5 most common problems when migrating from Trello to Jira


A lot has been said about the differences between the two project management tools: Trello and Jira.


Many comparisons have been made to prove one tool’s superiority over the other or – on the contrary – to show distinctions that make each tool more or less useful in various use cases. Surely, Trello allows teams to organize their projects visually while Jira is unbeatable in its management structure – it can keep even large teams well-coordinated and on track.

It is true that from a collaborative perspective, both tools make a huge difference in teams’ work, enabling team members to view all stages of the project and reducing the need for constant communication and updates. However, as teams grow and the workflows become more complex, Trello users often start to search for a tool that would provide better task tracking functionality as well as more advanced planning. And there Jira comes into play.

Undoubtedly, Jira is one of the best tools when it comes to tracking the stages of teams’ projects easily. It is also perfect for companies that are trying to move towards a more agile work environment.  However, migrating from one project management tool to another is rarely smooth and easy – despite what their producers may say ;). The truth is that you may encounter quite a lot of problems there. Running workflows with large amounts of data efficiently and customizing the transformation for your exact needs is, of course, doable – but challenging, too!

Here we listed some of the most common problems faced by teams when they decide to migrate their projects from Trello to Jira.


Importing checklists from Trello

Trello import

When migrating from one system to another, it’s good to take your data with you, isn’t it?

Well, it’s not always so simple. Although checklists are an in-built functionality for Trello, Jira does not support their migration. It does offer subtasks instead – however, for some users, it is a too time-consuming option. But at the same time, losing business-related data that was initially documented as checklists may be highly frustrating, especially if you think checklists help you raise your work efficiency. So what is the proper solution here?

Naturally, writing a migration script is always an option. But because this is a time-consuming and error-prone process, it may not be the best idea for every team. Fortunately, there are some add-ons that you can acquire straight from the Atlassian Marketplace that allow users to add multiple checklists to a single Jira issue – just like you add multiple checklists to a single card in Trello. One of them is Multiple Checklists for Jira by SolDevelo.

Multiple Checklists for Jira aims at helping its users in organizing work on a particular task. It is designed for creating checklists directly in Jira issues and – what’s the most important – their number is unlimited. In order to achieve a desired level of organization, you can freely add new checklists to an issue. Additionally, you can prepare useful templates and upload them to the chosen issue. It is a great solution for repetitive sets of tasks or requirements.


No ticket templating

No one likes to be creating the same document over and over again, don’t they? Creating templates, on the other hand, may save you from hours of repetitive work and boost your overall productivity. In order to help the users build a seamlessly repeatable workflow, many software programs do include different types of templates. Thanks to coping key information over from the template to a new card, you can work in a clear and consistent way. A template serves as a master copy for replicating processes and enables teams to begin with the exact same content every time.

In Trello, you can create template cards by simply making the card and easily duplicating it whenever necessary. Then you can copy that card, and choose to copy over checklists and attachments. What is more, you can create new templates just by clicking the card template icon at the bottom right corner of any card. You have to admit it sounds pretty smart!

Unfortunately, Jira doesn’t include feature ticket templating. We bet you agree with us that issue creation is an exceptionally time-consuming process there. Especially if you have to re-create the same epics, stories, and sub-tasks over and over again. Jira users are often complaining about scrolling through the same fields and typing in the same data repeatedly. If you and your team often face the challenge of repeating standard tasks, you may be unpleasantly surprised when migrating from Trello to Jira.

What to do then? Again, Jira add-ons, available on Atlassian Marketplace, can come to your rescue.


Multiple assignees? Not in Jira!



Adding multiple assignees to a single task is a good idea, allowing you to distribute the work and share responsibility. It seems understandable and quite useful.

However, in JIRA an assignee means just one person. Why? Because having one issue assigned to multiple assignees seems to be against the principle of how Jira operates. The task owner is the assignee. They have to deal with it. They may have helpers, but the single-person responsibility must be a rule. Otherwise, the situation becomes vague and unclear. The same in real life – if one task is assigned to several people, it can simply be overlooked.

It all seems reasonable but – at the same time – it may be quite a nuisance. What is more, it is really hard to imagine a situation when everybody responsible for a task fails to notice it at the same time. With Jira being so flexible in every aspect, it is difficult to understand why this little detail is impossible to be changed.

Of course, users try to work around this problem and, for example, create a multi-user picker field which later they use to store multiple assignees. It is also a good idea to add that field in notifications so that all the assignees will be notified of any changes to the issue.


No similar add-ons available

Trello, known for its flexibility, offers rather simple and basic functionality in its standard form. However, its core feature set may be impressively extended through power-ups, add-ons, extensions or integrations. And when you already think that you have tailored Trello to your needs perfectly with these additional tools, the decision about migrating to Jira pops up unexpectedly.

Well, it quickly turns out that some of the add-ons you liked and used extensively for Trello, do not work for both project management tools. In fact, you will have to start the whole process of adjusting the new tool to your needs basically from scratch. But do not worry – Jira will compensate for all this initial inconvenience. It is an amazing tool offering a greater number of features that come in handy for everybody who wants to improve their workflow and apply it to a variety of work situations and project sizes. And what’s the most important – it greatly surpasses Trello with its wide library of integrations and add-ons. You’ll soon be on your way to maximizing your project management experience – we promise you that!


Too much of a fuss over configuration

Trello surely differentiates itself from its competitors with its simplicity. It is really easy to have this tool get up and running in a couple of clicks. Actually, you can easily begin using it within minutes of setting up your account.

Jira, on the other hand, would never be classified as an easily customizable solution. In fact, it may be overwhelming if you’re using it for the first time. Sprints, epics, and issues can all blend together, making the whole experience a bit daunting and it takes time to get full advantage of its power. That was also one of the reasons why Jira’s next-gen projects were invented. Both their design and functionality bear a lot of resemblance to Trello, blending together power and simplicity. Next-gen projects are new project types in Jira Software, built with the most important features of the classic version but much more easily managed and customized.

Surely, migrating from Trello to Jira may seem challenging at times. Sometimes you may feel to be overwhelmed by mountains of information and will miss the simplicity offered by Trello. As always with tools, remember that both can get the job done for you – the question is: how they do it? If you’re looking for a tool that can do it all with agile project management – we highly advise you to open yourself to all the possibilities available in Jira. Transitions are rarely easy – no one promised they’re going to be so. However, everything worthwhile takes time and commitment, doesn’t it?



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