Improving user retention for Microsoft 365
Our subscription management experience lets our customers cancel their current Microsoft 365 subscriptions. As part of modernizing our commerce approach, we aimed to build a new cancellation process that boosts customer retention by explaining subscription value, while still keeping the cancellation process simple.
Company
Microsoft Corporation
Role
Design lead
Year
2023
status
Shipped
SKILLS
User research, Prototyping, Stakeholder management
Overview
Research
Research goals
1
Identify the driving reasons behind subscription cancellations.
2
Uncover user pain points within the current cancellation process.
3
Determine how competitors handle cancellations and retention efforts.
Research methods

Quick user chat
Chatted with 12 users who recently canceled or considered canceling their subscription to understand what motivated them to make the decision.

USAGE data analysis
Analyzed usage data from canceled and retained accounts to identify patterns. For e.g., users with low OneDrive usage showed a higher likelihood of canceling.

REFERENCES
Evaluated the cancellation flows of popular subscription services like Netflix, LinkedIn, Slack etc. Noted consistent patterns in persuasive messaging and retention.
INSIGHTS RELATED TO OUR existing EXPERIENCE
Confusion
Users canceled their subscription immediately due to unclear cancellation options that made it seem like it was the only choice.
DIFFICULTY in RECALLING
9 of 12 users didn't remember the key benefits of their subscription, like advanced security tools and OneDrive Storage, while cancelling.
Lack of personalization
Multiple users mentioned how our cancellation experience lacked any form of personalization and did not encourage them to reconsider their decision.
OTHER INSIGHTS
Cost sensitivity
The most cited reason for cancellation was cost, particularly among users who felt they weren’t utilizing enough features to justify the expense.
trust BUILDING FACTORS
Across services like LinkedIn, Netflix, and Slack transparency, flexibility, and confirmation were a consistent theme in their cancellation flows.
BEHAVIORAL DATA Observation
KEY FINDING
Users who showed low engagement with core features had a significantly higher likelihood of canceling their subscriptions.
INTERPRETATION
It wasn’t just about disliking the product; it was more about not fully realizing the value of what they already had access to.
IMPACT
This informed our personalization strategy to begin highlighting underused benefits like security tools, and family sharing in the new cancellation experience.
Navigating design decisions
#1 ADDING FRICTION

Leyla Dalton (She/her)
We should add a friction point and look at routing them through support, especially for enterprise customers. Thoughts?

Siddharth Naik (You)
I get the intention but forcing support as the only option might feel manipulative. Let's look at other options that would add gentle friction.
Challenge
During early explorations, a stakeholder suggested routing all users to contact support before they could cancel. While this approach could potentially reduce churn, it risked frustrating customers who had already decided to leave and creating unnecessary support cost. The challenge was to balance the business goal of reducing cancellations with the user need for a clear, self-service path that didn’t feel manipulative.
SOLUTION
I recommended a hybrid approach that maintained transparency while introducing purposeful, user-respectful friction. Rather than forcing every customer through support, I proposed a design that would present thoughtful retention options like complimentary subscription period, plan downgrade, or a chat with a product expert, before completing cancellation.
#2 balancing minimal steps and simplicity

Sam Morenza (He/him)
Do you think we can simplify the cancellation flow by limiting it to 1 step?

Siddharth Naik (You)
Yeah, we could, but 1 step might cause more overrload. Let's try a multi-step approach.
Challenge
One of the core challenges in this project was balancing the need for minimal steps with the wide scope of information we needed to present. Our product team wanted a single-page cancellation flow, but early prototypes suggested that we couldn't fit all the required content without overwhelming users.
SOLUTION
We implemented a concise, 2-step flow that guided users through the process with clarity and confidence. By displaying multiple visually clean and digestible sections, we reduced the cognitive load, minimized errors, and made the overall cancellation process less overwhelming.
Design principles

Transparency
Build trust by clearly explaining each step and potential consequences, ensuring users feel respected and valued.

Flexibility
Keep the cancellation process flexible by providing users multiple ways to cancel, or offer a way to downgrade their plan.

HUMAN SUPPORT
This will introduce another layer of decision making, which might convince users to reverse their choice to cancel.

Value-based
Highlighting key features reminds users of what they stand to lose, thereby encouraging them to reconsider their decision.

personalization
Offer personalization by delivering tailored experiences that address individual needs to enhance customer retention
Flexible cancellation options
We now provide users with clear cancellation options, straightforward language, and visible exit points. This approach built trust and reduced frustration.
Dynamic value highlights
We integrated subtle, dynamic reminders of subscription benefits. For instance, users who have utilized their Office apps saw prompts highlighting top features in Word or Excel.
Support touchpoints
Added a live chat option for users hesitant about canceling. Our expert agents have context-aware scripts emphasizing relevant benefits or flexible options.
Personalized retention options
Made it easier for users to opt for alternate options rather than canceling their subscription. For e.g. downgrade to a cheaper plan, get training on how to use your subscription etc.
No unnecessary roadblocks
While we presented relevant value propositions, benefits, and alternate actions at every step, we wanted to ensure that users could still cancel their subscription easily.
Clear confirmation
A clear confirmation step ensures that users know their action has been successfully processed. This would reduce unnecessary support tickets or dissatisfaction.
A/B testing
To validate the design at scale, we launched an A/B test involving a flight of 10,000 users over a two-month period:
A
Group A experienced the original cancellation flow.
B
Group B used the redesigned flow with improvements.

Increased retention
Group B's interaction with the new flow retained 22% more users compared to Group A.

engagement
~44% of Group B's participants explored the Cancel before next renewal option.

USER SATISFACTION
Group B users reported higher user satisfaction rate by almost 45% as compared to Group A.
Final impact
resulted retention against an estimate of 15-25% retention rate within 3 months of launch.
users saved against an estimate of 140,000 users within 3 months of launch.
Key takeaways

Balancing persuasion with user autonomy
Finding the right tone was crucial. We didn't want the new experience to be perceived as too pushy, which led to refining the messaging to focus more on education than persuasion.

Integrating data driven personalization
We realized that we were working with user data and leverage it responsibly was key. We ensured that all personalized messages respected privacy norms and avoided feeling invasive.