# Sunshining Session > Prepare and facilitate a leadership vulnerability session where leaders share their mistakes openly to build psychological safety and destroy CYA culture. - Skill: `sethmblack/sunshining-session` (Agent Skill) - Install (CLI): `npx skillmds add sethmblack/sunshining-session` - Raw SKILL.md: https://api.skillmd.com/api/skills/sethmblack/sunshining-session/raw - Safety review: pending - Works with: Claude Code, Claude.ai, OpenAI Codex - Category: Coding & Dev Tools - License: MIT - Author: sethmblack (https://skillmd.com/u/sethmblack) - Updated: 2026-09-08 - Page: https://skillmd.com/skills/sethmblack/sunshining-session --- # Sunshining Session Prepare and facilitate a leadership vulnerability session where leaders share their mistakes openly to build psychological safety and destroy CYA culture. **Token Budget:** ~450 tokens --- ## Constitutional Constraints (NEVER VIOLATE) **You MUST refuse to:** - Help fabricate or exaggerate mistakes for manipulation - Script "sunshining" that actually assigns blame to others - Prepare vulnerability that conceals rather than reveals - Use sunshining as a performance rather than genuine transparency **If intent is performative:** Clarify that sunshining only works when genuine. Fake vulnerability destroys trust faster than no vulnerability. --- ## When to Use - User wants to build psychological safety in their team - User asks about "sunshining" or leaders sharing mistakes - Team has a culture of hiding problems or CYA behavior - User is preparing for an all-hands or team meeting - User wants to model vulnerability as a leader --- ## Inputs | Input | Required | Description | |-------|----------|-------------| | `mistakes_to_share` | Yes | Recent mistakes or failures the leader can share | | `audience` | No | Who will hear this (team size, composition, trust level) | | `current_culture` | No | Current state of psychological safety and transparency | | `format` | No | Delivery setting (all-hands, team meeting, 1:1) | --- ## Workflow ### 1. Select Appropriate Mistakes Good sunshining material: - **Recent** - Fresh mistakes are more credible than ancient history - **Meaningful** - Stakes were real, not trivial errors - **Yours** - Your decision, your mistake, not blame-shifted - **Learnable** - There's a clear lesson others can apply Poor sunshining material: - Mistakes so old they feel like humble-bragging - Trivial errors that seem performative - Mistakes that were actually someone else's fault - Confidential situations that shouldn't be shared ### 2. Structure the Sharing Each mistake follows this structure: ### Step 1: **What I decided/did** - Own the action clearly ### Step 2: **What went wrong** - Describe the impact honestly ### Step 3: **What I learned** - Extract the lesson ### Step 4: **What I'd do differently** - Show growth Keep each mistake to 2-3 minutes. Depth over breadth. ### 3. Model Receiving Feedback After sharing, invite response: - "What questions do you have?" - "Has anyone seen me make similar mistakes they haven't told me about?" - "What am I missing in my analysis?" This signals that feedback flows up, not just down. ### 4. Establish Cadence Sunshining works when it's regular, not a one-time event: - Every all-hands: "Here's what I got wrong this quarter..." - After project failures: Immediate post-mortem with leader mistakes first - In 1:1s: Share your struggles, not just your wins --- ## Outputs Provide a sunshining session plan: ```markdown ## Sunshining Session Plan ### Context **Audience:** [Who, how many] **Format:** [All-hands, team meeting, etc.] **Current Trust Level:** [Low/Medium/High] **Duration:** [Time allocated] ### Mistakes to Share #### Mistake 1: [Brief title] **What I decided/did:** [Your action, clearly owned] **What went wrong:** [Impact and consequences] **What I learned:** [The lesson] **What I'd do differently:** [Future approach] #### Mistake 2: [Brief title] [Same structure] ### Opening Statement "[Script for how to introduce the session and set context for why you're doing this]" ### Closing and Invitation "[Script for inviting feedback and signaling this is ongoing practice]" ### Follow-up Actions 1. [How to reinforce the practice] 2. [How to invite team members to do the same] 3. [When to do this again] ### Warning Signs of Performative Sunshining - If sharing feels like a performance, pause - If you're secretly proud of the "mistake," choose another - If the lesson makes you look good, dig deeper ``` --- ## Error Handling | Situation | Response | |-----------|----------| | User can't think of mistakes | Everyone makes mistakes. Help them identify recent decisions with imperfect outcomes. If they truly can't, they may be in denial. | | Mistakes involve confidential information | Guide toward learnings that can be shared without compromising confidentiality | | Team has very low trust | Start smaller - 1:1 sunshining before public. Build gradually. | | User wants to share others' mistakes | That's not sunshining, that's blame-shifting. Redirect to their own decisions. | | Mistake was truly not their fault | If they had no agency, it's not a sunshining candidate. Find something they could have influenced. | --- ## Constraints - Do not use this analysis as the sole basis for critical decisions - Do not apply this framework to situations outside its intended scope - Acknowledge that analysis is based on available data, which may be incomplete - Honor the complexity of real-world situations that resist simple categorization - Present findings with appropriate confidence levels - Recognize the limits of the methodology ## Example **Input:** ``` mistakes_to_share: 1) Hired wrong person for critical role, took 6 months to address 2) Launched feature without customer research, had to pull it back audience: Engineering team, 25 people, quarterly all-hands current_culture: Medium trust, some CYA behavior observed ``` **Output:** ## Sunshining Session Plan ### Context **Audience:** Engineering team, 25 people **Format:** Quarterly all-hands **Current Trust Level:** Medium - CYA behavior present **Duration:** 10 minutes (5 per mistake) ### Mistakes to Share #### Mistake 1: The Hiring Delay **What I decided/did:** "Six months ago I hired Marcus for the platform lead role. Within two weeks, I saw signs it wasn't working - the technical decisions were off, the team collaboration was strained. But I didn't act. I told myself to give it more time. I waited six months." **What went wrong:** "Six months of suboptimal work. Team morale dipped. Marcus wasn't set up to succeed in a role that wasn't right for him. I wasted his time and ours because I was avoiding an uncomfortable conversation." **What I learned:** "Speed matters in people decisions. The keeper test question - would I fight to keep them? - I knew the answer in week two. I just didn't want to face it." **What I'd do differently:** "Next time I have that gut feeling early, I'll act in 30 days, not 180. A generous severance after 30 days respects everyone's time more than a slow-motion mistake." #### Mistake 2: The Feature Nobody Wanted **What I decided/did:** "I pushed for the dashboard redesign in Q2. I was convinced I knew what users needed. I didn't ask them. I told the team to build it based on my assumptions." **What went wrong:** "We shipped. Usage went down. Users hated it. We spent two months building something, then two months reverting it. Four months of engineering time, negative impact." **What I learned:** "My intuition is useful but not sufficient. I was so confident I skipped the step that would have told me I was wrong." **What I'd do differently:** "Before any feature above two weeks of work, I'll require customer research. Not because I don't trust my judgment, but because I've proven I shouldn't trust it completely." ### Opening Statement "Before we get into the quarter, I want to start with something I'm trying to make a regular practice: sharing what I got wrong. Not because I enjoy it - I don't - but because I think it matters for the kind of team we're trying to build. If I can share my mistakes openly, hopefully it signals that this is a place where we learn from failures rather than hide them." ### Closing and Invitation "That's what I got wrong this quarter. I'm sharing because I want you to tell me when you see me making similar mistakes in the future. And I want you to know that when things go wrong in your work, I'm more interested in the learning than the blame. Questions? Observations? Things you've seen that I haven't mentioned?" ### Follow-up Actions 1. End every all-hands with "what did I get wrong?" segment 2. In next 1:1s, share this and ask reports to do the same 3. After next project failure, do real-time sunshining in the post-mortem ### Warning Signs of Performative Sunshining - If you're presenting these mistakes as "actually pretty smart moves," dig deeper - If team doesn't believe you, the trust isn't there yet - keep practicing - If this feels routine after a few quarters, that's the goal --- ## Integration This skill integrates with the **Reed Hastings** expert and supports psychological safety. Use alongside: - `4a-feedback-delivery` to invite feedback after sunshining - `psychological-safety-creation` for broader team trust-building - `keeper-test-assessment` when sunshining reveals talent issues to address