Conversations Module

OVERVIEW

Workpath is an enterprise SaaS platform helping organizations adopt OKRs. While teams could set and track objectives, ongoing alignment between managers and employees was inconsistent. The Conversations module aimed to close this gap by embedding structured, guided check-ins directly into the platform.

GOAL

Enable teams to maintain alignment mid-cycle by improving visibility, structure, and accountability within 1:1 and team check-ins.

UI minimalistic widgets

YEAR

2022-2023

ROLE

Product Designer
Product Strategy


SKILLS

UX Strategy
UX & UXR
UI & Design Systems

THE CHALLENGE

Workpath helped organizations define what to achieve, but not how to stay aligned while doing it.

Teams often set ambitious OKRs but lacked a shared understanding of progress throughout the cycle. Performance reviews became retrospective rather than ongoing progress. Managers wanted more transparency, and employees wanted clearer feedback loops.

THE IMPACT

Q4 '22 - Q2 '23: Closed Beta rollout


Metric

Before

After

Change

Weekly active users

94

250

+166% increase

Retention

24%

35%

+11 percentage points

Talking Points per active user

2.3

3.0

+30%

🚀 These results validated the redesign’s value ahead of the full rollout to Workpath’s broader customer base.

Image of two smartphones with a gray background

The Problem

Our users struggled to understand the true status of their OKRs.

Key gaps identified:
  • No visibility into whether goals were on track during a cycle

  • 1:1 conversations lacked structure and consistency

  • Progress updates were scattered across tools and meetings

Research and Insights

Why are teams unable to report effectively despite having a solid grasp of OKR methodology?

Key insights:
  • Accountability gaps: Employees weren’t clear on what to report or when.

  • Manager burden: Conversations varied widely in quality and depth.

  • Disconnected tools: Updates in spreadsheets, Slack, and meetings never fed back into our platform.

Snippet of synthesis showing overlapping vs divergent ADR elements across customers

Solution:
Step 1

Focusing teams on the right conversations.

The first step was helping teams discuss OKRs, not tasks.
I redesigned the existing module using our Datagrid component to display selected OKRs and their current status as part of the check-in agenda.

Design decisions:
  • Omitted global navigation on the detail screen and replaced with back button to reduce distractions

  • Improved Datagrid component usability to support deeper and more flexible drill-down into OKR levels

  • Reduced cognitive load by keeping only essential elements on screen

Solution:
Step 2

Guided "Talking Points" for strategic updates.

Teams needed guidance on writing relevant updates. I introduced Talking Point categories with inline guidance text to steer users toward strategic reporting instead of operational chatter.

Design decisions:
  • Limited categories to improve clarity and focus

  • Allowed updates across all entity levels (Objectives, Key Results, Initiatives, Aligned Goals)

  • Clarified intent and context for each Talking Point to improve reporting quality

Solution:
Step 3

Making Talking Points transparent across the platform.

Previously, check-in data was siloed within the module. I proposed linking outcomes of conversations back into the broader OKR framework through a new “Updates Feed” tab visible across Datagrid instances.

Design decisions:
  • Exposed conversation data beyond the module

  • Enabled company-wide visibility into check-in discussions and progress updates

Limitations

Our small team faced significant engineering constraints.
Developers preferred investing their time in lasting code rather than quick prototypes.

To balance speed and scalability, I proposed leveraging our design system component library for rapid iteration. This approach allowed us to build testable experiences faster while also improving the neglected design system.

This strategy later evolved into my role as primary stakeholder of the company’s design system initiative, a scalable outcome that extended beyond this project.

Future opportunities

After improving communication, the next step was turning insights into actions.
I explored concepts such as:

  • Action Items: enabling teams to assign, track, and close follow-ups after check-ins.

  • Reactions: lightweight ways for managers to acknowledge or celebrate progress.


Smooth Scroll
This will hide itself!

Conversations Module

OVERVIEW

Workpath is an enterprise SaaS platform helping organizations adopt OKRs. While teams could set and track objectives, ongoing alignment between managers and employees was inconsistent. The Conversations module aimed to close this gap by embedding structured, guided check-ins directly into the platform.

GOAL

Enable teams to maintain alignment mid-cycle by improving visibility, structure, and accountability within 1:1 and team check-ins.

UI minimalistic widgets

YEAR

2022-2023

ROLE

Product Designer
Product Strategy


SKILLS

UX Strategy
UX & UXR
UI & Design Systems

THE CHALLENGE

Workpath helped organizations define what to achieve, but not how to stay aligned while doing it.

Teams often set ambitious OKRs but lacked a shared understanding of progress throughout the cycle. Performance reviews became retrospective rather than ongoing progress. Managers wanted more transparency, and employees wanted clearer feedback loops.

THE IMPACT

Q4 '22 - Q2 '23: Closed Beta rollout


Metric

Before

After

Change

Weekly active users

94

250

+166% increase

Retention

24%

35%

+11 percentage points

Talking Points per active user

2.3

3.0

+30%

🚀 These results validated the redesign’s value ahead of the full rollout to Workpath’s broader customer base.

Image of two smartphones with a gray background

The Problem

Our users struggled to understand the true status of their OKRs.

Key gaps identified:
  • No visibility into whether goals were on track during a cycle

  • 1:1 conversations lacked structure and consistency

  • Progress updates were scattered across tools and meetings

Research and Insights

Why are teams unable to report effectively despite having a solid grasp of OKR methodology?

Key insights:
  • Accountability gaps: Employees weren’t clear on what to report or when.

  • Manager burden: Conversations varied widely in quality and depth.

  • Disconnected tools: Updates in spreadsheets, Slack, and meetings never fed back into our platform.

Snippet of synthesis showing overlapping vs divergent ADR elements across customers

Solution:
Step 1

Focusing teams on the right conversations.

The first step was helping teams discuss OKRs, not tasks.
I redesigned the existing module using our Datagrid component to display selected OKRs and their current status as part of the check-in agenda.

Design decisions:
  • Omitted global navigation on the detail screen and replaced with back button to reduce distractions

  • Improved Datagrid component usability to support deeper and more flexible drill-down into OKR levels

  • Reduced cognitive load by keeping only essential elements on screen

Solution:
Step 2

Guided "Talking Points" for strategic updates.

Teams needed guidance on writing relevant updates. I introduced Talking Point categories with inline guidance text to steer users toward strategic reporting instead of operational chatter.

Design decisions:
  • Limited categories to improve clarity and focus

  • Allowed updates across all entity levels (Objectives, Key Results, Initiatives, Aligned Goals)

  • Clarified intent and context for each Talking Point to improve reporting quality

Solution:
Step 3

Making Talking Points transparent across the platform.

Previously, check-in data was siloed within the module. I proposed linking outcomes of conversations back into the broader OKR framework through a new “Updates Feed” tab visible across Datagrid instances.

Design decisions:
  • Exposed conversation data beyond the module

  • Enabled company-wide visibility into check-in discussions and progress updates

Limitations

Our small team faced significant engineering constraints.
Developers preferred investing their time in lasting code rather than quick prototypes.

To balance speed and scalability, I proposed leveraging our design system component library for rapid iteration. This approach allowed us to build testable experiences faster while also improving the neglected design system.

This strategy later evolved into my role as primary stakeholder of the company’s design system initiative, a scalable outcome that extended beyond this project.

Future opportunities

After improving communication, the next step was turning insights into actions.
I explored concepts such as:

  • Action Items: enabling teams to assign, track, and close follow-ups after check-ins.

  • Reactions: lightweight ways for managers to acknowledge or celebrate progress.


Smooth Scroll
This will hide itself!

Conversations Module

OVERVIEW

Workpath is an enterprise SaaS platform helping organizations adopt OKRs. While teams could set and track objectives, ongoing alignment between managers and employees was inconsistent. The Conversations module aimed to close this gap by embedding structured, guided check-ins directly into the platform.

GOAL

Enable teams to maintain alignment mid-cycle by improving visibility, structure, and accountability within 1:1 and team check-ins.

UI minimalistic widgets

YEAR

2022-2023

ROLE

Product Designer
Product Strategy


SKILLS

UX Strategy
UX & UXR
UI & Design Systems

THE CHALLENGE

Workpath helped organizations define what to achieve, but not how to stay aligned while doing it.

Teams often set ambitious OKRs but lacked a shared understanding of progress throughout the cycle. Performance reviews became retrospective rather than ongoing progress. Managers wanted more transparency, and employees wanted clearer feedback loops.

THE IMPACT

Q4 '22 - Q2 '23: Closed Beta rollout


Metric

Before

After

Change

Weekly active users

94

250

+166% increase

Retention

24%

35%

+11 percentage points

Talking Points per active user

2.3

3.0

+30%

🚀 These results validated the redesign’s value ahead of the full rollout to Workpath’s broader customer base.

Image of two smartphones with a gray background

The Problem

Our users struggled to understand the true status of their OKRs.

Key gaps identified:
  • No visibility into whether goals were on track during a cycle

  • 1:1 conversations lacked structure and consistency

  • Progress updates were scattered across tools and meetings

Research and Insights

Why are teams unable to report effectively despite having a solid grasp of OKR methodology?

Key insights:
  • Accountability gaps: Employees weren’t clear on what to report or when.

  • Manager burden: Conversations varied widely in quality and depth.

  • Disconnected tools: Updates in spreadsheets, Slack, and meetings never fed back into our platform.

Snippet of synthesis showing overlapping vs divergent ADR elements across customers

Solution:
Step 1

Focusing teams on the right conversations.

The first step was helping teams discuss OKRs, not tasks.
I redesigned the existing module using our Datagrid component to display selected OKRs and their current status as part of the check-in agenda.

Design decisions:
  • Omitted global navigation on the detail screen and replaced with back button to reduce distractions

  • Improved Datagrid component usability to support deeper and more flexible drill-down into OKR levels

  • Reduced cognitive load by keeping only essential elements on screen

Solution:
Step 2

Guided "Talking Points" for strategic updates.

Teams needed guidance on writing relevant updates. I introduced Talking Point categories with inline guidance text to steer users toward strategic reporting instead of operational chatter.

Design decisions:
  • Limited categories to improve clarity and focus

  • Allowed updates across all entity levels (Objectives, Key Results, Initiatives, Aligned Goals)

  • Clarified intent and context for each Talking Point to improve reporting quality

Solution:
Step 3

Making Talking Points transparent across the platform.

Previously, check-in data was siloed within the module. I proposed linking outcomes of conversations back into the broader OKR framework through a new “Updates Feed” tab visible across Datagrid instances.

Design decisions:
  • Exposed conversation data beyond the module

  • Enabled company-wide visibility into check-in discussions and progress updates

Limitations

Our small team faced significant engineering constraints.
Developers preferred investing their time in lasting code rather than quick prototypes.

To balance speed and scalability, I proposed leveraging our design system component library for rapid iteration. This approach allowed us to build testable experiences faster while also improving the neglected design system.

This strategy later evolved into my role as primary stakeholder of the company’s design system initiative, a scalable outcome that extended beyond this project.

Future opportunities

After improving communication, the next step was turning insights into actions.
I explored concepts such as:

  • Action Items: enabling teams to assign, track, and close follow-ups after check-ins.

  • Reactions: lightweight ways for managers to acknowledge or celebrate progress.


Smooth Scroll
This will hide itself!

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