Upcoming Project: JIRA Worklogs Microsoft Teams Bot

I’ve been working on a concept over the last month, to explore a different way of inputting time reports on Fridays with Atlassian’s JIRA Worklogs module.

To exercise my system design thinking and writing muscles, I put together a design for my solution. The solution is running locally, but still not working with an actual live Teams instance. Debugging Microsoft Teams Apps Marketplace is… painful.

Code is here, demo coming soon!

Exploring UX Tradeoffs

A bug fix this week opened up bigger conversations about UX tradeoffs, first principles, and system design.

What started as a fix turned into 3 key milestones — each one clarifying what matters most in the product.

The bug was around state being lost in our front-end app. The fix was straightforward – re-fetch the data from the API.

1. Data may not be available anymore.
The API is returning JSON blobs from a model, being produced every minute. Refetching might mean that the data is gone.

– If we cache it, the data may be stale.
– One first principle: data must be real-time and useful.

We considered redirecting the user back to the landing page to restart the flow.

2. Not great UX?
– Redirecting users without explanation isn’t ideal.
UX and I talked about adding more copy about what happened and giving context.
– We settled on clear, simple copy to keep the UI clear.

3. Could users miss out on data?
UX was front-of-mind at this point, I wondered if a user was missing out on data?

– We debated changing the model or storing the data differently.
– We could flatten the data and store it sequentially.
– But that would impact internal calculations and they were vital.

We decided to keep the existing data architecture.

Lessons learned:
– Tradeoffs deserve time. Rushing decisions often means missing hidden costs.
– Technical choices ripple into UX and product – talk early, not under pressure.
– First principles matter. They keep decisions honest.

If you’re designing flows like this, I’d love to hear what worked for you.

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