It’s All About the Journey: How We Mapped Onboarding at DonorsChoose

Josh Rosenberg
Making DonorsChoose
8 min readJan 8, 2020

As DonorsChoose grows, more teachers are finding our site through word of mouth, but don’t have a solid understanding of how the site works or what’s expected of them. Providing a simple and easy onboarding experience is critical so teachers can spend less time navigating our site and more time teaching their students.

We recently redesigned our sign-up flow as part of an effort to get teachers up and running as quickly as possible. But signup is just one piece of onboarding. In addition to registering, teachers need to confirm their email address, write a request for resources, shop for what they need, post a picture of their classroom, and help fundraise by sharing their request with their networks. Before we could even begin thinking about signup, we needed to know how it felt to be a teacher facing all of these potential hurdles. A journey mapping workshop was the perfect platform to get our colleagues in one place to sketch out the full experience. Read on to learn how we did it.

It’s important to have photos of sticky notes.

But First…What Is Journey Mapping?

Journey mapping allows you and your colleagues to step into your users’ shoes as they try to complete a task using your product. You do this by mapping out the actions, reactions, thoughts, feelings, and questions that a user goes through as they interact with your service, step-by-step. Then, you add the teams and tools on your company’s side that are responsible for the experience, assess the health of each step, and identify key problems that, if solved, would improve the journey.

The result is a holistic, often messy, map of the UX, which is a useful reference in its own right. But the biggest wins come from the process. Teams walk away from the workshop with a shared understanding of the problems that exist and a motivation to solve them.

How We Journey Mapped

You might be thinking to yourself, “But Josh, how do I pick a journey to map? How do I know what a user is thinking or feeling? Who do I even invite to this workshop thing?”

These are good questions. We had the same ones! While it might’ve been useful to dive right into the mapping process, we took a couple of weeks to dig into these questions and plan our approach. Here’s how we prepped to get the most out of our workshop.

Defining the scope. Although our users and their paths are certainly unique, we needed to pick one or two journeys to map that would help us understand onboarding. The goal was not to map out every possible twist and turn; this would be time-consuming and too overwhelming to be helpful. We needed to place some constraints in order to be productive. We chose to start at the moment a teacher decides to try DonorsChoose and to end when they finish writing their first project request. Because we needed a better understanding of both mobile and desktop experiences, we settled on mapping both mobile and desktop journeys in our workshop.

To help us focus even further, we created personas and scenarios — representations of the users we wanted to focus on and their context for using DonorsChoose — for both the mobile and desktop journeys. These would help us stay on track and make realistic decisions about user actions and thoughts. Would our users leave after a certain obstacle or persevere? How much patience do they have? Do they need to switch devices? Our personas and scenarios helped us answer these questions and more. More on this in a sec.

Conducting upfront research. We’re fortunate at DonorsChoose in that we’ve collected tons of research over the years, our analytics are built out and accessible, and many of our staff members are themselves former teachers. Heading into our workshop, we already had a decent understanding of our users and some of the problems they faced.

That said, we had some gaps to fill in, so we surveyed around 500 teachers who recently joined our site to gather demographics like age and to validate their primary goals on the site.

Sample findings from our survey.

Crafting personas and scenarios. Survey findings in hand, we met with a group of teacher-facing colleagues to outline two provisional personas, one for each journey. A couple of key findings from the survey helped us define our personas:

  1. A significant chunk of respondents had been teaching for over 10 years.
  2. Most teachers sign up for our site already knowing what resources they need.

Our colleagues told us that more experienced teachers often have accumulated supplies over the years and tend to seek enrichment items on our site. We wanted to support these teachers but also ensure a first-rate onboarding experience for the new teacher who urgently needs basics for their empty classroom. As a result, the persona for the mobile journey was brand new to teaching, while the desktop persona was a classroom vet. And because most newly-registered teachers in our survey knew what supplies they needed when they came to DonorsChoose, we knew that both personas should be goal-directed in their behaviors. No browsing here!

To make the personas believable as people and to provide the proper context for their behaviors, we named each persona (Carolyn and Sofîa), wrote a backstory, and crafted a scenario that would surface the challenges users face as they onboard.

One of our provisional personas, Sofîa, and their scenario

Choosing workshop participants. When picking participants, it was important to consider factors like group size, how well personalities meshed, and whether we had a mix of people with varied expertise. We chose a group of colleagues whose work impacts the onboarding experience, ensuring that we had representation from various corners of our org, including folks from Marketing who manage our email campaigns and oversee our Facebook community of teachers, people from our Product & Engineering team who design and build site improvements, and members of our Operations team who make sure resources get shipped to the right classrooms and help us mitigate risk. We had 11 participants in total (5 to 6 per journey map), which was large enough to have a breadth of knowledge but not so big that people could feel off the hook for participating during the workshop.

Workshop Day

On journey-mapping day, our group of 11 met offsite for the 4-hour workshop. The day was split into 4 sections: presenting goals, socializing personas, mapping the journeys, and sharing learnings.

Presenting the goals. We began with an overview of the motivations for the workshop and the mapping process that we would be using. This included an introduction to the personas and their scenarios.

Socializing the personas. Participants split up into two groups, one for each persona. To empathize with our personas, each group added detail and color to their persona’s backstory. How does Sofîa commute to work? What does Carolyn do in their downtime? The guiding principle was to have fun but be realistic.

Mapping the journey. Next up was the journey mapping itself. Each group had a moderator, whose task was to challenge assumptions and keep their team moving. The other participants were charged with building the map itself, which was broken out into 5 rows capturing:

  1. User thoughts — what the user is feeling and thinking at each step
  2. User actions — what the user is doing at each step
  3. User touchpoints — what devices, people, or services the user is interacting with at each step
  4. DonorsChoose teams — what teams on our side were responsible for making each step great
  5. DonorsChoose tools — what software, 3rd-party services, and processes were involved in producing each step
Carolyn’s journey begins.

We assessed the health of the journey by labeling each step with colored dots to mark it as positive, neutral, or negative, and labeled 3 to 5 key moments with stars. Marking the key moments helped us identify the biggest opportunities for improvement and to highlight what was already working well.

Sharing out learnings. Before leaving for the day, each team chose a representative to share their team’s journey map. The share outs set the stage for the future work we’d tackle in the weeks and months to come.

Here were a few of our learnings:

  1. Our donor-focused homepage wasn’t providing enough context for teachers, who need to know if they’re eligible to use DonorsChoose without doing a lot of poking around the site.
  2. Onboarding is inherently disjointed. We often think about onboarding as a single experience, but there are plenty of opportunities for teachers to leave the funnel and come back (or not) because they need more information or time (like Carolyn, who needed to find out her students’ coat sizes).
  3. Some parts of the flow weren’t feeling great on mobile. Sofîa, who started onboarding from a bus, eventually gave up until they could get to a laptop. Sorry, Sofîa!

After the workshop Participants revisited the insights and created action plans for their teams. The Product team made improvements to the homepage and used learnings to guide the sign-up redesign.

The Moral of the Story

You know those problems in your flow that everyone is aware of but no one really talks about? This is how you talk about them! Sure, journey mapping can help you find new problems, but it’s really best at helping you understand the overall impact they’re having on your users. And because you’re figuring that out with teammates — like that person from Legal who you assume exists for the sole purpose of hampering your creative freedom but really is perfectly nice and reasonable and volunteers on weekends and hosts really great Friendsgivings but you wouldn’t know that because you’re still mad about that one time they told you you couldn’t make people choose their passwords from a dropdown menu — where was I? Oh, and because you’re figuring that out with teammates, everyone walks away with a shared understanding and is motivated to take action. It’s about the journey, folks! So here’s to you and lawyer-person solving problems together and roasting up a mean tofurkey next November.

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