Authentic sharing builds powerful connections, but requires thoughtful boundaries. This framework helps you decide:

1. What to share,
2. Where to share it,
3. When to share and
4. How to frame it for maximum impact.

1. Vulnerability Assessment Grid

Before sharing a business challenge, assess it using this grid:

Examples: — investor disputes — team performance issues — legal/compliance issues | Selective Sharing

Examples: — serious cash flow problems — (resolved) leadership mistakes | | Low Risk to You | Personal Discretion

Examples: — minor operational hiccups — everyday frustrations — personal productivity challenges | Share Openly

Examples: — product development — marketing experiments — customer feedback loops |

2. Context-Based Sharing Guidelines

Different contexts require different sharing approaches:

Public Platforms (LinkedIn, Twitter)

Best for: “Share Openly” quadrant items and carefully framed “Selective Sharing” topics Approach: Focus on lessons learned, questions for the community, and structured insights Caution: Establish a pattern of sharing successes before vulnerabilities to maintain credibility

Semi-Private Communities (Industry Slack groups, Facebook groups)

Best for: “Selective Sharing” topics and specific “Personal Discretion” challenges Approach: More detailed about challenges, with specific requests for feedback Caution: Remember that screenshots can travel beyond these spaces

Private Peer Groups (Mastermind circles, trusted founder networks)

Best for: Most “Selective Sharing” topics and carefully chosen “Keep Private” items Approach: Comprehensive breakdowns with context, emotions, and specific requests Caution: Establish group confidentiality norms explicitly

One-on-One Conversations (Mentors, advisors, peers)