Cowboys, Bureaucrats & Pirates

One of the biggest challenges of any startup is dealing with the cultural battles that arise when a company starts to implement structure and process into its operations. Communication and coordination are easy when the entire company can sit around a single lunch table, but once you have a lunchroom life becomes a little more complicated. Increased size and scope of business operations drive the necessity for formality and process. I have always thought of organizations as having two archetypes: the cowboy and the bureaucrat. The cowboy is the lone wolf nomad who operates best with total freedom away from the formalities of society. The cowboy’s credo is just get’er done. That is a great credo until customers start having an opinion on how things should be done (e.g., in accordance with ISO registration), or God forbid they want two of their products to be the same. That’s when the nomadic cowboy shows his limits. Once the ‘wild west’ [phase of your business] has been won, the cowboy’s role must be complimented with somebody with an eye for structure and repeatability. Enter the bureaucrat - the kind of person that understands the power and necessity of administration and process. To a bureaucrat, true beauty lies in efficiency and effectiveness, and so the bureaucrat is driven to tame the wild and bring order to things by building structures.

Unfortunately, cowboys and bureaucrats hate each other with a passion. The cowboy sees the bureaucrat as wanting to stifle innovation and creativity, and the bureaucrat sees the cowboy as a petulant child that cannot do anything without leaving a mess for somebody else to cleanup. It is an all-out cultural war that constantly shifts as the ratio of cowboys to bureaucrats changes along with the maturity of the company.

The truth is that companies need both cowboys and bureaucrats. The normal management strategy is to keep the warring parties apart, and just hope their cages (i.e., cubicle walls) are enough to keep them from fighting. I have come to think however that there is a third archetype out there – somebody that can cowboy when it is necessary but also build organizational capability along the way. It needs to be somebody that understands the value of process and infrastructure, but not in a dogmatic way. I struggled with the appropriate name and description for this archetype until my friend Ken Cook suggested the notion of the Pirate.

Pirates are masters of their craft. Yes, they are driven by the quest for the bounty, but more fundamentally they are sailors – great damn sailors. Sailing is one of those activities where coordination is an absolute necessity and each crewmember must master their role to perfection. Mastery in any field is achieved through discipline. It is this combination of superb skill and discipline that makes them masters. Seeking challenge (i.e., great bounties) in their work often places them in the role of pirates.

Most masters have a simultaneous distain and understanding of the need for rules and process. Their own personal discipline means that they do not need process or rules - control comes from within. Masters are given the tough jobs (i.e., sent into "no mans land") so they often run into situations where everyday rules, processes and standing orders are not relevant to the situation at hand, and stand in the way of getting the job done. At the same time, the master knows where his mastery starts and ends, and realizes that where there is not mastery, one needs processes or rules to follow to prevent harm to themselves or others.

The cowboy and the bureaucrat share a common attribute in that they are not masters nor do they understand mastery. The bureaucrat values blind adherence to procedure without insight or skill in a subject, and the cowboy values his personal insight and skill without appreciating the power of procedure. The bureaucrat will smother peak performance in the name of consistency. The cowboy will have occasional moments of glory punctuated by spectacular failures that take forever to clean up.

So, small startups can tolerate the cowboy because the organization needs their brilliance, and are nimble enough to contain the inevitable failures. However the small startup, when successful, quickly outgrows its ability to tolerate the downside of the cowboy. It usually takes a long time before the organization is large enough to tolerate the inflexibility of bureaucrats, but once they take root they tend to be a force to be reckoned with.

Overcoming the inevitable cultural battles that arise by trying to maintain some sort of détente between cowboys and bureaucrats is a losing proposition. Neither has the right answer and they will never agree to a ‘reasonable balance’ between their views. But there is a way forward: the relentless quest for mastery and the associated discipline it entails. Strive to build an organization whose culture values mastery toward the corporate mission above all else. Like the pirate sailor, set sail for blue oceans, endeavor to be a master of your crew position (be it captain or seaman), respect and coordinate your actions with the other crewmembers, and never lose sight of the bounty. It's the perfect cultural archetype and many thanks must go to Ken. The pirate culture - bounty-obsessed sailors with a healthy disrespect for the law.