Calendly

Designing scheduling experiences for trust and simplicity

ui/ux, user research, product design & strategy

Portfolio-Image_1x1_Calendly

Project Overview

During my time at Calendly, I transitioned into a UX design role embedded on the billing and clients squads.

My work focused on helping develop better cross platform experiences and helping people pay for their subscriptions. I paired closely with the product managers to define the end to end product from research to development. Basically, I spent a lot of time thinking about how people spend their money and time.

my role

UX designer; including responsive design (web app), user flows, ideation, product strategy, and user research

key collaborators

Developers, Product managers, UI/UX designers, User researchers

timeframe

1 year

selected projects

I’ve written up a brief overview for two of the projects I worked on during this time. Please reach out if you would like details about other projects.

1. Creating conversational experiences

The Clients team at Calendly owned the email embed experience — a popular feature among power users. This feature that allows users to “copy/paste” their available times in their email from Calendly. But it had a few problems....

“I’m trying to schedule time with investors, but the tone of voice in the prompts makes me sound pompous. And the design takes up the whole email.”
“I wish you could customize this so that you could allow more than just the first three available times for each day to show. ”
“Calendly implementing the ability to paste in many times would be even better. Right now the number of time slots you can put in an email is way to small. ”
— Feedback from in-app surveys

I collaborated with the product manager to synthesize years of user feedback from surveys and user calls on this feature. We identified three major user pain points:

  • Limited ability to display more than three dates with times
  • Language in the template is not conversational
  • Design takes up too much space in the email window

We also had technical limitations within the current design that affected performance across different email services. Part of the challenge for this redesign was to create a native email experience that was cross-platform and email client compatible.

the power dynamics of sharing time

Email Embed feature has multiple access points across the product (web app, mobile app, and browser extensions).

User-Journey

The quick user journey sketch marks where users were coming from, and when the experience changes.

Within this flow, the experience changes from the person sharing the times to the person receiving the times. This is an area of tension because of the politics of asking for someone's time that include age, social hierarchy, role, and need.

Because of this I wanted to keep in mind the inherent power dynamics in sharing time and availability. I created user scenarios that encapsulated the emotional and social dynamics of sharing your time (click/tap to enlarge).

Scenario 1
Explores how giving a time range could improve the experience for the person booking.

Range-Choice

Scenario 2
Explores how giving multiple time slots chosen by person sending the link could increase agency.

Multi-Choice

I also researched how their customers on other scheduling platforms were talking about what they did or did not like about emailing times by looking at hundreds of product reviews.

2×2

I compared where Calendly fit in the current competitive landscape to determine where the next iterations of the email embed design would make the most user and business impact.

balancing design with development

When creating the drafts for this project, I cast the net wide for the possibilities of the next iteration. I wanted to find the most natural way to send times... regardless of technical or design constraints.

Draft-4

Low technical cost,direct choice

Draft-2

High technical cost, range choice

Draft-1

Low technical cost, range choice

One possibility at this stage addressed the power dynamics of sharing by showing a range of times. This, however simply it appears, is actually very difficult technically to implement on the backend so we had to scratch it.

I held several ideating sessions with the PM to define what would be the next steps. After considering the several different design approaches, we pursued three different designs each addressing a different subset of user feedback.

One possibility at this stage addressed the power dynamics of sharing by showing a range of times. This, however simply it appears, is actually very difficult technically to implement on the backend so we had to scratch it.

We held several ideating sessions with the PM to define what would be the next steps. After considering the several different design approaches, we pursued three different designs each addressing a different subset of user feedback.

horizontal view

Approach-1

This design most closely matches the current design, but shows more times.

calendar picker

Approach-2

This design shows the most options but takes up too much space.

conversational (winner)

Approach-3

We ultimately chose the conversational design because it best reflected the nexus of these concerns. This design best reflects how people are using their email already.

reflection

I enjoyed working on this project because it’s one of the product enhancements that builds towards having tools and technologies that reflect how we as human think and share. It addresses how people still feel awkward about asking for and giving time. We need tools to help us but they don’t have to be bulky or cold. They can be simple, conversational, and minimal — getting the job done and getting out of the way.

2. Localizing the billing flow

As Calendly expanded into global markets an increasing number of users joined from outside the US. I worked with the product and engineering managers on the billing team to define what were the most strategic areas to improve the billing flow UX for both US and non-US customers.

Many of the issues with the billing flow crossover with the research I did for a previous project to understand user pain points when upgrading. So in addition to adjusting the payment methods, I also wanted to use this opportunity to improve parts of the overall billing experience.

I centered my research and design around two key principles:

Building trust

Indicate to users a level of trust and security in our payment process and give them access to a method they know and trust already

Over-explaining

Anticipate where users might need additional assurance in the billing process and adding language to address these concerns

building trust internally and externally

This project had a lot of stakeholders because it directly affected revenue. I had to balance several different stakeholder viewpoints with contrasting desires —keeping changes minimal and updating an antiquated flow.

The PM’s research revealed that Paypal is one of the top preferred payment methods globally. I analyzed current UX flows and UI patterns for adding payment methods for how we might add an additional payment method.

user flows

With the PM, I defined the multiple user scenarios for adding a payment method for new and current users. I used these as the base to map out the current billing flow, marking where the “new” features would be added.

Scoping

To maintain the project scope, I also documented areas for possible improvement in the future. I wanted to ensure any solution implemented now would support adding more improvements in the future with lower lift.

Ideating-Bin-Med-Lift

Medium - Lift

The wireframes focused on exploring specific solutions for the various scenarios. To manage stakeholder expectations, I separated the solutions into 'bins' based on the estimated level of development and user testing effort they would require.

Ideating-Bin-High-Lift

High - Lift

The wireframes focused on exploring specific solutions for the various scenarios. To manage stakeholder expectations, I separated the solutions into 'bins' based on the estimated level of development and user testing effort they would require.

The wireframes focused on exploring specific solutions for the various scenarios. To manage stakeholder expectations, I separated the solutions into 'bins' based on the estimated level of development and user testing effort they would require. We implemented a version of the medium-lift solution highlighted above.

The wireframes focused on exploring specific solutions for the various scenarios. To manage stakeholder expectations, I separated the solutions into 'bins' based on the estimated level of development and user testing effort they would require.

over-explaining what is happening when it involves money

From user surveys and think-aloud testing, I identified where trust declined in the billing process. This happened at two key points: when choosing a plan, and when entering their payment information.

CP_Content-Strategy

I worked with a content strategist to change the language used on the payments page to give users a clear indication of the next steps, and mitigate any surprises or fears during the payment process.

reflection

I worked on other projects in the billing experience but almost all of them stemmed from the initial research and design of these billing flow improvements. It’s hard to get billing experiences right but a lot of it comes down to adding clarity and building trust. These billing flow changes set the stage for future improvements that helped increase user understanding, and hopefully create a more seamless process.

get in touch
linkedin // email // read.cv

Designed by Rachel Arredondo