On having Pirates and Black Sheep as your Advisors

Image by Rujhan Basir from Pixabay

Black Sheep

There is a park next to my parents’ house in Grenoble. In this park, the gardeners decided to set a flock of sheep to graze the grass. They call this “eco-pastures.” It allows to save costs (I guess), but moreover to have this sweet presence of animals in the park, and having less CO² emissions than using lawnmowers. The other day, I looked at the sheep: 6 white ones and a black ones. I observed that it was always the  black one leading, and the other ones following. That observation was counter the usual “Black Sheep” expression we use to describe someone rejected by the clan. This black sheep was remarkably different, and yet able to lead and influence his peers. Furthermore, I never saw that black sheep get in any kind of trouble with the others (even though I saw a white sheep bullying one or two other white sheep.) Occasionally, the black sheep would wander off, and do its thing, grazing alone. He didn’t seem sad nor abandoned. He was in peace.



Pirates were legendary figures. We all know of the dark side of this archetype from the pupular culture: ruthless, violent, stealing, killing and raping. Yet, there were Pirate Codes  that were established. Pirates lived by their own rules. Yet, there was another part to them, which is the light side: unconventional, determined, and risk-taking. One of their strategies: “Burn the ship”. You can use it in your projects:

When they wanted to board another ship, one of their strategies was to  set fire to their own ship. That created a powerful psychological momentum for knowing that there was no way back, no safety net. When you need to get somewhere, that could be a good option.

In other moments, you might need to feel that you are keeping a safety net, so you might want to use the Spiderman technique, that Rich Litvin mentions in his article.

Pirates have another quality to them: they don’t care what other people (the Victorian society) think about them. They just do their thing. They are not afraid to say they love money. They love adventure. They go for what they want. They are enterprising. They do things differently, and they live from experience, not from a bunch of theories (although I love theories too!).

Some leaders don’t like Black Sheep nor Pirates

Last year, I felt inspired to connect with a business owner in France, who produced a herbal-based product that I love. We met at a restaurant, and he was kind to let me in the production facility for I was curious to see how he operated. I offered him some coaching, which he accepted. I saw him as a very spiritual person though, but I saw that he was not open to much feedback. I tried to find different ways in which I could serve him, and I sent him some ideas to improve his marketing and his branding. He did not see value in my propositions.

The business owner wanted to discuss the ideas I had given him, so I made time for a call with him. During that call, he counted every point I made in that document. I felt rejected, inadequate, and that I had gone too far in my service for this man who had not asked for it !

On the call, I asked him:

“I hear that there is a lot that you disagree with, and that most ideas seem irrelevant for you. In my whole document, is there one single idea that seems interesting to you?”

He paused for a moment.

Then he went on to ramble again on some ideas that were irrelevant and did not match his “facts”. (There is no such thing as dry facts. There is only interpretation and selection on facts based on our mindset.)

I closed the conversation, thanked him, and that was that.

I felt confused and sad after this call. Only later did I realized the blessing in disguise:

This man could not be a healthy client. Not with this closed and “know it all” mindset.

“A sage can learn from a fool, but a fool can’t learn from a sage.”

It was a mistake on my side, for he had not asked for my feedback nor my work. I was doing more work than he was, and that is not the way to go for a coach.

Capitalizing on Black Sheep and Pirates

Whatever project you are carrying out, you need at least a black sheep or a pirate in it. Someone who will go against your ideas, or be willing to challenge you and push back. If someone in your team is doing this, thank them for it. If you hate it, open your mind: you have a teacher in disguise in front of you.

Your job as a leader is to create more leaders, more black sheep. Not a bunch of followers. The world already has enough white sheep.

Everybody can be a black sheep, in their own way.

Listening to Black Sheep and Pirates with an open mind and an open heart will save you time, money, disappointment, mistakes, and failures. If you don’t yet have any, search for some. In the fields of cybersecurity, airport security, the military and intelligence agencies, project leaders designate a “Red Team” who’s role is to challenge operational planning by playing the role of a mindful adversary. In major law firms, they also practice mock trials, so that the attorneys can prepare their best defense and take into account opposing arguments for the case. They have a team from the law firm play the Devil’s Advocate, which improves their thinking and the outcomes for their clients.


If you are running a project, you need trusted advisors. There are several kinds of advisors. Some advisors try to please you. They try to be nice, and don’t rock the boat.

Some advisors try to manipulate you, to steer the project in the way they want it to go.

The priceless advisors are those who are not attached to the results of the project, yet they care deeply about it.

In a recent coaching retreat I led for clients, I told the three co-directors of the company:

“I am not attached to the outcomes of this retreat. Yet, if in a year, nothing had changed, it would hurt my heart.”

You need an advisor that can support you when needed, but also challenge you when you need to be challenged.

Who challenges your views in your world?

Do you have a Red Team, a coach or an advisor?

What is one point that they are constantly making, that if taken to be true, could improve your project?

If you would like some challenging feedback on your project, reach out, I would be glad to help you see some blind spots.

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