Your team estimates a ticket on Monday and by Friday, they can’t remember what the task even meant. What felt clear during grooming now feels ambiguous. Everyone has lost context and now, your engineers are reaching out, asking you to re-explain work they already committed to.
This isn’t just inconvenient. It derails your sprint velocity and forces you to become the team’s memory bank. The usual advice—“Just add more detail,” “Write better acceptance criteria,” “Be more proactive”—misses the point entirely.
This is because you don’t have a laziness problem or even a documentation problem. You’re dealing with a context loss problem. Context doesn’t live in checklists. It lives in conversations, in whiteboard sessions, in the decisions made mid-meeting. And unless you intentionally preserve that context, you’ll lose it.
Most engineering teams don't have a reliable way to capture and carry forward the context from their planning. So in this article, we’ll share why engineers forget what they estimated, why common fixes fall short, and what actionable steps can create lasting change.
The Planning-to-Execution Gap
In theory, grooming sessions are meant to set you up for successful sprint execution. You break down tasks, estimate effort, and commit to goals. But in practice, the gap between planning and execution grows wider by the day.
By the time engineers start work on a ticket:
- They’ve forgotten the rationale behind certain decisions.
- They weren’t the ones who created the subtasks.
- They may not have been present during the original discussion.
This leads to repeated clarification requests, lost time, and mounting frustration. The root cause isn’t poor documentation as you’ve been led to believe. It’s the absence of a bridge between planning and execution.
Why Agile Teams Keep Losing Context
- Context fades quickly. Cognitive science tells us that without reinforcement, people forget up to 90% of what they’ve learned within a week. That’s the “forgetting curve” in action.
- Estimation is treated like a chore. Most teams rush through estimation to get on with the sprint, without having conversation around the ticket. This leads to half-written subtasks with little rationale or helpful context.
- Information is scattered across different tools. Details are fragmented across Jira, Slack, Notion, Confluence, and meetings, none of which integrate context effectively.
- No one owns the narrative. Engineers inherit vague tickets. PMs assume others remember planning sessions conversations. The result? Misalignment and inefficiency.
The problem isn’t just tactical. It’s systemic. So adding more detail to the ticket, writing better acceptance criteria, and being more proactive won’t work. Though these are well-meaning, they put the burden on individuals without changing the system that brought the problem in the first place. The result is low compliance and eventual resentment.
What teams really need are structures and rituals that support memory, clarity, and shared ownership. Not more rules. Here are practical ways you can solve this problem.
Related Reading: Agile Theater: 5 Signs That Your Team is Performing Agile Without Real Progress
How to Prevent Context Loss in Software Teams
Let’s break down how teams are approaching grooming and estimation and what to do instead.
Problem 1: Grooming is treated as a formality
Most grooming sessions are fast-paced. You skim the ticket, make assumptions, estimate quickly, and move on. No one slows down to ask, "Do we understand this well enough to commit to it next week?"
What this causes:
- Engineers forget what they agreed to because they never really understood it.
- Tickets lack nuance and rationale.
- Estimations are disconnected from reality.
A better way: Make grooming a conversation, not a checklist. Instead of rushing through tickets, use them as prompts for team discussion. With Rally, when a ticket enters a grooming session, the AI generates clarifying questions automatically—"What dependencies does this have?" "Is this part reusable or new? "which sparks deeper thinking. The answers live directly inside the ticket thread, so anyone can revisit the discussion even days later.
Problem 2: The burden of documenting falls on one person
Usually, the PM writes the tickets, and the rest of the team barely interacts with them until execution. That leads to a knowledge bottleneck where one person holds all the context, and everyone else has fragments.
What this causes:
- Engineers ask questions mid-sprint that were answered in grooming.
- PMs become blockers because they’re the only source of truth.
- Tickets get reinterpreted differently by each person who touches them.
A better way: Shift from one-person ownership to collaborative context building. In Rally, every Jira issue becomes its own discussion space. Engineers can ask questions directly on the ticket, reply asynchronously, and mark discussions as resolved when they reach alignment. PMs no longer need to repeat themselves—and everyone sees the full context when execution begins.
Problem 3: Estimation doesn’t account for real execution variables
Even when a team does slow down to estimate, it often happens without context: who’s doing the work, how complex it really is, and how experienced the assignee is.
What this causes:
- Teams underestimate tasks by ignoring execution details.
- Story points or hour estimates get gamed or misused.
- Work spills over—not because of poor effort, but poor framing.
A better way: Use estimation as an opportunity to model reality, not just assign numbers. Rally’s AI-powered estimation analyzes task complexity and even adjusts based on the experience level of the person doing the work. It encourages teams to ask, "What would make this harder or easier to ship?"—and captures those discussions in the estimation record.
Related Reading: How to Provide Valid Estimates During Sprint Planning
Problem 4: There's no system to reconnect with the "why"
By the time a developer picks up a ticket mid-sprint, the original intent might be forgotten. If they weren’t in grooming—or if they were multitasking during it—they now face a pile of tasks without a narrative.
What this causes:
- Engineers slow down to ask for clarification.
- Work starts on incorrect assumptions.
- Output drifts from the original goal.
A better way: Create continuity between grooming and execution. In Rally, each ticket carries forward the highlights of planning: grooming takeaways, related diagrams or documents, and decision summaries all live inside the same space. Even if someone missed the meeting, they can get up to speed in minutes. It’s not just about preserving notes—it’s about making them usable at the moment of execution.
See How Rally Helps You Capture Context
Conclusion
If this sounds familiar, it’s because you’ve dealt with it: engineers asking questions mid-sprint and work getting delayed not because people aren’t trying, but because the you didn't carry the important details over.
This isn’t just a documentation issue. It’s a gap in how your team keeps track of decisions and explanations after planning ends.
Rally helps you fix that. It keeps the reasoning, questions, and key takeaways from planning visible inside the ticket so your team can stay on the same page without needing to follow up later.
The longer you wait, the more time gets wasted re-clarifying tasks and repeating conversations. Rally gives your team a simple way to keep the full picture in front of them, right where they need it.
Try Rally and help your team work with more clarity and fewer interruptions.