Framing a Failed Initiative with Lessons Learned

presentationMid10–15 min
How to Use This: Run this roleplay with 2–3 people, or try it solo by voicing each role. Add curveballs to test adaptability. Reflect afterward to see what went well—and what didn’t.

Roleplay Scenario

Scenario Overview

You’re presenting a post-mortem on a recent initiative that didn’t quite hit the mark. Although the project didn’t go as planned, you’ve picked up some valuable lessons, and it’s important to share these insights with your team. The goal is to keep spirits up and focus on how we can do better next time.

Roles & Setup

Role A – Team Lead (You)
You’re presenting the post-mortem to the team.
Your goal: Focus on what you’ve learned and how to apply those lessons in the future, while keeping the team motivated.

Role B – Team Member
You worked on the initiative and want to understand what went wrong.
Your goal: Learn from the experience and offer any ideas for improvement.

Role C – Stakeholder (Optional)
You were invested in the initiative and want to see how things can improve.
Your goal: Make sure lessons learned are applied and keep everyone accountable.

Suggested Openers

Team Lead:

  • “Hey everyone, thanks for coming. Our last project didn’t turn out as we hoped, but we’ve learned some important things that’ll help us next time.”
  • “I want to chat about what happened with [Initiative] and focus on what we can take away from it to improve in the future.”

Team Member:

  • “I’m curious about where things went off track and how we can avoid that in the future.”
  • “I’d like to know more about the challenges we hit and how we can tackle them better next time.”

Stakeholder:

  • “I’m here to see what we can learn from this and how we’ll use these lessons in future projects.”
  • “I’d like to understand how these insights will shape our strategy moving forward.”

Sample Roleplay in Action

Team Lead:
“Thanks for joining, everyone. While our latest project didn’t quite hit the goal, it taught us a lot. Let’s talk about what went wrong and, more importantly, what we’ll do differently next time.”

Team Member:
“I’m interested in knowing where we veered off from our plan. Are there specific areas we should focus on?”

Team Lead:
“Good question. One big issue was that we underestimated how complex some of the integrations were. This showed us that we really need to dig deeper into technical scoping before setting timelines.”

Stakeholder:
“Thanks for being honest. How will we make sure we scope better in the future?”

Team Lead:
“We’re going to add a more thorough review step before we finalize deadlines, involving both engineering and product teams. Plus, we’ll do smaller pilot tests to catch any integration issues early on.”

Team Member:
“Those sound like good changes. I also think regular check-ins with stakeholders could help keep everything aligned as we move forward.”

Team Lead:
“Exactly. More communication will help us pivot sooner if we need to. Let’s make sure to document these insights and revisit them before our next project kickoff.”

Stakeholder:
“Sounds like a plan. Thanks for handling this constructively. I’ll be interested to see how these changes play out.”

Team Lead:
“Thanks, everyone, for your input and support. I’m confident that with these adjustments, we’ll be better positioned to succeed in our next initiative.”

Post-Scenario Tools

Curveball Mode (Optional)

Introduce one of these mid-roleplay to test adaptability:

  • The stakeholder expresses frustration about repeated patterns.
  • A team member feels the failure wasn’t fully explored.
  • Mid-discussion, new data emerges that changes the understanding of the failure.

Reflection Checklist

As the Team Lead:

  • Did you frame the situation positively, focusing on growth?
  • Did you encourage input from the team and stakeholders?
  • Did you outline actionable steps for future improvements?

As a Team Member:

  • Did you express constructive curiosity about the failure?
  • Did you suggest improvements or insights based on your experience?

As a Stakeholder:

  • Did you maintain a supportive yet accountable stance?
  • Did you seek clarity on how lessons will be applied?

Common Mistakes to Avoid

  • Focusing too much on blame rather than solutions
  • Overlooking team input and feedback
  • Providing vague action items without concrete next steps

Pro Tip

Emphasizing a culture of learning over a fear of failing fosters an environment where innovative solutions can thrive. Encourage open dialogue and continuous improvement to turn setbacks into stepping stones.