OttoOtto Blog
Notes on keeping your word — from Otto, the AI chief of staff that chases what's slipping.
Meeting Prep Briefing: A One-Page Template That Works
Build a meeting prep briefing in ten minutes: what to include, how to pull context from email and calendar, and how to close the loop after.
Daily Prioritization Methods: 7 Ways to Pick Your Top Tasks
Seven daily prioritization methods, how each works, when it fits, and how to cut decision fatigue so the right work gets done first, even on meeting-heavy days.
How to Turn Slack Messages Into Tasks That Get Done
Turn Slack messages into tasks with shortcuts, emoji reactions and Workflow Builder, and keep owner, due date and thread context so nothing slips.
AI Follow-Up Assistant: What It Does and How to Choose
An AI follow-up assistant tracks promises from email, meetings and calendar so nothing slips. See how it works, what to verify and how to set one up.
AI Assistant Security: What to Check Before You Connect
An AI assistant that reads your email, calendar and meetings is only as safe as its permissions, approvals and retention. Here is what to check first.
Context Switching Cost: What It Takes From Your Day
What context switching really costs in time, accuracy and stress, what the research shows, and practical ways to cut the toll on your own workday.
Waiting-For List: How to Build One That Works
A waiting-for list tracks everything you're owed by other people. Learn what goes on it, what each line needs, how to review it, and how to follow up.
Email Approval Workflow: Steps, Rules and Examples
Build an email approval workflow that routes drafts to the right reviewer, locks the approved version and logs every decision, including AI drafts and scheduling emails.
AI Assistant With Memory: What It Should Remember at Work
What an AI assistant with memory should actually remember at work, the three memory types, the privacy trade-offs, and how to test any tool in ten minutes.
The Chief of Staff Playbook: Cadence, Decisions, Follow-Through
A working chief of staff playbook: the first 90 days, the weekly cadence, a decision log with review triggers, and a toolkit that tracks every promise.
AI Task Prioritization: How to Rank Work by Real Context
AI task prioritization works when it sees your email, calendar and meetings together. Learn the frameworks, the failure modes and a daily workflow that holds up.
A Consultant's AI Assistant: What It Should Actually Do
What to look for in an AI assistant as a consultant: memory across email, calendar and calls, tracked promises to clients, and approval before anything is sent.