Mentoring Leadership

You cannot hope to experience the best lessons of leadership until you are truly in a position to fail. But very few leaders are willing to give their subordinates enough rope to hang themselves; having a subordinate fail brings into question their competence as well. But an effective leader understands this is the best way to grow future leaders and is a risk worth taking.

If you've been given the chance to lead, either by formal position or just an informal result of chance, you will sooner or later get some kind of feedback. I think it is very important to listen especially to the negative feedback. But even when all the feedback is positive, you may find clues as to what you are doing wrong. For example, if the next level of your organization thinks you are the best, it could be that the bottom level is wondering why you aren't protecting them from the abuse of your subordinate leaders. I think the best leadership teacher is experience, but if you aren't in a position to gain from that experience you can still learn from the experiences of others. So let's get started.

1 — Why mentor?

2 — A negative example

3 — A positive example

4 — How to mentor

It is hard to think of a more autocratic leadership environment than aboard a U.S. Navy submarine. The captain's word is absolute and hesitating when following orders can have dire consequences for the mission and one's career. But how do you grow captains who can handle this responsibility when they come up in the very system that denied them that chance? Retired Navy Captain L. David Marquet writes about this in his book Turn the Ship Around! The subtitle gives the reason for mentoring in a nutshell: "A True Story of Turning Followers into Leaders."

Mentoring: "The Cons"

• Short term time constraints — It takes time to mentor a subordinate, especially at first.
• Short term risks — The most effective way to mentor someone is to give them just enough rope so that they can learn, but not so much rope so they can hang themselves. They will make mistakes and there is a risk those mistakes could be costly. Ideally you will be there to catch the mistakes before that point, but to be properly mentored, the "mentee" has to perceive there is risk.
• Short term failure — Not everyone is up to the tasks presented and some people cannot be mentored because they simply are not qualified. A person's suitability isn't always apparent at first and you may find yourself having to pull back from a promising candidate after the mentoring process is begun.
• Career threat — As the saying goes: "A's hire A's, B's hire C's." You could very well be mentoring your replacement or your future boss.

Mentoring: "The Pros"

• Long term time savings and flexibility — If you take the time to grow subordinate leaders, they will soon learn to relieve you of many of your time consuming tasks and free you up from the tactical to become more strategic. Additionally, these people will be able to pinch hit for others in the event of personnel shortages, illness, or other unforeseen circumstances.
• Improved use of talent — Increasing the number of people thinking outside their individual areas of responsibilities increases the chance one person comes up with an idea others would have missed. Almost as importantly, it also improves the odds someone catches a critical error others might have missed.
• Long Term Success — The more people you mentor the greater the odds you will find a superstar in the making.
• Career flexibility — If you build yourself a part of an organization where you have become indispensable, the organization may be loathe to promote you knowing your former section will fall apart. Knowing that you have a cadre of replacements ready tells the organization not only that you are free to move up, but that you have a record of growing future leaders.

I have seen the high cost of failing to mentor many times over the years in the military but one of the most poignant examples I've witnessed was in the civilian world. I've changed the names, aircraft type, and a few other particulars. But all of this happened fairly recently.

Cinderella Story

I've flown for a number of management companies as a check airman and standards pilot where I sat on the jumpseats of various aircraft to observe crews in action. My job was to ensure they were following company standard operating procedures and to provide them an avenue to provide the company with feedback to management. I like to learn about the crews I was observing and spent some time in "chat mode." I met many pilots with very different backgrounds, none of those more interesting than Clyde Hackworth.

We were flying one of the nicest Falcon 900s I had ever been on and both pilots were doing a fine job until the Top of Descent (TOD). For some reason their Flight Management System (FMS) indicated that TOD was about 100 nautical miles too early. We were at 35,000 feet descending into an airport near sea level. The "TOD" symbol appeared at 200 nautical miles and that's when they started down. I was happy to have a few innocuous critique items for the first leg.

After we landed and their passengers departed, we left for the hotel and the next scheduled event was dinner. It was a regular city for them and they chose a German restaurant with a great wheat beer and an even better selection of schnitzels. Since the first day only had minor critiques, I asked if they would like the first day's critiques over beer. Of course they thought that was a great idea.

"I'm not a Falcon pilot, but I have a few questions," I started. "I am surprised we cruised at 35,000 feet for hours and wonder if you would have gotten better fuel economy higher."

"None of us are really comfortable much higher than the mid thirties," Clyde explained. "So we pretty much avoid the forties."

"I am also wondering why you started down so early," I said. "You ended up flying below 10,000 feet for quite a while as a result. That has to cost some extra gas too."

"The airplane tells us when to descend," Mark, the other pilot, said. "That's pretty much what we have to do in this airplane." Clyde nodded in agreement,

"Your FMS is pretty much the same as mine," I said. "There is usually a good reason for a TOD error but sometimes the box gets confused. You can double check it by multiplying the thousands of feet to descend by three to get an ideal descent."

"I think doing mental math in the cockpit is usually a bad idea," Clyde said. "The computer is smarter than we are."

"It wasn't so smart today," I said. "Besides, the math is easy. Today at 35,000 feet you just multiply 35 by 3 to come up with 105. When the FMS told you to start down at 200, you would have known it was a mistake."

Both pilots gave me the standard look all pilots have for examiners when they don't agree but want to end the discussion. They promised to give my method a try, and I knew they would not. The schnitzel arrived and I wanted to turn the discussion in another direction. "So Clyde, how did you get your start in aviation?"

Clyde revealed what I can only liken to the aviation version of the story of Cinderella. He was a copy editor for a local newspaper stuck in an office that overlooked Logan International Airport. His job was to read everything written by the newspaper while checking for grammar and typographic convention. He explained that meant simply ensuring the newspaper's style preferences were consistent. "Mind numbing," he added.

"I came to work on my fortieth birthday and got the usual birthday cupcake and card signed by the rest of the office," he said. "I sat at my desk thinking about how much I was hating life when this business jet took off and turned west instead of east and I got a close up view. Right then and there I decided that's what I wanted to do with the rest of my life."

Clyde got a familiarization flight in a Cessna 152 at Hanscom Field, Bedford, Massachusetts that weekend. He enrolled in a local flight school that day and quit his job the next Monday. He had his private pilot's license in a few months, a commercial instrument rating and his instructor's ticket before the year was up. The next year he became multi-engine qualified and the year after that got his first job flying a King Air.

"On the day I turned 45 I got hired by this company to fly a Challenger," he said. "Three years after that we got the Falcon and they day I turned 50 they made me the chief pilot."

The next day we flew back to Bedford and Mark proved himself also competent, but not as knowledgeable as I would have expected from a Falcon pilot. Once again TOD had misbehaved and both pilots blamed the FMS. I flew another ride with two other pilots from Clyde's operation. It was remarkable, in a way. Four competent pilots who didn't know when to begin their descents. Years later Clyde's airplane moved to Oregon and Clyde moved with it. They kept two pilots at Bedford and two in Bend, Oregon.

A few years later our management company went out of business and I was forced onto the job market. I heard that one of Clyde's Bedford pilots had just retired and they were hiring. "Ah, not really," he said when I called. "We are just going to have one pilot in Bedford for now on." Oh well, I thought.

Five years later I ran into Mark at a convention and asked about Clyde. "He's about to retire," Mark said. "At the end of this year, as a matter of fact."

"You must be in line to take his place," I said. "You must have ten years with the company by now."

"Twelve," Mark said. "But they haven't made any announcements and I am wondering if I have what it takes. Clyde pretty much keeps everything he does secret from the rest of us. I've never had any kind of leadership training. I don't have a clue how to get started."

Over the years I've noticed that this situation is more the rule than the exception. I referred Mark to the series of articles I've written on the subject, Leadership. As it turned out, their company didn't think Mark had what it takes and ended up hiring another chief pilot from outside the company. Mark and the two other pilots ended up frustrated and within a year all three quit. I think the company looks back on Clyde as a great leader they had the good fortune to have hired; there just aren't any others out there like him.

Colonel Henry Goldstone was a navigator by specialty, economic guru by skill. Unlike pilots, most navigators aspire to leave the cockpit as soon as possible and Goldstone was no exception. He was put in charge of a large maintenance squadron at an early point in his career and had spent the last twenty years leading men and women. His current assignment was as the chief of one of the Air Force's most prestigious Pentagon offices. When he hired me, I had already been promoted to lieutenant colonel, but still had another three months before I could pin on the rank. So I was still a major, but what was called a "lieutenant colonel select." I was one of three selects in the office and we each outranked the five other majors in the office, as well as the five captains. Our job was to "program" the Air Force's airlift budget. I mention the office was prestigious which seems an odd thing to call an office. Prestige came because the office hired Air Force airlift "rock stars" who got promoted without fail and those eligible always got selected for command tours. Colonel Goldstone was up for promotion to general and the odds favored his chances.

"The chief wants a briefing on aircraft sat phones this afternoon," Colonel Goldstone said from the head of the table. It was my second week in the building and I was still a new face to my new officemates. "Major Haskel, can you handle that?"

"Yes, sir," I said while wondering how I was going to handle that. I spent the rest of the morning getting smart on what it was about satellite phones that the Air Force Chief of Staff wanted to know. I presented myself to the four-star general's office on time, waited twenty minutes before seeing the general, less than five speaking and another five answering questions. "Good job, major," was my only feedback from the chief.

Colonel Goldstone wanted to know what the chief's questions were and how I answered. "Good job, major." I later found out just how rare it was for a colonel to give up a chance to brief the four-star. Or, to put it another way, to risk his career by entrusting his fate to a subordinate.

A month later I felt that I understood my role as a "Program Element Monitor," or PEM. Each of us PEMs controlled a program element by approving spending for aircraft operations, maintenance, and acquisition. My PE was known as VIP/SAM, the VIP and Special Air Missions fleet. Our office also had the tactical airlift PE, strategic airlift PE, tanker PE, and training aircraft PE. Our five PEs were competing with just over 100 other PEs in the Air Force and nearly 500 PEs in the Department of Defense.

"PEM Parade!" Colonel Goldstone said at a Monday staff meeting. The other four PEMs groaned and I just sat quietly wondering what it was all about. "Unfortunately, I will be out of town the next two weeks," he continued. "So newly promoted Lieutenant Colonel Haskel will be in charge of the murder boards." He looked at me while the other PEMs seem to be relieved they hadn't gotten the duty. "James, do the murder boards as you see fit, but get everyone ready."

"Yes, sir," I said. I didn't know what a PEM Parade was, much less a murder board. But as soon as the meeting was over I followed Goldstone into his office and closed the door. "Perhaps a little background, sir?"

Goldstone explained that every PEM in the building would get ten minutes in front of a team of budget cutters from their service to explain where all their money was going, and then five minutes to defend their programs against budget cuts. The murder board was our office's practice runs where an executioner, me, would play the role of the budget cutter.

"We got creamed last year, James," Goldstone said. "A lot of that is the environment we live in, of course. The current administration doesn't think much of the military and we've seen our budgets cut viciously every year they've been in office. But we in the tanker/airlift world did worse than the rest of the Air Force. We told ourselves that it was because in times of budget cuts tanker/airlift isn't as sexy. But I think our lack of polish had a lot to do with it. Other than you, all our PEMs have been through this before. Between you and me, they didn't do a very good job of it. I think a lot of the problem was nerves. But I also think they were over-prepared. Your job is to teach them to think on their feet. I think we worry too much about the ten minute speech and not enough about the Q and A. I won't be back until the day of our PEM Parades, so all of the prep is up to you." He pulled out a calendar and started ticking the days. "You have ten work days before the big show. Get to it."

I called everyone into the office that afternoon and announced my strategy. "Well strategy is the wrong word," I started. "Having never seen a PEM parade before I have some extra distance to travel. But here's what I want to do. We have five PEMs and ten days. Let's have one PEM do a practice run every morning at 0800 and another at 1300. Everyone, even those of you who aren't PEMs will be in attendance." Groans. "This is an exercise in stress, so if you feel like this will be an exercise in 'rent a crowd' it might be. But the more eyes on our PEMs the more pressure. The more pressure now means being better able to deal with the real pressure later. So right now I need two volunteers to kick us off tomorrow."

"I'll go first, sir," Major Mark Rader said. He was the strategic airlift PEM but a fellow veteran of the 89th Airlift Wing from Andrews. It may have been that he was providing support to a former wingman.

"I got the afternoon," Lieutenant Colonel Earl Hooper said.

I spent the rest of the day tracking down PEMs from the fighter and bomber worlds to learn what their secrets were. But they each seemed as terrified by the PEM Parade as we were. "You ever have a civilian bean counter call you an idiot?" the F-16 PEM asked. "It's like they are trying to piss you off so you lose your cool and that gives them an excuse to cut even more. Bastards." I was starting to understand the PEM Parade.

The next morning I settled into Colonel Goldstone's office and read through the morning paperwork and realized my workload was more than just PEM parades. I was fully engrossed in these new duties when a rap of knuckles on the door brought me back to the task at hand. "We are ready, sir."

I sat at the head of the table, flanked my the rest of our office staff as Major Rader stood at the opposite end. He spoke confidently at first but then reverted to alternating his eyes between the audience and notes he had on index cards. He took care to detail his costs to the nearest dollar and program dates to the nearest month and year. "The FY96 budget shortfall stands at 37 point four, ah," he stammered, shuffling through his cards. "Point five," he correct himself, "it is 37 point five million dollars." All things considered, he had done well. He stopped talking, stood at attention and looked directly into my eyes. All eyes, in fact, were on me.

"Why am I spending close to a billion dollars on putting glass in an airplane I am going to retire in five years?" I asked. "Why should I spend that kind of money so you pilots can have fun at the expense of the tax payer?"

Rader looked at me, almost in anger. But he finally smiled. "Very good, sir." Everyone else exhaled.

"I'm serious, major," I said. "The C-141 is twenty-five years old. It may not make 30. Why does it need a new cockpit?"

"Ah, the ROI," he said. "The current avionics break at a rate that grounds the airplane every twenty hours. We can barely fly two or three times before having to replace a cockpit instrument. The new glass cockpit pays for itself in less than a year."

"Fantastic," I said. "I think you will get a lot further with saying the airplane breaks down every twenty hours than spouting return on investment stats. Good job."

The afternoon session was an inversion of the morning. Lieutenant Colonel Hooper's ten minute speech was disjointed, unorganized, and difficult to listen too. He repeated Rader's obsession with decimal points on his million dollar program totals. But his Q and A was very good. The next day's effort was much worse. Both PEMs seemed afraid to be defending their programs in front of me, one of their fellow PEMs. They did little more than read from their note cards and they both folded like a deck of cards at my first mean-spirited questions.

"Okay, I think I know how to proceed," I said after the second day's afternoon session. "We have three days left this week and five next week. I'll do my PEM presentation tomorrow morning, you pick your most merciless executioner but don't tell me in advance. Then everyone gets to pick on me. Tomorrow afternoon we'll meet to come up with a game plan going forward."

The next morning I entered the conference room to find Mark Rader at one end of the table holding a machete. "Here comes my breakfast," he said. I smiled and stood in front and started to talk.

The thing I had noticed most during the previous four PEM presentations was that each presenter seemed unsure of themselves. Each time they looked at their note cards it appeared they didn't know their subject matter and needed reassurance. The irony was that each PEM knew their programs better than anyone in the building. I didn't use any note cards at all. After ten minutes I concluded. "As you can see, the VIP/SAM program is high visibility, high stakes, and has a high cost for failure. The program is already lean and any further cuts will come at a cost. I look forward to your questions."

Major Rader sat at the head of the table, speechless. The rest of the staff was silent too. "Well?" I asked."

"How did you speak for ten minutes on all those different airplanes without notes?" Rader finally asked.

"I know my programs better than any of you," I said. "Just as you know your programs better than me. I memorized a leading sentence for five different areas of my program and ad libbed the rest for two minutes on each. Looking confident telegraphs that your are confident. I think everyone here can do that. Besides, its easier than talking off note cards. How about some questions?"

The questions were merciless but here again I went without notes. "How can you replace seven Boeing 707s with only four Boeing 757s without coming up short on airlift?" one of the non-PEMs asked.

"The older 707s use a depot maintenance model," I said. "They are designed to spend 18 months operational followed by 6 months of maintenance. The 757s use what is known as an A/B/C/D check system. They can go 10 years before any extensive downtime."

"Has that proven to be true with the airlines?" one of the PEMs asked. "Can you back that up with data."

"It has proven itself in practice," I said. "I don't have the stats at my fingertips, but I can get them."

"That's not going to fly," Earl Hooper said. "You have to have the numbers or you shouldn't mention them at all. And absolutely don't make numbers up or make a mistake."

"I agree you shouldn't make anything up," I said. "But we all make mistakes. Just be honest and if you don't know, say you don't know but will get the answers."

After the last question was asked and answered, the staff sat quietly. "This will knock their socks off," Rader said. "Or they will throw us out on our asses for not following convention. It's a helluva risk."

"Try it this way," I said. "At least once. If you really think it is too risky, then you can use the conventional tactic. But if you try it my way and it fails, you can blame the new lieutenant colonel. I'll be your flak magnet."

For our afternoon session each PEM proposed five topics for leading sentences and we spent the rest of the week practicing presentations. One of the non-PEMs proposed a game of "PEM twenty questions" where they would come up with a list of questions and we PEMs would field them at random. Points were rewarded for speed and subtracted for "ahs," "ums," and other signs of weakness.

On the day of the real PEM parade we presented ourselves to the conference room adjoining the office of the Secretary of the Air Force. Seated at the head of the table was the top Air Force civilian flanked by two three-star general officers. The balance of the head table was filled by civilians with ledgers and thick binders. In the audience behind them we spotted a collection of Air Force officers, including our boss, Colonel Goldstone.

Major Rader was in charge of our largest program and led us off. As he spoke, without notes, members of the audience started to whisper in amazement. After ten minutes he answered three questions confidently and without jargon. "The current C-141 fleet is averaging an airplane grounded every 20 flight hours," he said. The glass cockpit addresses 90 percent of these events for the same cost of one year of repairs. The program pays for itself in a year, at the current rate of airplanes breaking. And we know that rate is going up unless it is addressed."

The civilian at the head of the table looked to her left and then to her right. Each person at the table nodded. "Program is approved as proposed," she said. "Next."

The rest of us followed Mark with similar results. As the final speaker I thanked the members of the board and turned to walk out. The lead civilian stopped me. "Good job," she said. Behind her Colonel Goldstone shot me a thumbs up. Back at the office everyone, of course, was on an emotional high and there were smiles all around. At the end of the day, after most had left, Colonel Goldstone asked me into his office.

"The rest of the Air Staff is talking about us today, James," he said. "I think we've reinvented the PEM parade. But, more importantly, I think you've given each member of this office a new way to look at problems and solutions. Good job."

"Thank you, sir," I said. "But I have to think it was a high risk strategy on your part. You gave the job to the least experienced PEM in the office. You risked our budget on an unproven officer."

"You've proven yourself before you got here," he said. "Your reputation preceded you. Besides, that wasn't my primary objective."

"So I have to ask then," I said. "What was your primary objective?"

"I wanted to throw you into what might have seemed like a no-win situation to see how you would react," he said. "To see if you could lead the group through it all. And maybe learn how to lead them in the process. And you did. We got beaten up pretty bad a year ago and I think everyone was so gun-shy about making mistakes that they forgot that the best defense is a good offense. We always had good esprit de corps in this office, but it was lagging. This year's PEM Parade gave us a needed shot in the arm."

It was a learning exercise, to be sure. "I'm glad it turned out the way it did," I said. "Thank you for the opportunity."

"Did you ever stop to wonder why I gave you the opportunity?" he asked.

"As a matter of fact, I am curious about that," I said.

"The other two lieutenant colonels have already had their trials by fire," he said. "They did well, but not as well. It was your turn. The commander selection boards are coming up and I have some recommendations to write. I need you to do something unpleasant: get the other two to start thinking about non-command assignments."

"I think they are both counting on getting commands," I said. "One of them said this office has never had a lieutenant colonel ever fail to get a command."

"That is the way it used to be," Colonel Goldstone said. "The Air Force is smaller these days and getting smaller. There are only half as many squadrons available. You need to prepare them to be disappointed."

Of course he didn't need to say I should prepare myself for disappointment too. But as it turned out, two of us got squadrons. Earl Hooper was the first lieutenant colonel from our office in anyone's memory to be denied. My efforts to prepare the others for disappointment in the end convinced Earl that I knew something he didn't and was somehow responsible. That ended up being a good lesson for me too.

Over the years I used the lessons I got from Colonel Goldstone (later General Goldstone) to mentor those working for me. They are lessons I could not have picked up from textbooks or listening to lectures. Sometimes the best way to learn is to do.

Let me first say there is no one way to do this, how you mentor others to be leaders depends a great deal on your own leadership style and how you were mentored. It depends on the successes and failures you have witnessed, as well as those you were personally responsible for. So what follows are my steps. They've worked for me, I think they will work for you. But only you can be the judge of that. At the very least, these steps will give you a head start on developing your own techniques.

• Lead by (Conspicuous) Example

Before you can be identified as a leadership mentor worth emulating, you need to be seen as an effective leader in your own right. This becomes complicated in aviation and other technical fields because you also have to be seen as an expert in your profession. If, for example, you are a pilot leading a flight department, your leadership will be greatly hampered if you are not seen as a good pilot. Step one, then, is to become a good pilot. (Or doctor, or mechanic, etc.)

Good leadership is so rare that it should be noticed, but you can help the process with a little strategic timing. There is a fine line between a self-promoter and someone who just gets the job done without thinking about getting credit. It is easier than you might think, however. Let's say one of your subordinates realizes no one from your staff remembered to attend an important and mandatory meeting with the FAA. The person attends for you, takes diligent notes, and leaves you a detailed accounting of what was said and what is due. You could thank the person in private and believe that you did a good job leading because you acknowledged the person's vital contributions. But what if you saved that thank you for when the subordinate was in front of his peers? Now a pat on the back from the boss goes a lot further. Here are a few more examples: Stories: Lead By Conspicuous Example.

• Survey Your People

In just about every organization you will find people who openly aspire to leadership positions, people who secretly want the chance, people who are ambivalent about the subject, and even those who are openly fearful of the possibility. But you may also find there is an acknowledged hierarchy of informal leaders. If everyone senses you have made a choice of who to mentor and, more importantly, who not to mentor, morale can be impacted. Playing "favorites" might be the right call and the best use of your time, but it can also be a poison pill in an organization with more than one aspiring leader.

Another reason to canvass the troops is to learn what the organization is thinking about you and your potential "mentees." This can help you address potential problems and to anticipate what these mentees need to work on.

• Sponsor / Develop Relationships / Counsel

It may be a common practice in business to identify a "mentee" and then schedule time together to develop a mentor/mentee relationship. This makes it clear that the leader has full faith in the mentee, putting pressure on both to follow through with the relationship.

I've never found it advantageous to formally sponsor a mentee, but perhaps that is because I've never felt that I was being formally sponsored. I have felt that leader was pushing opportunities my way and actively sponsoring me up the hierarchy, but I never felt their fates were tied to mine. I like this method better than active sponsorship. Over the years I've had several people openly refer to me as their mentor, even though we've never discussed any kind of formal sponsorship. I consider the fact they think of me as a mentor to be the highest compliment a leader can receive.

• Advocate and Challenge

You will often hear that the best thing about having a sponsor is that they will advocate for you up the hierarchy, getting you noticed and opportunities for further advancement. I think that is true, but I think a good leader should be doing that for everyone with the potential, not just a chosen mentee.

You should always strive to challenge your people to the next thing just out of their grasp. If a person has zero leadership experience, give them a task that will eliminate "zero experience" to "some experience." If a person has done everything possible from their level in the organization, try shifting them to someplace that broadens their horizons. When these people do well, sing their praises up the hierarchy. If they fall on their faces, take full responsibility, give them a few pointers, and look for another opportunity for them.

• Teach

Regardless of how you intend to mentor, your position as a mentor should mean that you have something to offer those being mentored. You are an instructor and should be aware that not only are your actions being used as lessons, but everything you say can (and will) be used. Everything is a teachable moment.

Marquet, L. David, Turn the Ship Around!, Penguin Random House LLC, New York, 2012