in development
Ask Twennie
Twennie’s AI learning assistant is in the development queue. The first stage is planned for fall 2026 and will focus on helping members find useful Twennie units based on real workplace questions.
Ask in plain language
Members will be able to describe a problem, question, project situation, or learning need without knowing exactly which unit to search for.
Find relevant Twennie content
The first version will use Twennie’s existing content library to suggest articles, videos, prompt sets, exercises, templates, missions, and topics.
Move from problem to action
Ask Twennie will help members turn vague workplace friction into a clearer learning path, using Twennie content as the starting point.
watch
AI rollout update
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planned feature
What Ask Twennie Will Help Members Do
Twennie is built around practical, problem-triggered learning. Members often arrive with a situation before they know which topic, unit, prompt set, exercise, or template will help. Ask Twennie is intended to close that gap.
In the first stage, Ask Twennie will not try to replace human judgment or act as a full workplace coach. It will begin as a focused learning assistant that draws from Twennie’s own content library and suggests relevant units based on specific requests.
Ask Twennie will help members find the right learning faster.
What members might ask
A member might ask, “My client keeps changing scope,” “I need to prepare for a difficult kickoff meeting,” “My team is burned out,” or “We need better proposal evidence.” Ask Twennie would then recommend relevant Twennie content and explain why those units are useful.
What the first stage will include
The first stage is expected to use retrieval-augmented generation, or RAG. That means the assistant will search Twennie content first, then use AI to organize and explain the recommendations. The goal is not to invent answers from nowhere. The goal is to connect members with the most relevant Twennie learning resources.
What may come later
Later stages may include learning path generation, diagnostic support, proposal Red Team reviews, mission recommendations, and competition adjudication. Those features will be considered after the first stage is tested and we understand how members actually use the assistant.
rollout
Rough Rollout Schedule
Content and metadata preparation
We continue strengthening Twennie’s topics, summaries, tags, unit descriptions, and relationships between learning resources.
Stage 1: RAG-powered recommendations
The first version of Ask Twennie is planned for fall 2026. It will focus on helping users find relevant Twennie content based on practical workplace questions.
Refinement and member feedback
We will review how members use the feature, improve recommendations, and adjust the rollout schedule based on what we learn.
Possible advanced AI tools
Future possibilities include learning paths, Red Team-style reviews, diagnostic workflows, mission suggestions, and structured competition support.