Program Management

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.

Weaving alignment and empathy into team dynamics can revolutionize software delivery. So why aren't we all doing that?

It's a real challenge for organizations with numerous teams contributing to complex software, to achieve real alignment and consensus on user needs. But it's one well worth pursuing. Striking a balance between alignment on business goals and customer empathy ensures that the software your teams are developing truly resonates with users and fulfills those business goals.

Why Alignment Matters in Agile Programs

Alignment is more than just goal setting across teams. It's about connecting workflows, acknowledging challenges, and crafting solutions that encompass everyone’s perspectives, including the needs of your users. As Tony Camacho shared on the Easy Agile Podcast:

"Alignment isn’t just about goals—it’s about understanding each other’s workflows, needs, and challenges to create solutions that work for everyone."

This comprehensive strategic alignment is crucial for steering teams in the same direction. In large enterprises, team alignment means that agile release trains can function cohesively, and strategic business goals are successfully translated across diverse teams and departments. Strong alignment empowers cross-functional teams to sustain momentum and unity at scale, even as the product roadmap evolves. For agile release trains, effective alignment means that everyone is doing their part, pulling in the same direction, and delivering successful software.  

Customer Empathy and User-Centric Development

Customer empathy is the cornerstone of aligning business goals with user needs and developing software that delivers a seamless user experience. It's about getting to know your users, their needs, and their experience with your product so that you can create better solutions for them.

"The key to meeting user needs is empathy. When teams deeply understand their users, every product decision naturally aligns with providing value."

Tony Comacho

This ethos fuels decision-making and design that prioritizes user needs and values over functional deliverables. It's great to build and release something, but not-so-great if nobody uses it.  Agile leaders who embed empathy within their teams cultivate a customer-driven culture, resulting in software solutions that address genuine challenges and delight their audience.

Empathy enhances the process of gathering requirements, conducting user testing, and embracing iterative design. Combined with effective agile program management, empathy aligns business goals with user expectations, and is a great way to improve engagement with your software and reduce churn, paving the way for successful software delivery and user retention.

Building Clarity for Effective Collaboration

Building impactful software at scale demands effective collaboration and clarity.

"Effective collaboration is rooted in clarity. Teams need to feel supported by having a shared vision and understanding of the product journey."

Tony Comacho

Cross-team alignment revolves around establishing a unified vision and setting clear goals and expectations across the agile release train. For enterprise agile solutions that support PI Planning and Product Roadmapping, upholding this clarity allows large teams to work independently yet cohesively, ensuring a targeted approach to addressing both business and user needs.

How to Achieve Agile Alignment at Scale

To encourage team alignment around user needs in your organization:

• Invest in User Research & Design: Start talking to your users; and keep talking to them. Implement user-focused design practices, gathering insights from users throughout the development stages to effectively align user needs and business goals.
• Share Vision and Goals: Regularly communicate with your teams about business objectives and user needs, ensuring they are central to your agile program.
• Use Alignment Tools and Frameworks: Leverage agile tools that help you track objectives and development milestones to ensure team alignment and cross-team collaboration. Make goals and priorities easily accessible for all your teams.
• Encourage Transparent Communication: Cultivate an environment where feedback crosses team boundaries, maintaining cross-team alignment and empathy.‍

The Benefits of Alignment and Empathy in Software Delivery

Better outcomes for your software start when business goals are aligned with user needs. Programs that place strategic agile alignment and customer empathy at the forefront, not only meet user expectations but improve the value they offer to their customers. With good agile program management, the outcome is a streamlined, effective agile release train that consistently delivers exceptional software solutions. Which is what we all want, right?

As you work towards better alignment in your agile program, nurturing empathy and clarity can unlock significant gains in satisfaction for your users and for your teams, which is great news for the overall success of your program.

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🎧 Want to hear more from Tony? Listen to The power of team alignment on the Easy Agile Podcast.

Agile is about being flexible and always getting better—essential for delivering great software. But when scaling agile across teams in a program, being adaptable and flexible is easier said than done. In this post, we'll dig into the ins and outs of agile program management to help you:

• Tackle common challenges
• Use metrics and feedback loops to keep improving
• Leverage leadership for the best chance of success

By identifying some clear and actionable steps that you can start implementing now, you’ll improve your approach to program management and make your software delivery smoother and more efficient.

Overcoming Common Challenges in Agile Program Management

From dealing with dependencies to managing stakeholder expectations and balancing speed with quality, here are some challenges you might face now.

Dealing with Dependencies

Dependencies are a necessary part of working on complex software, and they need to be managed carefully to avoid disrupting delivery schedules.

Identifying dependencies early is key to keeping things running smoothly. By spotting potential bottlenecks early, like during PI Planning, we can nip them in the bud before they turn into major headaches, and:

• allocate resources more effectively
• streamline communication across teams
• keep everyone on the same page with a shared timeline.

Maintain clear communication channels and regular alignment meetings to address dependencies swiftly and efficiently. This helps everything stay in sync, and hopefully avoids last-minute 'surprises', for a more reliable delivery.

Managing Stakeholder Expectations

We can't deliver complex software on our own, so ensuring that our colleagues are informed and onboard is critical. Managing expectations across a large program is a complex challenge, but you'll be off to a great start if you are able to keep communication consistent:

• Regular Updates: Keep the lines of communication open and honest, and provide frequent updates to keep everyone in the loop.
• Be Transparent: Maintain a central source of truth for project information that everyone has access to, ensuring that objectives, milestones and priorities are clear.
• Set Realistic Expectations: Avoid over-promising and stay realistic about what can be achieved.
• Prioritize and Manage Feedback: Inevitably, there will be changes in priorities or feedback from stakeholders. It's important to have a process for managing these requests and ensuring they align with the program goals.

Agile tools that offer clear visibility into objectives, dependencies, and progress, can be the bridge between your development teams and stakeholders in leadership and other parts of the business.

By focusing on these areas, you’re not just managing expectations—you’re making sure everyone is part of the process.

The bridge between development teams and leadership, with objectives, milestones and dependencies all in one. Watch a demo or try for yourself.

Easy Agile Programs

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Balancing Speed with Quality

In a perfect world, we would all deliver amazing software that our customers love, at lightning speed. But the reality is that balancing time-to-market with quality is an ongoing challenge.

Agile practices like organizing work to deliver incrementally are part of the solution; they help identify problems early and deliver in a way that makes more sense than following a Gantt chart until the timelines blow out and it all falls over.

So while agile won’t make your development teams type faster, it can help them, as well as your colleagues in Product, and QA, learn what works faster, and how they can collaborate better to deliver work with quality.

Metrics and Feedback Loops

Metrics can be a powerful tool in agile program management. Velocity, burn-down charts, cycle time, lead time, and dependency reports can give valuable insights into how our teams are performing and how our projects are progressing.

• Velocity: Long-term trends help us understand team commitment over time, and estimate what can be achieved going into a sprint.
• Burn-down charts: Valuable for gauging progress throughout execution and spotting barriers to delivery.
• Cycle time: Uncover inefficiencies or bottlenecks where tasks are likely to get delayed or stuck.
• Lead time: Use the difference between an expected lead time and the actual lead time, as a starting point for understanding where delivery is being held up.
• Dependency reports: Use a snapshot of dependencies in your program to understand how teams are dependent on each other and where the biggest risks are.

Monitoring these metrics will give you a clearer picture of where work is progressing well and where you might need to make adjustments. Think of them as your project’s health check-up; a temperature check that can improve the predictability of your release.

With powerful dependency reports, you can identify bottlenecks, streamline communication, and keep your projects on track.

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Establishing Effective Feedback Loops

Feedback loops are integral to delivering software with market fit. Sprint reviews and retrospectives offer teams the opportunity to reflect on their performance, identify areas for improvement, and make necessary adjustments. DevOps practices like continuous integration further ensure that the code is consistently tested and integrated, reducing the risk of significant issues going unnoticed.

Using metrics and feedback loops allows teams to deliver software with greater predictability and transparency. Applying these practices consistently across a program means that you're better able to manage the planning and execution of work to deliver complex software to your customers in a predictable way.

The Role of Leadership in Agile Program Management

Great leadership is key to building an agile culture. It's not just about making decisions from the top; it's understanding team needs and clearing the way for them to be effective. But old 'command and control' habits are difficult to break.

As a program manager, you're the glue that connects the strategic vision of leadership with the hands-on work of development teams. Keep those communication lines open and reciprocal, so everyone understands the business goals and the strategic importance of their tasks, as well as progress and barriers to execution.

• Use agile tools to maintain a central source of truth, to give everyone a clear view of project progress and potential roadblocks.
• Foster a culture of regular feedback and continuous improvement. This proactive approach helps tackle challenges head-on and keeps everyone aligned with business objectives.
• Promote transparency and adaptability to help teams quickly adjust to changing priorities.

Keep these things in mind to help you plan and deliver with confidence. You may be the glue that holds it all together, but you can't be everything for everyone. Enlist help where you need it, and encourage an open and transparent culture where strategic priorities are understood, and everyone can see how the focus of their work contributes to the bigger picture.

An Agile Approach to Change

Taking a new approach to program management doesn’t need to be daunting. Once you’ve identified the changes that make sense for you, take an agile approach and implement incrementally. Every small change you make adds up over time and can lead to measurable improvement.

How Easy Agile Programs Can Help

Easy Agile Programs is a Jira integration that supports agile program management. It is a central source of truth for the issues, milestones, team objectives, and dependencies that make up a program of work.

Dependency maps and reports help you see the nature of cross-team dependencies clearly, so you and your teams can reorganize to avoid roadblocks that would otherwise blow out timelines with unexpected delays.

Easy to set up and tightly integrated with Jira, Easy Agile Programs supports scaled team planning and execution so you have greater confidence in delivering great software as each program increment begins.