Estimating with Jira: import your tasks and send the points back

Most teams already keep their work in Jira, and most estimation sessions still end the same way: someone copies the numbers from a meeting into the tickets, one by one. It is slow, it is easy to get wrong, and it is the first thing to be skipped when the week gets busy.

Connecting your estimation sessions to Jira removes that step. You bring the issues into the room, the team estimates, and the accepted number goes back to the issue on its own.

What you need

• A Jira Cloud site. (Jira Data Center is not supported.)
• A Jira account that can see the project and edit the estimate field of its issues.
• The permission to manage Planning Poker in your organization, to connect Jira. Owners have it by default.

Step 1: connect Jira

1. Open Settings → Integrations and choose Jira, then Connect.
2. Connect in the way that suits you:

• OAuth: you are sent to Atlassian, approve the access and come back. There is nothing to copy. This option appears when it has been set up for your workspace.
• API token: a personal access key. Fill in three fields: your Jira site (for example https://your-team.atlassian.net), your account e-mail and the API token. You create the token on Atlassian's own page: id.atlassian.com → Security → API tokens.

1. Use Test to check the connection. Your key is stored securely and is never shown again.

Step 2: choose where the estimate goes

Right after connecting, a Configure step asks whether the accepted estimate should be sent back to Jira, and into which field.

• Turn on Send the accepted estimate back.
• Pick the Jira field that holds your estimates. The list shows the number fields of your site, and Story point estimate is already selected when it exists.
• You can change this later in Estimate settings.

A tip: Jira has two similar-looking fields, Story points and Story point estimate. Pick the one your board actually displays, and make sure it is on the issue's screen, otherwise Jira will refuse the update.

Step 3: bring the issues into a room

1. Create a room (or open an existing one) and choose Import in the Tasks panel.
2. Pick Jira, then your project.
3. Narrow the list down with the filters: sprint, epic, issue type and status. You can also search by text.
4. Select the issues you want, or all of them, and import.

Issues that are already in the room are marked, so nothing is added twice. Each task keeps its Jira key (such as PROJ-142), a link back to the issue and the first lines of its description.

Step 4: estimate

Run the session as usual: open a task, everybody votes, reveal, talk about the differences, and accept the estimate. When you accept it, the number is written to the Jira issue within moments, without making the room wait. The room history then shows Estimate sent, or the reason it could not be.

What is and is not sent

• Numbers are sent. Half points work too, since Jira's field is a number.
• The ? and ☕ cards and T-shirt sizes are not, because they are not numbers. They are kept in the history as "not sent".

If your team estimates in T-shirt sizes, keep using them in the room, and write the story points in Jira by hand, or agree on a numeric deck for the sessions that feed Jira.

Estimating well, with or without Jira

• Estimate before the sprint, not during it. Look at the backlog items that are next in line, so the sprint starts with numbers everyone has already discussed.
• Use one scale and stick to it. Switching between Fibonacci and sizes from one session to the next makes your history impossible to compare.
• Points measure effort and uncertainty, not time. Avoid translating them into hours: the velocity of past sprints will tell you how many points fit in the next one.
• Re-estimate when the scope changes. A task that grew after the discussion deserves a new vote.

If an estimate was not sent

• "The field is not on the screen" or a permission error: check that the field is on the issue's screen in that project, and that the connected account is allowed to edit it.
• The connection stopped working: the token may have been revoked or expired. Use Test on the Integrations page, and Reconnect if needed.
• Something is not a number: the ? card, ☕ or a T-shirt size. This is expected.

Connecting takes a few minutes, and from then on the numbers from your sessions land in the right place without anyone copying them.