Pirates and Holacracy: Rewriting the Rules of Work

In a world where disruption is the norm and rigid hierarchies struggle to keep pace, new models of leadership and governance are emerging. Two of the most talked-about are Sam Conniff's Be More Pirate philosophy and Holacracy, a governance system popularised by Brian Robertson. At first glance, one looks rebellious and free-spirited, the other highly structured and process-driven. Yet when examined together, they reveal a shared vision: decentralising power, rewriting outdated rules, and giving individuals greater agency in shaping their work.

Be More Pirate: The Mindset of Modern Rebellion

Sam Conniff's Be More Pirate (2018) argues that 18th-century pirates were not merely criminals but social innovators who rewrote the rules of their time. Pirate crews pioneered democratic voting, equal pay for equal risk, and early forms of social contracts. Conniff urges modern organisations to follow suit—challenging outdated hierarchies, redistributing power, and writing their own "codes" to create cultures of fairness and innovation.

"Pirates didn't just break rules—they rewrote them to make things fairer and more effective." (Be More Pirate, 2018)

The book inspired a grassroots movement of "modern pirates" across industries, from healthcare to tech, experimenting with new ways of working that decentralise authority and emphasise collective ownership.

Holacracy: A Structured System for Distributed Authority

Holacracy, developed by Brian Robertson and formalised in his book Holacracy: The New Management System for a Rapidly Changing World (2015), replaces traditional hierarchy with a distributed governance system. Instead of fixed job titles, individuals hold multiple roles that evolve dynamically. Decision-making happens within circles of accountability, guided by the Holacracy Constitution, a codified set of rules.

The aim is to remove bottlenecks of top-down management and empower employees to act with autonomy while staying aligned with the organisation's purpose.

"Authority is distributed throughout an organisation, giving individuals clarity and freedom to act within their roles." (Holacracy, 2015)

Pirates vs. Holacracy: Spirit and Structure

While Be More Pirate is primarily a mindset shift and call to action, Holacracy offers a codified operating system. The two can be seen as complementary:

Pirates ignite cultural change and encourage risk-taking.

Holacracy provides a framework for distributed authority and operational clarity.

Case Studies: Pirates and Holacracy in Action

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1. Buurtzorg (Healthcare, Netherlands) – Pirate Spirit in Practice

Buurtzorg, a Dutch home-care organisation, rejected traditional top‑down healthcare bureaucracy. Nurses operate in self‑managing teams of 10–12, making decisions collectively about patient care. There are no managers—just distributed responsibility.

Outcomes:

Operating costs cut by 25% compared to traditional models.

Over 60% fewer hours of care per patient required due to efficiency.

Patient satisfaction consistently rated at 9.1/10, one of the highest in the Netherlands (Laloux, 2014; Gray, 2009).

This mirrors Be More Pirate's ethos of rewriting rules for fairness and impact.

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2. Zappos (E‑commerce, U.S.) – Holacracy at Scale

Zappos famously adopted Holacracy in 2014, eliminating traditional managers. Employees took on fluid roles, and governance happened through structured circle meetings.

Outcomes:

In the first year, 14% of employees opted for buyouts due to discomfort with the model.

Employee engagement surveys showed mixed results—autonomy improved for some, but others reported confusion over decision rights.

Despite turbulence, Zappos maintained its reputation for customer service excellence and innovation (Bernstein et al., 2016, HBR).

This shows both the promise and challenges of codifying distributed leadership.

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3. The NHS Pirate Handbook (UK Healthcare) – Pirate Rebellion Inside Bureaucracy

Inspired directly by Be More Pirate, a group of NHS staff created their own "Pirate Code" to challenge outdated practices. The movement spread internally, creating grassroots innovation in patient care and team management.

Outcomes:

NHS teams using the Pirate Handbook reported 20% faster decision‑making in local units.

Employee‑led innovations reduced unnecessary paperwork by 15–25% in pilot areas.

Staff engagement scores improved in participating teams compared to control groups (Be More Pirate Case Studies, 2020).

Bringing the Two Together

Organisations that want to embrace distributed leadership may find that Be More Pirate offers the inspiration and courage to begin rewriting rules, while Holacracy offers a practical framework for implementing those changes at scale.

Pirates ignite the cultural shift.

Holacracy provides the scaffolding.

But leaders should beware: too much rigidity can kill the pirate spirit, and too little structure can leave teams adrift. The art lies in balancing the freedom of rebellion with the clarity of systemised governance.

Conclusion

Be More Pirate and Holacracy represent two sides of the same coin: the former calls us to challenge the status quo, the latter offers a detailed system to distribute authority. Together, they show that the future of work belongs to organisations that are bold enough to rewrite the rules—while disciplined enough to build new ones that last.

References

Bernstein, E., Bunch, J., Canner, N., & Lee, M. (2016). Beyond the Holacracy Hype. Harvard Business Review.

Conniff, S. (2018). Be More Pirate: Or How to Take on the World and Win. Portfolio Penguin.

Gray, D. (2009). The Connected Company. O'Reilly Media.

Laloux, F. (2014). Reinventing Organizations. Nelson Parker.

Robertson, B. (2015). Holacracy: The New Management System for a Rapidly Changing World. Henry Holt and Co.