An Introduction

How Sherlock Holmes can help you be a better investigator and why examining fictional and real-life investigations can be important

I investigated crimes for 11 years as a federal prosecutor, but I had very little official training for that part of the job.

I went to a great law school, but it provided me with little preparation for the actual work of being a lawyer.  In law school, matters are typically presented to you from the back end – the judicial opinion that pronounces the relevant facts and sets forth a legal principle from on high. 

In law school, the facts are usually clear-cut and only the law is disputed.

But that is not how it works in the real world. 

In the real world, facts are messy and disputed - not just lying around for lawyers and judges to simply pick up and apply.  In the real world, I spent far more time as a prosecutor interviewing people and developing and analyzing evidence than I ever did doing legal research or even appearing in court.  And the same applies now that I am in private practice.

The famed legal scholar Blackstone recognized this in the civil context:

“Experience will abundantly show, that above a hundred of our lawsuits arise from disputed facts, for one where the law is disputed of.” 

Yale professor John H. Langbein put it even more simply:

“Find the facts and the law is usually easy.”

I learned how to investigate not in law school, but before - when I was a reporter – and after – when I was investigating cases on the job.  As a journalist, I spent years interviewing people, trying to interview people, staking out buildings and homes, poring through documents, and analyzing data – and then explaining what I had learned to strangers.  As a young lawyer, I worked closely with some great former prosecutors on some intense and complicated matters.

Over the years, I’ve wished that there were resources or guides that I could provide my colleagues or other lawyers so that they could be better at investigating (I did write one article for the U.S. Department of Justice to explain how to use data and documents more effectively).  And then I read the Sherlock Holmes stories and realized that the great detective felt the same way (or at least his author Sir Arthur Conan Doyle did).

Sherlock Holmes was a great detective not because of supernatural abilities or magical insights, but because of the training he underwent and the experiences that he had, things that he wanted to pass along to the police whom he viewed as incompetent.

For example, from A Study in Scarlet, the very first Holmes story:

“[I]f you have all the details of a thousand [misdeeds] at your finger ends, it is odd if you can’t unravel the thousand and first.”

And here’s the advice he gave to a young detective in The Valley of Fear:

“The most practical thing that you ever [could do] in your life would be to shut yourself up for three months and read twelve hours a day at the annals of crime.”

Basically, it is easier to solve a particular crime if you know how similar crimes were solved.  Find the right facts for your case by knowing (1) what facts worked in other cases and (2) how those facts were found.

So it was for me. 

When I first became a prosecutor, I learned from others how to solve certain types of specific crimes - bank robberies, drug cases, child exploitation cases.  And I later taught people how to solve certain types of white-collar crimes that I had successfully prosecuted, passing on the techniques that I had developed so they would not have to re-invent the wheel themselves.

Holmes had other lessons for investigators that are scattered throughout the stories, lessons that I’ve shared myself in a webinar for the Federal Bar Association.  Compiling these lessons was Holmes’ dream: “to devote my declining years to the composition of a text-book which shall focus the whole art of detection into one volume.”

Holmes may not have gotten around to writing this textbook, but I am going to give it a try here.  Think of this as a quasi-sequel to the book that Sherlock Holmes would have written if he were real.  Here, I will share my advice and thoughts about investigative techniques and strategies using real-life and fictional examples. 

I’m going to discuss topics such as:

• How to interview someone, including the key sixth question that many investigators do not ask,

• How to review emails, something that Sherlock Holmes never had to deal with but is a huge part of modern investigations, and

• How to evaluate evidence, both in court and in your everyday life.

And I plan to use real-life and fictional examples that hopefully you will find interesting, such as:

• Sir Arthur Conan Doyle’s Sherlock Holmes,

• Agatha Christie’s Hercule Poirot,

• Operation Varsity Blues,

• The O.J. Simpson murder trial, and

• The Bible, which, after all, does describe the first homicide and the first criminal investigation!

I think this will be useful for investigators of all kinds, and that includes you, no matter what you do for a living.  These days, our public discourse and the success of our democratic system depend on people being able to sort through facts and arguments for themselves, being able to evaluate evidence, and being able to make decisions based on that analysis.  I have lots of thoughts about this and hope to share them with you in an interesting way.

I hope you join me!  Please subscribe, and please contact me with any questions or suggestions.

I was a federal prosecutor for 11 years and also worked at big law firms for 10 years. I now am a solo practitioner focusing on white-collar criminal defense, health care fraud, and data analytics in litigation.