How three strangers built a lasting peer leadership support group

Executive overview

Many leaders feel isolated despite being surrounded by people — they lack honest, unbiased input from outside their organization and industry. Three podcast listeners met in a virtual breakout session, clicked, and kept meeting monthly for years across two countries and three time zones.

Their model is simple: a monthly hour split equally three ways, explicit group agreements, and a norm of saying "thank you" rather than debating advice. Challenges are transferable — a difficult conversation looks the same in healthcare tech, business coaching, or higher education.

A small, consistent peer group outside your industry can replace the board of directors most leaders never have.

How the group formed and why it works

• Met in a Zoom breakout during a live podcast event in 2017; the host gave one question to discuss and told them to just say thank you to any feedback
• Chose to continue independently — no external facilitation after the first session
• Span healthcare tech, solo business coaching, and higher education Salesforce administration — different enough that advice carries no industry bias
• Being in different countries and time zones removes any risk of feedback getting back to someone in the organization
• Challenges are transferable: difficult conversations, career moves, and people problems look similar regardless of industry

Agreements and structure

• Set explicit group agreements from the start: monthly cadence, fixed time slot, agreed platform
• Each call divides the hour into three equal parts so no one person dominates
• Built in an annual review: does everyone still want to continue?
• Confidentiality named explicitly, not assumed
• At least two members show up every session — consistency is treated as a commitment, not a preference

Accountability

• Members follow up on goals stated in previous calls — not a courtesy, a real expectation
• Accountability holds because these people actually follow through, unlike casual requests to friends who drop off
• For a solopreneur without staff or a board, external peer accountability is the only version available
• The hard part is making the commitment honestly, not executing the follow-up itself

Celebration

• Deliberately surfacing wins prevents defaulting to challenges-only conversations
• Celebrations are repeatable: examining what went right reveals patterns, not just outcomes
• One member actively pushes the others to pause and name what went well — the others benefit from being nudged
• Safety to celebrate matters; many professionals suppress it as self-indulgent

The fear of having nothing to offer

• Every member worried initially about contributing to people from different fields
• Reality: asking genuine questions in a safe space reveals knowledge you didn't know you had
• A rejected suggestion (e.g. software blocked by industry regulation) costs nothing — it narrows the solution space
• People who invest in self-development consistently underestimate what they know

Resources mentioned

• Atomic Habits by James Clear — identity-based habit change; every action is a vote for the person you want to be; start small rather than goal-setting
• The Coaching Habit by Michael Bungay Stanier — simple questions, especially "And what else?"; shaped one member's decision to stay true to his coaching style rather than follow a client's new direction
• Values clarification tool — surfaces what "enough" looks like across money, travel, time, and relationships; used as a filter for career move decisions
• Related episodes: Ep. 237 (Michael Bungay Stanier), Ep. 395 (Priya Parker on meaningful gatherings), Ep. 397 (John Stepper on Working Out Loud circles)

Starting your own group

• Find two or three people outside your organization or industry, set explicit agreements, and start
• The "say thank you" norm keeps ideas flowing and prevents defensiveness from shutting down input
• Works within an organization, across industries, or through shared communities like podcast audiences
• The barrier is commitment, not difficulty — the conversations themselves are not hard
• You have more agency over who influences you than most people assume