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Episode 10: Future-proofing your work and wellbeing strategy with Cassandra Rose, Head of People @ Fringe

Wel­come to Episode 10 of How Peo­ple Work, where Jason and Cas­san­dra Rose, Head of Peo­ple at Fringe, dis­cuss how putting peo­ple at the cen­ter will future-proof your company’s work and well­be­ing strat­e­gy. In today’s busi­ness land­scape, com­pa­nies that pri­or­i­tize their employ­ees are the ones that stand out in tough times.

Cas­san­dra and Jason begin by dis­cussing the impor­tance of mak­ing employ­ee-cen­tric deci­sions, espe­cial­ly dur­ing dif­fi­cult times. They explore ways to pri­or­i­tize employ­ees’ well-being and sat­is­fac­tion, lead­ing to bet­ter busi­ness outcomes.

It’s an age-old say­ing: peo­ple don’t leave bad jobs; they leave bad man­agers. The role of peo­ple lead­ers is cru­cial in cre­at­ing a peo­ple-cen­tric cul­ture. Empow­er­ing and equip­ping them with the tools they need to sup­port their team mem­bers is key to build­ing a suc­cess­ful employ­ee-cen­tered strat­e­gy. Cas­san­dra also shares some best prac­tices for devel­op­ing and train­ing peo­ple lead­ers to fos­ter a cul­ture that val­ues employ­ees’ contributions.

Although there are few peo­ple who spend their whole careers at a sin­gle com­pa­ny any­more, employ­ees can still have sig­nif­i­cant impact at a com­pa­ny in 3 years. Jason and Cas­san­dra explore the impor­tance of not look­ing at one’s tenure at a com­pa­ny, but the employee’s life­time val­ue when look­ing at the impact made in time there.

Your peo­ple are your great­est asset, and invest­ing in them will ulti­mate­ly dri­ve your com­pa­ny’s success.

Now avail­able on Spo­ti­fy | Apple Pod­casts | YouTube

Key ideas and highlights

  • Com­pa­nies that cen­ter around their peo­ple are the ones that dif­fer­en­ti­ate them­selves in bad markets.
  • The best way to have a peo­ple-first peo­ple strat­e­gy is to empow­er and equip their peo­ple leaders.
  • What your employ­ees say about your com­pa­ny after they leave can be so much more pow­er­ful than what they said when they were an employee.
  • Deloitte Work­force Well­be­ing Imperative.

Word of the day

  • We haven’t for­got­ten about the word of the day! We’ll pick back up when Jor­dan returns.


  • 0:00 Intro
  • 4:58 How peo­ple-first com­pa­nies dif­fer­en­ti­ate them­selves in the midst of eco­nom­ic turmoil
  • 6:46 The key to your peo­ple strat­e­gy lies in what you as a com­pa­ny are aim­ing for
  • 8:34 How to meet the needs of a diverse workforce
  • 13:17 Why the best com­pa­nies equip peo­ple leaders
  • 15:30 The evo­lu­tion of work and why we must rethink how we think about work
  • 17:40 Three ways peo­ple lead­ers can empow­er their direct reports
  • 19:46 How to bal­ance flex­i­bil­i­ty and the needs of the business
  • 25:03 The pow­er of a boomerang employee
  • 25:29 Life­time employ­ee value


Jor­dan (00:05):

How many hours and years of our lives do we spend on work for near­ly all of us, we spend 30 plus years and one third of our days in our voca­tion, more time per­haps than we spend at rest or at play. But this isn’t a prob­lem. Why? Because work is good. Work needs to be inte­grat­ed deeply into our lives and must be in line with our most impor­tant goals and val­ues. And if it is, we have a far more com­plete and ful­fill­ing life expe­ri­ence. Wel­come to the How Peo­ple Work Pod­cast, where we explore the inter­sec­tion of how humans think and act and how they apply them­selves to their work. When you under­stand both of these things, you’ll be equipped to be insight­ful, com­pas­sion­ate, and com­pelling leaders.

Jason (00:50):

Wel­come back to the How Peo­ple Work Pod­cast. It’s me, Jason Mur­ray. I am host­ing tonight. Jor­dan is actu­al­ly not here, but I have a very spe­cial guest, Cas­san­dra Rose, who hap­pens to be the Head of Peo­ple here for Fringe, and she’ll prob­a­bly be a reg­u­lar guest from time to time on the pod­cast here. We’re excit­ed to have her. And so Cas­san­dra, say hi to every­one here.

Cas­san­dra (01:13):

Well, hel­lo. I’m so hon­ored and real­ly excit­ed to be jump­ing on the pod­cast. I love pod­cast­ing because it allows me to mul­ti­task and learn at the same time. So thank you for allow­ing me to be part of this journey.

Jason (01:24):

Absolute­ly. So for every­one lis­ten­ing, Cas­san­dra’s far more expe­ri­enced in the area of how peo­ple work than Jor­dan or myself. So we are very glad to have her on the pod­cast today. And so I think it’d be great for peo­ple to just hear a lit­tle bit about your sto­ry. So if you don’t mind, maybe just share a lit­tle how you got into peo­ple work, maybe how you end­ed up here at Fringe.

Cas­san­dra (01:47):

Yeah, I’ll start at the very begin­ning. So I was born on a Tues­day after­noon. No, I’ll go a lit­tle fur­ther than that. But yeah, my name is Cas­san­dra Rose. I’ve been in the HR space for near­ly two decades, which I can’t believe, I don’t think any­one goes to kinder­garten and says, I want to be a human resource pro­fes­sion­al when I grow up. But that’s shift­ing a lit­tle bit, which is excit­ing because I think for a long time HR was this thing to just kind of be han­dled. It was all the awk­ward pieces of the busi­ness that just did­n’t fit some­where else. So they gave it to human resources. And now that peo­ple have tru­ly under­stand that to have a thriv­ing busi­ness, you real­ly have to have peo­ple who thrive and come togeth­er as a col­lec­tive. And that HR can be a North star to that.


I think that real­ly changes the con­ver­sa­tion. So it is great to have been part of this 20 year arc of how the HR space is evolv­ing as well. Though I fell into HR, one of the things that I made sure I did was go back and get a mas­ter’s degree in human resources because I think it’s impor­tant to under­stand how the aca­d­e­m­ic and the the­o­ret­i­cal por­tion of it can also apply to the real life expe­ri­ences. What you learn in a class­room does­n’t always trans­late into real life. And some­times real life sit­u­a­tions require frame­works to real­ly push things for­ward. So I’m hap­py to have both of those things. I’ve also been cer­ti­fied, I’m say­ing all these things just to show­case that I real­ly tru­ly believe in this dis­ci­pline, and I real­ly believe in the fact that if you have enough peo­ple who come togeth­er and say, if I care about my peo­ple and I pay peo­ple to care about my peo­ple and focus on them, that actu­al­ly frees up oth­er lead­ers with­in the orga­ni­za­tion to focus on what they do best. And that’s how we all rise to the top.

Jason (03:31):

Do you remem­ber when we first met?

Cas­san­dra (03:34):

Per­haps, it may have been over a call, a demo? Is that right?

Jason (03:39):

Yes. It was, yeah. The fun­ny thing is, I don’t know if I’ve ever told you this, but when I first met you, it was on a dis­cov­ery call where some­how we had got­ten con­nect­ed. You were at Sprin­klr at the time. That’s right. There was some at least mod­est inter­est in Fringe. And I got on the call and I recall think­ing to myself when we were hav­ing that con­ver­sa­tion, if we ever get a chance to hire this woman, we should hire her. And lo and behold, here we are. You’re our Head of Peo­ple here at Fringe. So serendipitous.

Cas­san­dra (04:12):

Amaz­ing. If you can also hope for me that I win the lot­to next week, because appar­ent­ly your pos­i­tive think­ing works.

Jason (04:20):

I hope I could do that for you. But then you’d prob­a­bly leave us, so…

Cas­san­dra (04:24):

No, it depends on the lot­tery winnings.

Jason (04:28):

So some­thing you said, and I’m actu­al­ly inter­est­ed in your thoughts on this ques­tion, you know you men­tioned that because you’ve been in peo­ple work for two decades, you’ve seen some of the changes, some of the trends going on. And so for you, what are some of the biggest things that have been chang­ing in your line of work over the last 20 years and maybe in the last cou­ple years espe­cial­ly? It feels like some of those things are real­ly chang­ing for the good, I think, but would love to hear what you’re see­ing in peo­ple work and how that’s changing.

Cas­san­dra (04:58):

I think there’s a lot of cycli­cal trends that are appear­ing, and I think we just rebrand them. I got into the HR space and pri­mar­i­ly into the finan­cial indus­try, right around the time that we had a finan­cial cri­sis in this coun­try. And so it went from the hey­day of bank­ing being the big thing that every­one want­ed to go work in, and a pull­back of that because peo­ple saw some­thing that they saw as a liveli­hood that they could have for 40 years, retire rich­ly — just be so neg­a­tive­ly impact­ed. And we’re see­ing that now in the tech space where tech was the hot thing. Every­one was telling every­one, go to col­lege, get a tech job, you’re going to be safe. It’s all on the rise. And now we’re see­ing this dis­pro­por­tion­ate amount of lay­offs that are hap­pen­ing and qui­et quit­ting, and just see­ing com­pa­nies that were what uni­corns and deca­corns fall from grace.


And so I don’t think nec­es­sar­i­ly that there’s just bad lead­ers who just move from one space to anoth­er. What I think hap­pens is that we move away from the pri­ma­ry respon­si­bil­i­ty of what we’re sup­posed to be doing at work. And what that tru­ly means is that there’s some focus that’s lacked or some­times bad actors, let’s be hon­est. But I think this gives us anoth­er oppor­tu­ni­ty to look behind the cur­tain and say, what about the com­pa­nies that aren’t lay­ing off? Or what about the com­pa­nies that are doing it in as much as pos­si­ble a very eth­i­cal way? What are they doing that’s so dif­fer­ent that they have boomerang employ­ees? They have peo­ple who come back. And I think that’s when you’re putting peo­ple at the cen­ter of your deci­sion mak­ing, whether you have a bad econ­o­my or a good econ­o­my, you can still move for­ward and con­tin­ue to grow because you’ve actu­al­ly cen­tered humanity.

Jason (06:46):

Right? Yeah. Well, and that’s kind of in line with some­thing, Jor­dan and I have been talk­ing about a bunch in the episodes that we’ve had pre­vi­ous to this, which is this idea of human flour­ish­ing. And so what are we as com­pa­nies aim­ing for? Is it just bot­tom line prof­its? Is it what­ev­er our com­pa­ny’s about? Or do we have some kind of sense of greater pur­pose here? Is it some­thing that we can do good in the world for indi­vid­u­als, for com­mu­ni­ties, for soci­ety as a whole? And I like to believe that that’s pos­si­ble here and hope­ful­ly we’re doing our lit­tle part of that. It’s what we’re doing here at Fringe.

Cas­san­dra (07:23):

I def­i­nite­ly know that’s what we’re doing here at Fringe. At least that’s what you’re pay­ing me for. So look­ing at an arti­cle, a study that came out from Deloitte that you shared with me, actu­al­ly, the World Health Orga­ni­za­tion actu­al­ly looks at work as a very vital part of well­be­ing as a hu — just as human­i­ty. And when we think about it, one of the main ques­tions that we ask chil­dren are What do you want to be when you grow up?

Jason (07:48):

What did you want to be when you grew up?

Cas­san­dra (07:49):

I actu­al­ly want­ed to be an astro­naut. I thought it would be so cool to be able to go out­side of the earth and look down and do some­thing that if you think about it, even the smartest, rich­est peo­ple a hun­dred years ago, a thou­sand years ago, could nev­er even dream.

Jason (08:03):

Now you can pay to do it.

Cas­san­dra (08:04):

Now, you can pay to do it for about 11 min­utes, but you’re not total­ly going to out­er space. But that’s a dif­fer­ent top­ic for anoth­er day. Just blend­ing sci­ence, math, art, and what does it mean to be alive to me is some­thing inter­est­ing. And hon­est­ly, I feel like I do that every day. Being in HR and being not just in the peo­ple space, but work­ing at a com­pa­ny that talks about how to help peo­ple flour­ish because there is art to it and there’s sci­ence behind it. Being in the well­be­ing space does­n’t mean that you’re doing soft things or things that aren’t mean­ing­ful. You’re tak­ing dol­lars to make sure that you’re invest­ing in peo­ple in a way that shows up for them out­side of the four walls or the Zoom walls that they’re work­ing in. How do I make sure that par­ents in the work­place or peo­ple over 50 in the work­place or peo­ple who are just start­ing their career in the work­place, feel seen and heard and know where to go to find resources that they need to meet the needs of their lives in the sea­sons that they’re in.


There’s a lot of work that goes behind that. And for a long time, I think peo­ple were just throw­ing mon­ey at it and just putting perks in like hav­ing a ping pong table, but then they real­ized, hey, peo­ple actu­al­ly flour­ished when they were able to come togeth­er, right? And human­i­ty is about com­mu­ni­ty. Peo­ple flour­ish when they can have health insur­ance and know that their needs are cared for. So there’s so much more to it. And the fact that Fringe does this in a way that is, to me, rev­o­lu­tion­ary, makes me proud to work here two-fold.

Jason (09:39):

That’s excit­ing. Well, we hope to do that and we hope to inspire oth­ers. And I think that for Jor­dan and myself is a big part of what’s excit­ing to us about this endeav­or to begin with. Because when I look at my own jour­ney, there’s real­ly no busi­ness I have doing what I’m doing right now. I was a reli­gious stud­ies major in col­lege. I have no tech back­ground what­so­ev­er. I mean, there’s just a bunch of time in non­prof­it. And so in some ways, I look at what we’re doing here with Fringe and feel like, well, I real­ly have no busi­ness what­so­ev­er doing that. And Jor­dan has a very sim­i­lar sto­ry to myself, odd­ly enough. And I think we feel excit­ed and priv­i­leged and hum­bled in a lot of ways to be in a posi­tion where hope­ful­ly we can do this well for whomev­er we get to impact that as part of Fringe direct­ly in what we do and gets to be an employ­ee here.


But also for the com­pa­nies that we inter­act with. We hope even through this pod­cast, to inspire oth­ers to maybe think dif­fer­ent­ly about what they’re doing out there in the world. And I think some­thing you said, it real­ly res­onates with me because this whole notion of work-life bal­ance and the way peo­ple think about well­be­ing even I real­ly think needs to be dis­pelled to some degree. And even the fact that we talk about, and I know I’ve done this too, talk about some of these maybe more qual­i­ta­tive aspects of the work expe­ri­ences, soft mea­sures or soft met­rics. And just even as I’ve learned more being in this space and doing what we’re doing here at Fringe, I’ve come to see and actu­al­ly learn from the research I’ve delved into around human psy­chol­o­gy even that these things that we tend to say are soft in the busi­ness area real­ly aren’t psy­chol­o­gists that look at things around human psy­chol­o­gy and even self- report­ed mea­sures of hap­pi­ness and so forth. They’re actu­al­ly very high­ly sci­en­tif­ic and quan­ti­ta­tive. And so I think that’s rel­e­vant as we talk about this Deloitte study, for exam­ple, around well­be­ing, that it’s not just an entire­ly sub­jec­tive point of view, but I do think it’s help­ful to prob­a­bly think about, well, how should we be think­ing about well­be­ing? What’s a good frame­work for it? And I think this research starts to lay some of that out for us.

Cas­san­dra (12:15):

And I would even go as far as to say that it’s very easy to point to lead­er­ship, top line lead­er­ship and say, these peo­ple should be mod­el­ing what well­be­ing looks like, or to go to HR and say, hr, you’re respon­si­ble for cre­at­ing that for us. But it’s real­ly the peo­ple man­agers, the every­day line man­agers who are either push­ing for­ward some­thing that sup­ports every­one or with­draw­ing from their peo­ple and not real­ly shar­ing that infor­ma­tion. So one of the things that I’ve made sure to do at any orga­ni­za­tion I work for is to go, how can I empow­er peo­ple who lead oth­er peo­ple? And I think that’s where the rub­ber meets the road, because at the end of the day, you’re not call­ing up your CEO to say, Hey, I don’t feel like I have work-life bal­ance. I need you to make this bet­ter. It’s you call­ing your man­ag­er to say, Hey, I’m run­ning late.


I had to take my kid to soc­cer prac­tice, or I have this doc­tor’s appoint­ment. They don’t do week­ends. It’s that inter­play where we have to go, how can I equip some­one who’s a peo­ple leader to feel resourced, to feel like they are empow­ered, to be able to tell their peo­ple, I can, I got your back. I can sup­port you. I can give you that flex­i­ble sched­ule, or I can tell you about a pro­gram that we’re rolling out, or I can reward you and rec­og­nize you. Most peo­ple leave. I know this is some­thing that’s been said a mil­lion times. Bad man­agers, even if you have a great orga­ni­za­tion, if you have a bad man­ag­er, you’re going to have a bad expe­ri­ence. But if you can cre­ate bet­ter peo­ple lead­ers, you’re going to see that in your bot­tom line.

Jason (13:53):

So I think it would be real­ly inter­est­ing to dig into that a lit­tle bit, because some­times I feel like maybe I’m just igno­rant. Some of those things seem like com­mon sense to me, and this is me speak­ing as some­one com­ing from out­side of the HR space, even com­ing from out­side of the tech space. I haven’t run a com­pa­ny or been part of the lead­er­ship com­pa­ny pri­or to Fringe. And so there’s some things that we do that to me seem like, well, that’s obvi­ous. I have chil­dren. Some­times you’re late. Stuff hap­pens. And you know, can’t just pre­dict that all the time. And so I’m inter­est­ed your take on why is it that there’s this gap some­times where maybe the expec­ta­tion is like, Hey, just show up and do your job. We give you a pay­check. Why do you want any more than that? I mean, I cringe when I hear peo­ple say that kind of stuff, but more com­mon­place than I might expect. You’re prob­a­bly a lit­tle less sur­prised by that giv­en some of your expe­ri­ence. But what is the dis­con­nect there? Why down at the man­ag­er lev­el where some of these things hap­pen and peo­ple lis­ten­ing to this pod­cast, many of them lead peo­ple, what is going on at that lev­el that’s cre­at­ing maybe some of that dis­so­nance that peo­ple don’t maybe under­stand or empathize with just the human experience?

Cas­san­dra (15:19):

I think I’ll approach it from two dif­fer­ent places. One, the Indus­tri­al Rev­o­lu­tion. You haven’t prob­a­bly heard that word since 11th grade.

Jason (15:27):

We’ve actu­al­ly talked about it actu­al­ly on the podcast.

Cas­san­dra (15:30):

That’s right. So when we think about where human­i­ty was pri­or, you either were a farmer, you were just doing things to sur­vive with­in a com­mu­ni­ty or with­in an aspect. The Indus­tri­al Rev­o­lu­tion brought for­ward an abil­i­ty for peo­ple to make mon­ey and take that mon­ey and go do what­ev­er they want­ed to do with it with­out nec­es­sar­i­ly being con­nect­ed to a com­mu­ni­ty. And those who rose to the top, the Hen­ry Fords of their day made it so that way work was just that. It was this thing that you came to do. It was­n’t meant to be fun. It was hard. It was dif­fi­cult. So when you cre­ate an assem­bly line and teach dif­fer­ent aspects of peo­ple to just do one func­tion, what you actu­al­ly take away from them is inno­va­tion, is cre­ativ­i­ty, is the abil­i­ty to actu­al­ly grow. And I think even though we’re a hun­dred years plus for­ward in time, what’s actu­al­ly hap­pen­ing is that men­tal­i­ty still exists, that you’re replace­able. And peo­ple feel that in their job descrip­tions. They feel that in the lack of growth. When I talk to my man­ag­er, I’m like, what’s next for me? And you give me a blank stare. It makes me feel like you haven’t thought past that. For me, if we’re ask­ing peo­ple to stay with us for four or five years, but we only have plans that exist for six to 12 months, there is the dis­con­nect right there. And that’s not nec­es­sar­i­ly a peo­ple prob­lem, that’s a struc­tur­al prob­lem. We need to rethink how we think about work.

Jason (16:56):

How do we start to do that? Because I, I’ll admit for myself, when I was lead­ing a team here at Fringe that had quite a num­ber of peo­ple a part of it, I’m not sure I always did as good of a job as maybe I could have around some of those things. And I’m just won­der­ing for peo­ple who are lis­ten­ing that might be think­ing like, Hey, how do I do that bet­ter? How do I help peo­ple that I lead or influ­ence maybe feel like they have a path for­ward or not just treat it as kind of a cog in the wheel, so to speak? How could peo­ple be think­ing about that maybe more proactively?

Cas­san­dra (17:40):

Yeah well, three things I would always rec­om­mend. One, the sim­plest and least expen­sive way to do it is just ask them what they want. We may assume, Hey, hey, go do this learn­ing devel­op­ment thing. Go get this cer­ti­fi­ca­tion. Oh, have you explored this pro­gram? But some peo­ple like the job that they want and maybe they just want to be able to do that for two to three years, keep it sta­ble for them­selves. Or maybe you have some­one who’s like, I real­ly like what I’m doing, but I’d love to be able to learn a lit­tle bit more about this. Give them a stretch project. Or maybe they’d want to do some­thing com­plete­ly out­side of the realm of the work that you’re doing, but they want to have the per­mis­sion to be able to do the side hus­tle. And if your com­pa­ny allows for those things, encour­age them to do that.


We dis­con­nect these things and say that you must be one per­son at work and then every­thing else, you can be out­side of my para­me­ters. A man­ag­er, a real­ly good peo­ple leader will say, how can I incor­po­rate the desires of what you want to become and help you achieve those things? And that makes you a bet­ter employ­ee just psy­cho­log­i­cal­ly. So that would be step one. Step two would be to explore the pro­grams avail­able. I think we lim­it our­selves by think­ing that we always have to be the solu­tion to some­one’s prob­lem. And that’s what sys­tems are cre­at­ed for. So if there are oth­er resources with­in the orga­ni­za­tion, refer, advo­cate, spon­sor some­one and say, Hey, I see this per­son as an emerg­ing leader, or I want them to be able to stay here at this com­pa­ny. What can we do for them to devel­op them in their career in some­thing else and make sure that they’re get­ting con­nect­ed to that resource. And then the last thing I would say is take a chance on peo­ple. If there is an inter­nal mobil­i­ty oppor­tu­ni­ty, and maybe they don’t have the skillset, but they have the dri­ve, go to bat for them and say, I think you should go try some­thing else. Worst case sce­nario does­n’t work. We can bring you back on the team and make sure that’s a true state­ment, but real­ly take the time to see how I can devel­op some­one with­in an orga­ni­za­tion before exit­ing is a part of that strategy.

Jason (19:46):

Well, and I think what’s inter­est­ing about that, and I gen­uine­ly don’t know that I know the answer to this, but it feels like one of the ten­sions that can arise when you’re in a posi­tion of lead­er­ship is, well, if we start giv­ing peo­ple oppor­tu­ni­ties over here, what does that mean for the needs of the busi­ness, whether per­ceived or real? We’ve hired peo­ple to do cer­tain roles or ful­fill cer­tain respon­si­bil­i­ties. And so if we start maybe cre­at­ing some of that flex­i­bil­i­ty, how do we man­age the ten­sion then that comes with, Hey, we’re try­ing to give peo­ple oppor­tu­ni­ties to grow, try new things with — the busi­ness has cer­tain things that need to take place or cer­tain roles that need to be exe­cut­ed in a cer­tain way. I think that’s a challenge.

Cas­san­dra (20:34):

Oh, absolute­ly. And I think there should be gov­er­nance to it. It should­n’t just be ad hoc or — No one has a cer­tain strat­e­gy to it, but what I would say is that any com­pa­ny that’s grow­ing always has an oppor­tu­ni­ty for some­body. You’re either giv­ing it to the peo­ple who are cur­rent­ly with­in the orga­ni­za­tion or you’re giv­ing it to peo­ple who are new to the orga­ni­za­tion, but noth­ing that’s liv­ing, which an orga­ni­za­tion is, does­n’t come with new chal­lenges pre­sent­ed, whether it’s the econ­o­my, whether it’s a polit­i­cal cycle going on, whether it’s just your own orga­ni­za­tion going through its matu­ri­ty phas­es, you’re always going to find oppor­tu­ni­ties. So I can’t imag­ine there’s ever a time that you’re so stag­nant that that’s not a possibility.

Jason (21:16):

Yeah, no, I think that’s true. And I think it’s prob­a­bly then incum­bent upon man­agers of peo­ple then to be hav­ing these con­ver­sa­tions proac­tive­ly. And it’s prob­a­bly help­ful to have frame­works for under­stand­ing like, Hey, how do I have con­ver­sa­tions with my peo­ple that can help guide them towards places that give them life, help them feel more con­nect­ed to the work that they’re doing. So one of the things to me, I don’t know that I always did this well, but I would always ask peo­ple, what are you most excit­ed about? So to the degree that you can do work that you’re good at and that you feel excit­ed by and have most of your day filled with those kinds of things, then your work expe­ri­ence is going to be more pos­i­tive. And so try­ing to ori­ent maybe projects that employ­ees are part of towards that kind of work, seem­ing­ly is more crit­i­cal. But I think what’s inter­est­ing then is man­agers then need to feel that they have that autonomy,

Cas­san­dra (22:20):


Jason (22:20):

And lat­i­tude to be able to maybe give peo­ple work that’s a lit­tle bit out­side of a real­ly for­mu­la­ic kind of job descrip­tion. Because I think what you’re describ­ing is a vision of work that helps peo­ple feel more con­nect­ed, helps peo­ple grow, feel more alive in what they’re doing, but also requires a lev­el of, Hey, we don’t, maybe the out­come every sin­gle time isn’t going to be exact­ly what we expect­ed. Or maybe some­times this project that we assign some­body to, it’s just going to kind of bomb out, but we should­n’t have that indi­vid­ual feel­ing that their job is jeop­ar­dized because that par­tic­u­lar project maybe did­n’t go well because we’re will­ing to exper­i­ment, we’re will­ing to let peo­ple fail. And I think that’s prob­a­bly an impor­tant part of the expe­ri­ences, let­ting peo­ple know that hey, fail­ure is part of growth, not just for the indi­vid­ual, but also for the orga­ni­za­tion to learn in giv­ing peo­ple these oppor­tu­ni­ties to grow. It’s not always going to go exact­ly the way that we think.

Cas­san­dra (23:23):

Oh, I think that’s a beau­ti­ful segue into that sec­ond part. So we’re think­ing about one, just the struc­ture of work and rethink­ing it, the sec­ond com­mu­ni­ca­tion. Because I think exact­ly to your point around A) man­agers hav­ing the author­i­ty, do we empow­er our peo­ple lead­ers to actu­al­ly lead, or do we just give them a bunch of ran­dom infor­ma­tion and say, best of luck if your team is suc­cess­ful, that was us and you. But if your team fail, it was com­plete­ly you. And leav­ing them up to try in that way.

Jason (23:55):

Unfair respon­si­bil­i­ty.

Cas­san­dra (23:57):

A hun­dred per­cent. And so when I think about what you say­ing, giv­ing peo­ple appro­pri­ate space to fail, a lot of times peo­ple just are ter­ri­fied to fail because some of it is school­ing. If you just got an F, there was real­ly no com­ing back from that. But some of it has also been, again, this idea of if you sep­a­rate work. So that way I only work on one thing. If I do feel like that one thing, there is no space for me to go and try some­thing else. And one of the ways that I live my per­son­al life is to focus more on what I’m good at and just man­age the things I’m bad at. And some­times we try to get peo­ple to be bet­ter at the bad things and -

Jason (24:35):

Improve your weaknesses

Cas­san­dra (24:36):

And improve your weak­ness­es. But what you should do is be sharp­en­ing your strengths.

Jason (24:40):

So be real­ly good at what you’re good at.

Cas­san­dra (24:41):

You should be great at what you’re good at, and let’s fix the oth­er things. Let’s tweak it. So that is real­ly where you get peo­ple to under­stand their assets. And some­times I think orga­ni­za­tions may be wor­ried that what if we get some­one so good that they leave us? And one of the things that we have to real­ize is there is no 40 year career anymore.

Jason (25:02):

Not any­more.

Cas­san­dra (25:03):

Peo­ple are going to leave us, but if they leave you and they cham­pi­on you after, they can actu­al­ly some­times do even more for you than when they were a cur­rent employ­ee. And that’s why you’re see­ing boomerang employ­ees con­tin­ue to grow as a huge pop­u­la­tion of peo­ple who come back to an employ­er because they need to go out, get the expe­ri­ence that they need to get, but they want to bring it back because you’ve cre­at­ed such a place that makes them desire to come back and do great work.

Jason (25:29):

So that brings up an idea that I’m kind of inter­est­ed in. I’m curi­ous what you think of it. And then I don’t have ful­ly formed opin­ions on it yet nec­es­sar­i­ly, but we’re a soft­ware com­pa­ny here at Fringe. And so as a soft­ware as a service,SaaS com­pa­ny, as peo­ple call it, there’s cer­tain met­rics that you think about. And so life­time cus­tomer val­ue is one of them. And I came across a post, I think it was on Medi­um recent­ly, where they talked about life­time employ­ee val­ue. And so obvi­ous­ly when you first hire an employ­ee, there’s a cost, you got to bring them on cost of hir­ing, et cetera, et cetera. And so real­ly it’s a sunk cost until a cer­tain lev­el where an employ­ee reach­es pro­duc­tiv­i­ty. And so I think the ten­sion that I’ll acknowl­edge is always, well, peo­ple aren’t num­bers, peo­ple aren’t just mon­ey. And I ful­ly agree with that point of view, but there’s some­thing I think to what you just said, which is, well, peo­ple aren’t going to be here 40 years, but in order for it to work eco­nom­i­cal­ly for busi­ness­es is like, well, you need peo­ple to be at an orga­ni­za­tion long enough that they reach a lev­el of pro­duc­tiv­i­ty or life­time employ­ee val­ue that is at least greater than what it costs to bring them on.


And so I’m curi­ous what you think about that as a par­a­digm, maybe how we think about the time that employ­ees spend at an organization.

Cas­san­dra (26:48):

Yeah. First of all, I want to bring that here. Because I love that con­cept because it’s not just about the dol­lars and cents, but it’s also help­ing peo­ple to under­stand their own val­ue of what they bring to the work­place. When you come in, can you bring in the val­ue of what your salary is rep­re­sent­ing? Not because I’m just try­ing to get you to a hard and fast num­ber, but it helps you to bet­ter nego­ti­ate for your­self to under­stand your true val­ue from an eco­nom­ic stand­point of finan­cial sta­bil­i­ty. And that’s what we’re all seek­ing. Work should be fun, but work also gives us the abil­i­ty to seek out things that maybe for myself grow­ing up in an envi­ron­ment where both of my par­ents were blue col­lar work­ers, I did­n’t need for any­thing, but we did­n’t nec­es­sar­i­ly have a lot of excess. And so for me, their wish was that I would go to col­lege and be able to have more options in career, have more options in finan­cial sta­bil­i­ty that they were seek­ing by com­ing to this country.


So I think we need to get very com­fort­able with hav­ing employ­ees talk about mon­ey, what it means to them, and how that shows up in their well­be­ing and in their hap­pi­ness as well. So when peo­ple under­stand their val­ue, they under­stand, wait. As an orga­ni­za­tion, not only can I bring val­ue, but how can I help oth­ers bring val­ue? How can I be a leader among lead­ers? Or if I’m an indi­vid­ual con­trib­u­tor, how can I still have influ­ence? Now we’re all think­ing in a busi­ness mind­set, now we all bet­ter under­stand how we influ­ence that bot­tom line. And some­times I think that dis­con­nect is that ten­sion that has been uncom­fort­able for so many decades.

Jason (28:27):

Well, and I may be guilty of being ide­al­is­tic around these things, but I like to believe that there can be kind of a win-win-win sce­nario where what’s good for the indi­vid­ual is also good for the orga­ni­za­tion. And so I think that’s what I like about this notion of a life­time employ­ee val­ue. It rec­og­nizes the fact that, well, some­body prob­a­bly won’t be here for­ev­er. That’s just not the way the world works any­more, that peo­ple’s growth oppor­tu­ni­ties. And I see that even here at Fringe, it’s like the needs that we have at Fringe, there’s prob­a­bly a ceil­ing for some indi­vid­u­als in terms of what they’re capa­ble of or what they want to do. And so if they move on from here, it’s prob­a­bly very rea­son­able and prac­ti­cal for their own career advance­ment that they may need to take anoth­er step beyond what Fringe is able to pro­vide them right now in terms of career oppor­tu­ni­ty. But at the same time, think­ing about it in such a way that you know what the indi­vid­u­al’s con­tribut­ing, what the busi­ness needs, like those things aren’t total­ly at odds with one anoth­er. And I think that’s a more pos­i­tive vision, I hope, where the needs of the busi­ness, the needs of the indi­vid­ual can be matched up in such a way that every­one’s kind of win­ning in that scenario.

Cas­san­dra (29:43):

I’ll even boil­er­plate it. I saw a meme once where some­one asks in an inter­view, why are you inter­view­ing for this job? And the per­son answered, well, aren’t you hir­ing? The employ­ee employ­er rela­tion­ship has always been sym­bi­ot­ic. It’s always been some­thing that you need ful­filled and I can ful­fill that need. And if you just make it trans­ac­tion­al, that’s when it feels like I can just leave. I can just walk away. But if I can add val­ue to your life, not just finan­cial­ly, but who you are as a per­son, and you can add that val­ue through your cre­ativ­i­ty, through your inno­va­tion, and some­times just through your dili­gence in get­ting your job done and doing a good job, how could that not be a win-win situation?

Jason (30:28):

I mean, what you said there is some­thing we talk about a lot here at Fringe and I think is real­ly prob­a­bly at the crux of the mat­ter, which is work sim­ply a trans­ac­tion or is there some­thing poten­tial­ly more mean­ing­ful? And I think some­thing we’ve been try­ing to put forth in the con­ver­sa­tions that we’ve been hav­ing on this pod­cast is that work is a more sig­nif­i­cant part of our lives, even just as human beings, than a sim­ple trans­ac­tion of time for mon­ey. And I can appre­ci­ate how peo­ple maybe have got­ten there. And I have a cyn­ic in me that can under­stand that, hey, insti­tu­tions as they grow don’t always have the best inter­ests of indi­vid­ual human beings in mind, but in a world that we’re try­ing to aim for human flour­ish­ing, which again is some­thing that we talk about a lot here, I like to think that there’s an oppor­tu­ni­ty where the rela­tion­ship between an employ­er and employ­ee isn’t sim­ply transactional.

Cas­san­dra (31:37):

I think that hap­pens day in and day out. I think the good com­pa­nies that do it do it so well that their peo­ple just nev­er leave. So maybe they’re not telling oth­er interviewers.

Jason (31:48):

Are you say­ing there are 40 year careers?

Cas­san­dra (31:50):

I’ve done anniver­sary par­ties, I’ve seen peo­ple work some­place for 50 years. But I think you could also have an amaz­ing career arc in three. And I’m very thank­ful to the Mil­len­ni­al gen­er­a­tion, which I may or may not be part of, and even Gen Z who are solid­i­fy­ing that that could be an exam­ple of a great career. And if you are hav­ing these three year arcs, but the com­pa­ny real­ly is being pro­pelled for­ward by the inno­va­tion and cre­ativ­i­ty of hav­ing new peo­ple come in with fresh ideas all the time. And we lever­age that instead of think­ing of it as a dis­ad­van­tage. Think about where we’ll be as a soci­ety, as a whole human race in 50 years.

Jason (32:32):

Yeah, absolute­ly. Well, we real­ly did­n’t get to a whole lot of that Deloitte study that I know we want to talk about. Yep. But this is a real­ly good stop­ping place for the con­ver­sa­tion today. And so thank you, Cas­san­dra, for join­ing us. Cas­san­dra’s actu­al­ly going to be join­ing us again for the next episode. And so every­one stay tuned and we will actu­al­ly dig in a lit­tle bit more into that study because I think there’s some real­ly inter­est­ing data and some top­ics that stem from the con­ver­sa­tion that we had today. And so thank you every­one for join­ing us on How Peo­ple Work.

Cas­san­dra (33:05):

Thanks for hav­ing me on.

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