How Imaginative is Your Investigator?

But tough cases can turn on an investigator thinking, “I should be seeing X but I’m not.” Why would a money manager for very rich people have an office in that part of town, amid abandoned houses and lots of crime? Databases won’t tell you to think this way.

British codebreakers during the Second World War woke up each day faced with the task of breaking the codes set by Nazi Germany’s famed Enigma encryption machine. Every day, the British would intercept coded German messages, knowing they would have no more than 24 hours to break the code because Enigma would use one of trillions of new encryption combinations every day.

The breakthrough came when team members put themselves in the shoes of the people they were fighting. The team realized that the phrase “Heil Hitler!” probably appeared at the end of each message the Germans sent. It was a fatal flaw that helped to break Enigma (without letting the Germans know, of course) and turn the tide of World War II.

The codebreakers could never be 100 percent certain that the messages ended in “Heil Hitler,” but it was a sensible bet. Sensible, because they used information they had from open propaganda, articles meant for wide dispersal, and they imagined (i.e. assumed without proof) that the pattern they had seen could have been repeated in secret code.

One of my best imaginative cases was helping a European investor decide whether an Italian American company was linked to organized crime. There was absolutely no evidence of this, but unfortunately it was not the first such assignment I had been given.

In addition to telling the client I saw no evidence (including reading a couple of books about organized crime in that state and looking into associates as well as the principals themselves), I imagined what a company with criminal links might be like. It would be reluctant to sue people a lot, because opponents could get discovery of its books and records and see where the money was going.

It would probably not use a large and prestigious law firm with lots of blue-chip corporate clients. Those firms like to steer clear of the mob.

And it would probably go into less competitive businesses that would minimize the need to deliver the best service for the best price.

I found this company sued people a lot, had the most prestigious law firm in its state on call, and was in all kinds of competitive industries. To this day, there has never been a whiff of evidence or innuendo about any illegal activity on the part of the company.

What’s the most imaginative, creative (and still legal) thing you’ve ever done on the job?