Wisary AI

Reimagining AI as a Collaborator, not just a Tool

About the Client

Wisary is an early-stage, AI-powered collaboration platform built to support Product Managers in creating, updating, and managing key product documents. Created by founder Ala Stolpnik, Wisary transforms AI into a real-time collaborator, helping PMs generate high-quality documentation, surface critical insights, and communicate more effectively with stakeholders. By integrating seamlessly into existing workflows, Wisary reduces friction, boosts productivity, and supports faster, more informed decision-making

Platform : Web App, Confluence AI extension

Industry: Project Management, AI Software

Project Overview

Despite its innovative features, Wisary faced a critical challenge: users were churning. Product Managers weren’t sticking with the platform, and it wasn’t clear why. With limited UX capacity in-house, the team brought me and 3 other designers on board to help uncover what was causing the drop-off and how the product could better support its intended users.

Services: UX Consulting, UX redesign and opimization, UX

UX Team : 3 other designers

Our Approach

Understanding the industry, Wisary's platform, and its users

Before diving into research, our first step was understanding Wisary’s why. What core problem was this platform built to solve, and what data have they already collected that could help identify why the platform wasn’t gaining traction?

Challenge through the lenses of the Wisary Team

Wisary set out to tackle a common but critical challenge in the product development world: misalignment. With over 70% of software projects failing due to poor communication between stakeholders, the founders envisioned a tool that would centralize documentation and keep teams aligned from MVP scoping to launch.

Their goal was to reduce confusion, prevent project delays, and streamline collaboration by integrating essential planning documents into one intuitive, AI-supported workspace. However, despite the product’s potential, users weren’t staying. From Wisary’s perspective, something was getting lost between intention and execution, and that’s where we came in.

Research Insights

In the define phase, we did a thorough exploration to identify the reasons behind user churn. This involved a detailed product walkthrough, stakeholder interviews, industry research, and competitive analysis. We engaged directly with key users of Wisary: engineers, project managers, and QA professionals, to gain insights into their experiences with the platform. Our objective was to uncover how they interact with Wisary and their perspectives on the potential contributions of AI in enhancing their daily workflows.

Research Assets

Competitive Analysis

Affinity map

What did we learn

In our research and analysis, we have gathered a wealth of valuable insights that are crucial for understanding user behavior and preferences.

  • AI Feedback Lacked Context
    While users appreciated that the AI identified areas for improvement, many found it difficult to understand what specifically to fix or how to address the issues. The feedback felt disconnected from the document itself, creating more cognitive load rather than saving time.

  • Insights Were Hard to Track
    In walkthroughs and interviews, users reported that receiving multiple insights at once was overwhelming, as it lacked a clear connection to where they applied in the document. This made it difficult to act on feedback efficiently and reduced the perceived value of the AI.

  • Critical Information Got Lost After Meetings
    PMs expressed that decisions were often made in meetings but not reflected in documentation. Without a clear process to capture and incorporate those updates, important context was regularly lost, leading to misalignment across teams.

  • Documentation Often Took a Back Seat
    Product managers shared that with so many competing priorities, keeping documentation up to date often fell through the cracks. They needed tools that could support and simplify this process, not add more steps to it.

  • Disconnected from Real-World Workflows:
    Many PMs didn’t see how Wisary fit into their existing processes. While the platform offered powerful features, it didn’t immediately solve their most pressing problems, like staying aligned after meetings or keeping documents updated under time pressure. As a result, engagement dropped when the value wasn’t quickly perceived.

With these insights in hand, we turned our attention to designing solutions that would address these pain points directly, bridging the gap between intention and execution

Usability feedback from Wisary users revealed that manual input of documentation into the webapp and a Chrome extension for Google Docs limited flexibility and caused friction. Users felt overwhelmed by too many insights at once, making it hard to connect relevant information.

Wisary AI multi-document function (Before Update)

AI Review (before update)

Wisary AI insights (Before Update)

AI suggested edit (before update)

Aha Moment: From Tool to Teammate

As we synthesized our research findings, one insight stood out and reshaped the direction of our project: Product Managers didn’t want another tool. With their plates already full, the idea of learning a new, complex system, especially one powered by AI, felt more like a burden than a benefit. While some PMs were experimenting with AI, their use was limited to basic research or ideation, and often required knowing exactly what to ask. This made the technology feel inaccessible, inefficient, or simply irrelevant to their daily work.

This was our turning point.

We realized that PMs weren’t rejecting AI, they were rejecting friction. They didn’t need another interface or a steep learning curve. What they truly needed was a collaborator: an intelligent assistant that could reduce their cognitive load and proactively support them in getting work done.

This shift in perspective became the foundation of our design strategy. We reimagined Wisary’s AI not as a passive tool waiting for perfect prompts, but as an intuitive, proactive partner, one that anticipates needs, simplifies workflows, and enhances creativity without requiring mastery of the tech itself.

Turning Insight into Ideas

This part of the process required the most iteration. With our new understanding of the user’s point of view and their initial opposition to the Wisary AI, we worked closely with Wisary’s founder and engineering team to brainstorm solutions that aligned with the users’ existing workflows. We needed to strike a balance: designing something intuitive and powerful that felt like a natural extension of how PMs already worked, but flexible enough to adapt to the wide variety of styles and preferences across teams. One key insight that reinforced this direction came from users who described how decisions often got lost in the noise of meetings and constant updates. This communication gap was precisely why Wisary was created, and our research confirmed just how valuable a living, central document could be when it’s easy to update and always reflects the latest context.

With this in mind, we explored how Wisary’s AI could reduce the burden of documentation by transforming it into a collaborative, almost conversational process. PMs often admitted that while documentation is critical, it's also the first thing to fall through the cracks due to time constraints. We saw an opportunity to shift the AI’s role from a passive tool into a true partner, someone you could brainstorm with, who would help capture ideas, track decisions, and keep documents up to date without adding to the mental load. Every feature we considered was filtered through this lens, ensuring it not only met a real user need but also aligned with Wisary’s long-term vision and technical capabilities.

Ideation Assets

User Journey map

User flow

Turning Ideas into Interface

📝 AI Document Generation

Start smarter, not from scratch.
We built a feature that leverages AI to generate product lifecycle documents like PRDs from either guided prompts or uploaded files. Instead of writing from a blank page, Product Managers can provide high-level context such as goals, user needs, or timelines and receive structured drafts tailored to their workflow.
💡 Value: Reduces manual writing effort, ensures consistency in documentation, and gives PMs more time to focus on strategic decisions, not formatting documents.

🔄 AI-Assisted Document Updates

Keep documents fresh without the heavy lifting.
We designed a feature that enables the AI to suggest updates to product documents based on new inputs like meeting notes, decisions, or uploaded files. The AI identifies relevant sections of the PRD and proposes targeted edits, always with the user's approval.
💡 Value: Helps PMs stay aligned with their teams, reduces the effort of manually maintaining documentation, and ensures key updates never fall through the cracks.

📎 AI-Powered Meeting Integration

Turn meeting notes into meaningful updates.
We designed a feature that allows Product Managers to upload meeting notes as documents for AI analysis. The AI reviews the content, identifies relevant decisions or shifts, and suggests precise updates to the document, always with clear, contextual explanations.
💡 Value: Ensures product documents reflect the latest conversations, reduces the burden of manual updates, and keeps everyone aligned with minimal effort

✅ AI Review

Your second pair of eyes—powered by AI.
We created a feature that enables the AI to review product documents based on selected criteria like clarity, completeness, and potential risks. The AI highlights gaps, suggests improvements, and even asks clarifying questions to refine its recommendations.
💡 Value: Helps PMs strengthen the quality of their documents with minimal effort, reducing the risk of errors while maintaining full control over final approval

❓ Stakeholder Question Generator

Ask the right questions—before it’s too late.
We built a feature that generates tailored questions for Product Managers to ask stakeholders, based on the current state of the document. Whether there are missing details, conflicting information, or unclear goals, the AI identifies gaps and surfaces smart, contextual questions to help fill them.
💡 Value: Empowers PMs to uncover critical insights early, strengthen cross-team alignment, and ensure no key detail slips through the cracks during planning.

🧩 Stakeholder-Specific Summaries

Tailored updates for every stakeholder.
We created a feature that uses AI to generate customized summaries of product documents, highlighting only the most relevant information for each stakeholder. Whether it's engineering, marketing, or leadership, everyone gets exactly what they need—nothing more, nothing less.
💡 Value: Improves communication, reduces information overload, and helps PMs keep every stakeholder aligned without manually rewriting the same update multiple times.

💬 Stakeholder Comment Section

Centralized feedback, smarter follow-through—on your terms.
We introduced a dedicated space where stakeholders can leave real-time comments directly within the platform. Product Managers can choose to activate AI support, which analyzes feedback and suggests relevant updates to the document, always leaving the final decision in the PM’s hands.
💡 Value: Empowers PMs to manage and incorporate stakeholder feedback more efficiently, while maintaining full control over what gets changed and when, ensuring documentation stays aligned and intentional.

✏️ AI-Assisted Edits

Precision editing, powered by conversation.
We built a feature that allows PMs to refine specific sections of a document with AI support. Instead of rewriting from scratch, users can select a section, respond to a few clarifying prompts, and receive tailored edit suggestions they can review and approve.
💡 Value: Reduces the cognitive load of editing, helping PMs quickly improve clarity, consistency, and alignment—while staying in control of the final output.

Project Outcome

From tool to teammate, reshaping how PMs work.

The redesigned Wisary AI was met with strong enthusiasm from users, particularly for its intuitive, collaborative approach. Instead of feeling like yet another tool to master, users described Wisary as a knowledgeable teammate, one that fits naturally into their workflows and enhances their productivity.

On AI-Guided Questions:

“I kind of feel like I'm sitting down with somebody who works in product, asking me thoughtful questions. It felt like a discovery call.”
This reflects how Wisary's AI helped PMs think critically, fill gaps, and confidently move documents forward.

On Seamless Integration:

“You don't have to change how you're working. That's the biggest thing.”
The ability to work within familiar tools and processes (like Confluence) made adoption frictionless and practical.

On Templates and Structure:

“Being able to leverage an AI-driven wizard to give structure and trigger intuition is great. It produces a polished product.”
Flexible templates and guided document generation helped reduce effort while elevating output quality.

What Users Said

  • Uploading/Linking Documents: 5

  • Flexible Templates: 4–5

  • Reviewing Entire Document: 5

  • Meeting Transcript Integration: 4–5

  • Confluence Compatibility: 4–5

    Stakeholder Question Generation: 3–5

Top-Rated Features (Scale: 0–5)

Key Outcomes

Improved Productivity:
Users saved hours with AI-assisted document generation, contextual edits, and automatic updates tied to meeting content.

  • Enhanced Team Alignment:
    Stakeholder-specific summaries and real-time feedback options helped reduce miscommunication and kept everyone on the same page.

  • High Adoption Rates:
    Integration with Confluence and Slack enabled easy onboarding without disrupting established habits.

One user summed it up best:

“With Wisary, we’re not just documenting we’re building better alignment and making strategic decisions faster.”