Agents · 2026-11-06
How much should AI decide without asking you first
Zapier shares what it learned from its AI assistant Sidekick: asking for permission too often and acting with no limits both fail, so clear rules are needed.
The problem every AI product that takes actions runs into
Once an AI does more than answer questions, for example editing files or sending messages, it has to decide whether to ask permission first or act and report afterward. Both easy answers are wrong. If it asks every time, people stop reading the requests and click «yes» out of habit. If it never asks, things seem fine until it does something unexpected once, and that can destroy trust.
How it played out in Sidekick
At first, Sidekick asked permission for every action that changed data, such as writing a file, editing a document, or moving or deleting things. The choices were Block, Once, and Always. This caused several problems: the request disappeared if you closed the tab, you couldn't answer it from somewhere else such as Slack, and the «Always» choice was forgotten after a page refresh. The team saved approvals on its servers and rewrote the buttons to say exactly what was being allowed, for example «Allow editing files for this chat».
Then the team found a deeper problem: rules were tied to tools, but people care about risks, such as a specific folder, an important document, or a Slack account. So the rules were rebuilt around what is being protected. Now you can set rules like «never change anything in this folder» or «only send Slack messages to me». If any rule says «never», it wins. If a rule says «ask first», Sidekick asks. Without permission, it acts only when nothing blocks it.
What this means for an ordinary person
Frequent permission requests don't make you safer, because you stop reading them. What matters is that requests cover truly risky actions, not every file read. Also watch for vague buttons: if it isn't clear what you are allowing, it's better to decline.
In Sidekick, permission requests appear in a panel next to the typing box and in a shared inbox so they don't get missed. The team also did not want to force people to set everything up in advance, so the panel stays out of the way while the assistant works and opens when your decision is needed.
Sources: 🔗 Zapier Blog