Onboarding Microsoft To Do

Showing users what they get from To Do without having to log in, through storytelling experiences.

As the UX Designer, I:

• Led the end-to-end design of the onboarding experience from scratch
• Collaborated with PMs, engineers, and researchers to align on constraints and goals
• Brought motion design into the process to make the first moments with the app feel dynamic and polished
• Facilitated remote usability testing during the early days of the pandemic, adapting methods for unmoderated, distributed participants

• Enabled ~66% of new users in testing to reach the “aha” moment before sign-up, maintaining conversion while unlocking new trust and engagement benefits over the existing account-first flow
• Cut time-to-value to under 2 minutes and ~5 purposeful clicks, faster and more engaging than competitor flows
• Pinpointed why the remaining 34% dropped off and produced a validated concept for exploration-before-sign-up onboarding. Although it was not shipped due to pandemic reorgs, the findings informed later onboarding experiments within To Do

(Video: Final Onboarding Proposal — replace with high-res clip of your motion prototype)

Microsoft To Do required users to sign up before they could see any part of the product. For a productivity app, this created a major trust and friction barrier. My task: design an onboarding experience that let people explore value before committing, without breaking Microsoft’s account-first ecosystem.

When Wunderlist joined Microsoft, we set out to combine its simplicity with Microsoft’s ecosystem power. But in the process, we inherited a mandatory sign-up wall.

By 2020, To Do was seeing:

• 60% sign-up rate post-download, far below the 80 to 90% common in competitor apps
• A growing list of user complaints about being forced to create a Microsoft account to even try the app

We had no onboarding at all, only a sign-in screen. The absence of any preview was hurting adoption and trust.

Business problem: The onboarding funnel was “skinny”, with too few users making it past the first screen.

User problem: Productivity tools are personal, and users weren’t willing to commit without knowing if To Do fit into their workflow.

“Maybe I can use the app without having an account.” — User feedback

I ran a competitive scan of onboarding flows from leading productivity apps. Two consistent friction points emerged:

1. Mandatory sign-up before showing value
2. Extra step of creating a Microsoft/Hotmail account for new users

We also identified that “My Day” was To Do’s most unique and sticky feature, a daily reset list to plan your day. This made it a strong candidate for onboarding focus.

I explored four flow options, mixing carousels, coachmarks, customization, and a welcome list:

• Carousel + coachmarks
• Customization + coachmarks
• Carousel + customization + coachmarks
• Welcome list + coachmarks

(Replace with annotated wireframes or flow diagrams)

Motion was key to making onboarding feel alive. I:

• Added subtle transitions to guide focus between steps
• Used animation to introduce features rather than relying solely on static text
• Built motion prototypes to test timing, pacing, and tone

(Replace with looped short videos)

We tested the prototype remotely with 8 participants on usertesting.com, asking them to think aloud as they explored the onboarding flow.

Prototype success rate: ~66% completion without drop-off.

Top drop-off causes:

1. Copy clarity issues, with icons and text misunderstood
2. Optional step confusion, where skip behavior led to missed required interactions
3. Testing artifacts, including distractions in unmoderated sessions
4. Minor UI friction, such as unclear tap targets and pacing

• Chose Flow 3 for balance of speed and personalization
• Dropped certain customization prompts to reduce friction
• Recommended a modular onboarding that could adapt by platform

• Advocated for exploration-before-sign-up as a viable business path
• Introduced motion design to onboarding for the first time in To Do
• Aligned product, design, and engineering on a testable MVP

Although not shipped due to COVID-19 reorgs, the research and design artifacts became reference points for later onboarding experiments within Microsoft To Do.

This project taught me to:

• Build an entire onboarding from scratch in a system used to account-first flows
• Adapt quickly to remote testing in unprecedented circumstances
• Use motion as a functional onboarding tool, not just aesthetic
• Derive actionable insights from tests that remain valuable even when paused