AI interaction design
context
context
context
awork is a project management tool (like Jira or Monday.com). There was an AI feature implemented that lets users ask questions and get instant, context-aware answers about their tasks, projects, and team workload — no manual digging required.

Designing high-intent AI entry points to turn awork AI into a daily habit
Designing high-intent AI entry points to turn awork AI into a daily habit
Designing high-intent AI entry points to turn awork AI into a daily habit
Designing high-intent AI entry points to turn awork AI into a daily habit
problem
problem
problem
Despite strong AI capabilities, awork AI was not becoming a habitual part of users’ workflows.
» Users had to think too hard about what to ask the AI
» AI entry points felt disconnected from real work moments
» First-time usage required initiative and creativity
» Repeated usage required memory and motivation
Despite strong AI capabilities, awork AI was not becoming a habitual part of users’ workflows.
» Users had to think too hard about what to ask the AI
» AI entry points felt disconnected from real work moments
» First-time usage required initiative and creativity
» Repeated usage required memory and motivation
Despite strong AI capabilities, awork AI was not becoming a habitual part of users’ workflows.
» Users had to think too hard about what to ask the AI
» AI entry points felt disconnected from real work moments
» First-time usage required initiative and creativity
» Repeated usage required memory and motivation
solution
solution
solution
If awork AI is introduced at moments of highest user intent and powered by pre-filled, context-aware prompts—users can engage instantly, reach value faster, and build a habit of returning to the feature organically.
High-intent moments:
» Within a project: surface prompts to identify blockers, generate summaries, or assess project status.
» Within time tracking: offer prompts such as Weekly Time Report or Missing Time Check to support quick, task-driven insights.
If awork AI is introduced at moments of highest user intent and powered by pre-filled, context-aware prompts—users can engage instantly, reach value faster, and build a habit of returning to the feature organically.
High-intent moments:
» Within a project: surface prompts to identify blockers, generate summaries, or assess project status.
» Within time tracking: offer prompts such as Weekly Time Report or Missing Time Check to support quick, task-driven insights.
If awork AI is introduced at moments of highest user intent and powered by pre-filled, context-aware prompts—users can engage instantly, reach value faster, and build a habit of returning to the feature organically.
High-intent moments:
» Within a project: surface prompts to identify blockers, generate summaries, or assess project status.
» Within time tracking: offer prompts such as Weekly Time Report or Missing Time Check to support quick, task-driven insights.





Goals
≥ 500
Weekly Active Users (WAU)
20%
Prompts Opened
30%
Contextual Usage
Results
≥ 483
Weekly Active Users (WAU) / 🟠 97% of target
30%
Prompts Opened / 🟢 1.5× goal
73%
Contextual Usage / 🟢 2.4× goal
Goals
≥ 500
Weekly Active Users (WAU)
20%
Prompts Opened
30%
Contextual Usage
Results
≥ 483
Weekly Active Users (WAU) / 🟠 97% of target
30%
Prompts Opened / 🟢 1.5× goal
73%
Contextual Usage / 🟢 2.4× goal