What work management software should I choose?

And is Jira really always the answer?

Yasmin Clarke
6 min readJan 23, 2022

I see this topic come up a LOT. In organisations, in online forums, in social chat. Often (though not always) the questioner is looking for a silver bullet.

Jira, Trello, Asana, Notion…Which one should I use? Which one is the best?

Thinking about work management tools got you like 😖 😬 😱 ?

This is asked as if it’s possible that there is an objective answer. Which would be comforting, wouldn’t it? It’s a version of the IBM rule — if you’re responsible for choosing task management software for your team, and you choose ‘the best one’, then you feel safe in that choice. You have a defense if the implementation doesn’t work out.

I’m sorry to disappoint, but there is no silver bullet. The solution that works best for your team will not necessarily be the one that works best for another team, or for your team in 2 years, or for a different team that you managed in your last role. As in everything, context matters…a lot.

Context matters.

•What kind of work are you trying to get done? •How does your team communicate? •How comfortable is your team with tech tools? •What other software are you using, and what level of integration do you need? •What level of management oversight or reporting do you want? •How much automation do you want?

If you can answer these questions clearly, then your choice will become a whole lot easier. Even though all these software tools are nominally in the same category of ‘work management’, they all approach this problem in slightly different ways, with different features and trade-offs. (Notice that although I’ve used ‘work management’ here, I’ve also used ‘task management’ and ‘project management’ elsewhere — clearly this is a broad category of tech solution with various specialisations).

Having said that, I get that you don’t always have the time & energy to invest in exploring every single option. There’s a reason that people tend to choose software they’ve worked with before — it’s a known quantity, even if it doesn’t perfectly suit their needs. But if you’ve never worked with project management software before, where do you start?

Work management software tl;dr

I’ve worked with most of the major work management tech solutions, and with some custom-built ones, across 5 different organisations, and in most of those teams I’ve also been there for the implementation, sometimes in a key role and sometimes as a recipient. So I have a fairly broad understanding of the key points of similarity & difference for most tools.

As I mentioned above, each tool approaches the work/task/project management problem in slightly different ways. Depending on your team and your requirements, sometimes those aspects are trivial but sometimes they are the difference that makes a difference.

So here is my tl;dr version of the major work management solutions. From what I can tell (I admit no direct experience) most of the smaller/less-well-known solutions are usually more specialised versions of these, either designed for specific types of teams, for specific types of work, or with a particular emphasis on one aspect of the project management process.

👉 Jira

Jira is a spaceship. Expect to spend time configuring it to work the way you want. You’ll probably need to employ someone specifically to update & maintain your configuration (not necessarily a fulltime role, but requires specialised knowledge). If you don’t know what you want, then Jira is harder to get started on.

It has all the bells & whistles though! Jira is likely the best option for software teams, as this is what it was specifically designed for. In particular it has a lot of automation, integration, and notification options. If you need a spaceship, then definitely spend the time investing in a good set-up on Jira.

Jira can also be used well to manage other types of work, especially if those teams are working with software teams that also use Jira — it’s always cleaner when everyone is in the same space using the same tools — but if you’re doing that, you might find that some of the features are unnecessary or even get in the way. The major missing feature for me when it comes to non-software work is that tasks don’t have an obvious place to ‘put’ (either write directly or link) the work that you’ve done or the conclusion of the task. To be fair, none of the solutions below has this either.

👉 Asana

Asana is vastly simpler than Jira and is usually the go-to for non-software teams that want individual task management.

It feels more friendly than Jira too. It’s very easy to ‘write a task and do it’ — less clicks than Jira. However it has less bells and whistles (eg. no time logging), though it does have good notifications. There’s limited flexibility or customisation but compared to Jira I think this is actually a good thing, because you can just plug & play. I imagine it could be annoying if your project doesn’t fit how Asana structures things.

One Asana feature I really like is that it has built-in places for giving context to each project, eg. a project summary, a weekly status update, links to relevant info, etc. Jira doesn’t have this (I suppose you could get Confluence — the wiki tool — as well as Jira and put the info there, but it’s not as handy).

👉 Trello

Trello is easy to explain. It’s an online version of sticky notes that you can categorise into lists. So to do task management in Trello you could set up a ‘Board’ for each project with ‘Cards’ (post-it notes) categorised as ‘To do’, ‘In progress’, ‘For review’, ‘Done’ etc (or whatever makes sense for your project).

It has a few more very handy features (notifications, space for a detailed description, comments, task assignment, etc) and it does have some automation which I’ve not explored.

Trello is decent if you want very simple task management. I especially recommend it for ephemeral projects where once it’s done, it’s gone. It’s also extremely intuitive for non-technical people, because the concept of categorised post-it notes is so familiar.

👉 Notion

The interesting thing about Notion in this context is that it can do task management, but it is not just a task management tool. It is also a wiki and a lite database and a few other things.

When you use it for task management, you create a ‘database’ of tasks, and then you can display these however is useful — in a kanban-style board, on a calendar, on a project timeline, etc. If you’re not a super technical person, don’t be put-off by the ‘database’ language, just think of it as a list of tasks.

It’s highly highly flexible so you can pretty much make it do what you want! If you’re process-minded, you’ll probably love that. If not, you may need to invest a small amount of time to learn some good approaches.

It doesn’t have all the task management bells & whistles — the main missing feature for me is that notifications don’t work exactly how you’d expect from traditional task management software, because, well, it’s not designed to solely do task management. But has a lot of other good stuff that might be useful enough to trade off.

What would I choose? If I was starting a new project outside of any existing structure, I’d start on Notion because I can do more than just task management there. I’d only move to something else when I needed more structure or automation.

However if your team are used to more traditional task management tools, or need more automation, then it might make sense to use Jira or Asana or something similar. And if you want very lightweight or transitory, then Trello is a good choice.

Note that Trello is now owned by Atlassian (as is Jira). I haven’t explored whether there is any useful integration between the two. I also get the impression that Jira are trying to develop a simpler version that is less overwhelming — I believe this is the intention behind their ‘next-gen’ solution vs the ‘classic’ version, but I haven’t seen a good demonstration that it’s as simple as any of the other tools mentioned above, so I’m sticking to my spaceship assessment for now.

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