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Speaker 1: Welcome to the Eagles Transition podcast, where your host, financial planner, speaker, and author Curt Sheldon talks to senior military officers who have made the retirement transition before you. You'll hear about different hiring processes, interview questions, salary negotiations, and how each one of them successfully settled into a rewarding second career. Now, here is your host, Curt Sheldon.
Curt Sheldon: Welcome to episode 10 of the Eagles Transition podcast. Today, I'll be talking with Alan Berry. Alan is well into his second career and is currently Vice President for Cyber Security with a major company in the healthcare sector. Alan brings a unique perspective to the podcast, as he has been hired and is also a hiring manager. Make sure you pay attention to his observations concerning asking questions during an interview.
Alan is the first podcast guest that used a recruiter to help him with his career when he moved from his first position to his current position. There are some good nuggets there. But before I talk with Alan, I'd like to make a special offer for our podcast listeners. If you go to www.CLSheldon.com/Eagles, you can get a financial checklist to help you with your transition from active duty to the civilian world. It is designed for you and you can get it for free at www.CLSheldon.com/Eagles. Now, on to the show.
Alan, welcome to the show.
Alan Berry: Thanks Curt.
Curt Sheldon: I have to tell you, this is a milestone today for the show. This is episode 10. So, we're happy to have you here for this big huge milestone of 10 whole podcasts and talking to you about your post military career. So, to start that out, why don't you tell us a little bit about what you're doing right now?
Alan Berry: Sure. So, I am the Vice President for Cyber Security in a major healthcare company, where I helped defend the company. And by extension, our members, our providers, everybody that's involved, from any kind of cyber attacks. And it's a bit of a change from what I did in military. But in many ways, it's exactly what I did in military, just a different customer base.
Curt Sheldon: Okay, so speaking about what you did in the military, what was your last position in the Air Force?
Alan Berry: So in 2014, I retired out of the Air Force. I was at Fort Meade where I was the Chief of Staff for Air Forces Cyber. The way that we present forces, of course, in the military is the services generate and present to a joint command. And Air Forces Cyber is that joint presentation element for cyber. And I was the senior guy at Fort Meade, doing all the interface with U.S Cyber Command and National Security Agency.
Curt Sheldon: Okay, so your career ended in cyber. Did it start there? Kind of give us a thumbnail of how your career went.
Alan Berry: It did. It started in cyber and then took a few detours. In 1989, when I went on active duty, I was a Computer Security Acquisition Engineer. We didn't really know what cyber was at the time. It was still very new, but we knew we needed to do something. And in many ways, the Air Force was way ahead of the curve on this. So, one of my first jobs was building out the cyber security aspects for the advanced tactical fighter, which we all know is the F-22 today, but in that 10 plus year acquisition cycle, we had to decide very early on how to protect all the systems that are going to create the first truly flying computer that we had.
And we started off with a very rudimentary understanding and grew from there. As I went through my career, I sidetracked into many things and specialized a lot in combat communications and command and control and air operations, but it was always with a cyber aspect because the Air Force career field for communications computer systems was just assumed to be also the cyber security career field, whether it was officially designated or not. And then, it wasn't until about 2010 that we actually shifted from the support side into the operation side and were recast as 17 Delta's cyber operators.
Curt Sheldon: Okay, so after you retire, so you said you retired in ... I think you said it was '14. Did you land where you are today? Or how did your job flow work out after retirement?
Alan Berry: So, when I was in the process of transitioning and figuring out what I wanted to do, I had to make some big decisions. The easy button in my career field was to join a defense contractor to capture management business development, sell back to the military. A lot of my friends do that and they're very successful at it. But for me, I wanted to make a clean break. I wanted to continue to defend a company, an enterprise, something that was more of a ... Some might call it a noble mission. So, I made a very distinct decision to look for opportunities out in industry where I was doing what I did in military, where I defended the Air Force networks and the DOD networks. I wanted to be able to defend that corporate enterprise.
I interviewed with several different places for Chief Information Security Officer type positions and ended up taking a job with CVS Health up in Rhode Island, leading their disaster recovery programs. After three years, I found this new position where I've been for about 15 months, where I am the Vice President for Cyber Security operations, which is much more like what I did in the military, but still part of the overall cyber security responsibilities.
Curt Sheldon: Okay, so I guess we could talk in the case of both the jobs, how did you find out about them? And how did you first enter, I'd say, the application process if you will?
Alan Berry: Well, I did like almost everybody else does, especially retiring military types. And I beefed up my presence on LinkedIn and I built my resume and I trolled all the various job sites. And honestly for me, none of that really did me much good. It's almost table stakes. You need to have a strong LinkedIn presence so that you can have a place for people to go check you out, but it didn't generate any actual leads for me. All my leads came from personal networking.
My first position, a friend of mine knew about the position and told me I should consider it and interview, and I did. That's how I landed that job with CVS. And then, the one I'm in now, another mutual friend knew that they were looking for somebody and trusted the individual that was looking for a VP, and said that they should reach out and talk to me. And that was the introduction. I didn't know the position existed. They didn't know I existed. It was that personal contact of another former Air Force Colonel who connected us and got me the position.
Curt Sheldon: Yeah. It comes up pretty much every episode, that the network is really important. And at our level, it's likely that that's going to be the what opens the door for you versus putting in an application, but I assume you still had to go through an application process? How did that kind of look and you can compare and contrast or if they were both similar, How did the application and interviewing process go?
Alan Berry: For me, very slow. I'm probably very similar to other retiring officers and Senior NCOs where I wanted to go fast. You should be able to make a decision within a day or two. You probably know within 15 minutes of talking to somebody if you're even going to entertain hiring them. And yet, it can take weeks and months. And my current position, it was probably about a five month process as we went through the various levels of interviews and discussions. And then, once we had a formal position to interview for, the back and forth with the recruiters and the hiring manager. And it can be aggravatingly slow to folks who are used to high speed, low-drag, get things done kind of mentalities, but it's something that we as transitioning officers just have to get used to, and to a large degree. It's just the industry is built on a different paradigm.
Hire slow, fire fast. So, they're going to be very cautious when they're hiring somebody at a senior level because they don't want to make a mistake. It's very expensive if they make a mistake. So, you have to really change gears and change expectations to a large degree.
Curt Sheldon: During the interview process, were most of them one on one group settings? How did that work?
Alan Berry: They were mostly one-on-one and then I usually ... In both cases, I ended up doing some lunch interviews where it was more than one person. We're eating lunch and discussing possibilities. But for me, the experience was mostly one-on-one. Interestingly as a hiring manager, there's been more group interviews. And I think I like the one-on-one better. It's my preference. It's easier to have a discussion and not get distracted. But I see that a lot of companies prefer the group interview, not in a panel, not a formal panel, but an ability to have multiple people hear the answers and have different impressions to what the candidate talks about.
Curt Sheldon: You mentioned, and I heard this the other day, you mentioned meals as part of your interview process. And obviously, if you're ever working with someone from the company, it's an interview. But the thing I heard the other day is this ... I guess it's not just one company, but several companies in my industry, that they will set up a meal interview or event and they will instruct the restaurant to goof up the interviewees order, maybe bring the wrong side or something like that, just to test how they react when things don't go their way. The interviews always on, you're always on stage. I don't know how many people actually do that, but at least a few companies in my industry do and that thought had never even crossed my mind.
I wanted to follow up on one thing there. You said you are a hiring manager yourself. Any lessons learned, I would say, from there that might be worth passing on to other folks?
Alan Berry: Yes, there's a fine line. It's a balance when you're the new hiring manager and you're seeing it from the other side of the table. Sometimes interviewees flip the tables, flip the script, and it becomes more about bombarding the interviewer with questions. You need to have some. If at the end of the interview, whether it was 30 minutes or an hour, you say, "Nope, I don't have any questions." The interviewer is going to come away with the impression that you didn't really engage, do any research. You're just looking for the job but you didn't put any skin in the game.
But you have to be so careful because if you turn it around and you start to really inspect or drill the interviewer, then they can also have a bad impression. So, if I'm doing an interview for one of my positions and they have zero questions and zero curiosity, then I wonder if they're the right person for the job. In my world, my line of work, you need to be curious and you need to be suspicious. And if you're not showing that, exhibiting that, then I wonder if you're fit for what we do.
But you also have to figure out the fine line between being overbearing and dogmatic. And so, it is a tough one. It's one that I think we all struggle with. We don't want to be pushy, but if we're not a little bit pushy, than are we showing that we have that ability to ask the next level question?
Curt Sheldon: Okay, good. That's a good observation. And I think you're right. It's a really fine balance, because if someone has no questions or the questions are just about pay and compensation or things along that line, it's going to leave a different impression than someone who starts asking about the company itself, and in the way the way things go on.
During your hiring process, and I'm getting some anecdotal data points. But as far as salary negotiations, how did that work? Were there negotiations? Were you able to influence them much? Again, you're kind of on both sides, have been hired and are hiring manager. What are your observations on salary negotiations?
Alan Berry: Well, that's one area that our transition assistance program did not prepare me for at all. ETAP was a good program. But there's a lot of boiler plate, and when I ask those kind of questions, they tap danced and ducked. There's no other way to say it. They weren't wanting to go down that road for whatever reason. So, I was ill-prepared.
My first position, I did do a little negotiation because the first offer wasn't exactly where I wanted it to be, so I was able to move the number a little bit. But in my mind, what the candidate really needs to know is what does yes look like? You need to know what your yes is. And if the employer offers you something beyond yes, do you really want to negotiate at that point? So, I'm not the expert on this one. I'm far from the expert, but my second job, they matched my yes and then some. And so, I didn't even try to negotiate. For me, it was clearly the company I wanted to work for. It had the mission I wanted, had the location that I wanted, and so it ticked off three or four boxes. There was simply no reason for me to get into that.
The only thing I've heard from others who maybe didn't have my experience is that some companies do try to bring in your military retirement as part of that negotiation when they talk numbers, and I would walk away from those companies. If they think that's part of the puzzle, and it's kind of like going to a car dealer where they want to negotiate your trade-in before they tell you what the price of the new car is, you need to just walk away.
Curt Sheldon: Okay, thanks. It's pretty typical to what I'm hearing from most folks, again, with our sample size of 10. So, one of the things we're pretty good at in the military is bringing a new guy in and getting them up to speed pretty quick. He may have some training, but new organization, new job potentially.
What was your take on onboarding, getting settled into the new job, on the civilian side?
Alan Berry: Well, in my small sample set of two, companies don't do a very good job at this. We are used to military culture where not only were you on-boarded, but then you went to extended training before you're even allowed to try to do your job. Then you showed up at your first duty assignment and you were treated as a newbie and provided even more training. And in companies, it's four hours, is what I went through. Both cases. And in one of them, it was more about trying to sell me that I made the right decision. I'm already there. I've already signed up. I don't need to be sold. I need to know how to operate inside this culture. So, companies tend to not do as good a job.
I've seen some exceptions. The consulting firms seem to do much better job, where they have a week or two dedicated to new hires, even at all levels, and say, "You're going to come in. You're going to learn our culture. You're going to learn how we operate." But outside of that realm, I haven't seen it. They typically say, "Here's your computer. Here's your login, your desk or your office or your cube is over there. Get busy. Why aren't you producing yet?" And that's where I think we lack in the industry side how to bring people in, get them up to speed, and equip them and empower them to be productive right off the bat, versus throw them in the deep end, and if they swim, great. If they don't, well, it was an early exit.
Curt Sheldon: Okay, thanks for that. So, you mentioned that you use LinkedIn. You were I think you said trolling some of the job sites, and that your personal network was pretty much responsible for getting you connected with the people that led to both positions that you've had. How did you energize your personal network? How'd you get them working for you?
Alan Berry: Several months before, I actually went on terminal leave. I started .. Revitalized at that point. So, folks that had already left before me, I reached out to them. Let him know what my plans were, started talking to them. I had never really broken those connections. I had nurtured them my whole life, my whole career, but more as friends not really thinking of it as a hiring Network. I should have started that a little earlier in hindsight. I think everybody has that same advice. If you wait till three or four months out, you're late. Start earlier.
And then, as I got closer and closer, I leveraged any opportunity that presented itself to attend conferences or events in my area, especially when it was no cost and it was just a little bit of time. I did not try to use the Air Force to send me off to some fancy conference somewhere else just to look for jobs. I know some people have done that, but that just kind of went against my personal ethics. But if it was local, I went to it. I talked to people. I made sure I reintroduced myself and that started people to think about, hey, there's a position out there, Alan's going to be open in the very near future. And just by doing that that, I ended up with four or five interviews that I would not have known about. It was the fact that people knew I was retiring, knew what I could do, knew what I was looking for, and then opened up opportunities for me.
Curt Sheldon: Yeah. I think a very powerful tool that is out there is similar to what you described there of going to conventions and stuff of professional organizations. If there's an organization that covers the profession that you're going into, that's a great place to start opening up a network that goes beyond the people that you already know.
So, energized your network, found the job, got the job, started getting some money. How did the money transition work for you?
Alan Berry: Well, I think everybody will tell you that the first year's tax bill is a bit of a shock. No matter how many times someone tells you to be ready for, it's still a bit of a shock. There's so much of our military pay that has tax benefits that aren't obvious unless you're in the business. So, someone like you, Curt, in the business, you fully get it. But a lot of us, that's not what we do. We rely on other people to take care of us there. It's an interesting process when you transition out.
It's also interesting when you have to start setting up 401Ks or dealing with any of that side of the compensation. So, you don't really understand how that works. Sure, we have the ... I forget the name of it. The investment that you can do when you're on active duty, but-
Curt Sheldon: TSP.
Alan Berry: TSP, that's it. But we don't do matching in TSP.
So, you can use it and get some tax benefits, but the military doesn't match your donations. Whereas in the corporate world, they typically will to some degree. And so, understanding all the different wrinkles, how your taxes work differently, having to give up your nice tax free state, when you live in a state that doesn't do that anymore, you can't utilize the laws that protect service members. It's pretty big change. So, the tax bill goes up tremendously and at some point it feels like my military retirement pay just pays Uncle Sam.
Curt Sheldon: Yeah, that's probably not too far from the truth. And especially on the state side, if you don't set up withholding from your retired pay, if you don't tell DFAS to do it, they won't do it for you. Even if you update your address, they just won't withhold any for your state, so that can be one that catches people a lot. Any particular resources that you found that we haven't already talked about? Online, books, people that you follow, anything like that, that you found particularly useful?
Alan Berry: I made a decision to enlist a career coach, if you want to think of it that way, a career advisor, when I started my job search for my second position. And it was very helpful for me. I'm a smart guy. I write well. I can spend a lot of time and craft a resume and rebuild my LinkedIn profile and restate my career, but it would take me weeks or months and a tremendous amount of intellectual capital that maybe I just don't have time to dedicate.
So, I paid for it. For me, that was the right decision. It's not cheap if you get somebody good. It's not going to be cheap, but you have to think of it as an investment. You have to think about I'm finding an expert that really understands how to do this and what is actually working and providing benefit across the U.S, not just what maybe some barracks lawyer told me work for them, and helping me recast who I am and how companies would look at me. So for me, that was very helpful. Not everybody would get benefit out of that. So, it's a personal decision. But I thought it was a good idea for me to have somebody help me with the resume and help me with my LinkedIn profile and make sure that I wasn't overlooking something that others would think of as obvious.
Curt Sheldon: Yeah, kind of along that line, I kinda always say, at least I don't believe it so much anymore, but I always used to believe I can read a book about anything and figure it out. And I believed that until I tried to put up crown molding. And I did eventually get it done, but it took me probably five times the time it would have taken a real carpenter and it still doesn't look as good as if a professional carpenter had done it.
So, sometimes it is ... not always, but bringing in an expert for certain things certainly can make sense, and if nothing else, keep you sane and not get quite as frustrated. As you went through the process again, two times, anything really surprise you?
Alan Berry: The slowness of the process was the biggest surprise right off the bat. One of the positions I interviewed right as I retired was very interesting. Very large company, well-known. They needed a Chief Information Security Officer. They never had one before. They realized that they were behind the times. They viewed themselves as a business to business enterprise, and therefore, why would anybody come after them, until the FBI knocked on the front door and said the Chinese are all up in your chili and you really should change the way you do business.
So, it could have been a great opportunity. But the speed was so glacial that I just gave up on them after a while, because I was looking at the end of the Air Force line and knew I needed a job lined up. And there was no faith that they would deliver. So, that was the biggest aggravation and surprise. The other one is probably how many of the few people that went before me are willing to reach back out and help. And I wasn't expecting that. And so now, I do that for others. So, it's kind of a payback. I had several folks who had experienced this journey, gone through these problems, earned these scars before me, who are more than willing to spend time with me and help me understand the process and do a better job versus having to learn everything from scratch. So, that was a surprise. I didn't expect it, but it was a very pleasant surprise.
Curt Sheldon: Okay, interesting. Thanks. Any low points?
Alan Berry: You don't know what you're going to get into in the new job until you get there. It always looks rosy from the outside. So, my first opportunity could have been a great position. Had some bumps, which is why I started looking for the next one. And it was a little bit underwhelming or depressing in some ways about that. And it's not really a knock on the company itself. It's just that sometimes you don't fit in that culture and sometimes it's not where you need to be and it doesn't make your heart sing.
So, I would just suggest that people really look at a position and make sure the heart is going to sing. If you're just taking the position for a job, it may work out, it may not. But if it makes your heart sing, it really gets you excited. If you look forward to going to work in the morning, even if you're going to work in the office 20 feet from your bedroom, then you'll get through everything. It will be a lot more fun.
Curt Sheldon: Okay. Well, I always like to take a moment here and just kind of make it open mic, your chance to pontificate about anything that I maybe haven't hit on that you think is worth bringing up.
Alan Berry: Sure. One of the areas that I found really interesting is in my TAP class, we had a gentleman come in and talk about clothes. I spent 26 years wearing what the military told me to wear. And I had really zero education on suits and what was appropriate. And it was fascinating. And of course, then I got a little excited and I went and bought the $1,200 suit. In my first job, I didn't have to wear it at all now.
Now, I'm in a company where I do wear a coat and tie every day. Which is fine, but I found that I really didn't need $1,200 suits. Joseph Banks works just fine for just about everything that I needed to do, and then similar outfits out there. Not everybody's going to get that experience in TAP. We just got lucky because I was in the DC area and there was a gentleman that would come and do that for us. We really don't know how to dress. It was amazing that there's things that I just didn't know and understand. How weird is that? That as a 48 year old Colonel, highly successful in the military, I needed Garanimals for men in order to get dressed.
Curt Sheldon: Okay. Yeah, I agree. I went through TAP at DC a few years before you and the people have changed over time. But yeah, I learned a lot through the presentation that I heard and realized I didn't know anything, and that I probably needed somebody to help me as well.
So, as we kind of start to wrap things up, if somebody wants to get in touch with you, what's the best way for them to do that?
Alan Berry: Best way is probably LinkedIn. I'm the original Alan Berry on LinkedIn. I was an early adopter, and so it's easy to find me. A-L-A-N B-E-R-R-Y. So, anybody else out there has to have some number, something behind them.
And then, Curt, one other point I just wanted to bring up that maybe some folks don't realize. When you retire, you may be perfectly healthy and you may feel like you don't need any of the VA benefits or anything, or you may be disabled and you actually know you need them. But a lot of us get a little too much bravado and say, well, I'm not going to put in my paperwork for the VA and I don't know how to do it and it's hard. I used the VFW to do mine. But I was slow in doing it because I was in that position. I was like, well, I'm healthy. I can still go run 3 miles and play volleyball and softball. So, I really don't need it.
It's important that you do that. It's important that you swallow your pride if you're in that position. Reach out to one of these groups like the VFW, they're not the only ones, and get that paperwork submitted because it may not be a matter today, but 10 years down the road, if you didn't document that properly and it does become a problem, you don't have that and you don't have that prepared and ready to go and you may put yourself or your family at risk. So, it's really important for all of us to remember that it's not about pride and it's not about getting free money. It's about documenting what happened, so you have it should it ever become a problem in the future.
Curt Sheldon: Okay, thanks, agree with that entirely. So, to kind of wrap things up, I'm going to the question that I ask pretty much everybody when they come on. If you were to go back, 2013 or early 2014, 6 to 12 months prior to your retirement, what do you know now that you wish you would have known then?
Alan Berry: That's a tough one. We mentioned the network, early network, often. That's the biggest thing out there.
Curt Sheldon: Okay. Yeah, I agree. It's certainly worth it to start the networking process early, and network constantly comes up on the podcast. Everybody brings it up. Everybody used it. Everybody so far has been like you, willing to pay it back. But it does take time. I mean, people can't help you if they don't know. And so, I agree a 100%. And probably the same situation, I probably should have networked better earlier as well.
So with that Alan, we'll go ahead and wrap things up. I would like to thank you for coming in. I know you're a busy guy. I know your time is valuable. I appreciate you passing on what you've learned to the folks coming along. And again, thanks a lot for being here.
Alan Berry: Thanks, Curt.
Curt Sheldon: Okay. Take care.
Speaker 1: It's not easy balancing the demands of active duty and searching for your second career. That's why we put together a retirement financial checklist tailored for senior military officers. With it, you'll organize your financial affairs and avoid mistakes when you retire. And the best part is it's free. You can get it at CLSheldon.com/Eagles.