WHAT ONE FORTUNE 100 HIRING MANAGER WANTS TO SEE ON YOUR RESUME

Kip Boyle:        

Hi, everyone. This is YOUR CYBER PATH, the podcast that helps you get your dream cybersecurity job. I’m Kip Boyle, and I’m a experienced hiring manager of cybersecurity professionals. If you want to give me feedback on the show, if you want me to answer your question on a future episode, please visit the show page. You can find it at anchor.fm/yourcyberpath. When you get there, you’re going to see the message button, click on that and start talking. I am super excited to introduce my special guest. So, like me, he’s an experienced hiring manager of cyber security professionals, his name’s Wes, and I think you’re going to learn a lot from him. Hey Wes. Welcome to the show.     

Wes:  

Hey, Kip. It’s great to be here. Thanks for having me on today.

Kip Boyle:

Oh, man. Fantastic to have you here. I got to tell you, this is episode 17 or something like that, and I was getting really lonely being the only guy talking because I’m on another podcast and I have a co-host and I’ve had one, Jake’s been co-hosting with me from the first episode. So, this was really weird and quite relieving to have you here. And so, yeah. So, tell the audience who you are and why you’re here.

Wes:

You bet. So, it’s great to be here. My name’s Wes. I found my path into technology from an ATNT wireless call center up in Bothel Washington. I wanted to solve a thousand problems at a time, not just one problem at a time. And while in IT, I would run towards the biggest problem. The biggest challenge we had at the time was our single sign on. We had a single sign on product where the front door was down, but the applications were up, and the applications were taking operational hits against their availability even though it was a front door problem and not their actual application.

Kip Boyle:

Okay. So, when you started, you weren’t even in cybersecurity inform security or any of that in the beginning, right?

Wes:

I started as a call center representative, moved into IT doing it operations, right? Business analyst, functional analyst, tech writer. I wrote some code. I found out I was best at organizing people and stepped into a project management role. In project management I ran towards the biggest problem and the single sign on called me, right? That during the time that, that was 2002. That’s when Enron happened and MCI WorldCom happened, and with that Sarbanes Oxley happened. And so, Sarbanes Oxley is Sox. Sox is all about least privileged access or LPA and segregation of duties, SOD. At that time I was new christened a, what’s that security professional, right? If you’re doing single sign on and Sox happens, you are now a security.

Kip Boyle: So, that was your path into a cybersecurity career. Fascinating.

Wes:

And it really was all about understanding my business, right? Because what qualified me as an IT professional was understanding the business processes of a call center rep and being able to tie what we’re doing on the frontend to what’s happening on the backend. Since then, I’ve worked in a couple security groups at Microsoft and Nordstrom and Pricewaterhouse Cooper, and a couple others, lots of clients in the region.  I’ve had management responsibilities for most of the last 10 years. I’ve probably hired a hundred people in that time, contract or FTE or something. And so, really looking forward to our conversations today, I think there’s a lot to be said.

Kip Boyle:

Yeah. That’s great. And by the way, everybody, I think you know that I live in the Seattle area, so does Wes, which is fantastic for us to be so geographically close together. Hopefully when the COVID 19 thing goes away, Wes and I will be able to meet up for some beers and do some episode planning. So, I’m looking forward to that. Okay. So, let’s talk about the episode today, what I’d like to do and the reason why I asked Wes to join is because I want to talk about what is it like to be a hiring manager? And I want the people in the audience to better what is the work of a hiring manager? And particularly how do you find strong candidates to interview? Because that is kind of the behind the curtains problem that we face.

The other side of that curtain is, I want a job, right? And I’m trying and figure out how to get my resume into the hands of the hiring manager, right? And so, I’ve always found it interesting that our side of that curtain is so very different from the side of the job hunter. And I always think of job hunting as like trying to start a serious relationship. But the hiring process is highly regulated so it’s not a free for all kind of a situation, right? And as a hiring manager we need to be well trained. We need to stay within legal, ethical boundaries. We’re not illegally discriminating, we’re not advocating that. But Wes and I are going to explore, right the themes, I hire for a small company these days, Wes hires for a large company these days. And so, today what I want to talk about is-

Wes:

I would interject, I’m sorry to interrupt. I would interject that the market has for the last four years been one of, especially in the security space, a shortage of security workers and security managers who are complaining. I can’t pay enough to attract the kind of talent that I want. I need more money in order to attract talent. And I’ve got to say that I’ve never had that problem, right? If you can create the kind of atmosphere and environment that skilled professionals want to be a part of, then it’s not a problem. And so, I do a very transparent hiring process, right? One of come in and see a team meeting and see how we treat one another and how our customers treat us.

I invite you to an interview with only my customers and none of my team or my staff are in that conversation at all, because you can go find out what they really think about us. And we’re even a part of that conversation. So, we can talk about transparent hiring processes another day. Today I think we’re talking about the resume process and how we get there. I know that the market has shifted quite a bit in the last couple of months with this COVID where now there are plenty of staff available and we have an opportunity to find that right match and really step into these roles that are opening up.

Kip Boyle:

Yeah. So, let’s talk about this and particularly the resume. And I think in future episodes, it’s just going to be fascinating to be able to bring other things that you’re seeing and that I’m seeing. So, okay. So, from your point of view, Wes, what’s the purpose of a resume? How should our audience members be thinking about resumes?

Wes:

I want to start by saying that hiring is the most strategic thing a management team can do. I’m convinced that taking the time to hire great people makes my job easier. It makes my team better and improves everybody around us, right? We can level up. When you’re hiring great people, it makes everybody better with the energy and the enthusiasm that comes with it.

Kip Boyle:

Definitely. Yeah. And the hiring managers the gatekeeper, right? Of who gets on the team.

Wes:

That is the objective. Yes. What’s the purpose of the resume? Resume’s got a couple of purposes, but it’s a very limited scope purpose. So, let’s understand that before we go into how to craft a resume. No resume’s ever gotten anyone, a job period.

Kip Boyle:

That almost seems like a heretical thing to say.

Wes:

But it’s absolutely true. The resume’s job is to kick the door in for you so that you can have a conversation and you can win your heroes, but it does not get person’s jobs ever. It’s possible to get a job without a resume actually, right? If you have a strong reputation and relationships it’s possible to get one without a resume. So, you’re trying to accomplish four things when you put your resume in front of someone, right? First is you want to get through the artificial intelligence word search tools that choose who goes forward, right?

Kip Boyle:

Yeah. The applicant tracking system, right?

Wes:

Yeah. And then the second is you want to get invited to the conversation with the recruiter. The third would be to get invited to the conversation with the manager, and then use it as a springboard into the conversation, right? It’s going to be a conversation starter for you in those conversations.

Kip Boyle:

So, a conversation with recruiter and a conversation with a hiring manager, right?

Wes:

And that’s, it stops there. That’s all. After that it becomes an audit mechanism to make sure that you told me the truth when I’ve made a hiring decision and I have to do a validation check on those career statements.

Kip Boyle:

Oh, interesting. Another thing that happens that people hunting for cyber security jobs probably don’t think about is that audit and, the point that you made a moment ago about, it’s possible to get a job without a resume, boy I sure know that. And I’ve been very fortunate that I’ve actually been able to do that. And I remember distinctly one time being offered a job and then having the hiring manager say to me, “Oh, by the way, send me your resume. I need one for the file.” And it’s like it almost didn’t matter what was on the resume. You just needed one for the file.

Wes:

Well, and it better be truth that is on that resume. Truth is the only thing that matters there. But we can go into that in a minute.

Kip Boyle:

That’s a good point.

Wes:

In the meantime. Well, actually that leads into the four things that you want to keep in mind if you’re going to write an efficient resume.

Kip Boyle:

Yeah. Yeah. Let’s get into that. Tell us, what [crosstalk]-

Wes:

Real audits happen. Not just the interview check, not just when the interviewer looks across the table and says, “I see this bullet here. What does that really mean to me?” But there’s a real audit that happens when hiring that says, did this person work for you from this date to this date, doing this function? If the candidates found a creative way to say things, shall we say it can cost him a big opportunity.

Kip Boyle:

Have you actually seen that? Has that happened to you?

Wes:

No, not to me. I have seen it happen to others.

Kip Boyle:

Has it happened to a candidate, somebody that you were considering?

Wes:

Not to my candidates? No. I’ve seen it happen to peers.

Kip Boyle:

Have you seen it?

Wes:

Yes, yes. To peers.

Kip Boyle:

That just sounds like a terrible situation for everybody, right? So, the job seeker doesn’t get a job. The hiring manager has poured tons of time and energy into it and now can’t offer the job or has to retract the offer. Horrible.

Wes:

And one of the best ways to tell the truth is to make sure that if you’re using a resume writing service, that writing service, you’re editing and auditing that writing service is result for or resume, because you’re still the one speaking, no matter what someone else says about you, that’s you delivering your document to someone. So, it better be accurate, right? To what you would say.

Kip Boyle:

I’ve used resume writing service one time. It was a long time ago, but I felt so squirmy when I got it back because they were trying to position me as a really great candidate. And they said things that made me kind of go, I don’t think I ever would’ve written that.

Wes:

And that’s something that we have to come to terms with as we move forward, we’ve got a very international audience and having a resume writing service is a reasonable path for how do I communicate effectively in a language and a culture. And I’m going to say even the culture of Midwest America versus the culture of West Coast, America is very different. And so, hiring a local resume writing service for the area you are trying to get work in is a very reasonable thing to do, but understand you’re still accountable for what you’ve said in there.

Kip Boyle:

Right. Right. Okay. So-

Wes:

Another thing I would add is don’t get lost in telling stories about last year or yester year. Right? Don’t tell me stories about when you were 17 and working as a box boy, it’s time to tell the stories that are relevant to the role that you’re looking at. And buzzword bingo doesn’t help you. Right. I, I only have the tolerance for reading for so long. And so, if you’ve got a lot of big words that are fluffy, they’re probably not going to get you where you want to be.

Kip Boyle:

So, this is great advice. And I can only imagine you sitting at your desk with a pile of resumes, right? And they’re probably not printed out, but for whatever reason I can just imagine a big stack of papers in front of you. And you’re just going through them, right? One after the next, one after the next, because you probably get way more resumes to screen than you can hire. I mean, right? So, I mean, what’s it like for you?

Wes:

I’m about a five to one. I’m sorry. Once you get to interview, I’m about a five to one interview to hire. So, I’m a tough manager for hiring, but yeah. I probably look in a high in order to get to five resumes, conversations to get to one higher.

Kip Boyle:

Okay. Okay. So, here you are, you’re sitting there, you’re screening resumes. You’re looking for a good resume, right? Because a good resume probably means a good candidate, right? Somebody you want to talk to. So, what are you looking for?

Wes:

The summary. I’m going to give you a couple items here. That summary is probably the first thing. The summary at the top of the resume that says my name is, and I am, and this is what I’m looking for. It needs to be thoughtful. It needs to be efficient. It tells me how you’re going to communicate to an executive. If you’re working for me, right? That’s your executive summary. And if you can write to an executive that summary, then I know you’re going to be okay talking to my boss when you come into the office.

Kip Boyle:

Ah, okay. So, in other words, the person writing the resume is already preparing a work product for you.

Wes:

And that’s really true. That’s really true. That executive summary is a work product of how you’re going to talk to my boss. Then I’m going to look at your skills section, and the skills need to be organized and prioritized by what you’re selling to me. This is what you are bringing to the table and telling me, “I think I understand this job and these are the skills I think you are looking for. And I want to highlight them in priority order, not just in throw against a wall order.” And this is going to tell me that you understand my job and the skills that are going to be needed to do this job.

Kip Boyle:

There was one word that you said that really stuck out to me, selling, right? That a candidate is selling themselves to the hiring manager. And I think that most of the people who work in cybersecurity would probably say, “I don’t do that. I don’t sell.” Right? That selling is repellent or they imagine a used car salesman or something like that, and they’re like, “God, I don’t want to be like that.” So, what a paradox.

Wes:

And that’s a very difficult thing to navigate because you do, you want to highlight the things that you’re bringing to the table that are valuable. You don’t want to pretend or make anything fake about it. And you want practice the humility that is so valuable in these roles, right? If I can’t bring humility to the table am I really bringing anything else? This is probably a big question. And so, you’re right to call out, is it selling? No, but sometimes I have to convince myself its selling in order to highlight the things that I wouldn’t normally talk about myself about.

Kip Boyle:

Yeah. Well, Daniel Pink has a great book and he talks about how everybody is in sales, like if you’re married or if you have a significant other, at some point you convinced somebody else to be in a relationship with you. And guess what I mean, that’s kind of like selling. And when I think about going to get a job, I’m thinking about, I want to create a relationship with an employer, with a hiring manager. And so, it actually has been pretty useful for me to think about the whole thing as a relationship rather than selling a car or something like that. And it’s your brand, right? Your brand is going to be known. You’re going to work in this industry, in this market for the next 20, 30, 40 years. And when you do, people are going to know you by how you treated them and how you knew your topics and really your reputation and your brand that you bring to the table. Right. Okay. So, on the resume, what about, now I’ve got a work history, what are you looking for there?

Wes:

So, that’s a good question. That work history better have short descriptions, action verbs, subjects in the first five words. Can you glean the important topics effectively? I would almost say for that section, it’s worth having your mom read it. I mean that for real, right? If your mom can’t understand in the first five words of that sentence the action and the topic that we’re talking about, then you didn’t write that sentence effectively. If you’re starting with, -ing words you’re probably not conjugating your verbs correctly, right?

Kip Boyle:

Oh, so like planning or that sort of thing, right?

Wes:

Correct. Unless it’s the current job that you’re actually in and you’re actively doing it now, it needs to be a past tense verb. It needs to have a subject involved in it in the first five words. And it needs to be specific and clear so that I can understand both your role in the function and what the delivery was, right? Why that benefited the company.

Kip Boyle:

Okay. So, I think this is a great sort of summary of what you’re looking for in the resume. And I think we could go much deeper right into these and I would love to do that in future podcast episodes if you’d like, but yeah, let’s talk a little bit more about the hiring process for you as a hiring-

Wes:

Sure. So, the hardest part for me is sitting to read resume after resume, after resume. It’s a monotonous grind. It’s rough. And it’s not nearly as much fun as doing the job of security. So, I’m looking for you to help me help you, right? I actually want to hire you. I want to hire you, right? My life is better when I can get that hiring done, get that person in here and get them contributing.

Kip Boyle:

Yeah. Whenever I get into a situation where I’m saying to myself, “Okay, I have to hire somebody.” I have two feelings at the same time. I’m excited because I’m like, wow, this is really cool. I’m going to bring somebody onto the team. We’re going to get more done. We’re going to serve more customers. But then at the same time, I also kind of groan inwardly because it is not easy to do it. And it’s going to be a ton of work. It’s going to be really distracting from the things that I’m used to doing every day. Like an hour grinding through the pile of resumes is an hour I cannot spend coaching somebody on my team or having a valuable conversation with a customer. So, I feel conflicted. And that’s one of the things about the hiring process that I struggle with.

Wes:

So, I see some people go through resumes at 30 seconds a resume. I’m not sure I can quite do 30 seconds of resume. I’m pretty sure it’s not because they’re speed readers. And I think an important question to ask is how will I be represented in that 30 seconds?

Kip Boyle:

Right. So, if I’m seeking a job, hunting for a job, that’s what I’ve got to keep in my mind, right? Is that I might have 30 seconds of attention from the hiring manager on my resume. And that’s 30 seconds after I run the applicant tracking system gauntlet, right?

Wes:

True. So you’ve survived applicant tracking. Now you’re in the 30 second window of test. And if you pass the 30 second window of test, you get to continue to two minutes. At the end of two minutes I’m going to decide to bring you in for a phone call or not. And so, you’ve got that first 30 seconds of catch me, another two minutes of keep me, and then I’m going to make the phone call.

Kip Boyle:

Okay. So, everybody in the audience, hang on to that, that’s really, really important. And I think it really puts a sharp point on the need to be really excellent in your written communication skills. So-

Wes:

It’s something I would call out is, that executive summary needs to be very specific and purposeful, right? And we can talk about what goes into that at some point if you like. The next thing is the bullets for each job need to be specific and purposeful. If you’re going to give me a six page resume, I can’t get through all that. As a candidate, I need the candidate to filter their resume to the salient valuable points and deliver me a one to two page two and a half page tops resume of, two and a half pages for 20 years, right? Of the salient valuable points from each of their specific roles that filters it for me. Otherwise, I’m going to have to filter it for them. And they may not like what I filter.

Kip Boyle:

So, If a person doesn’t consider themselves to be an excellent writer, right? And they’re saying, ” Well, I’m a pen tester.” Or, whatever their skillset their specialty is, right? And they may say to themselves like, “Writing a resume is such a chore and now I’m listening to Kip and Wes talk about how great it has to be. And I’m just inwardly groaning myself right now because this isn’t what I do.” Then I suppose that’s a great use case for you to get some help.

Wes:

And use the resume writing services just for the record, I don’t think you’re recommending a referring any resume writing service specifically. Is that right kip?

Kip Boyle:

No, I’m not.

Wes:

We are just neutral dudes talking about hiring. So…

Kip Boyle:

Yeah. And trying to figure out if you are a person who is trying to get in front of a hiring manager and what we’re saying to you is, your writing has to be amazing to do that. That’s a crucial skill. But if you don’t have that don’t think that you’re doomed. [crosstalk]-

Wes:

No, and you’re not, you’re going to get better. Everything worth doing is worth doing poorly and awkwardly. And I want to say that one more time, anything, everything worth doing is worth doing poorly and awkwardly, because if you start poorly and awkwardly, you’re going to get better over time and you’re going to do it better and you’re going to present yourself better, and it’s going to be worth it. If it wasn’t worth it, then why do it at all? And so, please take that. I do want to jump into that resume.

That summary section, it’s how you’re going to communicate with executives. The skills section is how you’re going to communicate with your peers and tell me, you understand the priorities of this job. The past job descriptions, that’s how you’re going to write a status report for me. And if you can write a prioritized important list of the tasks that you’ve done at a previous job, and I know my status reports that I’m going to be reading are going to be reasonable. If you throw a picture of personal information in there, I’m not allowed to look at your resume anymore.

Kip Boyle:

What?

Wes:

That is one of those boundaries, right? Do not put your picture on your resume. That is not helpful to me as a hiring manager. And it almost immediately disqualifies you.

Kip Boyle:

Can you say why?

Wes:

It’s too much bias? It puts us in a spot where now I’m accountable for information in a resume evaluation that I shouldn’t be accountable for at that stage in the hiring process.

Kip Boyle:

So, that kind of goes back to this idea that hiring is a highly regulated process, and we need to be well skilled, and we need to be ethical and take our duties seriously.

Wes:

We do. And I would suggest that people carry two resumes. I would almost suggest you carry a duplication of your resume. One that is a machine readable keyword search matching long text, easily pastable into every one of these individual recruiter machines that every company has out there. And it takes an hour to paste all your stuff into every one of them and answer all of the questions that they have. And so, building yourselves a text formatted resume that has all of the search engine optimization in it is beneficial and valuable. As long as that is not the one you send me an email, right?

The one you send me an email in the human format, right? I’m going to call one the machine format, and I’m going to call one your human format. And the machine format one can have all your key buzz words in the right order and sell yourself to the machine. Then the human format one needs to be the two pages or less. It’s the one that we send through email, it’s the document or PDF that you upload into the program when it says, do you want to include a resume and cover letter? We didn’t talk about cover letter but I don’t spend a lot of time on cover letters. I would say just that that paragraph executive summary at the top is where you’re going to be communicating who I am, what I’ve done and what I’m looking for.

Kip Boyle:

Right. It almost seems like the applicant tracking systems has really shifted the burden a bit to the applicant, right? Because now I’ve got to have two resumes and I’ve got to have one for the machine. One for the person.

Wes:

I think this two resume thing is a new concept. And I don’t know that everybody knows that. And so, I do want to throw that out there. The facts need to be the same, right? You can’t have different facts between them, and it sure makes it easier if you’ve got the text based and the PDF version separate so that you can present to different readers in different ways, but that’s a very new concept and not always something people do.

Kip Boyle:

Yeah. So, you’re just knowing your audience, and you’re just trying to be respectful, like I have a machine audience and I have a human being audience, and I want to put the right thing in front of each one of them to optimize for the way that they’re going to consume that information.

Wes:

Absolutely. I do.

Kip Boyle:

Okay. Got it. Well, gosh, we’re coming to the end of the time that we have for this episode. Wes, this has been fantastic information.

Wes:

A lot of fun.

Kip Boyle:

You’ve been sharing. Do you have any final thoughts on the resume?

Wes:

This is the time, this is the chance to go take your chances, to get out there and put your best foot forward, use your resume to accomplish those four objectives. Right? Kick those doors open with that hiring manager, with the artificial intelligence search machine and with the recruiter, right? And then understand it’s their springboard into the conversation that you’re really selling yourself for.

Kip Boyle:

Great, thanks, Wes. So, as you all know, back in April, we did a beta test version of our masterclass that’s called how to get your dream cybersecurity job as told by hiring managers. And right now we’re working hard to get the revised masterclass ready for launch, and we’re going to be up and running by June 1st. And I’m excited about that. And I’m excited to be able to share more about that with you later, but that’s enough for this episode. And we hope you come back and join us for the next one. We’re going to continue, Wes and I to unpack resumes and the hiring process. So, anyway until next time, remember, you’re just one path away from your dream cybersecurity job.