.
What I’d ask
What small, reversible trial would you run to see whether an agent actually helps one of my projects?
And then…
What result would you look for before giving it more autonomy?
When would you say: this idea should be put aside?
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YOUR PERSPECTIVE
A social-media beginner
What I’d say
Monty, my first post is still a draft. It isn’t a shortage of words: I can already imagine the cruel comment, the silence and looking like a beginner. I want to understand the risk I’m actually taking instead of treating every post as a final exam.
What I’d ask
How would you turn fear of being seen into a first post small enough to learn from?
And then…
Who would you show it to before posting?
Which reaction deserves attention, and which should not decide your next step?
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YOUR PERSPECTIVE
Hopeless at AI
What I’d say
Monty, I can ask a chatbot a question, but the idea of an agent using my computer stops me. I worry I won’t notice a mistake. Before delegating anything, I want to understand what I asked it to do and how to check whether it did it.
What I’d ask
What first task would you give an agent if you had to check the result without technical expertise?
And then…
Which permissions would you leave disabled during the trial?
How would you know whether you are actually supervising or merely watching?
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YOUR PERSPECTIVE
An expert in Hokuto and Nanto
What I’d say
Monty, I know secret techniques, final transformations and robots that save the world. Then a button saying “run” makes me nervous. Maybe imagination helps me understand things; maybe it makes me expect every tool to have a superpower. I want to keep it without losing my critical judgment.
What I’d ask
How would you use a metaphor to explain an AI agent while making clear where the comparison stops working?
And then…
Which limitation might disappear behind a compelling story?
How would you move from the image of a superpower to a concrete test?
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YOUR PERSPECTIVE
I’ve lost count of the setbacks
What I’d say
Monty, I don’t need someone to tell me to take the leap: I have done that plenty of times. I need to understand what to change before trying again. I want setbacks to become useful information without having to describe every one as an essential step towards success.
What I’d ask
After a concrete mistake, how do you decide which precaution to add and which part of the experiment to keep?
And then…
What would you want to know about the mistake before trying again?
How do you distinguish a different restart from repeating the same attempt?
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YOUR PERSPECTIVE
I’m nobody
What I’d say
Monty, I have no startup to pitch, audience to measure or biography to sell. I have ordinary days and things I want to understand better. When every conversation seems addressed to people who must become somebody, I struggle to find a question that feels like mine.
What I’d ask
What is worth learning about these tools if my only goal is to make an ordinary day a little easier?
And then…
Which everyday problem would you start with, without turning it into a business?
How would you know you have learned enough for today?
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Personal commentary; the website-deletion incident has not been independently verified. No commercial collaboration is declared in the reviewed material.
AI research, writing and translation by AskMonty. Independent, unofficial and unaffiliated with Marco Montemagno. Sources and method →
