Failing Upwards: How to Rise in Cybersecurity by Finding and Exploiting Your Weaknesses

welcome to Higher Ground I'm Kathleen Smith yes it's Kathleen on Twitter it is just so exciting and emotionally inspiring to me to see this room felt um wow I promised myself I wouldn't cry anyway um I started this seven years ago because I'm in recruit my marketing and I knew that the conversation was not happening in a valuable and safe space for people in our industry to find a job so I asked a few friends to come in and do resume review and career coaching asked a few people to do presentations that would help you with your career and now over seven years it's grown to a full room wow so let's talk about failing because we

all know that we hate to fail God I hate to fail I'm the eldest of five kids I hate to fail I have to be perfect all the time but you know what failing is the best way to learn right yeah pretty much okay so Wes is going to talk about failing upwards in your career let's give it up for Wes

so for those unaware uh my the previous speaker did not drink his water so I have bonus water no no no my water my water anyway so yeah so thanks for coming to this talk uh you know what's kind of fun is um when I was looking at how to do this I was looking up like presentations like surely someone's talked about this before no one's presented this yet as far as I'm aware this is the first time anyone's presented how to fail upwards so everyone in this room is a trailblazer today so that's um that's news right that's pretty cool um and everyone can hear me okay yeah cool all right just for that Okay so

um one more thing to know and this is uh this is um just a little bit a little bit of a warning um as I spent far too much time on real cringe inspirational stock photos I spent real time on this I'm sorry I'm sorry in advance so failing upwards let's try this out let's start with who am I um my name is Wes hi how you going hey uh so you know I kind of move around a lot I currently live in Canada not Canadian um but before then I lived in the Netherlands Japan China United States these are places I've worked and lived uh for the last uh 15 years or so um also New Zealand UK and Belgium and

for a tough from time to time I it's that's a story on its own honestly that's not this talk that's another talk uh but it's it's just kind of what I do um my current role what I do these days is I'm currently the chief security officer for a company in the in Toronto called order grid um I'm also a data privacy Advocate I work with the I try to do what I can for Electronic Frontier Foundation uh feel free to support them a lot oh sorry I feel oh yeah the fan yeah that's that's my competition yeah okay I'm stepping forward so you can hear me better so anyway yeah um and I'm all and I'm also a hacker as

well um I put that on my professional list not that I hold that title it's more that that actually helps my job that actually helps me do my job so it's kind of what I do to help the main gig so to speak um on the personal side I do lots of running I do weight training um I play lots of video games when I have the time I walk around the world sometimes and I also hack in my free time my current hobby horse these days is RFID badge cloning who thinks that's cool because I think that's yeah oh so many friends yes okay um so and then but why am I like this

um I like Puzzles and I seek novelty that's kind of the short version uh also anxiety so that's enough of me um before we start on this though just a few things just kind of level set and manage expectations a little bit um I'm going to start with by explaining by clarifying what is failing upwards in the first place um I'm going to tell you my story I'm really sorry about that you're gonna have to sit through my story to hear how to do this thing um and I'm gonna set some scenes for you set some mental space on what mental angle you should find yourself in if to try this out uh then we're actually

going to get to the steps on failing upwards in the first place um and then we're gonna do some final final words as we go um and this is a really like long presentation because it's really nuanced and I'm sorry for that but uh if you want to ask questions feel free to you're going to dislodge me a little bit but I promise you're also going to put me back on track at the same time so feel free to yell things out hey you're wrong please do um that's gonna help that's help me Focus bring me up to speed some assumptions I'm expecting that everybody in this room has you want that you want to get ahead and that you know

where you want to go and that you have some idea of the job you want to have um this is largely based on the idea of rising into management because I think we all kind of at some point decided we don't want to be on call anymore so yeah uh it's kind of like that also I'm making another assumption which is that uh most of you are already inside the uh it or security space already if you're breaking into the field this is also applicable just less so and uh then also one another assumption is you have is that I'm assuming you're willing to get weird okay yeah yeah perfect perfect um some disclaimers your mileage your

mileage may your mileage will vary your mileage will vary because this is a very nuanced subject it's very personal to every person uh the reason why I'm telling you my story is because that's how I can give you examples it's going to be different for everybody another thing is I want to say out loud I see my privilege I recognize that I am CIS male I recognize I'm Caucasian and vaguely tall these things do contribute to this they do uh to the success that I've found that said the reason why I'm talking about it in the first place is because I have seen people who are ethnic minorities and gender minorities do the same process again just like me

accidentally because I don't think anyone tries to fail upward necessarily until tomorrow right but in any case it's almost always accidental and I've seen people who are not like me also succeed this way and this is and just a bit of a warning this looks easy and is hard by the by trying to go through this process you're basically putting yourself in a position of vulnerability as a means of succeeding long term you're putting your Stakes up high I don't expect anyone to risk their jobs over this another thing I want to say out loud but um the way this works is that you're going to have fun with it and I mean that it

really helps to have a good time doing this because that's going to sell the Charisma which is going to get you there in the first place so that's a lot of disclaimers I talk too long let's discuss failing upwards what does that even mean well if you look it up on Google these days it looks like this to advance in one's career despite failure and you know the thing is that's that's that's not exactly the thing I'm talking about today that's not exactly the process of failing upwards if you've ever had a boss who is just like how did how are you managing me you know he failed upwards he he found himself in a role that he is not trained

to do by doing a job this by doing a job above his above his rank too long and somehow he somehow he's managing others that's this sentence to advance in your career despite failure that's career resilience not failing upwards there's a very big difference here that's not what I'm talking about today you can you can be you can be strong and powerful and employed but what we're talking about today is how to rise so but why would you fail upward why not just go the normal path and work hard and get promoted because it doesn't work it just doesn't work there's no reason not one reason a manager has to promote you for a good job

they are literally disincent disincentivized at every single time how many Engineers analysts in the room like key stakeholders in the technology level yeah so I'm gonna guess each one of you has been told you're really important yeah yeah so the trick is is that if you why you would want to fit why you would want to fail upwards is because that's a because you want or need to get an advanced job maybe you have bills to pay maybe you've got maybe you've got maybe you've got goals you got that like eight mile energy on you um you know good employees don't usually get promoted frequently they do frequently they do but it's not guaranteed it's really not

and managers if you're looking to rise into management what does a manager do truly I mean they have job duties but what does a manager what does management quality even mean right and there's you can you can I mean can anyone give me n a manager quality babysitters what else what else these meetings meetings yes yes what's that carrot and stick yes carrot on a stick even better do it double it up

this is a special request thank you thank you this gives me Strife this is um I should explain it shouldn't I absolutely I did not expect you to do this thank you I made a special request when I submitted my talk uh to can I please have a giant picture of princess erulon from Dune in 1982 I am I I this this gives me strength thank you thank you very much I need yes oh my God this is a great thank you I'm gonna I'm gonna put it right here where she angling a little bit so I can see her no I can't you know what yes wonderful I did not expect this oh my God that is incredible never say

beadsides doesn't take care of their speakers that is incredible thank you thank you thank you so much this guy this guy thank you very much what the hell was I talking about anyway did I tell you the okay so do 1982 was a real classic but it's really no it wasn't that um let's move on how do but but the mechanics are failing upwards let's talk about that um how does how does failing upwards work mechanically like what is the process of failing upwards um I'm going to go into a greater depth on this this is just a bit of a summary but the short version is counter signaling which in this case actually bigger summary it's uh subtle emotional

um subconscious cues that you get and there's also social constructs like um which we'll get to in a moment so things like counter signaling which is for example to say something negative to indicate positive or to uh bias for Action you know just doing something is better than doing nothing um cronyism frankly that is the x that is the attack surface we're talking about today so cronyism how do you break into it it's exploitable print and principles of influence uh any social engineers in the room oh see I figured you would see that that much Style no that's a social engineer right there so right here the social Engineers are going to recognize the six principles of

influence I'm going to reference three of them which in this case is reciprocity I give you give uh social social proof we uh we all approve this or likability because frankly that's needed um and I just want to apologize in advance because the one thing that I really wanted to spend time on and I can't is how to how to build your charisma and your communication skills because that is how this comes together I'm sorry I have resources at the end at the end of the presentation but we're just gonna have to take me on faith that that one matters so sorry about that that said is it really truly a thing people still do is this does this happen all the time

as a matter of fact it does [Music] um two articles ten years apart these are things that actually are still subject matter today in business circles uh it is extremely normal to find people failing upwards people are seeing it as a problem because people are getting into jobs that they're not skilled to have but be that as it may uh this is actually a really really normal thing to do every company experiences this every company deals with this this is in fact a way of business that goes back as far as corporate life does so take me on faith on this believe me there's lots of examples of failing upwards now let me go through let me go through the

boring stuff then we'll get to the interesting stuff so I gotta tell you this for for the reasons of giving examples here's a here's here's kind of how I got into this and how I failed through this process on the childhood side you know I was I was into geek stuff you know video games and movies mostly kind of was the audio visual guy from my family small hands behind the TV sort of stuff and um and I also in my free time I I messed with my game genie it was a man in the middle device which allowed you to input new codes into games and change the gameplay this guy knows what I'm talking about game game shark is

good too okay that's that's PlayStation era I like it and um and so yeah but uh so I went so I and I was like and turns out old TVs older CRT TVs turns out you can brick them um by playing with the settings too much so fun fact um teenage years I got into martial arts that was helping my anxiety a lot still lots of geek stuff but now I'm into robotics now I'm now I'm now I'm like building stuff and I'm social engineering I did not know that's what I was doing but that's what I was doing in college Years I was into politics I I flunked out of a double major in

politics in fact um then I got a degree in education I couldn't quite pick a lane um and in my free time I was jailbreaking iPhones and writing a cyberbunk novel um still still in progress and um and then early career I you know while I'm flunking out of your University I figured I'd pick up some retail Hospitality work you know just kind of pay the bills and while I'm doing this people keep asking hey Wes knows that West knows that he can fix that um because it at no point in my entire childhood did I connect that I should probably get into technology not once it had occurred to me maybe I should pick up Tech work as a as a

profession um but I finally eventually did crawled my way into that space um starting with a job in China I was a technical pre-sales in China now uh for those less aware of the way China sells to China uh there is a there's a when you do a business conference and you want people to see your business as prestigious and international even if it isn't uh you hire a white guy to stand there in a suit and be Caucasian and white in your booth I was a booth babe for about a while um no no don't talk don't talk you're not supposed to talk do not use your terrible Chinese on your customers um stand there and be Caucasian uh but

in my free time I learned some of the technical stuff and that kind of but I was doing that to move to China to move to Japan because my goal of time was in education to be a teacher in Japan for the rest of my life you know that worked well um I went back and forth and back and forth for a while and I was doing Shadow I.T the entire time and it finally occurred to me maybe I should get into it eventually so I so I pick up this basic I.T job tier one help desk at a foreign currency trading foreign currency exchange company in downtown Tokyo and um yeah so there's all that I finally it

finally I finally got there I got like all they you know I can finally this is my job now now I can fix things all the time and of course everything's broken so I see everything needs fixing so I started off with help desk and then I see that no one's working on the data centers I think of some data center work then I then move more synthesis admin that it morphs into Data Center Administration I.T risk management I.T compliance um uh multi-data multi-data Center Administration project management for the Asia Pacific region um I burned out I burned out real hard just like university only much harder and uh there's a there's a separate and

parallel lesson to that which is that if you're gonna burn out just before you do let go of some of the things that are keeping you and that that you can actually like not burn out as hard so holding on to everything is how you burn out faster so Pro tip but anyway here's where the failure really kicks off is I I burned out so hard I had to fall back to the United States for a while and I picked up a cloud sysadmin job uh just something kind of basic just get the job done um it was easy to get work as engineers in the room probably are aware um especially when I was doing literally

everything for this company for like a period of six months and so but they hired me to just basically kind of be there but it kind of occurred to me as I was in the process of helping with their Cloud migration and their and their their systems Administration for AWS it occurred to me I'm not great at this like I am mediocre truly I am I am unexceptional and they they did not hire unexceptional they they hired this rock star from Japan uh but no no I'm basic I'm like super basic really um and I was tired and so as I was tired as I was trying to figure out how to go about this job that I've signed up for

that I you know I liked I loved technology and um what do I do what do I do and so it's like you know you look really pretty tired you want to just manage the content delivery network no one likes that um and that's true no one likes no one likes CDs no one not a one um and so I I liked the what I liked doing was fine-tuning the laugh I'm That Kind of nerd and um and it kind of got me into doing security Cloud Security Administration to a lesser degree very beginning of breaking into this into the security space but the pattern here I think you're going to start to see is that

I I kind of over delivered over here and under delivered over here and they just kind of moved me a little bit right that's kind of the the pattern is starting to form now that now here's where the task fails successfully um around 2016 it occurred to me maybe it's time to move overseas again no particular reason and um I moved to Netherlands I picked up a platform engineer job and at that point it was at that point about six weeks in my boss at the time I talked to him they say I talked to my boss and I said I I I say um you know no one's doing the security stuff in for this team should someone do

that it's like can you do it yeah I can do that I don't mind uh so I got my first security-ish job you know in 2016. not that long ago and um at that point they I look around I say well how exactly do I secure this company there's never been a security person there still isn't I'm kind of not it and it occurs to me I need to do everything again just like in Japan only this time I got to do it from scratch so I got to work I get to this I I go to these meetups after work and I go to conferences like this and learn about security from from zero

um I equate my I acquaint myself with the words and the terms of the people that are would be my peers and I start kind of like just picking services and Technologies off a shelf and I shove them into a box and make a presentation out of it put it to the CSO and the the CTO and um and I just I do everything I do the policy the design the architecture the everything but the implementation because I told you I'm a mediocre engineer right mediocre truly I had help putting in place but I designed it all I designed it all I organized it um I set up the set up instant response I wrote policies procedures the

governance I I chose my bosses off a shelf off the org chart I wrote it all up and I didn't ask permission I just started doing it um and I was also what because I was a mediocre engineer no one expected me to do much more in the job I was hired for I was doing my on-call rotation I was making sure the uptime was good I was okay at my job but I was also building security from zero um and so that's when that's when it truly failed that's when the fail upward truly occurred is right after that because um at certain point I finally a new ciso shows up and he takes a look at what I built and he says

hey I see you've built a lot of stuff it's like yeah yeah I'm really glad you're here because we got a lot of work to do and and he's and he looks and he says you know I've been I've been I've been hearing about the work you've been doing you did all the governance and the risk reg and the risk registration and the the the the the the stuff I do it's like yeah yeah I had yeah the previous ciso wasn't doing that bit um so so he's like hey would you like to just be an infosec officer because I think you're probably really good at that and I need like two guys so I'm like yeah that sounds good I'm

really tired and so yeah so that so I worked for 18 months to build an entire Security State from zero literally the entire thing minus the implementation because a mediocre engineer and uh I didn't even get to run it I didn't even get to touch the fruits of my labor I handed it off to somebody and I then ran risk management um that's the fail upwards I'm talking about in steps here uh just spoilers um the set the last part is actually pretty quick and less interesting which is once you're in management as a previous speaker was talking about once you're there you're kind of there you know so I was so a certain point about a

year into being an infosec officer I'm like you know I'm just I don't like I want a bigger View and I want to be able to talk to the board because that's easier for me to just talk to them directly so but the CSO was good at his job so I'm not going to take his job so I just took a different one different company and then I had to move back to North America for personal reasons and I like well if I'm gonna move I might as well join an executive team and uh so I just asked and here I am so um what he yeah I mean it really is truly like once your management your

management you can step down but you know it's easier to step up at that point it's just crossing that Rubicon into management that is the challenge that people generally have which is what we're talking about if I've yeah she distracted me okay anyway failing upwards how does that actually work here's the details the mechanics of failing upward countersignaling is the is basically when you when you indicate something with a negative you say something a negative to indicate a positive it's not exactly like like a like false praise or false modesty it's more like when I like uh uh who's the actor Tom Hardy is it not Tim it's Tom right I always get those mixed up thank you thank you

appreciate it he's a master at this he basically will you if you see him ever see ever see Tom Hardy talk about his movies he will like talk about like his personal struggles and he's not shy and people love him because he because he's counter signaling he's showing confidence in himself by explaining where he has failed in his life he's not shy about he's not he's not burdened by it that indicates strength and confidence bias for Action is another is another key piece of this puzzle even when people fail they've the fact that they tried in the first place means that they have actually put some effort into it they believe in themselves at least enough to put themselves out there

um learning from failure is one thing but failing again repeatedly it shows determination so Frankly Speaking the more failures you have the more determined you look um I'm going to talk about the 90s a lot if you ever if you ever get to talk to me in person in lots of 90s movies in my life uh one of them is Cool Runnings who's in Cool Runnings from 1994. oh my God fans I'm home anyway um there we go perfect everybody's involved um so what happens is is that they cross the finish line at the end spoilers um but they carry they carry their bobsled on their shoulders they don't they don't get offended they don't get a

Podium finish they don't get a medal but they get Applause they got a movie out of it they they're not good they're actively bad for like 90 minutes and you and you actually cry at the end because they're because they finish because bias for Action means something these are all subtle subtle um like signals that we send each other subconsciously we can't undo this this is where we're all hardwired in most cultures um let's talk about cronyism it's really about Circles of trust cronyism is negative because it involves some exclusivity that's that's why it's negative it's pushing people out not just keeping people in but here's the attack surface of it if you consider cronyism an attack surface

this is what it looks like here's the vulnerability circles equals trust equals bias what we're talking about is a circle of trust and when you are inside that Circle of trust you are naturally biased towards other members of that Circle this is not just cronyism this is families this is friends this is professional everything um the biases are not conscious once you're vaguely in the in the vicinity of the circle you're almost inside it directly just being near it in the orbit of the circle is generally close enough to gain a minimum amount of trust on its own so that's you consider that the the vulnerability the exploit in this context is trust is a measure of time

plus exposure this is networking 101. um literally everything comes back to this circles open with time and exposure so therefore the the the the actual the actual attack method on cronyism is to just be near it long enough that you finally get in but that takes too long I don't like that no one likes that so but countersignaling and bias for Action they kind of they kind of Click into each other and become a key to help you get through that barrier faster which we're going to talk about what's gonna what's gonna kind of um make this process go smoother are the principles of influence I discussed earlier reciprocity uh give some get something and you'll give in return this

is why you get free samples at the grocery store because they want you to buy something you feel if you if you have a soul which I'm assuming most do not all but most um You probably feel at least a little bit bad about taking a sample with with you know no intention of buying the thing right like you kind of do unless you're I mean there are people who don't sometimes me but frequently you feel at least a little bad um likewise if I tell you that like I fell off my Bice like if we're talking one-on-one I tell you I fell off my bicycle as a kid I hurt my shoulder real bad and I can't lift my shoulder too

high now you're gonna feel like oh wow that's why'd you tell me that Wes but then you're gonna feel like you're going to want to tell me something about you in return that's a natural give and take we we do as people as primates honestly reciprocity explaining your failures without any burden of guilt or shame or hesitance will give you a sense of not just not just you know showing that you you're willing to willing to work and you're willing to fail but also you're opening yourself up and that lets them open themselves up too and that creates connections connections which you can use to break into cronyism a little faster social proof is the next piece of this

ideas are stronger in groups or with backing of others um are there any Psychopaths just cross the street all the time without it without milking I mean there we go there's one there's always one in a room this big there's at least one uh but you find person you actually give permission to all of us so as soon as one person does it the rest of us will try it right that's how it is in a meeting room too if you get into a meeting room and no one says no to it you've just been approved so bear that in mind and then likeability again I'm sorry I want to give more topics to more more time to

that but you got to work on that too being being a good communicator um being a good listener and being able to be you don't I mean people talk about being persuasive you don't have to be persuasive you just need to be a be pleasant to talk to you know so in any case let's talk about the emotional energy we're trying to harness here we've got two role models Buzz Lightyear and uh Peter Gibbons again I promise more I promise 90s movies right we're all about that here so Buzz Lightyear I don't know how many how many of you grew up grew up with it but uh there's a scene where where woody challenges Buzz to you know prove that

he can fly and he doesn't fly he falls with style but he makes it look real good um Buzz Lightyear is cold it is confidence bold and incompetent he is very very capable of him in his own mind um and he's reaching for things he clearly should not be reaching for I would not give him a gun or a pilot's license um least of all at the same time uh Peter Gibbons from off in space um I would advise very very carefully that while office space is very very good to illustrate uh failing upwards uh don't take the career advice from this movie because he because he's he because he he commits crimes but before he

commits crimes it's a great example of failing upwards uh he's capable charismatic underperformer he basically just has a mental break at a certain point and start and starts kicking down cubicle walls so um and then and then they want to give him a promotion for it for not working so that's that's the emotional energy we're trying to harness here um but before we dive into the steps on how to fail upwards I just want to give a little inside management heads uh any managers managers in the room right now there's there's a few good good glad to hear it I'm feeling less alone now thank you um I think you're going to recognize this space and that is that from the

management side um I mentioned before there is no reason to promote a good employee there just isn't there is every reason to keep them satisfied and productive in their current Place uh you may get a pay raise you may get Cliff Bars you may get PTO but you're not going to get a job improve a job increase on working hard um personal story that I did not did not share yet is my first paying job was a cashier at a department store and at that job I was like I'm gonna work hard and get promoted so I was the best cashier they had in about three months and I asked for promotion that and they said why would

we promote you you're the best cashier we have so so there is no management and corporate structures are incentivized to not promote you based on the Merit or based on the Merit of your work you've got to you gotta color Outside the Lines if you want to be promoted and how you get how you demonstrate that again management does not know what they're hiring for most of the time they have duties and tasks but they don't know what qual how to describe the qualities of management they look for examples they look for real world situations that they can draw upon to say hey that's an example of management the way you would the way you would

illustrate that is with contrast if you want to truly give the give the understanding that you're ready to move up into management then you need to show the difference from your current role and failing up failing upwards indicates in this context in a kind of drop here and a rise here so the contrast is more obvious does that make sense kinda okay not everyone is asleep good to know okay so that's kind of the background uh we're almost there I promise because I got some prerequisites for you sorry I do compliance now so this matters to fail upwards you're going to have to get yourself in a very specific mindset with like what you're going to try to

accomplish nice to have as experience now what I mean by that is nice to have experience in management before you apply for it not necessary it's nice uh but you should have some background knowledge on the type of work you're wanting to get to so if it's like a you know you should have some understanding of what the job is like in a practical day-to-day sense um but you but you need to have a goal State you can't just do this without having a goal you've got to have a goal um I think the last hour before me was all about that in fact um nice to have as a startup mentality treat yourself like a project treat

yourself like you like not not the job not the not the company not the role treat yourself as the thing you're working to working to on leveling up that'll help uh but you should you should have a willingness to work outside business hours to to get that done um it's going to be really hard to fit that into a business day what I'm about to describe and you need to be good you need to be less good at your current job and risk it we all I mean we all whether we like it or not we're defined by the work we do we all have day jobs which we identify as part of who we are and you

got to be willing to let your ego take a bruise or two in the in service of your greater goals um and then the last the last nice to have is friends and I places if you've got a friend in management that definitely is a very big deal that does help um but you should have acquaintances in management they shouldn't at least know your name you know that's the goals they know your name they know what you do um but you need to have a high place with people in it to start with um now why I say that is because I actually had Consultants you know come and ask me how to how do I get better at

my job with consultancy it's like I don't know your management structure is over there I have no idea how you rise in that space you have to you have to be this one this process only truly serves people who are in-house and working to rise in-house so with that said oh okay um I still got time whatever failing upwards phase one here's how we do it phase one is all about laying is all about laying the groundwork for this for the steps to come this one's a fairly short list of steps in the Practical steps it starts off with begin to power down and what I mean by that is um if you're an overachiever if you work

really hard at your job stop that stop that right here right here is where you stop working hard I recognize so many Workaholics with the nervous laughter right now so many and if you know what if you're already powered down good job you're way ahead of the game keep at it um this is I mean this meet your kpis the employable do all the things you need to do just don't be a superstar anymore stop it right now and next step right there is to immerse yourself in the next steps culture so if it's management you're looking for go to um management meetups meetup.com for example has like these after hours like just groups of people who just hang out

and discuss what concerns them are interested sometimes it's in a hotel bar sometimes it's in a hotel conference room sometimes it I mean stuff like that uh Tech conferences if you're trying to break and break in besides is great for that right so immerse yourself in the culture don't worry about the technical or professional skills just kind of get the lingo get the get the mental space of this um and then while you're in the process of improving yourself also work on your personal Charisma I can recommend for example a YouTube channel called Charisma on command goofy to think about working on how to network with people but I promise you that's actually what we're doing here

mostly is just like we're going to be working people this is a social engineering space um so work on work on joint you know get good with the social engineering club get good with Charisma on command YouTube channel um I have tons of resources in the back of the slide deck so feel free to ask me Annoying questions about them because I want to discuss that that's so super important the goal with phase one though is you're employable but you're not a rising star yet phase two this is the hard yards this is where the work comes in um and this is also the longest point this can take months and this is extremely extremely relative to each

individual um the first step first phase is super easy you know just just be better this step you start making moves it's going to be reliant on your ability to read the room and to read the space if you do this wrong then you run you run certain risks so be very very careful and only step where you're comfortable stepping quietly try to do the next thing without permission um you may not you may remember my personal story about when I built that infrastructure without permission well yeah that's an example um just do so in a way that is non-disruptive if you're breaking into management then do there are management tasks that do not need a manager to do

them for example like maybe you can um help organize the Sprint calendar or maybe you can you know do some other like administrative tasks that the manager hates these are examples um but do the do them without permission but it's really critical right here and this is where this is where the mistakes come from and failing upwards don't make noise about it don't make noise about it don't be loud about it don't be proud about it don't share this with your boss don't be don't socialize that you're doing all this extra work that makes you a good employee that does not make you a rising star that makes you a good employee they go in the extra yard you're going to get

an extra four percent bonus on your on your paycheck this this next year do it quietly here that time will come that time is phase three spoilers make yourself familiar with the next steps peer group and and to the management so make sure if if you don't if you don't already have connections inside the Inner Circle you're trying to penetrate that's where you start making yourself familiar with them that's where they need to be familiar with you and the goal is that they're familiar with you they know your name they know your job they don't know what you had for dinner and they don't and they're not necessarily friends but they at least know who you are because that's going to

come in handy later and then here's where you start doing more and more of the next job after after the step one part you're going to be working towards increasing and increasing and increasing the amount of work you're doing that's not your job and while you're doing that don't burn out don't burn out and let go of the things of some of the things that are less important in your in your paying job that you're doing now so phase two goal is if you're doing this right over time everyone just feels like you're doing a better job over here than over there you know present job is it's okay it's okay but you're doing some doing some

interesting stuff over here that's the goal make a sense so far okay good good so phase three this is where this is where it gets real real this is where it gets awkward so do not begin phase three until everyone is comfortable and confident in your space if you're doing job here and job here and no one's mad then you're ready um and also you need to commit yourself too just be entirely clear so here's here's the point of no return step one invite yourself or Shadow someone into conversations or meetings you are not invited to if this can be as simple as I can give a personal example it's my I only know my

own story right um an example would be like uh you're a technical person and you need to provide technical feedback on a budget discussion you don't belong you're not you're not just you're not a CFO you're not a you're not you're not in a financial comptroller so you're not you're why are you there well you're there as a subject matter expert but why but what if you actually want to break into Finance do both so that's an example what I'm talking about get into these meetings one two go slow go carefully just Shadow someone and just walk in with them and when you do this um if you've done if you've done phase two correctly

No One's Gonna Be noisy about this No One's Gonna No One's Gonna be upset about this and by doing this you're getting the social proof because as soon as you go through one meeting just one without anybody complaining they have approved you whether they mean to or not they have approved you you penetrate the circle now you begin doing less of the current role and more of the next one because you have because at this point you've actually gotten inside that Circle of trust because you put because you've been working quietly over here I told you quietly it was going to be useful right here's where it's useful you've been working quietly over here that everyone just assumes you

should be in the meeting now now you're in these meetings by default now at this point you can start doing you can start missing your kpis you can start missing your indicate your performance indicators and who cares about your annual review now at this point you're doing two jobs they're going to measure you on two jobs no they're not it's not about your job anymore it's about your paycheck that's different here's where you ex but here here's where you create some carefully constructed noise express interest and intent to move upward to that inner circle you've just joined by default so you're in these meetings now you're doing this work now and here's we say you know what I'm just really liking

this team can I join just you know can I can I can I be part of the clubhouse and one or two things is going to happen they're either going to talk amongst themselves or they're going to send you to HR and HR is the bad HR is not success HR is what failure looks like the bad failure not the good failure so that's because if you've done phase two correctly then phase in phase three at this point you should be able to see them think it over should be able to see them work out like how you would fit and what you would do and what and if you've got a clear plan on what role to take

just give them details on what you want and what you would do explain how you would do this if they ask they will ask if they care and if you're in the circle trust that you say you are but here but you gotta wait you gotta wait and let them let them come to a decision and when they come to that decision they're either going to they're either going to give you some informal interview or a straight up job if you've done it really well um but they might also decide no talk to HR at that point start applying elsewhere now I think we've all been in the position maybe not you I think you're a little

too young to apply for jobs yet you might have views to go but most people in this room have had to change jobs uh at a certain point that they will come um and when you do you're always like um why did you change jobs well we all have different reasons here's one I've been working at this I have this job I want to do and I've been doing it for six months and I'm and they don't have a role for me now so now I'm looking elsewhere it's a natural progression into that role whether you whether you have done it on paper or not you now have the skill set and and talent and

frankly drive to go do the job for somewhere else and they should know that they should absolutely know that so either they're going to keep you or not keep you based on that so phase three goal is you you're better at you you're better in this you're better in this work and we'll do it here or elsewhere you're going to do it one way or the other you want you want you can pay me and save a lot of time and effort you know or someone else will pay me and you'll have to replace two jobs now so with that said those are the phases and it goes by kind of fast I wanted to give

this most of my attention um there's going to be questions but I just want to do a quick summary real quick um failing upwards is commonplace might as well work for you literally happens every day we all have bosses that are doing this now um it can ha it happens generally from a combo of normal human behavior which we frankly can't avoid from doing the reason why it happens everywhere is because it's Human Nature um and you can do it yourself if you are familiar with some social engineering tactics and a few specific social cues that will guide you into that process and also disclaimer used it is extremely personal experience if your story is

going to be different from mine but this is just what I've seen work for others and uh yeah don't come in don't come in on Saturday and fall with style I had to be glib at the end I'm sorry I'm sorry guys I I I wanted a better joke it's best I could find short notice um I promised you a lot too many resources um feel free to screen cap this for those on those on the internet um I will share this presentation with literally anybody who who asks um but I just have some articles on the on the on the far left got some media in the center and some books on the right

a few quick call outs um I reck I recommend uh specifically from the YouTube channel Charisma on command literally any and all of that is going to help you network and network and communicate with people better they do they actually was like like like uh like pop icons and like Marvel Superheroes to illustrate how people talk to each other it's really fun um books I'd recommend what everybody is saying and xfbi's next FBI agent's guide to speed reading people body language expert follow this man stalk him on the internet read his books he's incredible uh things like where people's feet are pointing and help you understand when you can talk and when you shouldn't stuff like that

um influence the psychology of persuasion six principles of influence that are used for literally every part of success and uh yeah I'm down there in the bottom right that's me um I'm on LinkedIn sometimes I usually just post memes from Twitter on LinkedIn that's kind of what I do I think I gave myself something stupid like the Tactical CSO um as a title and I know I'm out of time but other questions am I out of time oh I got time

realize that we do have a virtual audience as well so that's true did yes happy too happy too I'm not leaving this Podium until I get one good question okay [Music]

oh that's a really good question that's a really good question the question is how long do you wait in phase two with uh holding that like manager workload without without manager title so in that so that's a that's a really that's what I was talking about with being a really really personal experience with failing upwards because for my story because again my privilege I probably got it too quick um but in my case um it was a period of I think about nearly six or eight months um it can go slow or can go fast it depends on who you know um how comfortable you are with the organization how formal the organization is um it depends on like uh how many

stakeholders are involved in the role that you're seeking for example if it's like got like a finance and and all and regulatory requirements those then suddenly it's a lot more complicated so um it can and all and then I mentioned body language a lot I mentioned reading people and social engineering uh skill sets being able to know when to speak to people and when not to speak to people and to what degree it can push is going to be critical to how how quickly that process goes so it's going to be months expect months but uh how you can't really overdo that stuff um because if you do if you if you're in that step too long it just means that it

just means you need to start looking you just go straight to the next job when because they haven't given you it already so cool that's a good question who's done yes

[Music] I'll be honest with you I'll be honest with you I'm having a really hard time hearing you can you can you stand up mask off and speak louder please

oh that is that is an extremely good question how do you do this remotely so point I actually did this remotely um so my so my story is actually a remote a story that I got through remote now um that's harder that's a lot harder um establishing Rapport over remote over remote sessions is the challenge um a cup a couple quick couple quick tips just to kind of help that process along I can give you a couple of things right now for one is everyone sits like this don't do that sit sideways a little bit because it's actually it's because it's less confronting it's already just your body position while you're on webcam will actually help put the all put the

audience at ease whether that's a stakeholder whether that's just a one-on-one just just work on your body posture to help increase the level of Rapport but um additionally that's why this that's why the um principles of the principles of influence are in the slide deck because you have to get that reciprocity you have to get that give and take because that's how you because the goal is to penetrate that inner circle right so you do that by establishing rapport and you establish a give and take relationship which you do with you know explaining like you know your personal failures how I've done this I've done this it didn't work but man I learned a lot you know and then they're going to

want to feel to do the same and that just takes it just takes longer but you got to work on that you got to work on the on the social on the under on your presence on webcam will help a lot

yeah excellent that's a great question what other questions are there oh back there yes

oh that's a good one okay okay the question is how do get sorry can you repeat one more time for me okay I need I need I need the so how do you get how do you overcome the barrier of I need to know you can do this before you can do this okay so that's where phase two is largely built on is the idea that you're demonstrating these skills that are either direct or related to that that threshold if uh if you're getting that barrier over a period of time if you're in phase two so long like maybe too long and they're and someone's saying I need you I need I need you to I

need to see this before you get this it means you've jumped the gut it means you it means you've asked too soon this is where you this where you keep keep it on the download that you're doing all this stuff you just quietly do that because you let the expectations build around you you let your Legend grow the goal is that you're actually you're telling people that you're not telling people that you want the job you're showing them and once you've done it quite once you've done it and everyone expects you to do this job then when you ask it's organic so that's a good point

[Music] s

that is not only technical skills but people skills leadership skills and you are going to get more challenged being involved in a conference of this size that skills build your network and then you can say oh by the way this last weekend I ran the knock and someone goes you ran a knock I didn't know you could do that or something like that so do not Overlook volunteering opportunities as in your career development very good very good that's exactly what I'm talking about with um getting getting getting immersed in the culture of that job this is exactly how you do it as the volunteer opportunities it's a good point excellent excellent what other questions are there

anything else on mind another one perfect hit me

oh breaking oh like okay so the question is how do you modify this process for changing laterally into a different field okay okay so the process is I gotta admit that I kind of gave that disclaimer earlier that this process doesn't work as well for that but there are there are principles you can use for it um it comes back down to how to penetrate that inner circle uh that's that still applies the same way but even but in that case if it's an entirely New Field and you have zero zero experience in that field then it comes back down to the example like for example for um for volunteer work is a really good example things that kind of

get you into the space where you can talk about it confidently like you're an expert you don't have to like demonstrate that you do the job you can just talk like you know what you're talking about just be really good at faking it um in a matter of speaking through through some extensive personal experience shall we say and once you can do that it can do that long enough then you can start quietly like just join the conversation at a certain point they're just gonna feel weird not to hire you so if I could just add to that you would not be surprised that you will be surprised at how many different Industries are represented at this

conference Health Care Finance retail Hospitality networking within this industry through the conferences you would be surprised that you're working next to the you know for Bank of America or near the CFO of Health Care conglomerate building your network is another way of Crossing one industry to the other true story yeah perfect perfect okay yes another question

I've watched those videos

okay the question if I've got this right is uh I recommended some some resources Charisma command being one of them uh but the but doing the things that they show is hard is that right okay yeah doing is hard I completely agree so that that is that is where you have to be awkward um there is no substitute for that one unfortunately uh you gotta get weird you gotta get weird but if you treat it as getting weird instead of getting wrong then it suddenly becomes a game and if you treat it like a game you're just like you got no stakes in this right like who who's who's he I mean you're risking your ego but what are the real

table Stakes of you going out and talking to someone you know I mean I mean there's there's always that there's always that joke it's like well if if uh if Jeff Goldblum and Will Smith can upload that computer virus to that alien Mothership then you can talk to that bartender you know that that's really what this is about you know I mean it's it the muscles are hard to hard to build but the good news is they don't fade nearly as quickly as others so you start slow my I mean you've heard this advice I know but I'm sorry I'm gonna repeat it you start slow you work carefully through what you're comfortable doing no more than you're

comfortable doing but get a little uncomfortable as you go n plus one the whole way yeah good question there um did I answer that question okay okay that's a that's a that's a fuzzy one I like to make sure I'm clear on that anything else please

watching all of the presentations in their hotel rooms 10 years ago so they first started watching the videos and then they came and folded t-shirt s and then they ran the Reds team and then they moved up to sponsor and then they moved up to someplace else to the point that they're all now at senior executive positions within the organization but then guess what they had the same parallel development within their jobs so getting off work with a bunch of people here who got weird usually helps I mean I'm in it really am yeah but you're coming here and being with your tribe of where your people is totally cool you got to make it weird

you got to make it really weird like that's how this works