Atlassian is getting more powerful… and more complex. The “keep it simple” paradox

[#1]

I’ve been working with Atlassian tools long enough to notice a pattern: every year the platform gets more capable, more integrated, and more “enterprise-ready”… and at the same time it gets harder to keep the day-to-day experience simple for normal users.

It’s not a complaint post. It’s more of an observation and a paradox I think most admins and partners feel right now.

Why this happens

Atlassian is building a platform, not just apps. Jira + JSM + Confluence + Assets + Automation + Atlassian Intelligence + Analytics + Guard… each piece adds value, but also adds decisions:

• more configuration surfaces

• more feature flags and rollouts

• more “right ways” to do something

• more dependencies between products

• more “this is available only on plan X”

It’s not that any single feature is bad. It’s the accumulation. Complexity isn’t shipped in one release, it grows quietly, layer by layer.

The admin reality: every new option has a hidden tax

When Atlassian adds a new capability, the tool gets better. But for admins it also creates work that nobody sees:

• documentation and enablement (“what is this and why do we use it?”)

• governance (“who can configure it?”)

• support (“why did this change?”)

• training (“where did the button go?”)

• integration and security review

• rollout planning (sandbox, release tracks, feature rollouts)

So the paradox becomes: the platform improves, but the cost of adopting improvements rises.

The simplicity problem isn’t users. It’s entropy

Without guardrails, Jira/Confluence naturally drift toward entropy:

• custom fields multiply

• workflows grow “just one more status”

• labels become taxonomy wars

• automation becomes a spaghetti plate

• and suddenly nobody trusts reporting because definitions aren’t consistent

Teams rarely do this maliciously. They’re solving local problems. But locally optimal decisions add up to globally messy systems.

“Keep it simple” is easy advice and hard practice

Most admins know what good looks like:

• minimal workflows

• consistent fields

• clear ownership

• boring conventions

• templates that make writing easy

• automation that is readable and auditable

But the platform keeps offering more knobs to turn and the organization keeps asking for “just one more exception”.

So the real skill isn’t knowing what simple means. The skill is protecting simplicity while still enabling progress.

What’s helped me (and why I think it matters)

I’ve learned that “simple” doesn’t mean “no features”. It means:

• one standard way to do the common thing

• exceptions only when the business case is real

• controlled change, not unlimited customization

A few habits that keep things sane:

• start with the “why” before adding apps or new features

• set a small number of standards (fields, statuses, naming)

• treat automation like code (ownership, review, versioning)

• measure adoption and pain, not just “features enabled”

• keep onboarding docs up to date (or users will invent their own process)

The real question

How do we keep systems simple while Atlassian keeps adding power?

I don’t think the answer is “stop changing”. The answer is:

• adopt features intentionally

• design for humans, not for maximum capability

• and accept that simplicity is something you actively maintain

Curious how others handle this. What’s your biggest source of complexity right now  and what’s one rule or practice that helped you keep your Atlassian stack usable?

Im Happy to hear more about your Opinnions :)

[Dave Mathijs]

Unpopular opinion:

Stop the in-app advertisements in a product with an already hefty monthly/annual subscription (and a yearly increase well above normal inflation rates) to trick you into up-sell/cross-sell.

Plenty of examples:

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• Secure your organization's users and data Requires Atlassian Guard
• Protect top-priority projects and surface suspicious behavior Powered by Atlassian Guard Premium

[Arkadiusz Wroblewski]

@Dave Mathijs Great point ☝️, but what I find more crucial that the notification system for Subscription of news and generally notifications should be simplifized, it's easy to subscribe but unsubscribe is more and more Hidden.

Especially for Power User.

[Tenille _ Easy Agile]

@Dave Mathijs ooof, and the "new article" suggestions in Confluence 🤦‍♀️

Nice post @Arkadiusz Wroblewski, thanks for sharing your insight. One of the strengths of Jira is how configurable it is, and one it's biggest challenges is how configurable it is...

Treating simplicity as a design principle rather than a happy accident is a solid approach for most systems. Really understanding what's driving the request when a team asks for a customisation can often lead to a better solution that might apply across the instance. 

[Stephen_Lugton]

Thanks for your perspective on this @Arkadiusz Wroblewski you (and @Dave Mathijs ) have made some good points. 

We've found that simple works in different ways for different teams; one team wants to keep very few fields on work items - Summary, Description, Status and Assignee are enough for them, but another team currently has 40+ fields on their work items with automation for when fields values change. 

Luckily for that second team most of the fields are dropdowns, but they also have a fairly complex workflow, and I get to be admin for them!  You may say that's not simple, but they're meeting a regulatory need where they have to be able provide accurate information and auditability in a way that's easy for overworked team members to use, and I've set them up with reports and dashboards to be able to show that information in intuitive ways quickly and easily in meetings with the regulator.