How to Coach a Pirate

(NB Please do not quote without attribution)

As the final module of my coaching qualification with Meyler Campbell, I wrote an essay reflecting on what I’d learned, and exploring my emerging approach to coaching.

Throughout the course, I was drawn to three distinct types of clients, each representing pivotal moments where coaching has personally benefited me: Pirates, who seek to disrupt their industries, galvanize teams, or transform organisations from within; Firefighters, who face critical, time-sensitive challenges within the next 3-6 months; and Explorers, who are navigating new roles or exploring uncharted directions. My goal as a coach is to help leaders in these situations to thrive.

In my essay, I focused on the Pirates and explored whether they are truly coachable. I'm fascinated by leaders with disruptive, creative mindsets—those who’ve achieved success through self-belief and vision but may lack awareness of their weaknesses or the impact they have on others. These leaders could be founders, entrepreneurs, or creative mavericks; CEOs overseeing urgent turnarounds or corporate transformations; or intrapreneurs spearheading new ventures within legacy organizations. Can these leaders benefit from coaching? Will they engage with the process and its outcomes? Or would the self-awareness they gain act as kryptonite, undermining the strengths that fuelled their success?

To explore these questions, I drew on the wisdom of coaches in the Meyler Campbell community, as well as leaders, investors, and headhunters with firsthand experience. I distributed a short survey, asking them to identify the three greatest strengths and weaknesses of disruptive leaders and received over sixty responses.

The results (Exhibits 1 and 2) revealed that while strengths such as vision, communication, belief, and determination are common among disruptive leaders, these qualities are often offset by weaknesses in listening, empathy, arrogance, and self-awareness. Like many of us, the very traits that make Pirates great can also undermine their success.

I then asked respondents to rate, on a scale of 0 to 10, whether they believed disruptive leaders are aware of their strengths and weaknesses, and whether they are coachable. Exhibit 3 presents the results, with different colours representing instances where multiple respondents gave the same score. I believe this provides a valuable new tool for segmenting potential coaching clients in a practical and actionable way.

Respondents expressed confidence that most Pirates are both self-aware and coachable, with over 80% of scores being 5 or above on both axes. However, the responses also reflected a wide range of views, as highlighted by the quotes in Exhibit 4 below.

So, while Pirates may display vivid and extreme tendencies, they, like everyone else, possess unique attributes, varying levels of self-awareness, and different levels of commitment to coaching. As one Meyler Campbell faculty member observed:

“I think it varies between individuals. For some, part of their disruptive quality is an agility in taking onboard new thinking. They may see coaching as a sounding board for their innovative thinking and a way to support it and explore new possibilities. Others may suffer from hubris and believe they don’t have anything to learn from anyone. If someone…lacks even a chink of open-mindedness…my sense is they'd be fairly uncoachable...in any meaningful way”

Exhibit 3 is therefore a useful tool for identifying different types of disruptive leaders, offering a more nuanced method for assessing potential coaching engagements than the Coachability Index developed by the Lore International Institute.

The link to the survey is here: https://utb7kqgmbfu.typeform.com/to/j7DuUm

If you want to dive deeper and read the full list of qualitative statements I’ve posted them here.

If you’re interested in reading the entire essay it’s available here.

If you’d like to know more about my work as an adviser, coach and chair you can learn more here

And if you’re a pirate, firefighter or explorer, or a fellow coach, and you’d like to explore how we could work together I’d love to hear from you.