Advancing social connection via a mobile app that addresses the epidemic of loneliness and isolation

As the VP and Head of Design at Thoughtful, I led the design efforts (collaborating closely with the CEO) in shaping and executing the company's strategic vision, ensuring a cohesive and user-centric approach. I initiated the implementation of a comprehensive design system fostering consistency and promoting efficiency across all interfaces. I facilitated collaboration by systematizing our cross-functional workflows, which led to improved communication in a distributed team. By ensuring that our design solutions aligned with business objectives and customer needs, I prepared the team for launch.

The Vision

The COVID-19 pandemic has brought to the forefront that isolation and loneliness significantly affect mental health and well-being. Years of social distancing and lockdown guidelines left disruption to our day-to-day lives that had, for better or worse, changed our social circles, relationships, and appetites for connection.

Thoughtful makes it easier to fulfill our intentions to be considerate to our family and friends. The platform allows us to set aside time as we do for mindfulness, diet, and exercise. This app is a space dedicated to considering our relationships where we can note down thoughts, create reminders of important dates, and deepen our social connections.

Applications such as Calm and Headspace are excellent answers to mindfulness, as proven by their number of subscribers and valuation. Our user experience borrows the daily ritual as a habit-forming convention. Thoughful’s concept centers around strengthening social ties. It is grounded in wellness. However, it is what we would like to call Wellness 2.0, an ‘other-centric’ form of self-improvement.

Designing & Evaluating Solutions for Product Market Fit

We sought answers to questions on product-market fit by evolving a prototype of the onboarding flow. We analyzed each test's moments of interest, dislike/confusion, and delight. By identifying ideas that worked well and what didn't, we pieced together new narratives that increased the likelihood of achieving success by measuring NPS and a Disappointed KPI. With a few basic concepts in place, Prototype 1.0 scored 20 by NPS standards. By prototype 1.6, we saw world-class results with a score of 80 for men and women (25-40).

Through qualitative research and the Voice of the Consumer program, I learned much about people’s experiences during the COVID-19 pandemic. I observed aggravated social patterns in our respondents, and feelings of uncertainty arose, especially with no end in sight. There was a desire to strengthen social ties to remedy isolation and maintain a supportive community. Hearing their stories firsthand allowed me to further ideate on features that could be of most help.

Figure 1. A few screens of the onboarding flow branded by Red Antler

Figure 2.1. An early sketch of the user journey featuring the habit-forming Daily Guided tour that eventually became known as Daily Actions.

Figure 2.2. Since the early days of prototype testing, we’ve tinkered extensively with the onboarding flow. Our challenge was that the flow was long – we asked the user to input a lot of information to make their first-time use compelling. Our more impatient Enthusiasts (a persona), in particular, wanted the experience to be faster and more efficient (Their leading suggestions were integrating with Facebook or other sources).

Figure 2.3. Daily Thoughts (or Daily Actions) have been a staple of Thoughtful since our earliest prototyping days. Users have always loved Daily Actions because it makes it quick and easy to keep in touch with loved ones. Like meditation, it asks you to focus on one simple task at a time and provides all the tools you need to get it done and feel good.

Figure 2.4. Marc Lore (co-founder) wanted to access Siri to add his thoughts to the platform. As with all stakeholder feedback, we prioritized, designed, and prototyped for user testing. We discovered that voice command significantly contributed to the positive outcome of our KPIs.

Figure 2.2. Since the early days of prototype testing, we’ve tinkered extensively with the onboarding flow. Our challenge was that the flow was long – we asked the user to input a lot of information to make their first-time use compelling. Our more impatient Enthusiasts (a persona), in particular, wanted the experience to be faster and more efficient (Their leading suggestions were integrating with Facebook or other sources).

Figure 2.3. Daily Thoughts (or Daily Actions) have been a staple of Thoughtful since our earliest prototyping days. Users have always loved Daily Actions because it makes it quick and easy to keep in touch with loved ones. Like meditation, it asks you to focus on one simple task at a time and provides all the tools you need to get it done and feel good.

Figure 2.4. Marc Lore (co-founder) wanted to access Siri to add his thoughts to the platform. As with all stakeholder feedback, we prioritized, designed, and prototyped for user testing. We discovered that voice command significantly contributed to the positive outcome of our KPIs.

Figure 2.5. Shown above is prototype 1.6, where we met our NPS KPI for product market fit. The onboarding sequence above illustrates how we visualize user testing results to evaluate designs against user needs.

Figure 2.6. The above flow charts are a few examples of how our iterative design process affected the onboarding narrative. We hypothesized that deep architected flows would keep the users in a flow state, resulting in a satisfying onboarding process. We learned that intense activities such as preference selection and profile building are even more successful when spread out over time.

Features

Often what holds us back from reaching out is not knowing what to say to our loved ones, especially those going through a challenging time. Seeing a What to Say Guide at the right time increases the likelihood of contacting a person. Reading the guides in the context of a person proved to be a moment of delight for the user testers as they felt empowered with information and could act on their intention to speak confidently. The guides provide practical advice on appropriate and inappropriate things to say for everyday situations such as birthdays, anniversaries, holidays, and even in cases of a natural disaster.

Having a person top of mind with practical advice was enough to pique interest. Naturally, they wanted to copy and paste content from the guides to start a text message. For this scenario, when the user consistently finds themselves at a loss for words, they can opt-in for a pre-drafted message that would appear as an SMS ready to send.

The experience needs to help users with social competency. So we looked at a few different ways to achieve that. To start, memory-invoking prompts helped identify people to reach out to. Once the user has someone in mind, they can set the intention and frequency to connect. The completeness of a person’s profile indicated the steps taken toward social competency; however, streaks were the first manifestation of making user accomplishments visible. Lastly, a daily article was available for those that completed their Daily Actions. These features reward, inspire and keep the momentum to help users achieve social competency wherever they are in their journey.

The idea for a positive portfolio came to us via Dr. Samantha Boardman. It is a tactic that elicits positive emotions. The Full Person View surfaced together a collection of personal notes, memories, and milestones. Seeing the evidence reinforces a relationship's beneficial aspects, making it easier to reach out.

In parallel to creating new features, I applied half of my effort to reducing friction in areas of data collection. Here are some themes to the problems we solved:

• How might we practically and creatively convey a sense of progression?

•What gamification techniques can we leverage to encourage our users?

• How might we maintain trust throughout the experience?

Features

Often what holds us back from reaching out is not knowing what to say to our loved ones, especially those going through a challenging time. Seeing a What to Say Guide at the right time increases the likelihood of contacting a person. Reading the guides in the context of a person proved to be a moment of delight for the user testers as they felt empowered with information and could act on their intention to speak confidently. The guides provide practical advice on appropriate and inappropriate things to say for everyday situations such as birthdays, anniversaries, holidays, and even in cases of a natural disaster.

Having a person top of mind with practical advice was enough to pique interest. Naturally, they wanted to copy and paste content from the guides to start a text message. For this scenario, when the user consistently finds themselves at a loss for words, they can opt-in for a pre-drafted message that would appear as an SMS ready to send.

The experience needs to help users with social competency. So we looked at a few different ways to achieve that. To start, memory-invoking prompts helped identify people to reach out to. Once the user has someone in mind, they can set the intention and frequency to connect. The completeness of a person’s profile indicated the steps taken toward social competency; however, streaks were the first manifestation of making user accomplishments visible. Lastly, a daily article was available for those that completed their Daily Actions. These features reward, inspire and keep the momentum to help users achieve social competency wherever they are in their journey.

The idea for a positive portfolio came to us via Dr. Samantha Boardman. It is a tactic that elicits positive emotions. The Full Person View surfaced together with a collection of personal notes, memories, and milestones. Seeing the evidence reinforces a relationship's beneficial aspects, making it easier to reach out.

In parallel to creating new features, I applied half of my effort to reducing friction in areas of data collection. Here are some themes to the problems we solved:

• How might we practically and creatively convey a sense of progression?

•What gamification techniques can we leverage to encourage our users?

• How might we maintain trust throughout the experience?

Figure 3.1. What to Say guides: When we developed Thoughtful 1.0, guidance on how to help friends through difficult life situations was the most popular feature we proposed. Pairing content with reminders of important dates gave depth to the Thoughtful experience. It transformed us from a mere reminder system into a well-rounded tool for deepening relationships.

Figure 3.2. Pre-Drafted Messages: While doing Daily Actions, we make sending an SMS easy. In settings, you can select responses for everyday events, such as a birthday or an anniversary of a loss. Three choices per event provide variation in what to send. Shown above is a verbose option for a kid’s birthday.

Figure 3.3. Intention to Connect is a favorite feature of building a profile for testers and live app users in Thoughtful 2.0. Enthusiasts loved the idea of a reminder to connect with an individual.

Figure 3.4. Full Person View

Design System

It became worth investing in the design system shortly after the beta app went live—the features we were designing lacked cohesion and polish. Our problem-solving process resulted in siloed solutions that negatively impacted the user experience. Design critiques are often subjective, which causes quite a bit of churn. I documented our design decisions to steer the conversation toward uniformity.

I sought buy-in from my stakeholders to utilize a Style Guide and Library of Components. I shared relative industry knowledge on design systems followed by KPIs of what successful Design System utilization looked like. Shortly after, there was one source of truth—contradictions to design decisions were now a thing of the past. What works in one feature must do so in another in precisely the same way, regardless of who is working on it.

Organizing the libraries allowed me to spot inconsistencies through this holistic view of the application. At the time, roughly thirty atomic components and ten patterns comprised the entire experience. I made those patterns accessible via the library. Giving access to everyone was pivotal to saving my team hundreds of hours of pixel-pushing. When executing the rebrand, the design system proved worthwhile, updating 135 unique views in weeks versus months.

Design System

It became worth investing in the design system shortly after the beta app went live—the features we were designing lacked cohesion and polish. Our problem-solving process resulted in siloed solutions that negatively impacted the user experience. Design critiques are often subjective, which causes quite a bit of churn. I documented our design decisions to steer the conversation toward uniformity.

I sought buy-in from my stakeholders to utilize a Style Guide and Library of Components. I shared relative industry knowledge on design systems followed by KPIs of what successful Design System utilization looked like. Shortly after, there was one source of truth—contradictions to design decisions were now a thing of the past. What works in one feature must do so in another in precisely the same way, regardless of who is working on it.

Organizing the libraries allowed me to spot inconsistencies through this holistic view of the application. At the time, roughly thirty atomic components and ten patterns comprised the entire experience. I made those patterns accessible via the library. Giving access to everyone was pivotal to saving my team hundreds of hours of pixel-pushing. When executing the rebrand, the design system proved worthwhile, updating 135 unique views in weeks versus months.

Figure 4.1 Typography, Icons, & App Bars were the first design elements to be formalized into components.

Figure 4.2. The ten app view templates that all views within the app are derived from.

Figure 4.3. The eight libraries of Thoughtful.

Cross-Departmental Workflows

Figma is a powerful collaboration tool that is versatile and intuitive. I taught others how to use it systematically. We visualized the product roadmap on a Figma board once key stakeholders were comfortable and displayed basic proficiency. Within an Epic were Features, Research Insights, and Product Requirements, all of which I managed from a centralized repository. These boards were a digital gathering place to exchange feedback and align product management, research, design, development, and content. I worked towards continually improving the cross-departmental workflows resulting in consistent written requirements. By year two, we had managed an efficient process for production.

Cross-Departmental Workflows

Figma is a powerful collaboration tool that is versatile and intuitive. I taught others how to use it systematically. We visualized the product roadmap on a Figma board once key stakeholders were comfortable and displayed basic proficiency. Within an Epic were Features, Research Insights, and Product Requirements, all of which I managed from a centralized repository. These boards were a digital gathering place to exchange feedback and align product management, research, design, development, and content. I worked towards continually improving the cross-departmental workflows with Elizabeth Shaffer, CEO, resulting in consistent written requirements. By year two, we had managed an efficient process for production.

Figure 5.1. Shown here is a Figma board displaying features within an epic.

Figure 5.2. Requirements writing was simplified through the use of components.

Nurturing Design

It is challenging to keep up with the speed of an early-stage start-up. My junior product designer wanted to articulate her design decisions better. She aspired to speak with confidence and defend her design thinking. I challenged her to describe the process using a Problem/Solution framework. By reframing the problem statement (in her own words), she rationalized the outcome by connecting it to research insights. Preparing presentations for the quarterly reviews gave her the space to think critically about her impact on the business objectives.

I enjoyed my time at Thoughtful and was fortunate to be on a team of incredibly talented individuals.

For more information visit www.thoughtful.com