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Top Gun Secrets (That Every Advisor Must Know)

Lt. Col. Rob 'Waldo' Waldman brings his military experience in Iraq and Serbia to the business world.

Lt. Col. Rob “Waldo” Waldman is a bona fide hero for many reasons – and not just because he rescued the term “wingman” and the “top gun” concept from the cheesy clutches of the ’80s movie, Top Gun.

As a fighter pilot, he flew 65 missions in Iraq and Serbia, and now he is bringing those lessons to the business world. He is eminently qualified to do that because not only is he a graduate of the U.S Air Force Academy, he also holds an Master in Business Administration degree with a focus on organizational behavior. He melded his studies with his anecdotal observations from his military career into the book Never Fly Solo.

Readers might recall seeing Waldo in one of his many speaking gigs or media appearances. Although he looks the part of a dashing fighter pilot, he is an engaging, approachable guy with a knack for putting people at ease. He is comfortable with revealing his own foibles, such as overcoming claustrophobia and fear of heights to jam himself into the tiny cockpit of a sound-barrier-busting fighter jet.

He can relate to sales people because he was one himself. He was a top producing sales manager for several technology and consulting firms.

In this discussion with InsuranceNewsNet Publisher Paul Feldman, Waldo talks about how insurance producers can build their own squadron of wingmen for mission success.

FELDMAN: Being a fighter pilot and being an insurance agent or an advisor, it appears to be two opposite ends of the spectrum. What can insurance agents learn from a fighter pilot that would help them to close sales?

WALDMAN: A fighter pilot and a financial advisor or anybody who wants to achieve success has to execute with precision. As a fighter pilot and as a business person, you talk about motivation, attitude and mindset. But it’s how you are fulfilling the mission and getting the job done that counts. As fighter pilots, we didn’t have many options when it came to execution. We either hit the target, did our job or we might not come home alive. Obviously as a fighter pilot, your life is on the line and as an insurance agent, your life isn’t, thank goodness. But your lifestyle is. If you look at regulation in the financial services industry, the constantly changing products, the competition, the commoditization of your resources and your trade, there are a lot of folks eating ramen noodles instead of filet mignon because they are out of work.

So, accomplishing the mission with that sense of passion, commitment, focus on service and getting the job done is the impetus to what drives success, which drives performance excellence.

FELDMAN: Your message, and the title of your book, is Never Fly Solo. But a lot of our readers are solo entrepreneurs. They work in their small offices and not necessarily reporting to people. Sometimes they do feel like they are flying alone because they don’t have peers to build them up.

WALDMAN: A lot of us think we are flying solo but we are really not. As a fighter pilot, I may be strapped into the cockpit by myself but I wasn’t flying solo. I had other wingmen flying with me. We never went out there just as a single ship, we always flew as a team because we can get a lot more done.

As a team, you can build a picture. We called it situational awareness, a 360° view of the threat, the weather, the target, alternate airfields, things that are impossible to track and monitor on your own. But you fly with wingmen who build the picture both in the air and with support from units on the ground for maintaining the jet and making sure it does what it’s supposed to do. The intelligence officers telling you where the threat is, helping you prepare, allowing you to focus on the most important thing, which is executing that mission in the air with a $30 million aircraft under your butt and with a critical lifesaving mission to accomplish.

Now if you look at it from the perspective of a salesperson, an insurance agent who is in his office maybe not at 10,000 feet but at five feet. You may think you are flying on your own, but you also have wingmen who can help you build your picture, accomplish the mission where your threat is constantly changing, where you need to adapt to change and execute a plan.

Realize that as an entrepreneur, you have wingmen in your accounting staff, administrative assistant, referral network, your peers in the industry, wholesalers and mastermind groups. There are relationships with a whole host of other wingmen that you have to nurture, putting them into your formation and allowing you to execute your mission. I think it’s a key to any successful practice to leverage those relationships. Realize when you turn to your left and your right and call out for help when there’s a missile coming, it sure as heck helps when you have a wingman who is on your team who can build a picture, someone who can help you dodge the missile and even hit the target.

FELDMAN: So what makes a good wingman?

WALDMAN: You have two-ship, four-ship, eight-ship, sometimes even 16-ship formations. There’s only one leader and the rest are wingmen. Now, the flight lead is a wingman but the wingman is not a flight lead. The flight lead, that one fighter pilot, is executing the plan, delegating responsibilities and building the picture based on the communication that he or she receives from the wingmen.

A wingman has the back of the flight lead and checks the blind spots. You may be checking other wingmen at 6 o’clock [directly behind the plane] and building a picture for other members of your formation at certain times. Wingmen have assigned roles and responsibilities. They stay focused on that and then they are able to call it out to the leader.

For example, you have a high search and a low search. Let’s say the low search is from 0 to 15,000 feet and the high search is 15,000 to 30,000 feet. If your responsibility is to look from 0 to 15,000 feet, you are staying there and you are disciplined and focused on that. And if you see something, you call it out to the wingman. And everybody else is doing their job.

Now, if you have other people in your formation, administrative assistants, accounting, finance, your inside sales, the folks who are doing research or whatever, if your mission gets diluted and you don’t stay focused, you are not going to be able to build a big picture. So, to build that trust, your wingmen have to be focused on their perspective on what their responsibilities are and most importantly, call out the threat, share the information with the members of the formation and tell them often what they need to hear and not what they want to hear.

This concept of communication, what I call a “check six culture,” is absolutely critical and is what turns an average formation into an outstanding one, an average business to an outstanding one. The communication and the ability to give and receive feedback that you may not want to hear but need to hear is the foundation for successful business and any relationship.

FELDMAN: In the business world, it’s a little bit different than the military because you have trained fighter pilots who know what to look for and they know how to do the check six and they know how to communicate with you. In a non-structured environment like in the business world, how do you find and train people to be wingmen?

WALDMAN: The biggest thing that we do is hire on attitude. And especially in financial services, you need a committed attitude, somebody who has an amazing work ethic and values relationships and has a ton of integrity. These are all the things that are critical because not everybody can be a fighter pilot. You have to have that wherewithal, that background, the discipline. That’s why so few pilots make it to the fighter pilot world because not all of us have that. It doesn’t mean that you’re not good. It’s just not your environment.

As fighter pilots, we brief and debrief. This sets the tone of the mission and at the end of the mission, regardless of how it went, we debrief and we learn the lessons. Now, this formalized process allows us to really set standards.

When we go out there and say we’re going to see a client, going to work with some other vendor partners or go to networking events, we have to have an objective for that particular mission. We assign roles and responsibilities to everybody as we go out there to accomplish the mission. And if one person fails to do his or her job, we know there’s a consequence because if one person fails to do the job in that formation, the whole mission fails.

The last thing that we do before the briefing is we ask ourselves what if – what if the weather changes, the threat changes, or we have an emergency, who is taking over? Everybody understands these roles, responsibilities and actions and what we call standards. They are written, they are briefed and we are all marching from the same sheet.

So if you are building a business, everybody needs to know what the standards are in your organization. It’s a process, it’s written out, it’s understood by all so you can fall back on that all the time instead of guessing and asking how do I deal with this situation? And obviously you can’t dodge every missile and deal with every contingency, but it is a great place to start.

FELDMAN: You say that the debriefing is more important than the briefing. How does that work?

WALDMAN: When we come back from our mission, the members of the four-ship formation take off our rank and nametags, which are attached by Velcro, and sit down behind closed doors and do a debriefing. We don’t let our ego, rank, personality or names get in the way of being brutally honest and learning from the good, the bad and the ugly that went on in that formation. And I don’t care how great you think the mission went, there’s always something to be learned from each other.

Now, the first thing that you do in that debriefing is the flight lead shares his or her challenges, admits his or her mistakes. We call it exposing our chest to daggers, saying something like, I messed up today, guys – I didn’t call out on the emergency airfield like I was supposed to.

When you set the tone as a leader, admitting the mistakes, you are going to create an environment where others are going to bring you their problems and share their mistakes so that you can grow and learn from them.

Egos will be bruised. You may tick off people. You may get grounded. You may have committed some serious violations. But we know in the debriefing that the doors are closed, the training is sacred and this is how we do the growth and development. If you can’t handle that, then you don’t belong in the cockpit. Some folks will wash out of pilot training if they can’t maintain their ego and be open to feedback and be willing to give it.

It’s in that highly intense, rapidly changing environment where you want to be the best. That’s what differentiates the average from the excellent.

FELDMAN: A lot of our readers will go out on a sale by themselves. How could they effectively debrief? Is there a strategy to debrief yourself that you should be doing? What are steps to do that?

WALDMAN: Checklists are critical. I used them for years when I was in sales. I was in financial services, mergers and acquisitions, commission-only sales consulting for mergers and I was also in technology sales. Use a checklist along with a pre-mission and a post-mission briefing. When I sat down say with the VP of sales at Panasonic or UPS, I would go through this checklist. Before I met them, I would double check press releases, find them on Google and LinkedIn. Have a contingency plan in case you are stuck in traffic – what is their cell phone number? What is their email?

Come in with some preplanned questions. Clients love that. They want to see that you are prepared for this briefing so to speak, this one-on-one or one-on-five consecutive Q and A sessions where you are gathering intelligence and trying to come up with a solution to their issue or their challenge.

So, use those checklists. They will help you decommoditize yourself. Show prospects that you are different, that you value them enough to be different than the rest of the advisors giving them the same old pitch, trying to sell them life insurance and annuities and all of that.

On the debriefing, when I win the sale, I will always ask that person why did you hire me? When I lose the sale, I ask why you went with my competition? I am really curious. If you are lucky, they will be brutally honest with you – it was the price or you are a pain in the rear, you weren’t prepared, the competition was my cousin.

FELDMAN: You talk about chair flying missions, where you would visualize missions on the ground while seated in a chair. Is it true that you practiced missions on the toilet?

WALDMAN: It’s true, I practiced countless missions there. When you are in pilot training or F-16 training, you practice every waking moment. You live it, you breathe it. If you are financial advisor or an entrepreneur, you have got to live it, breathe it; everything that is going in and out of your brain has to be about your business if you truly want to excel. We all only have so many hours in the day.

The most important wingman in your life at the end of the day is yourself. You have to be your own wingman. You have to be committed, disciplined, accountable, prepared, resilient, focused, have integrity like a rock and you can’t outsource any of that stuff. And as fighter pilots, we are strapping into the single engine F-16 by ourselves and we are flying with other wingmen, we have other wingmen on the ground and in the air that are helping us out. We have our hands on the throttle and on the stick and if we are not ready to go to do battle, no amount of teamwork is going to be able to help execute the mission.

I don’t want to discount the fact that if you want to grow a business, you have to do the hard work. You have to study the threat, the competitors, the products. Go out there and meet all the wholesalers, find out the best of the best. Read the books on sales and personal development. It’s a lot of hard work for that “inner wingman,” as I call it. That inner wingman has to be critical in executing the plan.

The commitment is one part, but also important is the drive and the ability to keep going when obstacles are present, when the missiles of life are being shot at you. A real committed fighter pilot and a real committed business entrepreneur still presses on when the fun stops – when the sales are down, when the customer is saying no, when the products are changing or the economy fires missiles at us. That resilience and commitment have to be there when you jump out of bed every day. They have to be in your mind when you go to war and be willing to get shot at, which I did in combat 65 times.

FELDMAN: Can you tell us about a leader who helped you develop as a fighter pilot?

WALDMAN: There are a lot of fundamentals that differentiate average leaders from great leaders and poor leaders from average leaders. I will share what happened one time I was late for a mission briefing. If you are late for a briefing or a debriefing, you are always grounded. It’s a serious situation and you just can’t lack discipline because you impact the training of your whole squadron.

So, I was late. Instead of chewing me out, my commander, whose name was Psycho and a very intimidating guy, came up to me and said, “Waldo, listen, this isn’t like you. You are never late. Is everything OK at home? Do you feel all right? Do you need a day off? Talk to me.” I remember how shocked I was. I just did not expect to hear it from this guy. He was a senior leader and a former fighter pilot himself. He had a lot of combat experience.

And I remember thinking to myself how he appreciated me as a person first rather than a pilot. And he connected with me from the heart, not the head. And by doing so, he built my loyalty to him, which is a rare commodity these days.

I worked harder for that commander. I volunteered for the tough duties. I studied harder. I became a better pilot because of him. When I became a better pilot, I was able to execute better. I performed better because Psycho knew a thing or two about leadership.

A great leader, in any industry, asks the questions and treats people as people first rather than employees, because we are all going to have bad days. We’re going to walk into the squadron of life – be it an office or in that meeting or the sales arena or in a mission and we may have missile or engine failure, a gear may not be down and locked. A phone call may have come in and a spouse may be sick, the divorce paperwork is getting ready to be signed, the test results are positive. We have to still go out and execute the mission, close the deal, give the presentation, land our jets and make it home.

FELDMAN: Can you motivate people to become wingmen or do you have to hire the right people?

WALDMAN: Hiring good people is key. You can’t change the stripes on a zebra. But finding great qualified talent is difficult these days, so you have to hold them.

You can motivate them. More importantly, you can demotivate them. You can get a perfectly qualified wingman, an assistant, a member of your team that you are trying to get ready for battle. But if you don’t walk the walk, if you are not the example, not connecting with them, treating them with respect, talking to them from the heart, living the dream yourself and emulating the characteristics you are trying to get out of your team, they will surely look for work elsewhere. They will surely be mediocre.

Here’s the point: As a leader, we always have the choice every day to “push it up,” which is an expression meaning to push up the throttle. You’re either going to push it up and go to full power and commit yourself to excellence for yourself, for your team and for your family, or you are going to pull it back. It’s easier to give into the temptation to pull it back when we are overwhelmed – dealing with rejection and just so much is going on. It’s easy to say you know what? I’m going to get into work a little late. I’m going to sleep in. I’m not going to make the extra call. I’m just going to kind of give it half the effort.

Then what happens is complacency, and complacency kills. It kills the fighter pilots who don’t prepare and stay committed. It kills small businesses, entrepreneurial practices and relationships because that complacency will eat away at you and your values and everything that you stand for. Your wingmen will see that as well. So, like George Patton said, you are always on parade. And your people are watching you if you are pushing it up or pulling it back. If you are not willing to push it up on everything you do, they’re not going to want to do it either.

And guess what? Neither will your clients, because they are watching you, too. They are watching you when you enter the Ritz-Carlton Hotel. They are sitting down and watching what you do when you sit down with them. They are watching your eyes. They’re seeing if you follow up and do a handwritten personalized note. If you are delivering all the things that you briefed them on, all the small little subtleties that differentiate the average from the experts and the complacent from the committed.

FELDMAN: Do you have any examples of leaders who demotivated you?

WALDMAN: Yes, for example, there was a squadron commander of mine when I was a young captain. As a young instructor pilot, I exceeded the G limits of structural limit of a P37 twin engine jet that I was flying. Anytime you over G or maximize the G, the structural limit of the aircraft, you have to declare an emergency. Now, I was messing around with a P37 by myself. Every so often, you can go out and fly solo and practice all your maneuvers on your own. I was training. It wasn’t in combat or anything.

I was flying this trainer jet and I went to a traffic pattern and I wanted to see if I could hit the maximum G limit of 6.67Gs. I just wanted to see how close I could get to it. I was hot-dogging. I was lacking discipline. I accidentally over G’d the jet to 7 G’s because I hit some weight turbulence.

I could’ve punched off the G meter and zeroed it out like a stopwatch and nobody would have known about it. It was just .5 G, hardly anything. And it was 99.999999 percent certain it wouldn’t have done anything to the jet. It was a very rugged jet and what is a small little over G? But I knew in my heart of hearts it was the right thing to do, to turn myself in and then they would have to ground the jet.

So I came back in and my commander reprimanded me, rightly so. I was messing up. I had to give a presentation to my squadron mates on the emergency and the fact that I was hot-dogging it. They had to ground the plane and check for cracks. They had to literally rip the wings off of the plane and do an X-ray of the wings to see if there were any hidden cracks. If you over G the jet, you can turn a small crack into a big crack and exponentially cause a serious problem in the airframe. It could break apart in flight. The seats may not be able to eject. That plane would be grounded for two weeks and it would cost $25,000 to do the inspection.

My commander wiped his hands of me. He chewed me out. He cursed me out. I had never done anything like this before. I had a great reputation.

My buddy and I were at lunch and he said Waldo, if that were me and I over G’d a jet by as little as you did, I would punch off the G meter because I wouldn’t want to go through what you just went through the past two weeks. And I remember thinking to myself, how disappointing it was to know that despite my punishment, despite the example that was made of me, instead of creating a culture of courage where people would admit their mistakes and admit their problems, my commander created a culture of cowards. So I lost respect for him.

He made me think of what he could have done to instill a reprimand and a lesson. He could have said in front of the entire squadron I was briefing that Capt. Waldman messed up. He over G’d the jet. He lacked discipline. He was a hot dog or and he’s going to be grounded because of it and I don’t want anyone of you to do that. But I also want you to know is that Capt. Waldman turned himself in when he knew he could have punched that G meter and gotten away with it and no one would have known about it.

He could have said that’s the type of leader I want you guys to be. Waldo admitted his mistake. He is accepting the consequences. If he does it again, he’s going to be in even more trouble. He could have been ticked off at me but he still could have inspired my respect.

Those are the types of things that we can do. Be careful chopping off your wingmen at the knees, the folks that work for you when they make a mistake. If they admit their mistake, discipline them, reprimand them. If it continues, fire them if you have to. But if people make mistakes one or two times, use it as a learning lesson. Then they will be more apt to share more mistakes and learn from your example, more inspired to hold themselves to a greater standard as well. It’s about influence.


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