AI Assistant

Meet your productivity partner, two modes, 24 tools, transparent actions, and a memory that learns your preferences.

Not just a chatbot

Most AI assistants are spectators. You ask a question, get an answer, then do the work yourself.

CoachKeeper’s AI is different. It has hands. It can create tasks, schedule events, update notes, search your documents, and manage your workspace, all from a natural conversation. And everything it does is visible, explainable, and reversible.

Two modes

The AI has two personalities, switchable anytime from the chat header:

Assistant mode

Direct and task-focused. You say what you need, it does it. No extra commentary, no unsolicited advice. Ideal when you know what you want and just need it executed.

Coach mode

A thoughtful productivity partner. Coach mode opens with a brief check-in on your current state, how many tasks are overdue, what’s been sitting in progress too long, whether your priorities have scheduled time. It surfaces patterns, suggests what to focus on, and gently nudges you forward.

The tone is always an offer, never a guilt trip: “Shall we tackle…” not “You still haven’t…”. Think of it as a thoughtful colleague who happens to have perfect memory.

What it can do

The assistant has 24 tools organized by domain:

DomainCapabilities
NotesCreate, update, delete, search, summarize, rewrite
TodosCreate, update, change status, modify checklists, search
EventsCreate, update, delete, check availability, handle recurring events
SourcesList uploads, read content, search by meaning
SearchFind items across all entity types by title or content
SchedulingRead your availability windows, suggest time blocks
Web searchSearch the internet (when enabled in settings)
MemoryLearn and recall your preferences across conversations
UndoReverse any recent action, even multiple at once

How to talk to it

Just type naturally. The assistant understands context, it knows what tab you have open, what’s in your backlog, and what’s on your calendar.

Everyday prompts:

“What should I focus on today?”

“Create a todo to review the quarterly report and schedule an hour for it tomorrow morning.”

“Find my notes about the marketing strategy and summarize the key points.”

“What’s been in progress for more than a week?”

“Move my 2pm meeting to Thursday.”

Batch operations:

“Create todos for each action item in my meeting notes.”

“Schedule my top 3 backlog items this week.”

Knowledge queries:

“What did that research paper say about retention rates?”

“Summarize my notes from last Tuesday.”

Quick prompts

Pre-built prompts to get started fast:

  • “Plan my day”, reviews your backlog and calendar, suggests a plan for the rest of the day
  • “Schedule my week”, creates time blocks across your available hours
  • “What’s overdue?”, lists tasks that have been sitting too long
  • “Weekly review”, summarizes what you completed, what’s in progress, and what’s coming up

@Mentions

Type @ in the chat input to reference a specific note, todo, event, or source. An autocomplete popup helps you find the right item. The AI pins that entity to the conversation with its full content, so it has deep context without you needing to describe what you’re talking about.

The action log

Every action the AI takes appears in a live action log within the chat. You see entries like:

  • CREATE Todo: “Review quarterly report”
  • CREATE Event: “Deep Work: Q Report”, Thursday 9:00–10:00 AM
  • UPDATE Todo status: in_progress → done

Each entry has an “Open” button to jump directly to the affected item.

This transparency is a core design principle. You always see what changed.

Undo

Every AI action can be reversed. Click the undo button on any entry in the action log, and the change is rolled back instantly. You can also ask the AI: “Undo that” or “Undo the last 3 actions.”

For bulk operations (six or more changes), the AI automatically presents its plan and waits for your approval before executing. No surprises.

Context awareness

The assistant automatically knows:

  • Your open tab, if you have a note open and say “summarize this,” it knows which note
  • Your task state, backlog count, in-progress items, estimated hours of work
  • Your calendar, upcoming events, free time slots
  • Your availability windows, it never schedules outside your working hours
  • Your uploaded documents, searchable by meaning via semantic search
  • Your preferences, learned over time through its memory system

Memory

The AI learns your patterns and preferences over time:

  • How you like things scheduled (morning focus blocks, afternoon meetings)
  • Your naming conventions and recurring projects
  • Communication preferences (concise vs. detailed responses)

Memories persist across conversations. You can view and delete them anytime in Settings > AI Memory.

Tips

  • Be specific. “Schedule 2 hours tomorrow morning” works better than “schedule something.”
  • Try Coach mode when you feel scattered, the check-in and gentle nudges help you regain focus.
  • Use @mentions for long notes or documents, it saves you from describing them.
  • Ask it to plan, not just create. “Plan my week based on my backlog” gives better results than creating events one by one.
  • Trust the undo. If the AI creates something wrong, one click fixes it.