Lately the business books being published focus on contrarian concepts, such as Barking Up the Wrong Tree: The Surprising Science Behind Why Everything You Know About Success Is (Mostly) Wrong; Everybody Lies: Big Data, New Data, and What the Internet Can Tell Us About Who We Really Are; and the one that caught my attention, Warnings: Finding Cassandras to Stop Catastrophes, which came out on May 23, 2017, by Richard A. Clarke and R.P. Eddy. The book caught my attention because I have a Cassandra all my own, and he’s one of my most useful colleagues.

Because he is a very private person, I will just call him “Roy.”

Like Cassandra, the Greek prophet of doom, Roy has the difficult gift of finding fault in whatever he sees, and hence the seeds of future calamities. Like Cassandra — and all folks like Roy — he is also, often ignored, especially when all enthusiasm and illusion break loose, and he’s the only one with doubts about the project, or the product, or the prospects for success. I find his negative bent as one of the most useful perspectives among business advisors.

I like things to be right, and spotting the mistakes makes correcting them easy. But it’s easy to overlook mistakes, especially when fueled with enthusiasm and confidence. In Finding Cassandras, the authors focus on big issues, like emerging economic and political disasters. Cassandras also work on the mundane, such as personnel hiring, selecting clients, undertaking business ventures, and analyzing new products.

If you have a person like Roy in your life, I advise you to bring him or her close to you. Invite their opinion, even if you must do it in private. When I have a project in development, or a new business relationship, I will blind-copy Roy on my emails and planning. He will often pick up on the subtext of the interaction, highlighting double meanings and implied intentions I would not notice.

When I get ready to publish something, like a project manual or a brochure, Roy can see the errors in it, in Spanish and English, where the editors did not. He can spot mathematical mistakes, inconsistencies in logic, and the evolution of a defect from minor imperfection to major problem. In fact, over the four years that I have worked with Roy, I can say that I only regret not having heeded his advice more.

Care for your Cassandra

On the flip side, Roy can also see the blemishes in a beautiful woman, taste the imbalance of ingredients in a gourmet meal, and the decline in a lovely landscape. He finds it hard to find happiness. The Cassandra talent is a heavy gift, with a steep personal price to pay. I have developed a deep compassion for Roy, because as valuable as his fault-finding is to my decision making in business, it’s also what keeps him from joy, if ignorance is truly bliss.

Precisely because Roy sees the negative outcome, he sometimes circumvents good luck — which can be unpredictable.

Good luck, is the flip side of a black swan event, which is defined as a major event that nobody foresaw (except the Cassandras), and usually of negative consequence. The Great Recession was, for most of us, a black swan event. Roy foresaw it, and didn’t buy a house in Denver during 2004, believing the market would crash. Today that same house — despite the crash he predicted—has tripled in value, and he regrets his decision not to buy it.

So, the thing to keep in mind is change. Your personal Cassandra can help you find faults you would overlook, and correct them, or at least remain wary of the possible negative outcome. Thanks to Roy pointing out one business venture would likely end up in lawsuit, we kept perfect records, and made the effort to comply with all our contractual obligations. Now we are on the cusp of winning that lawsuit, and perhaps make more money than we would have with a successful project.

When you combine talents, such as the infectious enthusiasm of a young and talented salesperson, with the seasoned and reasoned oversight of an experienced businessperson, and the annoyingly accurate insights of a gifted Cassandra, you have the basis for a successful organization that can navigate toward your clear blue ocean, and sail through the inevitable storms.

Creative commons photo credit: Matt RF Webb