Weekly Wonder: Structuring a “Day in the Life” Session to Showcase Real Atlassian Workflows

[#1]

Hi CUG Leaders!

One of the most powerful formats you can run in a CUG is a "Day in the Life" session, where a real person walks through how they actually use Atlassian tools in the course of their daily work.

Not a polished product demo or training exercise, but a genuine peek behind the curtain at how someone plans their morning, triages their queue, collaborates with teammates, and closes out their day using Jira, Confluence, and whatever else is in their stack.

These sessions land differently because they're rooted in authenticity. Members see themselves in the presenter's workflow, spot tricks they've never tried, and leave with ideas they can apply immediately.

But a great "Day in the Life" session doesn't happen by accident - it takes thoughtful structuring to keep it focused, engaging, and useful for the whole room. Here are five tips to help you design one that showcases real workflows without losing your audience.

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1. Choose a presenter whose workflow is relatable, not exceptional

The instinct is to pick your power user: the person who's built the most complex automations or the most elaborate Jira setup.

Resist that. The best "Day in the Life" presenter is someone whose work looks familiar to most of your audience: a project manager running a sprint, an IT admin handling service requests, or a team lead coordinating across a few Confluence spaces.

Relatability is what makes the format work. When attendees see someone in a similar role navigating the same challenges they face, the tips and shortcuts land harder. They think "I could do that tomorrow" instead of "that's impressive, but my world is different."

If you do have a power user you want to showcase, consider pairing them with someone earlier in their Atlassian journey; the contrast can be instructive without making the session feel out of reach for the typical attendee.

How to do it:

• Write 2–3 outcome statements for your session, such as:

  • “Attendees can explain our standard Jira project workflow.”

  • “Admins can create a basic Confluence template for project kickoffs.”

• For each outcome, design a quick trio:

  • Visual: diagram, screenshot series, or short slide sequence.

  • Hands-on: a mini exercise in your actual Jira/Confluence environment or a sandbox.

  • Discussion: a prompt for small-group or whole-room conversation.

This keeps your agenda focused, since activities that don’t serve at least one outcome are optional. It also helps you explain the value of the meeting to leaders and invitees: “In 60 minutes, you’ll see the workflow, try it, and discuss how to adapt it to your team.”

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2. Structure the session around a real narrative arc, not a tool tour

A common mistake is letting the session become a feature walkthrough disguised as a daily routine. Instead, frame the presentation around the presenter's actual day with a clear narrative arc: what does their morning look like? What's the first thing they open? Where do bottlenecks show up? How do they hand work off or loop in colleagues?

Ask your presenter to map out 4–5 key moments in their day where Atlassian tools play a role. For example: checking their Jira board first thing, updating a Confluence project page after a standup, triaging incoming requests in JSM after lunch, and reviewing a dashboard before end of day.

By anchoring each segment to a real moment rather than a feature, the session tells a story that people can follow, and stories are far more memorable than click-throughs.

The narrative arc also gives the session natural momentum. Instead of jumping between disconnected features, the audience follows a thread from morning to end of day, which makes transitions feel organic.

Prep your presenter by having them literally narrate a recent workday to you in advance; you'll quickly see which moments have the most teaching value and where the natural pause points fall.

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3. Build in "pause and unpack" moments throughout the walkthrough

When a presenter is in flow, it's tempting to just let them keep going, but that's where you lose the room.

Plan 2–3 deliberate pause points where the presenter stops sharing their screen and you open the floor for a quick debrief: "What did you notice there?" or "Has anyone solved that bottleneck differently?"

These pauses serve two purposes. First, they give attendees time to mentally connect what they just saw to their own workflows, without that processing time, even great tips wash over people. Second, they create space for peer-to-peer knowledge sharing. Some of the best insights in a CUG session come from the audience, not the presenter, and a well-timed pause invites those contributions.

To keep pauses from stalling the session, prep 1–2 specific questions for each pause point in advance. If the room goes quiet, you have a prompt ready. If the discussion takes off, let it run for a few minutes and then gently redirect back to the walkthrough.

A good rule of thumb is to plan a pause every 10–15 minutes - i.e. long enough for the presenter to build context, short enough that no one zones out.

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4. Capture the "small moves" that live demos tend to skip

The highest-value moments in a "Day in the Life" session are often the smallest: the keyboard shortcut someone uses without thinking, the naming convention that keeps their Confluence space navigable, or the one-click filter they built to triage their Jira backlog every morning.

These micro-habits are invisible to the presenter because they're second nature - which means you need to surface them intentionally. During your prep call, watch for these moments and flag them. Ask questions like "Wait, how did you just do that?" or "Why do you name your pages that way?" Then build those moments into the session itself: have the presenter slow down at those points, or call them out yourself as the facilitator.

Consider assigning a "small moves spotter," someone in the audience whose job is to jot down every shortcut, trick, or convention they notice during the walkthrough. At the end of the session, they can share their list with the group and you can add it to your follow-up notes. This gives the audience a second lens on the content and ensures those easy-to-miss gems don't slip through the cracks.

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5. Close with a "steal this" takeaway list

Don't let the session end with a vague "hope that was helpful!" Instead, wrap up with a concrete list of 3–5 things attendees can take back to their own workflows immediately.

These should be specific and low-effort, not "redesign your Jira project" but "try pinning your most-used filter to your sidebar" or "create a one-line daily standup template in Confluence."

Build this list collaboratively during the session rather than preparing it entirely in advance. As the walkthrough unfolds, keep a running note (visible to the audience if possible) of the tips and tricks that surface.

By the time you reach the closing segment, you already have a crowd-sourced list that reflects what actually resonated with the room — not just what you thought would resonate.

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The best "Day in the Life" sessions feel less like a presentation and more like sitting next to a colleague and watching how they work. That's the magic of the format: it's grounded in real context, real tradeoffs, and real habits instead of idealized workflows no one actually follows.

When you pair a relatable presenter with a clear narrative arc, give the room space to unpack what they're seeing, shine a light on the small moves that make a big difference, and send everyone home with a short list of things to try, you create a session people talk about long after it ends.

And the more your members see themselves in the workflows being shared, the more likely they are to bring their own "day in the life" to the next meeting.

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Public Resources You Can Share with Your Group

• Atlassian University – Free Training & Tutorials 

  • Short, product-focused courses that can serve as inspiration for your series topics or pre-work for attendees.

• Work Life by Atlassian – Teamwork & Collaboration Articles 

  • Practical articles on team rituals, facilitation, and collaboration that can inform how you structure your recurring sessions.

• Atlassian Team Playbook 

  • Ready-to-use plays for running retrospectives, health monitors, and other team activities that make excellent recurring series formats.

[Jimmy Seddon]

That's a very interesting concept @Blake Hall!

I'm also wondering if the reverse might also be insightful - "A peek behind the curtain: The balancing act of being an Admin".

In my career, I have encountered many complaints about why we have workflows and fields setup the way we do and why are we telling them they can't have what they want. 

"It's JUST one more field".

But, a look at what we have to do to balance system performance along with the individual requests from hundreds of teams, might help to put that "one more field" in perspective.

Thanks for the inspiration!

[Blake Hall]

@Jimmy Seddon Great point! I could definitely see the admin perspective as part of this; I think showing it alongside other roles (even as a capping off session, like "...and here's what it takes to coordinate all these groups") could be really great as a rapport-building exercise.

You could even create mini-series of day-in-the-life walkthrough sessions, based on the latest products from the company - i.e. focusing on those teams for a series, a new team for the next, etc.