Pirates in the Navy (Ed Batista)

Pirate

It may sound odd, but pirates are a recurring theme in my executive coaching practice. I work with many startup founders, and it's not unusual for them to identify with or feel some affection for that other group of entrepreneurs who operated outside the bounds of conventional commerce. The concept is deeply rooted in the technology sector's collective narrative, and last year venture capitalist and LinkedIn co-founder Reid Hoffman published a compelling post that discusses this idea in depth:

One of the reasons the pirate label seems so appealing is that early-stage startups are a lot like pirates. They both lack formal processes, and are willing to question and even break rules to "steal" from incumbents (market share and booty respectively)... Pirates don't convene a committee meaning to decide what to do... [T]hey act quickly and decisively, and are willing to take risks because they know that the default outcome is failure and the death of the company. [1]

It's important to not to take this association too far, of course. As Hoffman also noted, piracy can be a problematic metaphor:

Much as with Silicon Valley's fondness for the term "disruption," piracy is a sexy label which projects the wrong image of entrepreneurship, and promotes connotations that can lead entrepreneurs astray... It may sound cool to say that you're a pirate, but to the rest of the world, you're essentially saying, "I'm a no-good thief." [2]

But he goes on to clarify that there are two different types of pirate: lovable rogues, who break rules but whose acquisitiveness is restrained by a code of ethics, and sociopathic criminals, who don't hesitate to harm others in the pursuit of naked self-interest. To be clear, my clients who respond to this theme are either lovable rogues themselves or enjoy leading teams composed of such characters--I don't work with sociopaths.

The antithesis of the pirate is the naval officer, and Hoffman argues that "startup pirates" eventually have to switch sides:

The impulsive Captain Jack Sparrow has to grow up and start acting more like the sober and responsible Captain Picard. This transition can be challenging; founders and early employees often resist changing their approach; after all, didn't it bring initial success? But failing to make the transition from pirate to navy can lead to disaster. [3]

I agree with Hoffman's thesis--growing organizations and their leaders must beware of the dangers of "failing the pirate-to-navy transition." But they must also be thoughtful about how they make this transition and what they evolve into. Just as some pirates are sociopathic criminals, some naval officers are by-the-book martinets and others are power-hungry political schemers. And just as some pirate ships are menacing threats, some commands in the navy are awful, soul-crushing bureaucracies.

The key is finding the right balance between the two identities, both for the individual leader and for the organization as a whole. Rather than being pirates OR the navy, perhaps being pirates IN the navy is a better way to think about it. Some of the leaders I've worked with are true pirates (the ethical kind) with no interest in serving in anyone's navy. As their companies grow they become increasingly uncomfortable with the routines, structures, and management style required to lead at scale, and eventually they're happy to recruit an "admiral" to take over, freeing them to pursue their next adventure.

But most of my clients want to remain with the organizations they've built for some period of time; even if they don't feel the need to stay permanently, they want to stretch themselves as leaders and reap the rewards (material and psychological) that will accompany a longer tenure in the role. In my experience leaders who make this transition successfully--pirates who've joined the navy, or who've transformed their pirate crew into naval officers--pay particular attention to these areas:

1. Self-Care

Pirates aren't models of healthy habits, and the same is true of many startup founders. Long hours, erratic sleep, poor diet, and minimal exercise are common. Effective leadership always entails hard work, to be sure, but a sustained tenure in a management role at scale is built on a set of self-care practices that are anything but piratical. [4] Among the practices I often discuss with clients are mindfulness and meditation, consistent exercise, and sufficient rest. [5] And yet the goal here isn't to compel a pirate to abide by a set of rules for orderly living but to help each leader adapt what we've learned about effective performance to their individual needs and preferences.

2. Work Style

One of the pleasures of being a pirate is freedom from routine, and many founders enjoy working in a similarly dynamic style. They focus on the problem in front of them until it's solved (or at least no longer an existential threat), and then simply move on to the next one that captures their attention. This approach works in a venture's early stages because every problem poses an existential threat. But what's necessary for early stage survival is sub-optimal for later-stage success, and if a leader maintains this work style beyond a certain point in the organization's growth, they risk wasting attention and energy (their own and others') on less-important problems. Related issues I often discuss with clients include treating attention as a resource, recognizing the difference between importance and urgency, actively ignoring some problems, and creating open space in order to think. [6]

3. Culture and Team Dynamics

From pirate ships to startups, every human system is characterized by a distinct culture, a set of norms that govern interactions and determine acceptable behavior. [7] These implicit rules begin to emerge immediately in an organization--as investor and JetBlue chair Joel Peterson once told an entrepreneur who denied that his company had a culture, "You have a culture. The question is: Do you want to influence it or not?" [8] And the challenge for a startup leader is to insure that the culture evolves to fit the needs of the business, while acknowledging the special contributions of the pirates who launched it. This is of particular importance among the executive team, where a leader has significant leverage to accelerate (and to resist) the pace of organizational change by personally modeling desired behavior, providing coaching and feedback [9], and by firing or levelling senior team members. [10] A leader who moves too quickly can trigger the unnecessary departure of early stage execs and a loss of trust within the team, but one who moves too slowly can allow a team to stagnate, creating a climate that's unwelcoming to new execs, making it difficult to add any "naval officers" to the team.

4. Structure and Systems

Finally, while the simple structure and improvisational nature of pirate life has its appeal, it generally fails to scale. As I wrote recently:

Growing organizations require increasing routinization of work. Tasks are transformed into processes, which are then combined into systems. This trend can be counterproductive, and I’m not suggesting that organizations should rush to embrace bureaucracy. But the fluidity and ambiguity that foster creative problem-solving in an early stage startup will feel like chaotic dysfunction at a later point in the company’s development. The dilemma this poses for leaders in growing organizations is that they typically prefer fluidity and ambiguity—this is why they launched the venture or took the job in the first place. They also generally have a bias for action, and when they’re faced with a system that seems to be slowing things down, they simply ignore it. This can be a great strength—but it can also be a crucial weakness, particularly when a leader’s reflexive disregard for systems prevents their healthy evolution in the organization at large. [11]

Footnotes

[1] Uber Needs to Transition from "Pirate" to "Navy" (Reid Hoffman, LinkedIn, 2017)

[2] Ibid.

[3] Ibid.

[4] "Work Hard or Work Smart?" Is the Wrong Question

[5] For more on self-care, see the following:

[6] For more on work style, see the following:

[7] Startups as Human Systems

[8] Joel Peterson on Organizational Culture

[9] Coaching and Feedback Tools for Leaders

[10] For more on removing people from their role:

[11] How to Scale: Do Less, Lead More