My Very Brief Career as the World’s Worst Detective – Smart Media Magazine

My Very Brief Career as the World’s Worst Detective

This is not an easy place to get hired,” said a fellow analyst at the company, an elite, private-sector global intelligence organization.

The vetting process was rigorous: an extensive background check, drug testing, fingerprinting, half a dozen interviews and months of waiting.

The company recruited highly decorated F.B.I. agents, state and federal prosecutors, and the most senior members of law enforcement.

I had worked as a gossip columnist and as an editor for a couple of celebrity weekly magazines. My expense account was $20,000 per week. I hustled, got drunk and got dirt. Somebody thought this qualified me to be a private investigator. That somebody was wrong.

“When we look into a new hire at a senior level, we treat them the same way we do a subject under investigation,” an executive said.

By the time I heard this, I had been at the company for two months and I was halfway through my 30-day P.I.P. (Personal Improvement Performance review). I didn’t need to be Inspector Poirot to detect that the jig was up.

My late father was a deal maker. I was raised to believe “real” men didn’t earn money. They made it: one big idea. Get to yes. But, after a yearlong stint of freelancing in search of that big idea, my son arrived. I needed a steady paycheck. My years of reporting had taught me how to ask enough questions to look the part and get hired.

The company’s clients came from the worlds of professional sports, Hollywood, Wall Street, aviation, oil trading, fine jewelry, cryptocurrency, mining and other big-money endeavors.

Every case was unique, but the questions were similar. Will online threats turn into real-world violence? Police were investigating a matter, but the client wanted their own report. Is this entrepreneur the next Elon Musk or a grifter in a tuxedo? A start-up needed to know if an investor was really in a position to put in billions with a “b,” what the source of that money was, and what else the investor was involved in.

I had been given the title of senior director and functioned as an analyst, which, among other things, meant a lot of background checks, identity verification and snooping into social media behavior over the last 20 years.

A month into the job, nearly a third of my brief career as an investigator, my cellphone rang. A male voice said his employer’s private bankers were getting calls from me asking questions about his finances.

“Sounds about right,” I said, swallowing a bite of a dry sandwich at my desk around 3 p.m. “That is what we do here.”

The caller wanted proof I wasn’t a con man. He also didn’t want to tell me his name or the name of his employer. I wanted to help, but I couldn’t just volunteer information.

“What we have is a standoff,” he said. I agreed.

Eventually we exchanged names and Googled each other. We asked and answered cryptic questions. Ultimately, he determined he need not report me to the authorities.

Colleagues would occasionally say to one another when confronted with some thorny situation, “You’re a professional investigator, you should be able to work it out.” No one ever said this to me.

Weeks earlier, an executive had called me into a conference room with a team of lawyers. My investigation had become the subject of a second investigation. Why? A client’s reference was unaware of the initial investigation and naturally creeped out by my questions about the client’s interests and character. It wasn’t my fault, but no apology was forthcoming.

I had read or watched hundreds of detective stories over the years. None of them showed the detective spending so much time defending himself against his own clients. The fantasy was Bond, Holmes and Serpico. The reality was Inspector Clouseau, had he been slightly less efficient than Dwight Schrute from “The Office.”

I was seduced by the trope of the best detective working under the worst conditions. Here, I felt like the worst detective working under the best conditions.

I learned that investigations usually weren’t conducted to apprehend bad guys. Clients just wanted to eliminate any surprises. Investigators can work around the clock to produce a report, and the client will only read the executive summary and will do the deal regardless of the findings. There was little opportunity to play the hero.

In fiction, spies are known for their breezy, impulsive approaches. In reality, investigations are laden with regulations and procedures. Arcane knowledge — real estate law, insurance titles, say — is often the key to solving these mysteries.

In fiction, the spy uses one of a half-dozen passports, well-rehearsed identities and Oscar-worthy disguises. In reality, misrepresenting yourself in any way is against the law.

In fiction, it’s honey pots and stylish spies bouncing from ski resort to beach club. In reality, I was glued to my desk, where I made calls on a headset, performed database searches and wore khakis.

I may have failed to finish reviewing orders of protection attached to divorce filings — if I understood what they said at all. This, along with many, many other mistakes I made while operating in a Mr. Magoo-like cloud of confusion, makes me wonder who screwed up when they were supposed to be investigating me.

A couple of weeks after I had started, we moved offices. By force of habit, I got off the subway and walked a few blocks to the old building. Later that week, when a colleague expressed mild confusion about the floor plan in the new place, I admitted I was lucky to have even found the building.

I struggled to understand the language used in federal, state and local litigation. There were dozens of databases, and I could hardly remember where I’d written my passwords. In one instance, when a case manager told me a client had a rolling deadline, I stuck the file in a drawer. When asked about my progress, I hardly remembered it was even on my to-do list.

At the beginning of the end, I was told, “Michael, in my 14 years here, I’ve never seen someone so disorganized when it comes to reports and billing.”

My first thought was that if anyone had been as confused as I was, my heart would go out to him or her. My second thought was: With everything you’ve identified that I’ve done wrong, you haven’t caught half of it!

When I showed up for the final meeting, on a Friday morning, the company’s human capital business partner dialed in. She announced that they’d come to a decision (decision?!), and handed the proceedings over to a managing director who made it clear I was toast. I fought the childish desire to ask where this was all coming from.

The head of the New York office, a former leader of a government intelligence agency, walked me to the lobby.

On the way to the elevator, I stopped and asked, “What about the Christmas party?”

He looked back at me with genuine concern. I cracked an impish smile. We hugged awkwardly by the security gate.

While getting hired as a private investigator may not have been easy, when it came to business intelligence, I wasn’t only miscast. I didn’t even have a clue.

Michael Rovner is a writer in New York City, where he lives with his wife and son.

Rites of Passage is a weekly-ish column from Styles and The Times Gender Initiative. For information on how to submit an essay, click here. ​To read past essays, check out this page.

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