How NOT To Tell Your Boss You’ve Applied to Another Job: A Story of How My Arrogance and Ignorance Got the Best of Me

It took me a couple tries to get into the CIA. The first time I applied, I didn’t hear anything, but the second time was different. I received an email from a man who wanted to interview me, and because I already had a professional career, I secretly called my grandfather from my cell phone in my car in the office building’s parking lot.

“Grandpa, this is the email he sent me,” I said as I then read word-for-word what the recruiter’s message said.

“Well that sounds pretty good,” he responded.

I called Chris, the man who emailed me and told him I was interested in hearing more.

“I’m going to be on the Ohio State campus in two weeks,” he told me. “I’d love to interview you.” I immediately accepted, but said there was one problem.

“The thing is, I actually already graduated, so I live in Cleveland now.”

“Oh, yes you did already graduate,” Chris said, taking another look at my resume. “Can you still come to Columbus?”

I agreed, of course, but I needed to figure out a plan.

Luckily, the job of a financial adviser is one that is spent away from your desk. You had to be out making relationships and meeting potential clients, so as a hopeful future CIA officer, I decided I would do a little covert action with my boss.

“Jeremy, I wanted to let you know that I’m going to drive down to Columbus in a few weeks. I set up some PMMs [preliminary money management meetings] with potential clients there, so I’ll leave in the morning and come back at night.”

He didn’t think anything of it and agreed to my day trip.

I did meet with some potential clients–all of whom were recent graduates like me and none of whom were ready for a full-time financial adviser–in addition to Chris, my CIA interviewer. I thought the interview went well and then went back to Cleveland and waited.

Then I received the Conditional Offer of Employment and the paperwork to sign to start the background check.

And this is where the story gets dicey…

The background check and screening process includes a required three-day visit to the Washington, DC area. It is where you have your psychological evaluation and polygraph examination. The problem was that I didn’t exactly have “vacation” days in my first year at my company.

It needed to happen, and I needed to figure it out, so I devised another plan.

There were a few other things that were going at home around this time, including the upcoming party for my grandparents’ 50th anniversary, as well as my grandmother having surgery to remove part of her kidney that was growing a tumor. While it wasn’t known if the tumor was malignant or benign, surgery was the best option to find out, and the surgery was scheduled for the Monday before the party.

So here was the plan I came up with.

I told Jeremy that my grandmother was having cancer surgery and that it was important for me, my family, and her that I was there with her in the hospital as she had the operation and recovered and that I would spend the rest of the week working out of the Ameriprise Financial office in Gaithersburg, Maryland, before attending the anniversary party the following weekend. I told him I would fly out Sunday night and return the following Sunday, reporting back to work the next Monday.

He seemed skeptical, but agreed to my plan. With his support, I contacted the travel agency that had booked my trip for the three-day visit to CIA Headquarters. I asked if they could book my flight on Sunday and not book my return until the following Sunday, if it was no difference. They obliged and I booked my hotel room in Tyson’s Corner for the nights of Sunday through Tuesday, and would stay with my family for the remaining nights.

With everything set, I booked appointments with potential clients on Thursday and Friday (after all, I still had a job to do).

The visit to CIA Headquarters went fine and I completed my three-day visit, except for the series of unfortunate events that started that Wednesday.

I don’t know how this happened, but my boss in Cleveland was under the assumption that I was going to spend two days with my family, not three, and report to the Ameriprise office in Maryland on Wednesday. When I didn’t report Wednesday, because I was still in the CIA’s three-day-visit protocol, he called the boss of the Maryland office to find out what was going on.

By the time I showed up to the Maryland office on Thursday and met with the boss of the office there, I already had messages and emails waiting for me. They were from my Cleveland boss, asking where I was and why I hadn’t shown up on Wednesday.

I called him back and tried to explain that I had been with my family for the three days and that we must have had a misunderstanding. I could sense his frustration and unhappiness on the phone, so I did my best to apologize and explain the work I had lined up for the remaining few days.

Also on Thursday, I received several phone calls from background investigators, asking for my references who could provide verifying information about my past work and the places I had lived. I wanted to support their work as best I could, so I provided them with the information they requested the same day. The next day, Friday, I received a request from the investigator based in Cleveland to interview my coworkers and supervisors.

Up until this point, I may have walked very close to the line, but in my next action, I definitely crossed it and did probably the stupidest thing I could have done.

Instead of calling my bosses and coworker to let them know about this request for the security interview, I sent an email. But it wasn’t a regular email with all the people on the “To” line. I put my boss on the To line and my manager and coworker on the BCC line. I did this thinking that, to send an email, at least one person had to be on the To line, or it wouldn’t send. I thought it would be best to give each of them a separate email, hence the BCC additions, and that, the way I did it, no one would know who else was receiving this request.

And here is what I wrote, on Friday, March 30th, at 11:30 a.m.:

I just wanted to let you know that an investigator wants to meet with you on Monday. He called me and said to let you know that he’ll be in our office to talk to you for about 15 minutes. I know your schedule tends to be kind of full on Mondays, so he said he could be a little flexible. To calm some nerves, I assure you that this is NOT securities related.  Thanks for your help.  Parker

[Insert facepalm emoji here]

What a blunder…what a terrible decision…what a terrible email. My manager and coworker knew that my boss knew, but they didn’t know about each other. My manager knew that he got this email, but that no one else did.

I didn’t get a response to that email, but when I returned to work on Monday, everything was at a boiling point, and it makes sense:

  • I told my boss I needed to be with my family, but didn’t report to the other office when he thought I would.
  • I was working in the other office, much closer to my hometown, so he is suspicious that I might be trying to make a switch out of the Cleveland office.
  • My boss got an email asking him to meet with an “investigator” the next business day, with no information what it was about, only a brief line about what it was not about.

When Monday, April 2nd, came around. I was nervous. The investigator showed up on time and I met with him in our reception area asking if he really had to interview my boss. I pleaded that he was my second-level supervisor, so the investigator would really only have to interview my direct supervisor (my manager) and my one coworker.

“Sorry, Parker, you put him on the paperwork, so I’ve got to interview him.” I acknowledged and gave the man one of our client meeting spaces to set up. Then, I walked into my boss’s office and let him know the investigator was ready for him.

My boss looked up at me–there was a fury behind his eyes–and he said to me, “What the hell is this about?” I hesitated for a moment, and he spoke again. “Parker, if I call my aunt who works for the Department of Defense and ask her what this is about, what is she going to tell me?!”

It was a silly question, but I was immature and decided to come clean.

“It’s a security investigation for a job I applied to before I started working here.” And that was a true statement, although a bit misleading. The first time I applied to CIA was during my senior year of college, so technically I was being honest, though I was hiding the fact that I also applied while working in Cleveland.

“God damn it, Parker! I know hookers with more loyalty than you!”

[Yes, he literally said that and I remember it like it was yesterday.]

Nevertheless, I needed him to conduct the interview, so I simply told him that the investigator was ready for him in the client room. My boss got up from behind his desk and stormed out of his office, passing me as I let him through.

The other interviews seemed to go fine, and once our cooler heads prevailed, I met with my boss to talk about what happened.

“I’m very disappointed in how you handled this situation,” he said to me.

I was arrogant back then, so I didn’t think much about it (although he was right), but just thanked him for doing the interview either way.

“The interviewer asked me if I trusted you,” he said. “I told him that I used to…before today.”

And that, my friends, is NOT how to tell your boss you’ve applied to another job. I was arrogant and ignorant. And in Metallica’s song Holier Than Thou, “Arrogance and ignorance go hand in hand…holier than thou, you are.” Back then, I probably did think I was holier than thou…untouchable…unbreakable.

But I learned a lot of lessons from this situation, ones that I applied to my most recent job change.

The story, however, doesn’t end there, and it comes a bit full circle.

Around this time, our boss had told us that he took a trip to a sister office of our company in Connecticut for some high-level management training. A few weeks after my incident, he got up in front of us at our Monday morning meeting and said, “I need to be more honest with you. I wasn’t in Connecticut for training, I was there to interview for the office VP position there.”

There were some gasps, some smiles, and even some “I knew it!” from a few others. He told us more about the position, and that he had been offered the job, and had decided to accept it, and he would be leaving in a few days to take the job.

Well, I was arrogant and ignorant, so I looked at the situation through those two lenses.

He did the same thing that I did, I thought. He lied about applying to a new job.

Shortly after the meeting, when he was sitting at his desk in his office, I knocked on his door. He looked up. “What’s up?”

“I just wanted to say that I’m very disappointed in how you handled this situation,” I said with a smirk.

His facial expression changed to one of displeasure and eventually anger.

“Are you fuckin’ with me?” he asked.

“I’m not. It seems to me that you did the same thing I did, yet for some reason it’s okay,” I said as I walked back to my desk.

That was the last time I remember speaking to him. The following week, his office was vacant as he had moved to new his city.

The Gemini Towers in Westlake, Ohio. My office was on the second floor in the building in the foreground.

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