Portfolio for Jira redesign

Atlassian, 2017 – 2018

I was the primary designer for the redesign of a project management tool which was considered too complex by many users. Over the course of a year we had to make bold changes to achieve product market fit.

Problem

Portfolio for Jira* is a product (and add-on for Jira) that helps product and program managers in large companies plan and track work that spans across multiple teams and projects.

The rigid workflow that Portfolio imposed made it very difficult to “put what is in my head, into the tool”. The tool was based on a sophisticated scheduling algorithm that couldn’t be overridden by the user. Our goal was to simplify the product so that users got value out of it much faster.

*In 2020 (after I had left) 'Portfolio for Jira' was rebranded to 'Advanced Roadmaps' and was made part of Jira premium.

Top constraints

In order to tackle this problem we had a few constraints along the way that influenced our decision making:

  1. Too much change risks losing existing user base.
  2. Maintain compatibility with the Cloud offering of the tool, should customers wish to migrate their data.
  3. Adopting a new front-end technology stack (moving to React).
  4. Our team started with 2 product managers, 1 designer (myself), and 5 developers. This eventually rose to about 12 developers after showing progress.
  5. Backwards compatibility with the previous generation of the tool.

Process

Now that we had understood why exactly users were struggling with the product, I wanted to make sure we knew exactly how product managers went about planning their roadmap today.

A whiteboard showing different people's strategies for creating roadmaps
To inform our user journey, I interviewed a variety of product managers and sequenced their planning into distinct phases. Comparing across the group revealed common patterns of planning.

From this and other research, I formed an end-to-end user journey represented the typical product manager. With this in mind, I started to work through the flow in a low fidelity. These are just a few key screens that explore basic hierarchy and structure of the page.

Those initial interviewees were brought back to give feedback on the lo-fi end-to-end journey. Over the course of many rounds of feedback, I increased the fidelity and polished both the overall flow, as well as designing how smaller tasks would behave.

This project would end up spanning over a year from initial kickoff to launching to customers, so I will only include some of the most interesting or relevant parts of the process here.

Creating a customer guild for this change ended up being one of the most helpful and important parts for setting us up for success. This was a small invite-only group of a mix of existing and prospective customers who gave regular early feedback on the development of the new version of the tool. 8-10 customers were recruited for this and represented a range of industries, maturity, and familiarity with the existing tool. In an ideal case we could attract new customers without alienating existing ones.

Both large strategic decisions and smaller feature level problems were brought to the customer guild. A common way this might play out would be:

  1. Initial discovery and enquiries with guild + other users to learn about a problem (e.g. How do you go about socialising roadmaps at your workplace?)
  2. After turning those research notes into insights, I would then create initial design concepts for solving a certain flow or task. (E.g. a share roadmap flow where you can embed the result in a slide show)
  3. A protototype or low-fidelity mock would then be brought back to the guild to get feedback on whether that would meet their needs and what changes could be made to better suit them.
  4. I would work with the product managers to prioritise which set of changes would be best overall trade-off. For example, you might get a very specific request from 1 member of the guild because of their unique business, but it might not make sense to include in our product as a whole.
  5. A refined design would then make its way into a future sprint or milestone. Once built, those guild customers could then try it out for real in their early-access preview and provide further feedback.
  6. Depending on if that feature/flow met our goals (quality/impact), we could then move on to the next thing. If it wasn't working for the guild customers, it would be a signal that it'd be unlikely to work at full public launch too.

During this phase I would create, print out and put up in our working area these customer sentiment cards. By the end hundreds of these were hung up (wish I had a photo!). Here are a few examples of them.

You don't want a major change like this to disrupt existing users who are just trying to get work done. I worked with product management and engineering on defining this rollout strategy:

  1. A invite only private alpha
  2. An opt-in public beta
  3. General availability (any newly created plans would be made in the new interface, but could be toggled off)
  4. (As of writing has not occurred yet)Future sunsetting of the old interface
One of the most crucial decisions we made was that there would be no data loss between switching between the old and new interface, despite this actually requiring a bunch of backend changes. Although this added a decent amount of engineering scope, it gave customers confidence to try the new interface and reverse the decision if it didn't meet their needs yet.

Solution

The project spanned over a year and I created 80+ Sketch files in that time. I'll include some of the key screens. To get a sense of the product in motion you can check out a video like this one from Atlassian on YouTube. If you're curious about some of the drag and drop experience see the Interaction design case study .

Success measurement

Our big goal was to find product market fit, which cannot be captured by just one metric. From a quantitative perspective, our ‘core metric’ to move was to reduce the weekly and monthly usage churn rate. This means for someone who uses the product week 1, what percentage don’t return week 2, and so on.

Since my work on this, Portfolio for Jira was rebranded into "Advanced roadmaps" and was so successful it became a pillar of the "Jira premium" package. The product experienced a 3 digit percentage increase in MAU over the first 2 years after my and the teams work was released to general availability.

In terms of quantitative feedback, there is strong signal that we’ve made the product much more intuitive, and easy to use. Negatives were mainly about missing functionality (to be expected in an early access phase). Here are a few examples of positive, neutral, and negative comments I’ve received about the design:

  • “I like the new cleaner look. The old look has too many options that we will not use or be able to use."
  • “This made my night! I am so happy to see the changes to the UI, drag/drop functionality w/ respect to scheduling, better transparency, simplicity, all really important.”
  • “This is a wonderful improvement to the Portfolio for Jira stack. The WebUI is very user friendly and the create issues on the fly is working a lot better.”
  • “I like the new planning experience - It greatly simplifies things and find that its the right direction.”
  • “In the "New Experience" there are less supported types than previously. Already one big issue with Portfolio was that not all the types were supported but it's now gone back”
  • “It’s really clunky to only have the 3M, 1Y Fit, time bar as a way to navigate the roadmap. There needs to be a horizontal scroll bar that affects the road map only, to allow the user to move freely”

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