Why Team Planning Will Feel Harder Than It Should in 2026 (and What To Do About It)
TL;DR
Sprint planning feels harder because distributed/async work, tool consolidation, and Atlassian AI expose priority noise, software estimation problems, and hidden dependencies. This guide shares three team planning best practices - set a clear order of work, estimate together to surface risk, and close the loop with action-driven retrospectives, so team alignment and team collaboration improve and plans hold up.
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Sprint planning should not feel like a shouting match where the loudest voice wins. Yet for many teams it has become a long meeting that drains energy, creates a weak plan, and falls apart by Wednesday.
The problem is not that your team forgot how to plan. The world around the plan changed. People work across time zones. More decisions happen in comments and tickets than in rooms. And the plan lives in tools that other people (and AI‑powered search) will read later. When the audience shifts from "who was in the meeting" to "everyone who touches the work", the plan must be clearer and better organised.
On one hand, AI and asynchronous collaboration are on the rise. On the other, we have a direct link between strong delivery capabilities and better performance. And those two lines meet in planning - if inputs are unclear, you simply do the wrong things faster.
Want to dive deeper? Get our Guide to Building Predictable Delivery with Jira in 2026.
We believe planning feels harder because three foundational elements have broken down:
- How priorities turn into an order of work,
- How estimates show risk (not just numbers), and
- How suggestions for improvements turn into real work.
When these are weak, planning becomes an exercise in managing metal overload rather than building a clear path forward.
This piece examines why sprint planning has become so difficult, what changed in 2025 to make it worse, and most importantly, how teams can fix those three foundations so your plan still makes sense when someone who missed the meeting reads it two days later.
The mental load of modern planning
"Cognitive load" is simply the amount of mental effort a person can handle at once. Every team has a limit on how much information they can hold at any given moment, and planning meetings now push far past it.
At the same time, teams are asked to:
- Rank features against unclear goals,
- Estimate work they have not fully explored,
- Line up with platform teams whose time is uncertain,
- Balance different stakeholder requests,
- Figure out dependencies across systems they do not control, and
- Promise dates that others will track closely.
Plans are often made as if everyone is fully available and not also working on existing projects and tasks. And we all know quite well, that is never the case. When the mental load is too high, teams cannot safely own or change the software they're working on.
Planning then becomes a bottleneck where teams spend more time managing the complexity of coordination than actually coordinating. Decisions slip, assumptions go unchecked, and the plan that comes out is not a shared understanding but a weak compromise that satisfies no one.
Where priorities fail
In most planning sessions, "priority" has lost its meaning. Everything is P0. Everything is urgent. Everything needs to happen this sprint. If everything is top priority, nothing is.
Teams struggle to prioritise because there are too many moving parts at once: lots of stakeholders, long backlogs, and priorities that change week to week. Most prioritisation methods like MoSCoW, WSJF, and RICE, work for a small list and a small group, but they stop working when the list and the audience get big. Meetings get longer, scores become inconsistent, and re-ranking everything every time something changes isn’t practical. People also learn to “game” the numbers to push their item up.
There’s a second problem: these methods assume everyone agrees on what “value” means. In reality, sales, compliance, platform, design, and support often want different things. Numeric models (like simple scoring) miss those differences, because some trade-offs (like brand risk, customer trust, regulatory deadlines) are easier to discuss than to put into a single number.
A flat product backlog makes this worse. As Jeff Patton says, reading a backlog as one long list is like trying to understand a book by reading a list of sentences in random order - all the content is there, but the story is gone. Without the story, “priority” becomes a label people use to win arguments rather than a clear order of work.
Put simply, when the work and the number of voices grow, the usual techniques can’t keep up. If you don’t have a way to surface different perspectives and settle the trade-offs, decisions drift from strategy, plans keep shifting because they were never tied to outcomes, and engineers stop seeing why their work matters.
The estimation show
Teams are generally too optimistic about effort and too confident in their estimation numbers. On average, work takes about 30% longer than expected. Even when people say they’re 90% sure a range will cover the actual effort, it only does so 60–70% of the time.
Translation: confidence feels good, but it does not mean accuracy.
The deeper issue is how we estimate. It often becomes a solo guess instead of a shared check on risk.
Here's what actually happens - someone sees a work item called “Update API,” give it 5 points based on the title alone, and the team moves on. No one tests the assumptions behind the number.
Nobody talks about the auth layer changes implied by "update." Nobody brings up the database migration hiding in plain sight. Nobody checks whether the frontend team knows this change is coming.
And when those show up mid-sprint, the plan slips and trust drops.
After a few misses, behaviour shifts for the worse. People start padding their estimates - quietly rounding numbers up to feel safe. Product then starts pushing back. And estimation turns into negotiation, not learning.
A healthier signal to watch is the spread of estimates. A wide spread of estimates isn't a problem to smooth over, but rather a signal to discuss assumptions. Most likely, there will be some difference in the initial estimates, giving each team member a great opportunity to talk about why their estimates were either higher or lower than the others.
The coordination cost of dependencies
When different teams own connected parts of the system, one team’s work often can’t move until another team makes a change. If those teams aren’t lined up, the change gets stuck.
This is common when how the software is wired doesn’t match how the teams are organised.
For example, the code says “Service A must change before Service B,” but A and B live in different teams with different priorities, sprint dates, and intake rules. The code requires coordination, but the org chart doesn’t provide it.
In large organisations, these small, work item‑level links are a constant source of delay. And it has only gotten worse in recent times.
Platform engineering has grown, with most features now touching shared services - auth, data platforms, CI/CD, component libraries. But planning often happens without the platform team in the room. No one checks their capacity, no one tests the order of work, and theres no agreement on intake windows or what to do when something is blocked.
So the plan looks ready on paper. Stories are sized. The sprint is committed. Then, three days in, someone says at stand‑up: “That API won’t be ready until next Tuesday,” or “The platform team is tied up,” or “Friday’s deployment window isn’t available.” Work waits, people wait, and money burns while nothing moves forward.
Dependencies increase complexity in any system. More complexity means more idle time as work passes between people or teams. Developers, then, often end up waiting for other work to wrap up before they can begin, creating inefficiencies that add no value but still cost payroll and budget.
What changed in 2025
Three shifts in 2025 made planning even harder:
1. Distributed work reduced live coordination.
Hybrid days replaced being in the same room every day. More work happens asynchronously. That means your written plans and notes like sprint goals, story maps, dependency notes, must explain what real-time conversations used to cover: why this work matters, what comes first, what won’t fit, who’s involved, and what could block you. Vague goals that could be fixed in person now fall apart across time zones.
2. Fewer tools, one system.
Teams cut vendors to reduce spend. Planning, estimation, and retrospectives moved into one solution, whether they fit well or not. While that reduces context‑switching, it also means that teams would have to lose specialised tools and custom workflows. It also means that stakeholders can see the full line from strategy to stories in one place, so your sprint goals, estimation notes, and retro/improvement actions will be read more closely.
3. Atlassian AI raised expectations.
Atlassian expanded Rovo across Jira and Confluence. Search, governance, and automation now connect conversations to issues and speed discovery. And the thing about AI is that it accelerates whatever direction you're already pointed. If goals are fuzzy, if estimates are guesses, and if dependencies are hidden - the automation will just help you go faster in the wrong direction.
The combination of all these changes is brutal - more coordination required, less overlap to coordinate in real-time, and higher penalties when plans fail because stakeholders can now see more of the picture.
Fixing the foundations in 2026: sprint planning best practices
The teams that will make planning work in 2026 will rebuild their foundations with three planning best practices. They’re simple, written rules the whole team follows. They live on the planning board and the work items, so they still make sense after hand-offs and across time zones.
1. Turn priorities into a clear order of work
“Priority” breaks when people don’t share the same idea of value. The fix is to agree on a single, visible order - why this first, then that, and what won’t fit this sprint.
Teams that get this right:
- Turn goals and outcomes into backlog work on a steady rhythm, not ad-hoc.
Once a month, product and delivery confirm objectives and break them into epics and small slices for the next 6–8 weeks. This keeps meaningful work in the pipeline without crowding the backlog assumptions and wishes that will change anyway.
- Write testable sprint goals using a consistent template.
Objective, test, constraint. Set clearly defined goals, objectives, and metrics. What is the definition of done? How will the team know if they are successful? You should leave the sprint planning meeting with a clear idea of what needs to get done and what success looks like. For example, "Users can complete checkout using saved payment methods without re-entering card details" is much better than "improve checkout UX" every time. If you can't verify whether you hit it, it's a wish, not a goal.
- Run a 30-minute review before scheduling anything.
Agree the order of work before fixing the dates. In 30 minutes with engineering, design, and platform teams: walk through the dependency list, check the capacity, and identify top risks. Output: ordered path to done, clear boundary of what won't fit that sprint, and a simple rule for how you’ll handle blocked items. This surfaces cross-team friction before it becomes a mid-sprint crisis.
- Make dependencies visible where people actually plan.
Use one standard dependency field and two to three link types in Jira. Review the highest-risk links during planning - not when they block work on day three.
Easy Agile TeamRhythm's User Story Maps makes this process concrete - Build goals and outcomes at the top, work items that connect to those goals, and sprint or version swimlanes to clearly group them. Turn on dependency lines so blockers and cross-team links show up in planning. When epics ladder to outcomes, when the order of work explains itself, and when dependencies are visible on the same board - you stop rethinking priorities and start shipping.
2. Estimate together to find risk early
Estimation is not about hitting a perfect number. It is a fast way to identify risk while you can still change scope or order. Treat it as a short, focused conversation that makes hidden assumptions visible and records what you learned.
- Estimate together, live.
Run Planning Poker from the Jira issue view so everyone sees the same title, description, acceptance criteria, designs, and attachments. Keep first votes hidden and reveal them all together (so the first number doesn’t influence the rest).
Easy Agile TeamRhythm help you run the estimation process in Jira, right where work lives. Capture the key points from the discussion in comments in the issue view. Sync the final estimate number back to Jira so your plan is based on current reality, and not old guesses from two weeks ago.
- Record the reasoning, not just the number.
If a story moves from a 3 to an 8 after discussion, add two short notes on the work item:
- What changed in the conversation (the assumption you uncovered), and
- What’s still unknown (the risk you’re facing)
This helps the next person who picks it up and stops you repeating the same debate later.
- Stick to clear, simple scales.
Time estimates vary a lot by person. Story points help teams agree on the effort instead. If you ask each team member to estimate the amount of time involved in a task, chances are you'll get 5+ different answers. Timing depends on experience and understanding. But most team members will agree on the effort required to complete a work item, which means you can reach a consensus and move on with your story mapping or sprint planning much more quickly.
Maintain a small set of recent work items (easy/medium/hard) with estimates and actuals. When debates don't seem to end, point to this known work: "This looks like that auth refactor from June - that was an 8 and took six days including the migration script."
- Limit committed work at roughly 80-85% of average capacity.
The space makes room for one improvement item, for unavoidable interrupts, and for reality. Setting unachievable goals sets your whole team up for failure. Failing to meet your sprint goals sprint after sprint is damaging for team motivation and morale. Use estimates to set reasonable goals as best you can. Consider team capacity, based on your past knowledge of how long tasks take to complete, how the team works, and potential roadblocks that could arise along the way.
Protect honesty in the estimate numbers. An estimate is a shared view of scope and risk, not a target to enforce. If it needs to change, change it after a team conversation - don’t override it. Remember what we said earlier - when estimation turns into negotiation, people start “padding” (quietly inflating a number to feel safe), and accuracy gets worse.
3. Closed the loop on improvements
Teams often fall into the trap of writing retrospective items as good intentions and not clear actions. Broad notes like “improve communication” or “fix our process” sound fine on paper, but they don’t tell anyone what to do next.
Action items are often ignored during a retrospective. Everyone focuses on engaging people in getting their ideas out, and not as much time is spent on the action items and what's going to be done or changed as a result.
- Start every retro by checking last sprint’s actions.
Ten minutes. Did we close them? If closed, did they help? What did we learn? This way, the team acts on what they learned straight away and everyone can see what changed.
- Turn insights into Jira work items immediately.
Each action needs an owner, a due date, a link to the related work, and a clear definition of done. If you can’t assign it immediately, it’s not actionable, it’s a complaint.
Easy Agile TeamRhythm's Retrospective lives right inside Jira, attached to your board. Turn retrospective items into Jira issues with owners and dates, link them to an epic or backlog item, and slot at least one into the next sprint. Track incomplete action items and repeating themes on the same page as delivery work.
- Make space for one improvement item every sprint.
Pick one action item for a sprint and finish it before starting another, so it doesn't get pushed aside by feature work. Treat action items like a feature: estimate it, track it, and close it with a note about the result and impact.
- Write a short impact note when you close an action.
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.
Write a one-line impact note for every closed action item, ideally with a small metric - for example, "Batched PR reviews into two daily slots - median review time dropped from six hours to 90 minutes." This teaches the next team, justifies the investment, and shows that retro action items increase the team's capacity to deliver, and are not admin overheads.
What changes when you follow the planning best practices
Teams with solid sprint planning foundations rarely talk about them. They’re not on stage explaining their process. They’re just shipping steady work while everyone else wonders what their secret is.
There is no secret. The best teams have simply stopped treating planning as a meeting to survive and started treating it as a system of best practices that compound over time.
The mental load of planning sessions does not go away. But it shifts. Instead of processing all of it live in a room under time pressure, these teams have recorded their answers into written plans and notes that do the thinking for them.
The user story map explains what matters and why. The order of work shows dependencies before they block work. The estimation scores and notes capture not just numbers but the assumptions behind them. Retro action items sit next to product work, so the next sprint benefits from what the last one learned.
Fix the best practices and your sprint planning challenges will reduce. Not perfectly. Not forever. But enough that planning stops feeling like a crisis and starts feeling like what it should be: a calm view of what is possible now, with simple ways to adjust as you learn.
The cost of unclear plans is rising. AI speeds up what you feed it. Stakeholders can see more details easily. Work happens across time zones. In that world, clarity isn't a nice-to-have - it's a basic requirement.
The teams that will do well in 2026 aren't the ones with better tools or smarter frameworks. They’ll be the ones with a few simple best practices written into the plan and the work items, so handovers are easy, others can check and understand them, and they still make sense after the meeting.
The Guide to Team Collaboration with Jira in 2026 examines how Atlassian's recent moves and other work trends in 2025 change the way team plan, and what you can do now to avoid falling behind.
Related Articles
Agile Best PracticeHow To Avoid These 6 Agile Planning Mistakes
Planning is a critical phase of the agile process; it's an opportunity to align on priorities as team and organize work in a sequence that will help it run smoothly. The planning process helps agile software development and other product development teams sort through new information, adapt to dependencies, and address evolving customer needs.
Agile is the opposite of traditional waterfall project planning, which takes a step-by-step approach. Waterfall has dominated project planning for many years, with detailed plans laid out at the beginning of a project that had to be adhered to rigidly. This may move a project or product forward, but it neglects to account for any new developments that could occur outside of the “master plan.”
Agile is an iterative process that helps teams reduce waste and maximize efficiency for the ultimate goal of bringing value to customers. This customer-first approach helps teams make informed choices throughout the development process — choices that continually and consistently provide value to stakeholders.
One of the greatest advantages of an iterative agile approach is that it enables early feedback from stakeholders. You don’t need to guess whether or not you’re making the right decisions — you can find out every step of the way by directly including stakeholders in your process. You can adapt your plan as you need to based on what will provide the most value to customers at any time.
Even if you are part of a seasoned agile team, there are always opportunities for improvement and processes to fine-tune. This post will outline some unproductive agile planning mistakes teams make, including how agile teams can avoid these common pitfalls.
Agile Planning Mistake #1: Not being on the same page as stakeholders
Do you involve stakeholders in your planning process? Do they understand your goals and why you are making each decision? Working directly with stakeholders, both internal stakeholders and the users of your product, will help you gain a clear view of both needs and constraints, and give you the information you need to determine what should be done when.
It's never a good idea to rest on assumptions. Your stakeholders live in a different world than the one you are deeply embedded in, with different priorities and assumptions of their own. So that you can produce deliverables that meet stakeholder expectations, you need to agree on what those expectations are. Involve your stakeholders in planning, but ensure everyone understands that expectations could evolve throughout the process based on new information gained from successes, failures, and customer responses.
Agile Planning Mistake #2: Not accounting for dependencies
Failing to account for dependencies in agile planning leads to bottlenecks, delayed releases, and undermines team collaboration. Collaboration within and across teams is needed for a business to deliver effectively. When multiple teams are working on interconnected features, if one team’s progress is blocked by another, the entire development cycle slows down. Without clear visibility of dependencies, work can be delayed and deadlines missed.
To minimize and avoid disruption to the flow of work, take the time to consult with stakeholders and anticipate dependencies early. Tools that help you visualise and map dependencies, and shared roadmaps to track cross-team dependencies, allow you to share an understanding of dependencies and sequence work in a way that avoids roadblocks. Proactively managing dependencies ensures smoother iterations, faster time-to-market, and a more predictable agile process.
Agile Planning Mistake #3: Using bland, flat product maps
Flat product backlogs are bland and boring 😴. Think carrot cake without icing. They lack the detail and functionality needed to realize the full story of your product backlog.
Plus, once you have more than a handful of items, they become overwhelming and difficult to organize in a meaningful way. It becomes less clear which item is the most important and more difficult to ensure your decisions align with the larger goal of the project.
When you plan out your roadmap, it needs context, and you must be able to clearly see the customer journey. User story maps visualize the customer journey in the planning process and throughout the entire process of product development. They utilize user stories — the smallest unit of work that can bring value to the customer — so you can plan and organize the backlog from the customer’s perspective.
📕 Read our ultimate guide to user story maps to learn more.
Agile Planning Mistake #4: Not allowing the plan to live, breathe, and adapt
As we've already discussed, agile is an iterative approach. This means your agile planning needs to leave room for changes. Your plan should be able to grow and adapt as you progress with each sprint or product roadmap.
At the beginning of a sprint, you lack the information needed to see the full picture. You don’t have everything you need to build the perfect solution, and that’s okay. It’s all part of the process. Spending hours or days trying to iron out the perfect plan just wastes time that could be better spent learning and solving problems as they come. What you thought would provide the most value during the planning phase could be completely different down the track.
You may need to alter your plan after a roadblock comes up in a daily stand-up, or you may learn about a customer concern that completely changes your direction. Iterations are inevitable and welcomed! They help you keep pace with incoming information as you learn from each other, stakeholders, and your customers.
Agile planning isn’t a promise. It’s an outline that will help you reach your goal, and that changes with your goals and circumstances.
Agile Planning Mistake #5: Not incorporating retrospective insights in the following planning session
Retrospectives are an essential piece of the agile process. They give teams a chance to reflect on everything that occurred in an individual sprint or after the completion of a product.
An effective retrospective asks the entire team key questions that can improve the process next time around. What went well? What’s worth repeating again? What didn’t go so well? What could be improved upon next time? What roadblocks or dependencies developed? What did you learn? How did you feel at the end of the sprint?
A retrospective provides insights that will improve efficiency, teamwork and team dynamics, the effectiveness of tools, and communication with stakeholders.
Simply holding a retrospective or collecting retrospective feedback is not enough to gain value. You need to ensure you’re incorporating the feedback into the following sprint planning meeting, and take action that leads to meaningful improvement. The next iteration will be all the better for the time you spend reflecting and improving based upon what you learned.
Agile Planning Mistake #6: Choosing tools that don’t take a customer-centric approach
Whether your team uses a Scrum process, kanban boards, or other agile methods, the tools you choose should always be customer-focused. And you need to continue using them in a way that keeps the customer at the forefront of decision making.
Teams can fall into a trap believing they’re focusing on the customer when they aren’t doing much of anything beyond following simple agile methods and generic processes. Customers need to be embedded in your development process right from the planning phase so that every decision a team member makes considers customer needs first.
Choose planning tools that help your entire team get to the heart of what makes your customers tick, and always check in to ensure you are making decisions in line with your customers.
For example, Personas provide a deep understanding of what customers want, need, don’t want, etc. They reveal key information about customer pain points, desires, demographics, goals, shopping patterns, and much more. We highly suggest developing customer Personas to get a rich picture of all the people who will use your product, but it’s not enough to just have Personas lying around.
You need to bring these Personas into your agile planning process and keep them front and center as you complete issues and continue to develop your product.
WorkflowWhen the Numbers Don't Matter: Why Teams Miss Deadlines Despite Perfect Estimates
TL;DR
Agile estimation challenges are rarely about the number. Planning poker is useful when teams treat vote spreads as signals about scope, risk, and dependencies. Software team alignment during estimation improves sprint predictability more than chasing velocity. Velocity alone cannot forecast capacity because context changes across sprints. Coordination work must live in Jira as first-class items, or retro actions will not get done. Easy Agile TeamRhythm keeps planning and estimation in one place: story mapping for sequence, planning poker on the issue for shared context, and retrospective actions that turn into tracked work. The new ebook, Guide to Building Predictable Delivery with Jira in 2026, explains how to plan with clarity, align on effort, and turn problems into progress. The outcome is fewer rollovers, clearer handoffs, and more reliable delivery.
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Estimation in software teams has become a performance ritual. Planning poker sessions run smoothly, story points get assigned, and even velocity charts trend upward.
Yet research analysing 82 studies found five recurring reasons why estimates fail: information quality, team dynamics, estimation practices, project management, and business influences.
The point is, the problem with estimations runs deeper than accuracy - it's about what teams miss whilst focusing on the number.
When a team estimates a story and three people say it's a 3 whilst two say it's an 8, that spread contains more value than whatever final number they settle on. The disagreement signals different assumptions about scope, reveals hidden dependencies, exposes risks before code gets written. But most teams treat the spread as a problem to resolve rather than intelligence to extract. They discuss just long enough to reach consensus, record the number, move on.
The estimation ritual runs perfectly, while the coordination that estimation should enable never happens.
Why the number misses the point
Communication, team expertise, and composition decide how reliable an estimation will be, far more than the technique itself.
A team of senior engineers who've worked together for years will generate different estimates than a newly formed team with mixed experience, even looking at identical work. Neither set is wrong - they reflect different realities.
Problems emerge when organisations ignore this context and treat estimates as objective measurements.
Story points get summed across teams. Velocity gets compared across squads. Estimates meant to help one group coordinate become data points in dashboards, stripped of the shared understanding that gave them meaning.
What planning poker actually reveals
Planning poker works when teams use it to promote collaboration, uncover risks, and address uncertainties proactively. Those benefits vanish when teams rush past disagreement to reach a number.
Someone who estimates low might:
- Know a shortcut from previous work
- Have solved something similar before
- Understand a technical approach others haven't considered
Someone who estimates high might:
- Have spotted an integration challenge
- Questioned an assumption in the requirements
- Remembered something that broke last time
- Identified a missing dependency
Both pieces of knowledge matter more than splitting the difference.
Teams that skip this interrogation lose their only reliable way to discover what they don't yet know. Later, when work takes longer than estimated, they blame the estimation technique. They should blame the coordination failure that happened during estimation.
How team members add context
Research indicates that even team members whose skills aren't needed for an item contribute valuable questions during planning poker.
The database person asks about data volume. The designer notices a missing edge case. The platform maintainer flags a version incompatibility.
None of them are trying to make the estimate bigger to protect themselves. They're raising legitimate technical considerations that affect how much work is actually involved. These questions reveal real complexity the team needs to account for. That's different from someone saying "Let's call it an 8 instead of a 5, just to be safe" without any specific reason (that's called "padding", and a team must avoid that at all costs).
When estimation becomes a solo activity or a quick management decision, all that context disappears. Work looks simpler than it is, not because anyone lied, but because key voices never got heard.
Why team coordination matters more at scale
Coordination ranks as one of the biggest challenges in large-scale software projects, particularly with complex codebases and multiple teams working simultaneously. As organisations scale, coordination problems increase:
- Dependencies multiply across teams. What used to be a conversation between two people in the same room now requires checking another team's roadmap, finding out who owns a component, and waiting for their sprint to align with yours.
- Handoffs increase between specialists. A feature that one full-stack developer could build now needs a frontend specialist, a backend specialist, a platform engineer, and a data analyst - each working on different schedules with different priorities.
- The margin for error shrinks. When you're coordinating work across five teams instead of one, a single miscommunication or missed dependency can block multiple teams at once, not just delay one work item.
- Assumptions travel further from their source. The product manager who spoke to the customer isn't in the room when the backend developer makes a technical decision. The context that shaped the original requirement gets lost through layers of handoffs and documentation.
Estimation sessions are often the only moment when everyone involved in delivering work actually talks about it before starting. Treating that time as a box-checking exercise to produce velocity data is one of the biggest mistake you could make as a team.
When estimates protect plans instead of revealing risks
Let's look at a familiar scenario. A team commits to eight features based on historical velocity. Three sprints in, two features ship and the rest need another month. Marketing campaigns get delayed. Customer pilots get postponed. Executive presentations need rewriting.
The team "missed commitment," so stakeholders lose confidence.
Next quarter, product managers add extra weeks to every timeline just to be safe. Engineering leaders give longer forecasts they know they can beat rather than their honest best estimate. Everyone protects themselves, the system slows down, trust erodes further.
Now, step back - why did the team commit to eight features in the first place? Usually because velocity suggested they could complete them.
The velocity number reflected what they'd delivered in the past. What it didn't reflect was whether those sprints had taught them anything, whether dependencies were worsening, whether technical debt was compounding, or whether the work ahead resembled the work behind.
Why velocity numbers mislead
Velocity treats delivery capacity as stable when it's dynamic.
Teams get faster as they remove friction and slower as complexity increases. Last sprint's number is already outdated, yet sprint planning sessions treat it as a reliable forecast.
Consider what velocity cannot tell you:
- Whether the team learned from previous mistakes
- Whether technical debt is slowing new work
- Whether dependencies have become more complex
- Whether the upcoming work requires unfamiliar technology
- Whether key team members will be available
Better agile estimation techniques won't fix coordination problems. But teams can fix coordination problems if they treat coordination itself as work that deserves attention.
Why fixing coordination problems matters for estimation
Teams that have messy estimation sessions usually know exactly what's wrong.
Someone will say it in standup: "We should really refine stories before planning."
Another person mentions it in Slack: "We need to check dependencies earlier."
It even comes up in the retrospective: "Our estimates are all over the place because we don't understand the work."
The insights are there. What's missing is follow-through.
Look at your last three retrospectives. How many action items got completed before the next one?
The average completion rate for retro action items sits around 0.33% - teams basically complete almost none of them. And that's mainly because the improvement actions exist outside the system that schedules work.
During retrospectives, teams identify real problems:
- "Our estimation sessions run too long because we don't refine stories beforehand"
- "We keep getting surprised by infrastructure work that's not in our backlog"
- "We never follow up on the spikes we create"
- "Dependencies block us mid-sprint because we didn't check capacity with other teams"
All true. All important. Then the retrospective ends, everyone returns to their sprint board, and those insights have nowhere to go.
The backlog contains features. The sprint contains stories. And improvement work lives in meeting notes, if anywhere. So it doesn't compete for capacity, doesn't get assigned an owner, doesn't get tracked, and doesn't get done.
How to make improvement work visible
Usage data from Easy Agile TeamRhythm showed teams completing only 40-50% of their retrospective action items. After releasing features to surface and track incomplete actions, completion rates jumped to 65%.
The mechanism was simple:
- Convert retrospective insights into Jira work items
- Give each one an owner
- Slot them into upcoming sprints like any other work
- Make incomplete action items from the previous retros more visible
When teams actually complete their retrospective actions, estimation gets better without changing the estimation technique. Stories get refined before planning, so there's less guesswork. Dependencies get checked earlier, so there are fewer surprises. The team builds shared understanding over time, so the spreads in planning poker get narrower and the discussions get shorter.
As you can see, this is a ripple effect.
Coordination problems compound when ignored, but they also improve when treated as real work.
A team that never fixes its planning problems will have messy estimation sessions next quarter, and the quarter after that. A team that deliberately improves coordination will gradually need less time to reach better software team alignment and their estimates will become more reliable as a byproduct.
What this means for tools and practice
Most planning tools were built to manage tasks, not support the conversations that help teams coordinate around those tasks. The challenge now is making coordination visible and trackable in the same place where delivery work happens.
Easy Agile TeamRhythm keeps coordination work alongside delivery work.
✅ User Story Map shows how work connects to goals, making sequencing a shared discussion instead of someone's private spreadsheet.
✅ Planning poker happens inside the Jira issue, where everyone sees the same acceptance criteria and attachments - so the spread of estimates becomes a trigger for conversation, not a number to agree on.
✅ Retrospective actions convert directly into backlog items that get added into upcoming sprints, so improvement work gets the attention it deserves.
The stakes for getting this right are rising. Atlassian's push towards AI assistance means your planning documents will be read by more people and processed by more systems. When Rovo searches your Jira instance, it surfaces whatever you've written - clear goals and explicit dependencies, or vague titles and hidden assumptions.
A fuzzy sprint goal doesn't just confuse your team. It confuses the dozen people across three time zones reading your board asynchronously, the automation trying to identify relevant work, the AI assistant trying to generate status updates, and the stakeholders trying to understand progress.
Where this leads
The teams that succeed over the next few years won't be the ones with the most sophisticated agile estimation techniques or the highest velocity scores.
They'll be teams where planning poker uncovers risks instead of producing commitments. Where retrospectives generate work items instead of wishful thinking. Where coordination shows up in Jira instead of getting discussed in conversations that disappear.
They'll be teams that figured out estimation was never about the numbers. It was always about getting everyone pointed in the same direction, with their eyes open, before the work starts.
The number is just what gets written down. The conversation that takes the team to the number is where the real work lies.
Agile Best PracticeAgile Team Trends 2026: Research Insights on Collaboration, Planning, and Delivery
Every year brings another round of agile predictions. Most are speculation dressed up as insight.
This one is different.
We surveyed 419 engineers, product managers, and project managers across companies ranging from 50 to over 5,000 employees in the US, UK, Germany, Canada, and Australia. We asked them how they actually work: how they estimate, how they plan sprints, how they run retrospectives, and where things fall apart. Here's the full version of the State of Team Alignment 2026, if you're interested.
And the findings revealed something interesting - teams are confident, collaborative, and still struggling to deliver predictably.
Here's what the data says about where product and engineering teams will need to focus in 2026.
Most teams are confident in their estimates. The data says they shouldn't be.
When we asked how confident team members feel about their estimates, 63% reported feeling "very" or "extremely" confident. Another 24% said "moderately confident."
That sounds healthy. But when we asked how often tasks end up significantly larger or smaller than estimated, 44% of teams said this happens on roughly half their work or more.
There's a gap between how teams feel about estimation and how estimation actually performs.
Part of the explanation lies in method. Only 31% of teams use collaborative estimation techniques like Planning Poker. The rest split between asynchronous or solo estimation (37%) and having a single person estimate for the whole team (30%). When estimation happens in isolation, there's no opportunity to surface the questions that reveal hidden complexity. The senior developer who knows the authentication system is brittle doesn't get to flag that the "simple" login change will require refactoring. The new team member doesn't get to ask the clarifying question that exposes a misunderstood requirement.
There's also the question of what teams are estimating. Most estimate time: 55% use hours or days. But time and complexity aren't the same thing. A junior developer updating button colours across multiple pages and a senior developer debugging a race condition in an API call might both get estimated at three hours. The difference is that the button task will probably take three hours. The race condition might take three hours or twelve, depending on whether the first hypothesis is right.
When most estimation is time-based and most estimation happens solo, variance is predictable.
What 2026 demands
Teams that want to improve sprint predictability need to move estimation from a box-ticking exercise to a conversation. That doesn't necessarily mean adopting Planning Poker wholesale. It might mean adding a five-minute discussion for any item flagged as high-complexity. It might mean asking "what could make this bigger than we think?" before committing to a number. The teams in our survey who estimate collaboratively report higher confidence, and their confidence is better calibrated to reality.
For a deeper look at estimation patterns and how teams are addressing variance, download the full State of Team Alignment 2026 report.
80% of teams roll work forward. Dependencies are the main reason.
Sprint rollover isn't a sign of failure. Some amount of incomplete work is normal. But the scale matters.
Only 20% of teams in our survey reported minimal rollover (0-10% of planned work). The remaining 80% regularly move incomplete work to the next sprint. Over a third are rolling 26-50% of their planned work forward.
When we asked what causes rollover, the top answer was dependency delays, at 36%.
This makes sense. Software development is interconnected work. Your feature needs an API from another team. Your frontend work is waiting on backend decisions. Your deployment is blocked by a security review that's running behind schedule. Any delay upstream automatically pushes your work downstream.
The challenge is that most teams lack visibility into these dependencies until they become blockers. When we asked about planning tools, 59% of teams use spreadsheets. Only 33% use Jira's native boards.
And most teams aren't using spreadsheets alone - they're combining them with two or three other systems, creating fragmented workflows where planning lives in one place, discussions happen in another, and work tracking happens in a third. That fragmentation hides dependencies. You can't see what other teams are doing or when blocking work will be completed.
The other causes of rollover vary by company size. Smaller companies (50-249 employees) struggle most with under-estimation. Mid-size companies (250-4,999 employees) cite scope change as the second biggest factor. Large enterprises (5,000+ employees) point to team capacity issues alongside dependencies.
What 2026 demands
The fix for rollover depends on its cause. If dependencies are your primary blocker, you need visibility into cross-team work before you commit to a sprint, not after you're already stuck. If scope change is derailing your sprints, the issue is likely upstream: requirements that aren't stable enough when they hit planning. If under-estimation is the problem, the answer loops back to collaborative estimation and better backlog refinement.
One tactical shift that works across all these scenarios: plan to 80% capacity. Assume 20% of your sprint will be consumed by the unexpected. That buffer gives you room to absorb delays without automatically rolling work forward.
The full report breaks down rollover causes by company size and includes specific strategies for each pattern.
Retrospectives surface good ideas. Half never get implemented.
Teams believe in retrospectives. When we asked how effective retros are at identifying meaningful improvements, 61% rated them "very" or "extremely" effective. Frequency is mostly solid too: 30% run retros every sprint, and another 55% run them every two to three sprints.
The problem is follow-through.
When we asked what percentage of retro action items get fully implemented before the next retro, the median was around 50%. Nearly 70% of teams implement less than 60% of the improvements they identify.
The biggest obstacle is that 29% of actions require changes beyond the team's control, and another 21% never get prioritised in sprint planning. Nearly half of retro actions fail before they start - either because the team can't fix the problem themselves, or because improvement work doesn't make it into the actual work queue.
The remaining obstacles are execution gaps: no accountable owner assigned (17%), no tracking of whether action was taken (13%), or vague action items that aren't specific enough to implement (15%). The report includes verbatim responses from survey participants on what they'd change about their retro process - worth reading if you're trying to diagnose where your team's follow-through breaks down.
Teams are identifying the right problems. They're just not set up to solve them.
What 2026 demands
The shift is simple but requires discipline: treat retro actions like real work. Create a ticket for every action item. Add it to the next sprint during planning. If it doesn't deserve sprint capacity, it probably shouldn't have been an action item in the first place.
For issues beyond the team's control—the 29% that require organisational change—escalate them immediately to stakeholders rather than letting them sit on a list that never gets addressed. And assign owners before leaving the retro. An action without a name attached is an action that won't happen.
Three changes to make this quarter
The data points to specific, practical shifts. Not a new framework. Not another meeting about meetings. While The State of Team Alignment 2026 report includes additional recommendations broken down by team size and role, these three apply broadly.
1. Add a complexity conversation to estimation.
Pick your highest-risk items each sprint and spend five minutes discussing what could make them bigger than expected. Surface the hidden dependencies. Ask the clarifying questions. That conversation is where estimation accuracy actually improves.
2. Map dependencies before you commit.
Before sprint planning, identify which items depend on other teams, external vendors, or sequential work within your own team. Reach out to those parties before you lock in the sprint. If you can't get clarity on a blocker, that item probably shouldn't be in this sprint.
3. Make one retro action a ticket.
Just the most impactful one. Give it an owner, acceptance criteria, and an estimate. Put it in the sprint. Track it like you'd track any other work. That single change closes the gap between identifying improvements and actually making them.
Get the full picture. The State of Team Alignment 2026 report includes detailed breakdowns by company size, role, and geography, plus additional findings on tool usage, planning methods, and team dynamics.
Download the full report →
Frequently asked questions
What are the biggest agile trends for 2026?
Research from Easy Agile's State of Team Alignment 2026 report, which surveyed 419 development professionals, points to three areas where teams will need to focus: closing the gap between estimation confidence and actual delivery accuracy, improving visibility into cross-team dependencies that cause sprint rollover, and converting retrospective insights into implemented changes. The data shows 80% of teams experience significant rollover and only half of retro action items get completed, suggesting these execution gaps, not new methodologies, will define team improvement efforts in 2026.
Why do agile teams struggle with sprint planning accuracy?
According to the State of Team Alignment 2026 survey, several factors contribute to sprint planning challenges. Only 31% of teams use collaborative estimation techniques, meaning most teams miss the discussions that surface hidden complexity. Additionally, 55% of teams estimate in time rather than complexity, which obscures the uncertainty inherent in difficult tasks. When estimation happens in isolation and focuses on hours rather than risk, variance increases. The survey found that teams using collaborative approaches like Planning Poker report higher and more accurate confidence in their estimates.
How can teams reduce sprint rollover?
The State of Team Alignment 2026 report found that dependency delays cause 36% of sprint rollover - more than scope change, under-estimation, or unplanned work. Teams can reduce rollover by mapping dependencies before committing to sprint scope, planning to 80% capacity to absorb unexpected delays, and addressing the specific rollover cause for their organisation size. Smaller companies tend to struggle with estimation accuracy, mid-size companies with scope change, and large enterprises with capacity and cross-team coordination.
Why don't retrospective action items get implemented?
Easy Agile's 2026 research found that 69% of teams implement less than 60% of their retro actions. The primary obstacles are that 29% of improvements require changes beyond the team's control, and 21% never get prioritised in sprint planning. Teams that treat retro actions as actual sprint work - with tickets, owners, and estimates, see better follow-through. The report recommends focusing on changes within the team's control, escalating systemic issues to stakeholders immediately, and assigning owners before the retro ends.
What estimation methods do agile teams actually use?
The State of Team Alignment 2026 survey found that estimation approaches split three ways: 37% use asynchronous or solo estimation, 31% use collaborative techniques like Planning Poker, and 30% rely on a single person (such as a tech lead or product owner) to estimate for the team. For units, 55% estimate in time (hours or days), 18% use relative sizing without specific units, 12% use story points, and 10% use t-shirt sizes. Teams using collaborative methods reported higher confidence and better calibration between estimates and outcomes.
How do team collaboration challenges differ by company size?
The State of Team Alignment 2026 report surveyed companies ranging from 50 to over 5,000 employees and found distinct patterns. At smaller companies (50-249 employees), under-estimation is the top challenge alongside dependencies. Mid-size companies (250-4,999 employees) struggle more with scope change during sprints. Large enterprises (5,000+ employees) face team capacity issues and cross-team coordination as primary obstacles. These differences suggest that collaboration improvements should be tailored to organisational context rather than applied uniformly.