Week 51 Day 7: Assignment: Tell One Failure Story to Your Team This Week

Choose the failure story that is most relevant to something your team is currently experiencing. If the team is under pressure to hire quickly, tell the bad-hire story. If the team is working on a project that is showing signs of trouble, tell the project-you-should-have-killed story. If the team is navigating a politically difficult situation, tell the comfort-over-courage story. Relevance makes the story land. Timing makes it stick.

Here is the step-by-step process. Step one -- select the story. Choose the failure story that has the most direct relevance to the team's current situation. The story does not need to be a perfect analogy -- it needs to address the same category of challenge the team is facing. If no current situation maps to your failures this week, choose the story that communicates the most important leadership principle you want the team to understand. Step two -- prepare but do not script. Review the story structure from Week 49: context (what was the situation), decision (what did you do and why it seemed right at the time), consequence (what happened as a result), and lesson (what you changed). You should be able to tell the story in under 3 minutes. Know the key sentences -- especially the moment of failure and the lesson -- but do not memorize a script. Authenticity requires some roughness. Step three -- choose the context. The best context is a natural conversation where the story is relevant. A team retrospective where a similar pattern is being discussed. A one-on-one where a team member is wrestling with a similar decision. A team meeting where you are introducing a new practice and want to explain why it matters to you personally. The worst context is an unprompted declaration: 'I want to tell you all a failure story.' That feels performative. The story should emerge from a conversation, not interrupt one. Step four -- tell the story and land the lesson. Tell the story with specificity and ownership. Then land the lesson: 'Here is what I learned from that experience, and here is why I am sharing it. I want our team to have the safety to acknowledge when something is not working before it becomes a crisis. The way I build that safety is by going first -- showing you that I have failed, that I own those failures, and that the failures made me better.' Step five -- open the floor. After telling the story, create space: 'Has anyone on the team experienced something similar? Or is there a current situation where this lesson might apply?' This invitation transforms the story from a monologue into a dialogue, which deepens the impact and builds the psychological safety that makes future failure disclosure safe for the entire team. Step six -- reflect. After the meeting, write a brief note in your Leadership Operating Manual: which story did you tell, how did the team respond, what would you do differently next time? This reflection closes the learning loop and prepares you for the next time you use a failure story as a teaching tool.

The in-person (synchronous) delivery requirement is supported by research on 'media richness theory' (Daft and Lengel, 1986), which demonstrates that communication requiring high trust, high vulnerability, and nuanced interpretation is most effectively delivered through rich media (face-to-face or video) rather than lean media (text or email), because rich media provides the nonverbal cues (facial expression, tone of voice, body language) that signal authenticity and create the emotional connection that makes vulnerability effective rather than awkward. The 'natural conversation' entry point implements what organizational development researchers call 'embedded learning' (Marsick and Watkins, 2001) -- the practice of integrating learning moments into the natural flow of work rather than extracting them into separate learning events (workshops, training sessions), which produces higher transfer rates (50-70%) than classroom training transfer rates (10-20%) because the learning occurs in the context where it will be applied. The open-floor invitation implements what Edmondson (2012) calls 'proactive psychological safety creation' -- the finding that psychological safety is not a passive state that develops naturally but an active construction that requires the leader to repeatedly signal, through specific behaviors, that speaking up is welcomed and rewarded. Her research found that single vulnerability disclosures produced temporary increases in psychological safety, but that sustained psychological safety required repeated signals over 8-12 weeks, which is why this assignment is positioned near the end of the course when the leader has already been building these habits for months.