Agile Retrospectives

Migrate your Jira project without drowning in it

Luis Ortiz

— 7 min read
Migrate your Jira project without drowning in it

Migrating your Jira deployment is a big deal. If your approach is not insightful enough, things can turn really sluggish. You can think of it as getting caught in quicksand: The more you struggle, the more you sink. That is why people in those types of emergencies require aid from a professional rescue squad.

Luckily, you cannot drown to death in Jira. Still, a failed migration will most likely hurt your team's productivity. Check this anonymous real-world story: "The migration from the legacy system brought in duplicates, incomplete and inaccurate information, leading to end-users raising incidents in ServiceNow for my team to fix. We have about a hundred of those. This is impacting our sprints, as the PO mentioned to prioritize urgent incidents…."

As mentioned, those kinds of situations require the assistance of pros such as Rachel Wright, a certified Jira administrator and experienced consultant. She travels around the US to help others successfully adopt the project management tool inside their business. She is also an active community member, with lots of published training courses and books, participation in conferences, and more.

We had the chance to talk with her about her most recent book, The Ultimate Guide to Jira Migrations - How to migrate from Jira Server to Data Center or Cloud, published alongside Botron. Take some shots from Rachel's wisdom and learn how to stay out of the Jira swamp.

Topics to check

  1. When and how to do a migration

  2. Assembling a Dream Team

  3. Retrospectives for constant improvement

When and how to do a migration

The first alarm sign is that Atlassian will end support for Jira Server after February 2024. If you are not in that situation, why your organization should do a Jira migration always boils down to specific needs. Maybe you are not even aware yet that you should do one. Hopefully, your Jira support agent has suggested doing so, and you are still reflecting if it makes sense, with no clear view of any advantages and, instead, seeing it as another project that consumes time and money.

Wherever you are already thinking of it or do not have any idea, Rachel suggests you think on three main factors: "Complexity, cost, and the apps you are using. There is no one solution." Going deeper, she considers that "It might be easier for a marketing team to move to Cloud than for a healthcare company. It really just depends on what compliance regulations you are subject to and what the organization's strategy is as a whole. Are they moving everything to Cloud or just some apps? And what does the future looks like in five years?"

Assess your situation and learn which Jira deployment might be the best fit for your migration project with her 21 question quiz, included in The Ultimate Guide to Jira Migrations - How to migrate from Jira Server to Data Center or Cloud book. It also includes other valuable templates to guide your process. Download the e-book for free here.

Now that we have discussed the when, we can focus on the how. First of all, the biggest don't: Do not start customizing stuff before you have a clear idea of how your teams' workflows unfold and the industry good practices and congruency with the overall organization's strategy. The best way is to understand how to effectively digitize your actual processes so Jira can support your organization for the long term.

In Rachel's words: "You should work with Jira in a way that helps your organization. Do not tailor the way you work to how Jira is set up". The key takeaway here is to make sure your team is aligned towards a strategy that includes the Jira migration as a tool to accomplish the primary goal.

Assembling a Dream Team

One of Jira's main strengths is that it can frame several of your teams' operations in one or various related projects, letting you keep a panoramic vision of how any project or workflow unfolds in great detail. That means that many people's daily jobs may depend on it, making it imperative to consider how migration could affect everyone involved.

You want to make sure to include as many perspectives as possible. One good starter could be to gather feedback across teams, using the template included in Rachel's book (remember it is free to download). Another critical step would be to reunite a Dream Team of specialists that can help you pull out a successful migration by supporting the project with their unique skills and background.

Depending on your organization's situation, finding the right champions inside its actual workforce might be possible. Otherwise, you might opt for other options, such as looking for temporary contractors. Please note, however, that forming the suggested Dream Team is not mandatory, but it can really ease things for you. Let's briefly check each profile:

Executive Sponsor - A member of the Leadership Team that can effectively communicate the relevance of performing the migration project to management and C-level. He is a decision-maker and helps verify everything stays aligned with the overall company's strategy.

Project Manager - A person focused on keeping the workflow, breaking down requirements into executable tasks, checking interdependencies, removing blockers, and sparking collaboration to meet deadlines would be one of your best allies.

IT Guy - A colleague who knows like his hand how your organization's network is configured and the technical requirements your project should match to be effectively supported and align with internal digital security measures.

Compliant Officer - An expert in legal affairs and the company's internal regulations will help you maintain a compliant project. Be sure that this officer gets a broad vision of all the data you store so he can do his best.

Jira Administrator - A member of the Jira administration team inside your organization who knows all about the current deployment. As he boasts all-level permissions, he will be a great partner to help you remove blockers along the road.

Power User - A mate whose job depends mainly on using Jira and has been for a while, granting him a broad usage cases perspective, meaning that he knows how to use the tool and understands how other teams use it.

Testers - One or several persons from different teams will try the new deployment in search of bugs and opportunity areas. You may want to ask your Power User to test as well, but it is better to choose another colleague with not so much expertise, so you can empathize with a 'casual' user.

So far, we have explored the why, when, and how. We have also suggested ideas to consolidate your Jira Avengers that can help you do a successful migration. But what about the day after your project has been migrated? "It is not that you have finished your migration, you come in on Monday morning, and everything is done, work gets back to normal. There is a post-migration phase". And running Retrospectives can be really useful for that moment.

Retrospectives for continuous improvement

"First, you want to make sure there are training materials for all the users. Your support team must be ready to answer questions. You may also need to review your test environment to try new things." As you can see, the Jira migration project does not end after you have changed your deployment license but rather when your team manages to get comfortable with the new setting.

Check out more insights about Retros from Rachel in the following video:

If people really take their time to understand their Jira configuration, it will obviously be easier to perform any migration. Rachel considers you should do two things: Document your migration project inside Jira so you can track the rationale on which the configuration is based, and keep checking for constant improvement by asking your end users, as they know better. "Ask them in a test environment, ask them in a production environment. Do not surprise them, and make sure you are collecting their feedback often."

A simple way you could leverage this feedback to keep improving your project settings is to run a Retrospective session. One exciting method you could try is Errors Conversation. You focus on discussing the mistakes originated by action and omission to develop better ways to deal with similar situations in the future. Just invite your team to join your session in Agile Retrospectives, available both for Jira or Confluence; ask attendees to bring their ideas, cast their votes, and come up with follow-up items.

If you need further guidance to set up your session, check this post to learn how to run your Errors Conversation.

We have learned a lot about a Jira migration thanks to Rachel Wright's experience and wanted to share her insights so you don't get trapped in the Jira swamp. We are really grateful for her time and suggest you check her courses on LinkedIn, look for more resources on her website Jira Strategy or even get personalized support. She won't let you down!

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