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Make Decisions Like a PI

A Leadership Discussion With Skipp Porteous: President & Founder of Sherlock Investigations

Skipp Porteous is the founder and president of Sherlock Investigations–a New York City-based private investigating business that has been around since 1995. He’s also the author of the book Into the Blast: The True Story of D.B. Cooper that explores the events behind the infamous in-flight hijacking of Northwest Flight 305.

Porteous got his start at the Los Angeles’ Department of Water & Power’s Special Collections Unit. He was a ‘skip-tracer’ and his job was to find people who skipped out on their bills. After his tenure in LA he became an undercover investigator with the Columbia County Sheriff’s Department in upstate New York. While he was there he specialized in narcotics investigations.

Since then Porteous has been involved with specialized investigative research and reporting as well as running his business.

I thought it would be interesting to talk to Porteous about leadership, management, and decision making because he not only operates a successful business, but he has to a lead a team through confidential and sometimes dangerous situations. Porteous generously set some time aside for some questions and answered them over email.

Leaders in any context can draw from Porteous’ experience and his methods of dealing with clients, younger team members, and uncertainty.

1. According to your website, you coordinate and direct four private investigators as well as work with outside consultants. Can you explain the process?

Our agenda is answering the questions (problems) that people ask. The clients tell us if we’ve answered their questions/problems correctly. We open case files of every client, ask specifically what they want, and find it for them.

2. In your field there exists a high degree of uncertainty and with that real danger. How do you deal with the prospect of day-in and day-out uncertainty?

We maintain low operating costs. We’ve been in business since 1995. That’s when we went on the Internet, too. People know we’re here. Also, I do bug sweeps for about 12 other private investigators. Bug sweeps are a technical skill, not an investigative one. So, I do about 2 or 3 bug sweeps a week.

3. The decision-making process of a private investigator must be quick. Sometimes, there’s no time to rub your chin and ponder alternatives. Although your private investigators are already trained and licensed, do you try to help them make best-case decisions by giving them defined instructions (ex: if X, do Y) or do you allow them to make ‘gut decisions’?

Almost no decision must be rushed. A plan must be followed. The clients who call at the last minute for a surveillance, or who want rush decisions are avoided. Sometimes we don’t take them as clients.

We work with intelligent people. As such, we allow them to make gut decisions.

4. Can you name a previous boss or role model that has shaped how you lead people and juggle different personalities? If so, can you explain how briefly.

Our heroes are Napoleon Hill, Abraham Lincoln, and Nelson Mandela. They’ve all worked successfully with people because they know themselves.

5. Have you ever made a mistake as a leader? If so, how did you learn from it and adapt?

Of course. I’ve learned to be very honest with myself and not make the same mistake twice.

6. How do you train the younger talent on your team? Do you work closely with rookies or do you let them learn for themselves?

We work very closely with them and teach them everything. Only when they’re ready in our opinion do we let them go on their own. Still, we keep an eye on them.

7. For people who want to know more about your business what book, movie, or website do you recommend they look in to?

I highly recommend The Complete Idiot’s Guide to Private Investigation by Steven Kerry Brown. Steve is a retired Special Agent with the FBI. He now has a private investigative agency in Florida.