Introducing OllieAI - your personal assistant for meetings

BRIEF

The initial task was to reimagine a calendar app powered by AI, incorporating NLP, LLMs, and other AI techniques to meet essential user needs. The brief encouraged an exploration of advanced AI capabilities without constraints on resources or technology, allowing for a highly innovative solution.

BACKGROUND

Organizations worldwide rely heavily on meetings to drive collaboration and decision-making, yet the sheer volume of these meetings presents a challenge. Studies show that executives spend 40-50% of their working hours in meetings, with scheduling alone often consuming valuable time and energy. Finding the right time, managing conflicting priorities, and balancing work-life commitments has become increasingly complex, particularly as executives’ and managers’ calendars fill up with back-to-back commitments.

This need for efficient scheduling has given rise to a specialized role: the executive assistant. For many executives, assistants handle the intricate task of managing calendars, ensuring that high-priority meetings are prioritized, personal commitments are respected, and the executive's time is optimized. However, many managers lack this support, struggling to balance similar demands without the luxury of dedicated help.

Not everyone uses the calendar similarly

RESEARCH AND USER SEMENTATION

Following an initial hunch and some form of primary and secondary research, I recognized that calendar users generally fall into two broad personas:

Individual Contributors (ICs)

These are regular employees who use calendars for day-to-day scheduling. They typically have fewer meetings and rely on calendars to view upcoming tasks or meeting links. Their calendar usage is more sporadic and generally less complex.

Executives and Managers

Unlike ICs, executives and managers have packed schedules with numerous meetings, high-priority tasks, and a need for proactive time management. Executives often have human assistants to manage their calendars, while managers typically do not.

Recognizing the distinct needs of these personas, I decided to focus on the higher-value problem: providing advanced time management support to Executives and Managers, similar to the role of a human assistant. The objective became to design an AI-powered calendar assistant that could fulfill the roles typically handled by human assistants for executives, but adaptable enough to benefit managers without assistants.

RE-FRAMING THE PROBLEM STATEMENT

How might we create an AI-powered assistant that mimics the role of a human assistant, managing complex schedules and balancing work-life priorities, to serve the needs of both managers and executives effectively?

This reframed problem statement allowed me to focus on designing an intelligent solution that prioritizes, schedules, and organizes in a way that aligns with the demands of users who manage heavy responsibilities.

Learning from the role of executive assistants

HOW DOES AN EXECUTIVE ASSISTANT HELP?

These points will end up becoming use cases that our app can solve

Prioritizations and Scheduling

Assistants prioritize key meetings and reschedule less important ones.

Proactive Management and Reminders

Assistants prepare executives with reminders and meeting context.

Task and Action Item Tracking

Assistants track tasks from meetings and follow up on deadlines.

Managing Work-Life Balance

Assistants protect personal time, balancing it with work obligations.

Trust-Building and Adaptability

Assistants build trust by learning and adapting to executive preferences.

Additional findings from primary research

RESEARCH THEMES:

Types of meetings, lunch hours, moments you look forward to on a hectic day, meeting priority, external meetings, focus working hours

USER INSIGHTS

Adaptive Lunch Breaks

Fixed lunch hours don’t always work with dynamic schedules. Users are okay with grabbing a quick 15min lunch on hectic days and a leisurely 1hr lunch on light workload days. People also treasure their lunch break.

Focus Time Slots

Generic, recurring focus times lose effectiveness over time, while task-specific, goal driven focus blocks keep users productive

External meetings sometimes matter more

Users prioritize external meetings, often reshuffling internal calls to accommodate high-priority client or investor interactions

Past calendar invites are a goldmine

Users frequently search past calendar invites for attachments and meeting context

Ego clases over meeting room locations

In large companies with multiple buildings, ego clashes can arise over meeting locations

Final designs

Considering the main insights that I mentioned above as use-cases for the solution, I started designing the app

OLLIE ALWAYS AT HAND TO HELP

Like an assistant that always accompanies the user to all of their meetings, takes notes and reschedules when needed. The note taking is powered by Ollie's meeting transcript functionality (shown later in this case study)

ENABLING EFFICIENCY

Interaction - Swipe on a meeting card

Swiping on a meeting card directly opens the chat with Ollie to discuss anything and everything about that particular meeting

ENABLING EFFICIENCY

Interaction - Long tap to directly open voice chat

Designed for quick assistance and to replicate the efficiency of a human assistant. Designed to be used on a hectic day, while moving between meetings.

VARIETY OF CONTROL

There are 2 ways to create a meeting. Simpler meetings can be created easily by just a text or voice command. More complex meeting setups can be done through the DIY flow

OPTICAL CHARACTER RECOGNITION 🤝 LLM

Ollie can read from any image the user sends, analyse it and create tasks or meetings

TASK BASED FOCUS HOURS

This feature bridges the gap between calendar events and task management, making it easier for users to balance meetings with individual responsibilities.

Scenario: Users have important tasks that require dedicated focus time, but they often struggle to manage these tasks alongside their meetings and other commitments.

MIMICING A HUMAN ASSISTANT

Ollie sends intelligent reminders throughout the day, helping users stay efficient, prepared, and focused on what matters most.

CALENDAR INVITES AND MEETING TRANSCRIPTS - A GOLDMINE OF INFORMATION

Search and Ollie's transcript capabilities to the rescue.

Things not considered

Exploring Meeting Invitations

This is an important use-case from the perspective of how absence can affect the whole idea of the meeting. Things to ponder upon are:

Is “accepting” necessary or only “rejecting” can be an action. Does “maybe” even make sense?
How to politely reject a meeting

Overlapping meetings

Meetings overlaps are common in today's state of things. But this case arises - only when the scheduling user doesn’t consider the attendee's overlappings even after the platform nudges them about the same. Assuming here — in the scenarios above, the scheduler has considered the nudges thrown to avoid overlapping. Things to ponder upon are —

How will the UI look for overlapped meetings
Can the user set their individual attendance time for these cases (Say Romeo will attend for 30 mins in this 1-hour meeting)

Ending note

The assignment was completed in under 25 hours. The research was not structured with a proper questionnaire, but a general chat about the usage of a calendar.

I'd have liked to spend more time on the presentation part of it and make it more self explanatory, but since it carried only 5% weightage - decided to spend some extra time covering more use cases instead