When you work with others, you need to be able to communicate quickly without wasting time in meetings. In Lupl, users could communicate through instant messages, but it wasn’t document- or task-specific.

After reading the requirements carefully and talking to the product manager about my questions, I began the design process for a comments feature.

Users who wanted to comment had to be able to:

It was not easy to decide whether to keep the interface simple or make the new feature stand out more.

Besides that, I had to figure out how to use different parts of the Lupl instant messaging interface to make it look different while still being easy to use.

If I had played too much of the card of novelty, I could’ve upset users and ended up with an uneven user experience. If I had used too much of an existing UI, it would have been hard to add things like tags and attachments.

Despite experiencing conflict, I was prepared to find solutions through experimentation.

I primarily looked at productivity apps that allow users to comment.

Flows in apps like Airtable, Asana, Wrike, ClickUp, Jira, and Microsoft Planner helped me understand better how to design the feature.

I had a few days until the first design review with the stakeholders, so there was no time to wait.

In the past, I used to spend hours searching for the perfect solution, worrying that if I didn’t go on the right path, I'd end up with a non-solution. However, this turned out to be a disguised form of procrastination, causing me to slow down and experience decision paralysis.

So I changed this strategy to the opposite. ‘Get started now, and you will discover the answer soon' started to be my mantra whenever I felt hesitant.

Adding a comment while hovering on the task was part of the requirements. But with all the other parts, this could not work. As is shown in the image below, there was not much space left for the task name. Therefore, I had to persuade the stakeholders to be removed from here.

Below is an early screen that I had to redesign because it did not work with the UI for instant messaging. In the design review session, we all agreed to leave the entry point only in the siderail. It felt like a small victory. 🙂

With helpful input from the design lead and the team, I was able to change the UI into something that worked better with what we already had. This got me approval on the design, and we were set to move forward.

On mobile, the same options had to be available. The user should be able to attach files, react with emojis, tag members and edit messages. I designed for both iOS and Android.

Thanks to the team's feedback, I was able to refine the design through trial and error and successfully incorporate it into the brand's guidelines.