Jira apps for agile teams

Retrospectives were meant to be agile’s secret weapon.

In theory, they’re a dedicated space for teams to pause, reflect, and course-correct. A recurring moment of clarity in the blur of sprints. But in practice?

“We show up, we talk about the same problems, we say we’ll fix them... and then we don’t.”
- Jaclyn Smith, Senior Product Manager, Easy Agile

This isn’t just dysfunction. It’s disillusionment. And it’s costing agile teams more than they realise.

In this post, we dive into the hard truths explored by Jaclyn Smith, Senior Product Manager at Easy Agile, and Shane Raubenheimer, Agile Technical Consultant at Adaptavist in:

• 🎙️ Easy Agile Podcast Ep. 32: Why Retrospectives Fail & How to Fix Them
• 🎥 Webinar: Retro Action – Stop Talking, Start Doing
• 📝 The Action-Driven Retrospective Template

Our goal is not just to fix retrospectives, but to reclaim them. If that resonates with you, keep reading.

TL;DR:

• Retrospectives often fail because teams repeat surface-level issues without resolving root causes.
• Action items from retros are rarely followed up, leading to distrust and disengagement.
• The Action-Driven Retrospective Template helps teams focus on fewer, more impactful changes.
• Trust is rebuilt through consistency, accountability, and small wins that compound.
• Real improvement happens not during the retro, but in what the team does afterward.

When we stop believing that change is possible

The quiet failure of retrospectives doesn’t happen in a moment. It happens gradually, invisibly, over the course of sprints where insights are voiced but not acted on. When teams invest time in talking about problems, only to see them persist, they don’t just lose momentum. They lose hope.

In the podcast, Jaclyn Smith, Senior PM at Easy Agile, reflected on retros where participation seemed high, yet nothing stuck:

“We’d have these beautiful, well-facilitated boards. But when we checked in a sprint later, people couldn’t remember what the actions were. Or worse, they remembered, and knew nothing had happened.”

That erosion of trust isn’t always visible. But it’s felt. It manifests as disengagement, short answers, vague observations. When a team feels like retros won’t lead anywhere, they stop offering anything worth leading with.

This is the paradox of failed retros: the form persists, even as its function evaporates. The team is technically “doing the retro.” But the retro no longer does anything for the team.

Normalising dysfunction and agile anti-patterns

In the webinar, Shane and Jaclyn dissect this disillusionment based on their experience of working with hundreds of real teams across industries. Most teams can relate to this problem - they're doing everything “right”: regular standups, retrospectives on the calendar, a backlog that moves. And yet, they somehow feel stuck in the same spot.

That's because of one or more of these anti-patterns, which have become dangerously common:

• Cargo cult agile: Following agile rituals without purpose
• Hero culture: Over-reliance on a few individuals rather than teamwork
• Water-Scrum-Fall: Mixing methodologies without clear boundaries
• Team velocity misuse: Tracking productivity by team velocity alone
• Backlog noise: Long lists of tasks lacking customer value

The issue isn’t awareness. Teams know these patterns exist. What’s missing is a structure that interrupts them - consistently, visibly, and meaningfully.

“The worst retros aren’t chaotic. They’re quiet. No conflict. No depth. Just a board full of things we’ve already said.”
- Shane Raubenheimer, Agile Technical Consultant, Adaptavist

This is why retros don’t just need better facilitation. They need a redesigned relationship with action.

Building action into the ritual

The most fundamental problem Jaclyn and Shane identify is that retros end with “next steps”, but those steps never reappear. Actions get lost in Jira, or exist solely in a facilitator’s notes. They’re rarely revisited. They aren’t owned. And without ownership, there’s no accountability.

That’s why they created the Action-Driven Retrospective Template. It’s not flashy. But it forces a shift in rhythm:

• Every retro begins with last sprint’s actions. Were they completed? What impact did they have?
• Themes are not just grouped - they’re challenged. Why do they keep showing up? What’s beneath them?
• One or two actions are selected - no more. And they are immediately assigned, tracked, and made visible.

“This is about restoring integrity to the retro. If we’re not checking what we did last time, what does it say about what we’ll do this time?”
- Jaclyn Smith

The brilliance here is in the restraint. Rather than generate more insight, the template helps teams create follow-through - the most precious and elusive outcome of any retrospective.

Why teams need fewer actions and more outcomes

In agile culture, it’s easy to mistake motion for progress. A retro that generates 15 sticky notes and 5 action items might feel productive. But it often leads to diffusion of focus and quiet inaction.

Shane is blunt about this:

“I’d rather a team act on one thing really well, than half-act on five.”

The Action-Driven approach discourages long lists. It nudges teams to choose actions that are both impactful and doable within a sprint. It acknowledges capacity. It invites discernment. And in doing so, it cultivates trust.

Because when teams start seeing change happen, even in small ways, they begin to believe again. And belief, more than any tool or process, is what fuels sustainable agility.

Retrospectives as emotional reset, not just process audit

Perhaps the most refreshing part of the conversation was how emotionally honest it was. Neither Shane nor Jaclyn treated retrospectives as an abstract exercise. For them, it’s about what people feel when they leave the room.

“A retro should give people energy. It should help them see that we’re improving, that their voice matters, that something got better because of something they said.”
- Jaclyn Smith

This is what most guides miss. Retros aren’t just functional. They’re relational. They tell a story about whether the team can learn, grow, and improve together. When that story breaks, when people stop feeling heard, or stop seeing results, the damage goes beyond a missed task.

It touches morale. Culture. Confidence.

Tooling and rituals are not the answers, but the amplifiers

In the webinar, Jaclyn goes on to show how Easy Agile TeamRhythm can help teams carry retro actions directly into Jira workflows. It’s not about selling a tool, but rather about shortening the distance between reflection and execution.

Jaclyn’s point is clear:

“The retro isn’t where change happens. It’s where it begins. The real test is whether your sprint backlog tells the same story.”

This is where tooling earns its place - not by replacing conversations, but by preserving context and sustaining visibility. When actions from a retro are visible in the planning session, on the board, and during standup, they don’t disappear. They become culture.

Start with mindset shift. Then build the habit.

What makes this approach so effective is its humility. It doesn’t promise transformation. It promises traction.

Start with one action. Make it visible. Talk about it next time. Build a habit. Trust the compounding effect of small, completed improvements.

“Agile isn’t about doing more. It’s about doing what matters - better, and more often.”
- Shane Raubenheimer

If your retrospectives feel tired, you don’t need a new format. You need a new relationship to action.

And that begins not with a workshop, but with a single, honest question:

“What did we change last sprint, and did it make anything better?”

If you don’t know the answer, start here:

📝 Download the Action-Driven Retrospective Template
🎧 Listen to the full podcast
🎥 Watch the full webinar

You don’t need to fix everything this sprint.

You just need to prove, to your team, and to yourself, that change is possible again.

High-performing teams don't happen by accident. They're built through intentional conversations about how to work together effectively.

Creating alignment isn't about one-off workshops. It's about clarity that sticks. A team charter gives agile teams the shared understanding they need to work better together, especially as teams grow, change, and evolve how they work. Without one, ambiguity creeps in, especially in remote or distributed environments where body language and hallway conversations aren't an option.

TL;DR

• A team charter is a shared agreement that defines how a team works together.
• It helps build trust, align expectations, and reduce friction.
• Creating one involves four stages: define purpose, agree on behaviours, map workflows, and embed the document.
• It evolves with the team and supports onboarding, retros, and continuous improvement.

What is a Team Charter?

A team charter is a living document co-created by the team. It outlines the team's shared understanding around purpose, values, responsibilities, and ways of working. It sets the tone for how people communicate, collaborate, and make decisions.

Think of it as a blueprint for a high-performing team: aspirational, but grounded in the daily realities of team life, and aligned with agile ceremonies like stand-ups, sprint reviews, and retrospectives that reinforce shared understanding. It reduces duplication, limits confusion, and gives structure to how we operate - even when the unexpected shows up.

Benefits of a Team Charter for Agile Teams

At its core, a team charter addresses the fundamental questions that cause most team dysfunction:

• What is our purpose as a team? Why do we exist?
• What is within the scope of our team?
• What outcomes are we accountable for?
• How do we treat each other as team members?
• How do we make decisions and communicate?
• What are our individual roles and responsibilities?
• How do we celebrate success?

What a Well-Crafted Team Charter Can Unlock

1. Clarity and Alignment

A team charter serves as a clear roadmap that defines the team's mission, goals, roles, and responsibilities. It ensures everyone understands how their work contributes to team success.

2. Better Decision-Making

When responsibilities and communication protocols are clear, decisions are made faster and more consistently.

3. Improved Communication

Establishing communication norms upfront ensures smoother knowledge sharing and transparency.

4. Accountability and Ownership

Team members know what they're responsible for, fostering commitment and initiative.

5. Trust and Team Cohesion

The collaborative process of creating a charter builds trust and empathy, and strengthens team dynamics.

6. Continuous Improvement

Team charters encourage feedback and reflection, evolving with your team over time.

7. Streamlined Onboarding

Team charter serves as a vital guide for new team members, offering clear insight into the team's norms, values, and workflows, accelerating their integration and boosting early productivity.

8. Living Reference Document

The charter acts as a reference tool that keeps everyone grounded and aligned as the team changes.

Four Practical Steps to Build a Team Charter

The team charter process is typically split into four interactive sessions. Each phase builds on the last and creates the trust, clarity, and psychological safety needed for the next.

Phase 1: Define Purpose and People

The team's mission refers to the objective or goal that a team is set to achieve. It is a clear and concise statement that defines the team's purpose and the value it aims to deliver.

Start by co-creating the team's mission statement. Team members contribute by answering: "What value do we deliver? What impact do we want to have?"

Everyone shares their input, then the team votes on the mission statements that resonate most. You can even combine parts from several to create the final version.

Once established, the mission should be displayed publicly where everyone can see it and team members can reference it.

Then we go deeper, with Personal Operating Instructions (POIs). This phase focuses on understanding team members as individuals. Each person answers questions like:

• What do you love about your job?
• What motivates you?
• How do you like to work?
• When do you work best?
• What do you want help to look like?

This helps us build empathy and challenge assumptions. It makes team members understand behaviours and uncover ways to support one another.

Phase 2: Create a Working Agreement

A working agreement is a team-designed agreement for an aspirational set of values, behaviours and social norms. Think of it as a vision for how it would be to work in an incredibly safe and powerful team.

This is where the real power lies, where you get specific about operations. Through a mix of guided reflection and group synthesis, the team explores questions like:

• What makes a great team vs. a terrible team?
• How do we communicate?
• How do we make decisions?
• What are our top responsibilities?
• What are our daily rhythms (e.g., stand-ups, reviews)?

And don’t stop at logistics, go deeper:

• How do we give feedback?
• What do we do when someone’s stuck?
• How do we balance collaboration and deep work?
• How do we share knowledge?
• How do we run meetings?
• How do we support remote or hybrid work?
• How do we protect focus time?
• How do we resolve disagreements?

From this, draft short, memorable working agreement statements. For example: "We default to asynchronous communication whenever possible," or "We commit to reviewing pull requests within 24 hours." Themes like "Diverse opinions welcome" or "Refactoring is a first-class citizen" should emerge.

💡 Tip: If your team uses Easy Agile TeamRhythm, you can incorporate these agreements into planning and retro directly.

Here are two examples of working agreements:

Phase 3: Map an Operational Agreement

Next, turn principles into rituals. Visualise your delivery flow using tools like Kanban boards, swimlanes, or service blueprints, whatever format helps your team see the full picture clearly:

• Who leads each stage?
• What’s working?
• What’s broken?
• What needs to be true for work to move forward?

Capture frictions around unclear ownership or ambiguous definitions. This surfaces hidden blockers and leads to better alignment.

💡 Tip: Consider using a collaborative tool like Miro, Easy Agile Programs, or whiteboarding sessions to map your current process together.

Phase 4: Make It Stick

A charter only works if it lives in your team’s daily rhythm. Otherwise, it risks becoming 'shelfware' that gets created once and forgotten. Keep it active, visible, and revisited to maintain its impact.

• Share and communicate: Make it accessible and visible.
• Live by the charter: Role model the behaviours you agreed on.
• Review and update regularly: Revisit and evolve it as your team changes.
• Use as a reference: Ground retrospectives and decisions in it.
• Reflect often: Use it to discuss what’s working and what’s not.

💡 Tip: Add your charter as a living page in your team workspace (like Confluence) and link to it in your planning tools.

Onboarding New Team Members with a Charter

When someone new joins the team, it's time to review the charter. Here’s a step-by-step onboarding process:

1. Initial walkthrough: A team lead introduces the charter and context.
2. Time to absorb: The new member reads and reflects.
3. Team review: The team invites their feedback and updates the charter together.

This creates buy-in and strengthens psychological safety.

💡 Tip: Schedule a 30-minute team check-in with each new hire after their first two weeks to revisit the charter together.

The Foundation of High Performance

A team charter isn’t just a document. It’s a shared commitment to how you work together. It evolves as your team does, helping you navigate change and stay aligned.

If there’s one thing we’ve learned, it’s that culture isn’t declared. It’s designed, together.

Whether forming a new team or elevating an existing one, your charter is a powerful first step toward intentional, aligned collaboration.

Suggested Next Step

Looking to embed your team charter into your team's everyday rhythm? Easy Agile apps like TeamRhythm and Programs help teams turn working agreements into action by aligning daily rituals such as sprint planning, stand-ups, retrospectives, and PI planning.

Collaboration in large-scale organisations often reveals friction in places teams expect to run smoothly. As product and development functions scale, the number of moving parts increases. So does the risk of misalignment.

At Easy Agile, conversations with our customers frequently surface familiar challenges. While each organisation is unique, the core struggles of collaboration are shared. To protect the privacy of the teams we spoke to, we’ve anonymised all quotes. But every insight is real, direct from the people doing the work.

This post is for anyone navigating the complexity of scaled collaboration, whether you're leading a team or working within one. Sometimes the hardest part is seeing the problem clearly. These are the patterns teams are running into, the questions they’re wrestling with, and the cracks that emerge when planning, alignment, and communication break down. Understanding and acknowledging these issues is the first step toward solving them.

Here’s what teams are experiencing and the key questions they’re grappling with as they scale collaboration.

TL;DR – Common collaboration challenges in scale-ups and enterprises:

• Teams struggle with communication and alignment, especially when working across multiple teams or departments
• Managing cross-team dependencies is a significant challenge, often causing delays and requiring frequent coordination
• Capacity planning and skill allocation are difficult, particularly when teams have to balance project work with ongoing operational tasks
• Teams face challenges in breaking down work effectively and maintaining visibility of progress across different teams
• Frequent changes in priorities and scope creep disrupt team planning and execution
• There are difficulties in translating high-level strategy into actionable team priorities and objectives
• Teams struggle with effective retrospectives and continuous improvement processes

What breaks down in cross-team communication?

Communication challenges tend to intensify with scale. As soon as multiple teams are involved, misalignment becomes more likely. A Senior Product Manager from a global HR tech firm described a pattern many teams will recognise:

"One of the main themes I heard in conversations with leadership was the lack of process, transparency, visibility, and dependency tracking. It’s always been manual across teams. We’ve done a really good job, but there’s an opportunity to do better."

Another team member highlighted how this disconnect tends to grow over time:

"At the start of each quarter, our conversations are strategic and cross-functional, involving sales and strategy teams. But as we dive deeper into execution, communication shrinks down to daily engineering huddles, and essential alignment details often get lost."

The problem isn't a lack of communication, but rather a shift in its focus. When delivery takes centre stage, strategic context gets sidelined. When teams move into execution mode, that shift in communication cadence creates blind spots across departments, leading to confusion, duplicated work, or misaligned outputs.

Why is managing dependencies across teams so difficult?

Dependencies create friction when they aren’t visible or clearly owned. Coordination across teams can be derailed by unclear sequencing, late handovers, or competing timelines. An Agile Coach at a financial institution shared:

"We had to run bi-weekly cross-program dependency calls just to stay on top of what was blocking who. We just list dependencies manually, there isn’t any unified visibility. At the ART level, it’s a mix of RTEs, Scrum Masters, and team members trying to link things, but beyond that, it falls apart"

A delivery leader at a global credit bureau reinforced the limitations of existing tools:

"I’ve never successfully been able to really tackle dependency visualization and put a process around that. It's always been manual. When I'm speaking to an executive, that means something... But when I'm speaking to someone on an agile team, it changes as it rolls up...Without proper plugins, even a robust tool like Jira struggles to provide clear dependency visuals. Planning becomes complicated quickly, leaving teams stuck."

Dependency risk increases when shared work isn’t tracked or visualised in a way that’s accessible to all stakeholders. Teams need to see not just their own work, but how it connects with others. Teams need more than awareness - they need shared visibility, clarity on ownership, and consistent ways to plan around dependencies.

How do teams manage capacity when demands keep shifting?

Planning team capacity isn’t just about headcount, but also about competing demands. Teams are often asked to deliver roadmap initiatives while supporting legacy systems, resolving production issues, or addressing technical debt. A product leader from a cybersecurity company shared:

"We’re always trying to achieve a lot with limited resources, and it makes roadmapping really difficult. We’ve made progress in estimating the team's bandwidth more accurately by looking at what they actually delivered last quarter. But we still hit the same issue - too many topics, too little time."

Another team shared how they introduced tighter prioritisation controls using a third-party tool, but even rigid structures have their limits:

"We use XXX as a source of truth for prioritisation. We have around 80 different initiatives prioritised from 1 to 80 of importance... no meeting can be scheduled if the project is not approved in the tool."

This helped formalise approvals and reduce noise, but it also revealed a deeper issue. Even with a strict gating process, the volume of initiatives stayed high, and prioritisation alone couldn’t solve for limited capacity. Clearer structures don’t automatically reduce the demand on teams or ease delivery expectations. That tension persists unless strategic scope is also narrowed.

What makes work breakdown and visibility so hard to maintain?

Breaking down initiatives into independent, testable stories is not always straightforward, especially when scope is uncertain or spans months. A software engineer working across multiple teams explained:

"Breaking work down is hard - some teams still think in layers. They say, ‘This only delivers value when the whole thing’s done.’ On top of that, we often run big planning in a five-hour day or stretch it awkwardly over two days. Third parties and shared services don’t get folded into teams, which makes breakdown and clarity harder."

Large epics often outlive the context in which they were created. As scope evolves, teams may struggle to maintain clear acceptance criteria and shared understanding.

An Agile Coach reinforced how hard it is to keep sight of progress:

"We break each story into smaller pieces as much as possible where it's testable by itself so the testing team can test it... But if it’s a lengthy project, spanning more than two months, it’s easy to lose clarity and effectiveness...Consistently tracking actions across multiple sprints involves endless toggling. It's difficult to quickly understand what's truly improving and what’s still stuck."

As work grows more complex, clarity suffers. Without reliable visibility, work risks stalling or repeating unnecessarily. Teams need tools, systems, and shared language to ensure breakdowns don’t get lost in the shuffle and progress remains meaningful.

Why do changing priorities and scope creep derail plans?

Frequent priority changes and scope creep disrupt planning discipline. They often signal deeper issues: vague goals, shifting leadership expectations, or unclear ownership. One product leader summed it up:

"Priorities used to switch constantly - sometimes halfway through a project, we’d have 30% done and then get pulled into something else. That context-switching really hurts. It demoralises engineers who were already deep into a feature. We had to raise it in a full engineering and product retrospective just to get some stability."

Another shared the toll it takes on delivery teams:

"We often found ourselves mid-quarter pivoting to newly emerging business needs, without fully aligning on what gets dropped. That lack of clarity meant engineers felt whiplash, and team goals kept shifting."

Without stable anchors in the form of clear goals and boundaries, even well-planned work can unravel. Work, then, expands to fill the available sprint, regardless of long-term impact, which brings us to the next challenge.

What stops teams from aligning strategy to daily work?

Teams need clear goals. But clarity breaks down when strategic objectives are too broad or when every team interprets them differently. A senior product manager explained:

"Prioritisation is only as good as your strategy, and ours wasn’t clear. The business goal was just ‘grow revenue,’ but what does that mean? Acquisition? Retention? Everyone wrote their own product objectives. It became a bit of a free-for-all. When goals are vague, it’s hard to prioritise work that ladders up to anything concrete."

Another added:

"We all set objectives tied to broad company goals, but when those goals lack precision, our objectives become misaligned, making prioritisation difficult and often inconsistent."

Without alignment between leadership priorities and team-level execution, valuable work can feel directionless. Objectives become outputs rather than outcomes.

What holds back meaningful retrospectives?

Retrospectives are intended to surface learning. But without consistent follow-through, they risk becoming routine. One Agile Coach shared how to keep them practical:

"We’ve tried tools where you just send a link and everyone rates how hard it was to get something done. But too often, it ends up with one person speaking and everyone else just agreeing. We’re trying to avoid the loudest voice dominating the retro. It’s still a challenge to get real, reflective conversations."

Another shared the risk of retro fatigue:

"To track action items consistently isn't easy... I have to toggle down and look at each one, which can make things cumbersome when ensuring certain behaviours have stuck...Effective retrospectives should surface recurring issues, not just review the recent past. Discussing ongoing challenges helps teams proactively tackle problems and move forward."

The barrier is rarely the ceremony - it’s the follow-up. Teams need lightweight ways to track retro actions, validate changes, and revisit unresolved pain points.

Where to focus

Improving collaboration means addressing the systems and habits that hold teams back:

• Keep strategic conversations active, not just at quarterly planning.
• Visualise and track cross-team dependencies clearly.
• Protect capacity for both roadmap work and operational stability.
• Break work into testable, clearly defined pieces.
• Reinforce the connection between business goals and delivery priorities.
• Make retrospective actions visible and measurable.

The teams we speak to aren’t struggling because they lack process. They’re navigating complexity. The opportunity lies in simplifying where it matters and supporting teams with the clarity to make progress, together.

The first step is recognising these patterns and giving them language. When teams can see and name the problem, they’re already on the path to solving it.

How Easy Agile can help

Whether you're dealing with blurred dependencies, vague objectives or sprint volatility, Easy Agile offers three purpose-built solutions to help teams stay aligned:

• Easy Agile Programs brings structure and visibility to cross-team planning in Jira. Perfect for managing dependencies and long-range planning across multiple teams and projects.
• Easy Agile Roadmaps gives every team a simple, shared timeline view, so they can prioritise and sequence work with strategic context.
• Easy Agile TeamRhythm makes sprint planning, story mapping, and retrospectives more engaging and purposeful, turning agile ceremonies into actionable, team-owned progress.