Weekly Wonder: “Show and Fail” Sessions - Sharing Missteps to Help Others Avoid Them

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Hi CUG Leaders! This week, we’re exploring a practice that can strengthen trust, accelerate learning, and make your CUG feel even more valuable: “Show and Fail” sessions, where members share missteps, lessons learned, and what they would do differently next time.

It can be tempting to fill community meetings with only polished wins, successful rollouts, and tidy best practices. Those stories matter, but they’re only half the picture. Some of the most useful learning happens when someone says, “Here’s where we got stuck,” “Here’s the assumption that cost us time,” or “Here’s the configuration choice we had to undo later.”

As CUG leaders, you can create a safe, practical space for these conversations. When members share mistakes openly, others can avoid the same pitfalls, teams build confidence faster, and your community becomes known as a place where real-world learning happens, not just highlight reels.

Below are five practical tips to help you design thoughtful “Show and Fail” sessions that turn missteps into shared wisdom.

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1. Set the tone: failures are data, not blame

Before asking anyone to share a misstep, make it clear that the goal is learning, not judgment. A “Show and Fail” session should focus on decisions, assumptions, constraints, and outcomes rather than assigning fault to individuals or teams. Open the session by reminding attendees that every Atlassian implementation, migration, workflow redesign, or automation experiment includes unknowns.

A simple framing statement can help: “We’re here to learn from what happened, what we discovered, and what we’d try differently next time.” This gives presenters permission to be honest while signaling to the audience that curiosity is expected. When leaders model this tone consistently, members are more willing to share the lessons that don’t usually make it into project updates.

2. Use a lightweight story format to keep sharing practical

Give presenters a simple structure so their story feels useful rather than uncomfortable. A helpful format might include: What we were trying to do, what went wrong, how we discovered it, what we changed, and what others should watch for. This keeps the session focused on actionable takeaways instead of turning into a venting exercise.

Encourage short, specific examples: a Jira workflow that became too complex, a permission scheme that blocked the wrong people, a Confluence space structure that confused new users, or an automation rule that created noisy notifications. The best “Show and Fail” stories are concrete enough that someone in the room can recognize a similar risk in their own work and take action before it becomes a bigger issue.

3. Start with small missteps to build psychological safety

If this is a new format for your CUG, don’t begin by asking for major project failures. Start with lower-stakes lessons: a naming convention that didn’t scale, a dashboard metric that was misunderstood, or a meeting format that didn’t engage members. Smaller stories help normalize the practice and show that “failure” can simply mean “something we learned from.”

As comfort grows, you can invite deeper examples from larger efforts like cloud migrations, Jira Service Management rollouts, governance changes, or cross-team automation projects. Over time, members will see that the community values transparency and improvement. That trust is what makes the format powerful.

4. Capture the lessons in a reusable “avoid this” library

A “Show and Fail” session becomes even more valuable when the lessons don’t disappear after the meeting. Create a Confluence page or section where you summarize each story in a short, reusable format: the situation, the warning sign, the fix, and the recommendation. Think of it as a practical field guide built from your members’ lived experience.

This library can become a go-to resource for new admins, project leads, and teams starting similar work. For example, a short note titled “Avoid over-customizing Jira workflows before validating team needs” can save another group weeks of cleanup later. The goal is not to document failure for its own sake; it’s to turn hard-earned experience into guidance others can actually use.

5. Celebrate the people who share lessons openly

Sharing a mistake takes courage, especially in a professional setting. Recognize presenters for helping the community get smarter. Thank them during the meeting, highlight the practical value of their takeaway, and reinforce that their openness may prevent another team from repeating the same issue.

You can also make this recognition part of your CUG rhythm with a recurring “lesson learned” spotlight, a small thank-you note, or a follow-up message summarizing the insight. When people see that transparency is appreciated, not penalized, they are more likely to contribute honestly. That creates a stronger, more resilient community.

Conclusion

“Show and Fail” sessions help CUG members learn from the real work behind Atlassian adoption: the experiments, course corrections, and unexpected consequences that rarely appear in polished success stories.

By setting a blame-free tone, using a simple story format, starting small, capturing lessons, and celebrating openness, your CUG can turn missteps into momentum. The result is a community where leaders and members help each other avoid avoidable problems, make smarter decisions, and grow through shared experience.

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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.