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Know your boss - the "head," toothpicks, and a pillow

Updated: Jan 17, 2023

This is a series of fun stories about the restroom, toothpicks, and a pillow and what each of the matters taught me about leadership and success.

This is a blog about leadership from the perspective of a lawyer and a naval aviator.

This is the fifth post about the many lessons I learned about leadership and success from an admiral when I worked as his flag aide over thirty years ago. I have discussed the job in great detail in my previous posts "What's a Loop?" and "It all began as a Loop."

As an admiral’s aide, you need to know your boss better than anyone else. Some say you get to know your boss as well as, if not better than, your boss's spouse. I was with the admiral from the time he woke up in the morning - usually well before the sun rose - until the time he went to sleep. This included many weekends and holidays. I woke up before him and went to sleep long after he did so I could use that extra time for planning, schedule review, engagement confirmation, and event preparation. Checking and double-checking every detail of the day was the only way to survive.

Being an aide is a "make or break career" job for a junior officer. You are only as good as your last dumb mistake, and you are not afforded too many of those. Just as the official Navy description of the position states, "[a]s an Aide, you get to handle many of the Admiral’s personal and administrative matters.

What I knew

I knew and handled a lot of personal and administrative details. For example, I knew the admirals' shirts and pants' sizes, whether they liked hot sauce or salt-and-pepper with their meals, whether they liked A-1 steak sauce with their steaks, and how they liked their steaks prepared. I knew their favorite alcoholic and nonalcoholic drinks, how many packs of sugar they wanted in their coffee, the time they usually went to bed at night, and the time they usually woke up.

I knew their shoe size, their golf handicaps, their wives' and children’s names and birthdays, their preference for soap and deodorant, and if they preferred a window or an aisle seat when traveling on a commercial airplane. I knew the prescription medication they took and what over-the-counter medication brands they preferred. I also knew their wedding anniversaries and of course, their dogs' names. I ate dinner with their families and went on working vacations with them. I picked up their dry cleaning and drove their cars and golf carts.

What I did

I helped write their speeches in their own words and style, wrote their official correspondence, and planned their daily schedule down to the minute. I attended almost all of their official classified and unclassified meetings and took mental and written notes of what they said and heard. I noted the questions they asked and the commitments they made.

I managed their long-term and short calendar and planned all domestic and international travel. I traveled with them around the world. I was an integral part of the admiral's staff, and my desk in the headquarters building was the first one outside his office door. I screened all their incoming calls, and I initiated all of their outgoing calls. No one got to see or speak to the admiral without going through me first. I was the gatekeeper.

What I saw

I also saw a lot. I saw them getting dressed in the morning and wearing only boxer shorts, white T-shirts, and black socks. I told them when I noticed they mistakenly left their zippers open after a head call. I assisted them if they cut themselves shaving or had bloodshot eyes.

I inspected their uniforms before they left their rooms to ensure that they had pinned on their gold aviator pilot wings, military ribbons, and uniform insignia perfectly per the Navy's Uniform Regulations: ribbons straight and parallel to the deck, name tags properly positioned a 1/4 inch above the pocket, and their “gig line” or belt line perfectly aligned. I ensured no long loose threads or “Irish pennants” were on their uniforms, excessive lint on their black winter uniform, or scuff marks on their summer white uniform shoes.

Being prepared

I carried with me wherever I went a special “admiral’s survival and repair kit” in my briefcase which included their favorite black pens, red felt tip pens for document editing (the color red is reserved for the admiral or commanding officer of a Navy unit), 3x5 white index cards (of course), an extra set of their military insignia including their uniform stars and ribbons, breath mints, aspirin, Afrin, a sewing kit, a shoeshine kit, an extra pair of contact lenses and prescription glasses and some toothpicks. Yes, toothpicks for Admiral Johnson. More to follow on that shortly.

The Head

During my one-week turnover with my predecessor Lieutenant Samuel Jackson, he told me to make sure I always knew where the nearest men's restroom or "head" was located in every building before we went to a meeting in that building. As part of an aide knowing precisely "where you're going before you get there," I would always have to make sure I knew exactly where that men's head was located along the travel path from the building’s entryway door to the room where we were headed.

The first couple of times I got out of the official Navy vehicle with the boss, and we walked inside a building for a meeting, Admiral Johnson would look at me and say, "I'm going to duck into the head quickly and be right back. You see Loop, at my age, you never pass up the opportunity to go to the head."

Very soon, it became automatic and beautifully choreographed that I would open the car door for the Admiral when we pulled up to a building for a meeting and whisper: "Admiral, the head is right down the hall, second door on the left.” Or, I would lead him right to the nearest men's head without him having to say anything. I knew the routine, and he knew I knew the routine. I would stand outside the restroom door using the time wisely to check details, make quick phone calls and review contingency plans for what could possibly go wrong in the minutes and hours ahead.

Good aides eventually know their bosses so well that they anticipate every move, action, and ultimate decision. Equally important, in the execution of the plan, a good aide ensures there is no visible confusion or fumbling along the way. An admiral has to look like an admiral.

"You never keep the admiral waiting and never, ever, want to embarrass the Admiral," Samuel had told me.

Wooden toothpicks

In addition to the importance of knowing the location of the men’s head, Lieutenant Jackson also briefed me that Admiral Johnson, upon the occasion of having finished a meal, would want a wooden toothpick. During my short week of a turnover with Samuel, I distinctly remember him opening up his small handheld portfolio (which we affectionately called our “brain"), and stating, "Now the admiral, he likes wooden toothpicks. So, I guess I won't be needing these anymore.” He pulled three wooden toothpicks that were individually wrapped in clear plastic out of his brain and handed them to me. “Make sure you always have these with you,” he said.

Before Samuel was commissioned as a naval officer, he had been an enlisted sergeant in the Army in the prestigious 101st Airborne Division. In many respects, he still spoke very directly like a sergeant. I was all ears, and he was all business during our turnover time together.

Of course, at this point, I was wondering what in the world had I gotten myself into. In addition to everything else I needed to worry about from before sunrise to well after sunset, including where the nearest head was located, I was told I always needed to carry wooden toothpicks.

I put the toothpicks in my new handheld portfolio brain without question or hesitation and forgot about them. Back then, much of the camaraderie in the Navy among shipmates was generated by pranks, many of which would be grounds for termination today. At that time, I wondered if this was simply a joke being played on me by my predecessor. I learned the answer to that question on my first overseas trip with Admiral Johnson.

The Admiral's pillow

About a month into the job, we went on our first trip out of the country to visit a P-3 aviation squadron participating in a military exercise in Thule, Greenland. We were flying up in a Navy P-3 from Brunswick, Maine, with some of the other more senior staff officers. We had just departed Canadian airspace heading over the Atlantic Ocean when Commander Timmy McNamara, the Wing Operations Officer, came over to me. The admiral had slipped into the cockpit to hang out there and fly for a while. Pilots love to fly no matter what age, and this also afforded Admiral Johnson the opportunity to chat with the junior officer pilots.

His being in the cockpit allowed me to relax somewhat for the first time after what was always a hectic and pressure-filled departure evolution. I was in the aft of the P-3 where there is a galley area with a table, a small refer, a coffee pot, and a well-used convection oven.

McNamara was also a pilot and nicknamed “Irish” for obvious reasons. He started to ask me how I was enjoying the job so far. Irish also told me to call him anytime he could help because he knew the aide job was very tough, and it was easy to “royally screw it up” and get fired. He then asked me if I had checked and double-checked the uniform of the day that the sailors would be wearing when we arrived at the air base in Thule so the Admiral was in the correct uniform.

"You never want to embarrass the admiral," McNamara said. I acknowledged I had checked every detail of the schedule multiple times before we left. He again graciously offered to help me on this first trip.

Then, he asked me, “Did you bring the Admiral’s pillow?”

I looked at him in disbelief. I didn’t know what to say. I knew I had the wooden toothpicks, but not a pillow.

“You're pulling my leg sir, aren’t you?” I asked.

“Nope,” Irish said, “Well known secret for those who have traveled with him. The Admiral always, always travels with his small personal pillow in a separate blue laundry bag.”

“Really?” I said.

“Good ole Sam didn’t include that in the turnover and pass down?” Irish asked, looking at me with his shiny balding head, coffee-stained teeth, and raised bushy eyebrows.

“Sir, you can’t be serious,” I said.

“Serious as a heart attack,” he said with no hint of a smile. "The Admiral will probably give you a break because it is your first trip, Loop, but I don't know. He might be pissed.”

By then I did not know what to believe. Another Navy commander on the Admiral’s staff, Commander Rob Ballard, joined us in the aft of the aircraft.

“Hey Rob,” Irish said, “New Loop here forgot the Admiral’s pillow.”

“What? He forgot the Admiral’s pillow? Oh no," Ballard stated.

“Sir, you guys are kidding me, aren’t you?” I asked.

“Of all things to forget, you forgot the pillow? Didn't Samuel tell you about that?” Ballard stated.

This had gone on now for about 5 minutes. McNamara was still looking very serious and shaking his head. Ballard was finally turning away when I saw him break a smile that turned into roaring laughter between him and Irish.

It was indeed good Navy humor at the expense of the new Loop. No pillow was needed, so it got me wondering about those wooden toothpicks that I had been carrying for several weeks now!

A Fine Navy Breakfast

Thule, Greenland is an incredibly beautiful place, but a very cold place. It was -10 degrees when we arrived. The sky was overcast and cloudy, and the wind made it feel much colder. We traveled there to visit the P-3 squadron that was participating in some interesting operations with U.S. Navy submarines operating under the polar ice cap.

The first morning we were there, we drove over the snow-covered roads on the base to the military galley to enjoy a fine Navy breakfast with a group of sailors and airmen. Thule was an Air Force base air, so there was a significant Air Force presence there.

In the military, you cannot always count on a Navy-cooked meal being a good meal. There were some well-known Navy classics like “monkey meat on a stick” (meat of unknown origin on a wooden skewer) and “shit on a shingle” (corned beef over toast). Typically, if I had to bet on a good meal, I could usually bet on a good breakfast. It's hard to mess up breakfast, and there was always an enlisted mess specialist there to cook a huge made-to-order omelet slathered in butter.

For my usual galley breakfast, I would enjoy a ham and cheese omelet, bacon, hash browns, toast, a glazed doughnut, coffee, orange juice, and an ice-cold glass of thick chocolate milk from a large stainless-steel dispenser. I got all that for about $2.15 back then.

We went through the cafeteria line in the galley, and the admiral and I sat with a group of sailors as we ate a great breakfast. After a lot of talk and a whole lot of "sir, yes sir" from the young sailors at our table, Admiral Johnson finished his meal, downing his last sip of coffee with both hands cupped around his coffee cup. He looked around the emptying galley. "Boy, I sure could use a toothpick. You don't happen to see any toothpicks around here or happen to have one, do you, Loop?" he asked.

There were no toothpicks on the tables and no toothpick dispensers anywhere in sight. This was the Thule Galley, not Cracker Barrel or our favorite Jacksonville barbecue restaurant.

Without saying a word, I leaned slightly over and opened my hand-carried binder “brain.” I pulled out a beautiful, individually plastic-wrapped wooden toothpick. I handed it to him. He grinned, "Nice job, Loop.”

In the P3 cockpit, over the Artic Ocean, 30-degree angle of bank, left turn.

“Thank you, Admiral,” I stated, grinning with pride.

“Sam gave those to you, didn't he?” the Admiral asked as he started working his front teeth with the toothpick.

“Yes sir, he did,” I said.

“Well, thank you for the toothpick. I think you're going to be okay, even though you forgot my pillow. Let's hit the head on the way out," the Admiral said.

"Thank you, sir," I said.

At that point, I could have hugged Samuel. While I did not know then where he was in the world, I could not thank him enough. I do remember running into Samuel about two years later and thanking him profusely for the toothpick tip. “Glad it worked out for you,” he would say. Like me, Lieutenant Jackson ultimately became the Commanding Officer of a P-3 squadron, retiring as Navy Captain in 2006.

The first trip was going pretty well so far, and having the toothpick provided me with some

much needed, advance political capital in the bank that I would soon need when things did not go so well in the very near future.

Lessons Learned

I learned quickly that knowing everything about my boss was critical to my success as admiral's aide. For me, the simple lessons about carrying a toothpick and knowing where the nearest restroom was located led to a flawlessly executed day. As odd as those actions might have been to me, they were important to the boss, and therefore important to me. We called that “attention to detail" in the Navy.

I realize the breadth of personal and professional knowledge about the admiral as the boss was exceptional and rarely expected in the civilian world. However, knowledge of your boss’s preferences, expectations, and desires will prove to be one of the keys to your success in every job. It is essential to know exactly what the boss prefers so you can deliver accordingly in your work statement and duties.

You can learn about your boss by watching, listening, and asking questions. You can learn by asking your boss’s administrative assistant, many of whom I have found to be lifesavers for me with their kind help and deep knowledge when faced with difficult situations. You can learn the boss's preferences by asking for a "go by" example of a previous presentation the boss liked. Just do not operate in the blind.

While new bosses might be afforded ninety days to get their act together and set the tone in a new job, I have found the runway in which the boss forms an opinion of me is usually much shorter.

Your job is to serve and perform well for your boss, and the boss is the one who will be evaluating you. Whether you like it or not, or whether it is "fair" or not, the reality is that your ultimate failure or success in your job usually depends on your boss. So, get to know your boss as well or better than anyone else.

I learned a lot from others about Admiral Johnson during my first few weeks on the job. However, the best knowledge came directly from him and what he told me in a fifteen-minute conversation my first week on the job about how to get the job done - with his stars. My next post discusses "use of the stars."

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