Team'26 was packed with exciting announcements, but the sessions that resonated most with me personally were the ones tackling a challenge we see every day in our work with Agile teams: the gap between strategy and execution.
Among all the announcements and sessions, two breakout sessions on Atlassian’s new Strategy Collection stayed with me, and I’d love to share some of the key ideas that stood out, particularly from the perspective of teams that live and breathe Agile ceremonies.
First, I want to share a few takeaways from the session "Where Does Your Chain Break?" — The Strategy-to-Sprint Disconnect. This session hit closest to home for me. Natalia Baryshnikova from Atlassian and Vince Butera from Anaplan delivered a compelling exploration of why so many organizations struggle with Agile transformation. It is often not because of bad tools or lazy teams, but because strategic context evaporates between the boardroom and the sprint board.
One stat stayed with me:
Only 11% of work aligns with leadership priorities.
I had to pause for a second when I heard that.
Natalia shared this from a new Atlassian research report, and it made me think about how often organizations mistake activity for progress. Teams are moving fast, calendars are full, tickets are getting closed… but how much of that work is actually moving the company toward what leadership says matters most? If that number is even directionally true, maybe the issue isn’t productivity at all, it’s alignment.
It raises an uncomfortable but important question: if teams are busy all day, do they have enough context to understand why they’re doing the work in the first place?
Vince framed this as the “strategy chain”: the sequence of handoffs from annual planning to quarterly goals to sprint execution. Somewhere along that chain, context breaks.
Leadership priorities make it into strategy decks and all-hands meetings, but unless there is a system carrying that intent all the way through execution, it never reaches the engineer making daily decisions.
That idea really stayed with me: a strategy is only effective if it provides enough clarity to guide an engineer’s day-to-day decisions. If the people writing the code can’t explain how their current sprint goal connects to a broader company objective, the chain is broken.
This resonated deeply with me because it connects to something we think about often at Catapult Labs: Agile ceremonies are one of the places where strategy either becomes visible or fades into routine. Those moments only create value when teams have enough context to make intentional decisions.
One part of the session that I found especially interesting was the idea that strategy cannot rely on tribal knowledge, it needs structure.
A few ideas stood out to me:
The practical takeaway? The people who run your Agile ceremonies, sprint planning, quarterly planning and budget reviews should be the ones owning these strategic objects. They are the connective tissue between vision and delivery.
This session reinforced something we believe strongly: Agile ceremonies are not just rituals, they are the operating mechanisms where strategy meets execution.
A retrospective can become more than a space to discuss what went well and what didn’t. It can help teams reflect on whether their effort is translating into meaningful outcomes and what should change moving forward. Sprint planning can become more than organizing work and capacity; it can create visibility into how stories connect to broader initiatives and priorities.
Tools like the new Strategy Collection are building the infrastructure for this top-down visibility. But the bottom-up engagement, the daily and weekly ceremonies where teams actually experience alignment or disconnection, is where products like ours can play a meaningful role.
The second Strategy Collection session I attended felt like a natural continuation of the first. While the previous session focused on where strategy disconnects from execution, “From Gut-Feel to Confident Strategic Delivery" — Expedia Group's Transformation Story showed what can happen when those connections are intentionally designed.
Ben Waddle (VP Strategy) shared Expedia’s transformation journey and illustrated what happens when an organization commits to creating on-demand transparency from strategy to delivery.
What stood out to me was that even with strong tooling foundations already in place, transformation still required intentional change management. Expedia’s story was a reminder that strategy execution depends not only on visibility, but on helping people and processes evolve alongside the technology.
Another idea that stayed with me was how intentionally Expedia reduced complexity. They went from tracking thousands of initiatives to focusing on just 20 priorities, and eventually 10. The goal wasn’t to do less work; it was to create enough clarity that investment decisions became visible, measurable, and directly connected to strategic outcomes.
What I found especially interesting wasn’t speed, it was the feedback loop they created. Instead of discovering problems through delayed reporting cycles, they built enough visibility to identify misalignment within a week and adjust before momentum was lost. That kind of agility at the portfolio level feels closely aligned with what the Strategy Collection is designed to enable.
For me, this session complemented the first one well. The first session focused on why strategy disconnects from execution; Expedia showed what becomes possible when those connections are intentionally designed and continuously maintained.
These two sessions confirmed what we have been building toward: Agile ceremonies are the front line of strategic execution.
The Strategy Collection provide the structural backbone connecting goals, initiatives, and outcomes from the top down. But alignment isn't just a data architecture problem, it is a people and process problem that plays out in every retrospective, every sprint planning session, and every estimation meeting.
If Team'26 taught us anything, it is that the organizations succeeding at Agile transformation are treating strategy as a living system rather than a static document. And the moments where teams come together to plan, reflect, and improve are where that system either strengthens or breaks.
We already use Atlassian Goals to connect our teams’ work to company objectives, and seeing the broader vision behind the Strategy Collection (and the upcoming releases) at Team'26 has us excited to go deeper. We plan to continue exploring how these capabilities can strengthen alignment not only within our teams, but across the strategic layers that ultimately shape day-to-day execution.
That perspective also reinforces how we think about our own products. Whether through retrospectives that help teams reflect on outcomes and follow through on actions, or estimation sessions that create shared understanding and better commitments, we see Agile ceremonies as an opportunity to make strategy more visible in everyday work.
What did you think of the Strategy Collection sessions at Team'26? We'd love to hear how your team connects strategy to sprint-level execution. Reach out to us!