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Episode 14: What it actually means to be a good leader

In this episode of How Peo­ple Work, Jason and Jor­dan explore the role of lead­er­ship in employ­ee well­be­ing and delve into the qual­i­ties and strate­gies that define excep­tion­al man­agers. They cov­er a range of top­ics, includ­ing the impact of man­agers on employ­ee reten­tion, the essen­tial traits of suc­cess­ful lead­ers, the per­ils of micro­man­age­ment and under­man­age­ment, and the chal­lenges faced dur­ing the tran­si­tion to a man­age­r­i­al role.

Jor­dan and Jason share per­son­al sto­ries of their expe­ri­ences in lead­er­ship and man­ag­ing a start­up. They dis­cuss the sig­nif­i­cance of trust, the impor­tance of both EQ and IQ in lead­er­ship, and the best prac­tices for devel­op­ing oth­er leaders.

Now avail­able on: YouTube | Apple Pod­casts | Spo­ti­fy

Key ideas and highlights

  • Lead­er­ship and orga­ni­za­tion­al struc­ture are key deter­mi­nants of employ­ee wellbeing.
  • One can be a com­pas­sion­ate but incom­pe­tent leader.
  • The tran­si­tion from indi­vid­ual con­trib­u­tor to peo­ple leader is a dif­fi­cult one. How to set your­self up for success.

Word of the day

  • Equiv­o­cal — Jason wins this week!


  • 0:00 Intro
  • 1:35 Deloitte Study Recap
  • 5:25 What it means if peo­ple leave a com­pa­ny because of a manage
  • 7:54 What the role of a man­ag­er needs to be
  • 10:52 Well­be­ing is a shared responsibility
  • 11:33 Which is worse: micro­man­age­ment or undermanagement?
  • 13:03 The bina­ry of lead­er­ship styles
  • 16:55 Why the tran­si­tion from an indi­vid­ual con­trib­u­tor to a peo­ple man­ag­er is so hard
  • 18:17 How trust­ing your peo­ple is one of the most impor­tant things you can do as a leader
  • 20:07 Which mat­ters more in being a leader: EQ or IQ?
  • 22:59 Here’s what the best lead­ers do to devel­op oth­er leaders
  • 25:57 Here’s what we actu­al­ly love receiv­ing from people


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.


Wel­come back to How Peo­ple Work. This is your host, Jor­dan Peace and your oth­er host, Jason Mur­ray. Hey Jason. Say hel­lo. Hel­lo. We have been fever­ish­ly talk­ing about the top­ic of well­be­ing. We got into the Deloitte Work­force Well­be­ing Study Imper­a­tive. They call it imper­a­tive in the last episode. Very self impor­tant. It is very self impor­tant. We got into that a lit­tle bit. There’s actu­al­ly far more to dis­cuss and to dis­cov­er today, so we’re going to do more of that. We’ll actu­al­ly share an info­graph­ic or two with you as we go along in the episode if you are look­ing at the video por­tion. But thanks again for lis­ten­ing in.


To recap last time where we land­ed, a few things. One, every­body needs to have in order to have true well­be­ing, you need to have sort of your own mis­sion, vision, val­ues in life and know who you are, inde­pen­dent of your employ­er, so that you can find the right employ­er, align to that right employ­er, and real­ly be bought in a way that’s real­ly inte­grat­ed and real­ly true to your nature and kind of your world­view. And then when we got into the Deloitte study, real­ly where we land­ed was again, with this info­graph­ic, this idea of what is the for­ward think­ing idea around well­be­ing and what’s the pur­pose of well­be­ing, which is defined by Deloitte. And we agree with this as the ambi­tion for human sus­tain­abil­i­ty. We end­ed the episode by talk­ing about the fact that work is a deter­mi­nant of well­be­ing. Well­be­ing is a shared respon­si­bil­i­ty between the indi­vid­ual employ­ee and the orga­ni­za­tion, the employ­er, that the employ­er must cre­ate an envi­ron­ment that is suit­able for well­be­ing, where well­be­ing can be cre­at­ed and sus­tained. And that last­ly, the orga­ni­za­tion­al struc­tures impact well­be­ing, not just throw­ing perks and ben­e­fits at the wall and see­ing what sticks, but real­ly cre­at­ing holis­ti­cal­ly an envi­ron­ment in a cul­ture where well­be­ing can take hold and be sus­tained. So we’re going to con­tin­ue with the Deloitte study today. And Jason, why don’t you take us and sort of tee us up, talk about the rest of this study and what you and I have learned through it.

Jason (03:12):

So we kind of went deep on a cou­ple areas of this study already that we’re going to gloss over this time, but I think there’s prob­a­bly two areas that I think are inter­est­ing and mer­it some dis­cus­sion. So one of those is the study out­lines three fac­tors that they say have an out­size impact on well­be­ing, and they call these the work deter­mi­nants of well­be­ing. And so in a sim­i­lar fash­ion to what we’ve talked about in pre­vi­ous episodes, the World Health Orga­ni­za­tion calls social deter­mi­nants of health and well­be­ing. This arti­cle has sort of tak­en a sim­i­lar par­a­digm and labeled these things work deter­mi­nants of well­be­ing. And so from their research and stud­ies or a sur­vey that was con­duct­ed that served as kind of the pri­ma­ry source mate­r­i­al for this report, they deter­mined that the three work deter­mi­nants of well­be­ing are lead­er­ship behav­ior at all lev­els of the organization.


So basi­cal­ly, I mean, I think you’d prob­a­bly sum­ma­rize this maybe as, hey, peo­ple don’t leave com­pa­nies, they leave man­agers. So it’s kind of maybe an encap­su­la­tion of that. The lead­er­ship behav­ior of indi­vid­u­als with­in the orga­ni­za­tion has a sig­nif­i­cant bear­ing on an employ­ee’s expe­ri­ence, seems self-evi­dent. How the orga­ni­za­tion and jobs are designed. So that’s some­thing that’s inter­est­ing. Prob­a­bly mer­its a lit­tle bit dis­cus­sion, maybe adding a lit­tle bit more col­or to what we talked about last time with the sort of inten­tion­al­i­ty behind design­ing employ­ee expe­ri­ence and then ways of work­ing across orga­ni­za­tion­al lev­els. And so some of what that means is are peo­ple just work­ing in silos by func­tion or is there more cross-func­tion­al inter­ac­tion? How does that work take place across teams? For exam­ple, is it per­haps more project based ver­sus just kind of func­tion based, some of those kinds of things. So I mean curi­ous, I know you have a lot of thoughts and ideas how some of those just strike you initially.

Jor­dan (05:25):

Yeah, I mean what I was sit­ting there think­ing when you were read­ing those is around job design and orga­ni­za­tion­al design. I think that as a leader for me, I’m prob­a­bly bet­ter at one and pret­ty poor at the oth­er. So orga­ni­za­tion­al design, I think I’ve got a decent idea at least around how we’re going to car­ry our­selves an orga­ni­za­tion, how we’re going to treat each oth­er, what our val­ues are going to be, where we’re going to hold each oth­er account­able from a human stand­point and a rela­tion­al stand­point. But the job design ele­ment is just not a strength for me. I’m like, well, I know I need these tasks done or I know that I need this goal to be aid­ed by the work of this per­son. But I think some­times we maybe fail to design a job as well as it needs to be ful­ly designed so that the per­son that’s placed in that role knows not only what’s expect­ed of them, but why what’s expect­ed of them mat­ters, and how it con­nects to the mis­sion and the vision of the orga­ni­za­tion. So I was think­ing about that hon­est­ly. But the lead­er­ship behav­ior at all lev­els, that is just, it’s kind of an old adage. Like you said, peo­ple don’t leave com­pa­nies, they leave man­agers. And I mean, there’s a lot of fail­ures there that are implic­it in that state­ment. One is if peo­ple are leav­ing a com­pa­ny because of a man­ag­er, then there is some sort of some very clear, to me, respon­si­bil­i­ty to the upper lev­el lead­er­ship of, well, you left a man­ag­er in place that would run peo­ple out of the job.

Jason (07:17):


Jor­dan (07:18):

What the hell? How could you leave some­one in place that is so dif­fi­cult to work with? Or so maybe even as far as abu­sive of their pow­er or what­ev­er the case may be, that peo­ple would actu­al­ly lit­er­al­ly quit their job, which is a very stress­ful thing to do and go look for anoth­er direct­ly as a result of a man­age­r­i­al rela­tion­ship. That’s a fail­ure on my part. It’s a fail­ure on your part as exec­u­tives to not see that. So that’s a big deal.

Jason (07:54):

I mean, I will say though, it feels like a top­ic that is maybe more com­plex than we want to acknowl­edge, because I think this to me feels like one of those areas where there’s a shared respon­si­bil­i­ty, right? And so if you think about


Man­agers, absolute­ly a thou­sand per­cent have a respon­si­bil­i­ty to care for their peo­ple, look out for their inter­ests. I would say the num­ber one job if you lead peo­ple, is to make sure your peo­ple are suc­cess­ful, right? Because what­ev­er you’re charged with as a leader of a team, let’s say, your suc­cess in accom­plish­ing your own goals is real­ly con­tin­gent upon how suc­cess­ful the peo­ple on your team are going to be. And so the peo­ple on your team aren’t a means to your own end, right? Your job, the means or your end rather, is help your peo­ple be as suc­cess­ful as they can pos­si­bly be in what­ev­er they’re doing. And I think that helps change the par­a­digm. But then on the flip side of that is none of us are mind read­ers. If an employ­ee has, we’re all wired so dif­fer­ent­ly. I’ve had this expe­ri­ence myself and work­ing with indi­vid­u­als who just like you miss each oth­er on com­mu­ni­ca­tion style, right?


Lead­er­ship style, some­thing gets said, maybe tak­en out of con­text, some­body feels a cer­tain way about it and it’s like, Hey, I need you to tell me, right? I need you to com­mu­ni­cate open­ly. And it’s my respon­si­bil­i­ty to make sure peo­ple feel safe. They can com­mu­ni­cate open­ly with me with­out threat or reper­cus­sions and what­not. But at the same time, it’s also the indi­vid­u­al’s respon­si­bil­i­ty. Say, Hey, this isn’t work­ing for me. I need some help here. Is there any­thing we can do? And a good man­ag­er prob­a­bly ought to say, Hey, yeah, let’s talk about it. Maybe we can’t fix all of this, but maybe we can fix some of this, right? Yeah. Or, Hey, I’m sor­ry, I did­n’t real­ize I was doing some­thing that was caus­ing you to feel a cer­tain way.

Jor­dan (09:56):

Yeah, I think you’re right. I mean, there’s two prob­lems there. If a leader real­ly tru­ly cares about the peo­ple that they lead and they’re pur­su­ing their well­be­ing and they’re pur­su­ing their suc­cess and all of that, then that ought to be enough. So long as the indi­vid­ual that’s being led has the courage to say, this is how I’m doing. This is what I need, this is how what you said, or the way that you lead makes me feel or makes me react. I think that the inten­tion is there, and the courage is there to be vul­ner­a­ble and to be forth­right on both ends. Then this type of thing’s not just not going to hap­pen, right? Because fail­ures are going to hap­pen and errors are going to hap­pen. But when the inten­tion is there to cul­ti­vate this envi­ron­ment of well­be­ing, then you know, you can solve a whole lot.

Jason (10:52):

Well, and I think, I’m curi­ous what you would say to this. I think it would be a mis­take to con­flate com­pas­sion with good lead­er­ship. It’s impor­tant that lead­er­ships, that lead­ers demon­strate com­pas­sion for their peo­ple. But that does­n’t, in and of itself com­prise all of what it means. And so there’s cer­tain­ly, there’s, you could be an incom­pe­tent, com­pas­sion­ate leader, right? And that’s not what we’re aim­ing for, right? We’re aim­ing for the leader has expec­ta­tions, right? And so, I mean, some of what this arti­cle points out is they’re on the job expec­ta­tion side. There’s micro­man­age­ment, which is a hor­ri­ble expe­ri­ence for you as an employ­ee if you’re being micro­man­aged. And then there’s under man­age­ment, which is prob­a­bly what I’m more inclined to do with indi­vid­u­als that have report­ed to me, which is, Hey, I don’t give enough direc­tion. I like giv­ing peo­ple auton­o­my, but I like it so much that some­times peo­ple are like, Hey, what the heck am I sup­posed to be doing here?


Am I doing the right stuff? Am I work­ing on things that are impor­tant? Am I focused on things that are aligned with what we’re try­ing to do here? And I think that’s a real­ly impor­tant part too. So we have to bal­ance all of those things, which I think ties into what we talked about in the last episode, which is we actu­al­ly real­ly need to focus on doing good work to man­age or lev­el up, let’s say, the peo­ple lead­ers, the peo­ple that man­age peo­ple with­in our orga­ni­za­tions, which is who our pod­cast is for. We need to help them lev­el up in how they think about the work that they’re doing with their teams.

Jor­dan (12:34):

Yeah. I mean, think again, we talked about in the last episodes that you don’t like bina­ries, right?

Jason (12:41):

I real­ly don’t.

Jor­dan (12:42):

And you should­n’t, right? Because they set up a false par­a­digm that one thing is right, and the oth­er thing is nec­es­sar­i­ly wrong. And in some cas­es that’s true. It’s just like toma­toes are poi­so­nous. That is a tru­ism. It is true. That’s just true, right? Yeah. There’s no debat­ing that.

Jason (13:00):

Espe­cial­ly that heir­loom kind. They’re all big, and it’s gross.

Jor­dan (13:03):

It’s a fam­i­ly trait. We’re not a toma­to fam­i­ly. But yeah, I think this, you’ve got lead­ers, I guess in that bina­ry. You’ve got lead­ers that are your friend and they under­stand and they heard you, and they know how you feel, and they’re com­pas­sion­ate and they care. But you can spend all of your time car­ing and feel­ing and empathiz­ing, and it’s not actu­al­ly lov­ing to peo­ple. It’s not actu­al­ly what they need. It’s just to feel and feel and feel. They actu­al­ly need to be aligned and remind­ed of the mis­sion and what are we here for? And how might we take our feel­ings and still feel them, but through those feel­ings con­tin­ue to strive, con­tin­ue to work, and con­tin­ue to pur­sue the mis­sion for which we are here. Right? And then you’ve got oth­er lead­ers. Again, it’s already set up this bina­ry sce­nario that it’s just screw your feel­ings, get the work done, get the job done. And I feel like as a leader, one of my fail­ures is that I swing a pen­du­lum from one side to the other.


It’s where I’m just like, man, I just hate that peo­ple are going through this. I hate that peo­ple feel what­ev­er that they’re feel­ing. Or our com­pa­ny, Fringe, lit­er­al­ly we are in the midst of an eco­nom­ic down­turn. We’re in the midst of like most com­pa­nies, just a hard time, a scary time of just like, Hey, peo­ple are going to con­tin­ue to buy this. They’re going to, are clien­t’s con­tin­ue to use this and appre­ci­ate this. Or their CFO’s going to get ahold of it and just slash the thing reck­less­ly, because it’s some­thing to slash. And so you can swing from like, oh man, I real­ly hate that peo­ple are feel­ing the fear of that. And then fail to lead from the stand­point of just like, yeah, but we got a mis­sion to ful­fill. Let’s go. And then swing too far that way and for­get to care for peo­ple and their feel­ings and so forth. So it’s easy for lead­ers to, when they’re not giv­en a real­ly good exam­ple of how to lead and how to man­age those aspects to fall into one bina­ry side or the other.

Jason (15:25):

Well, and I think this prob­a­bly gets us into some of the dis­cus­sion that we want to have around this info­graph­ic and these work deter­mi­nants, because the lead­er­ship side in par­tic­u­lar, it’s so dif­fi­cult. I mean, any­one that’s been in lead­er­ship, and any­one that’s been respon­si­ble for teams and lead­ing and man­ag­ing peo­ple would under­stand, it’s just a dif­fi­cult job. I mean, some­thing that I’ve learned and I say often or find myself say­ing often, maybe it’s advice or just some­thing you learn is like, Hey, if you’re in lead­er­ship, it’s always your fault. It does­n’t mat­ter. That’s just part of what comes with the job. And I’ve also learned that the job, it is real­ly dif­fi­cult. A lot of peo­ple, espe­cial­ly when you’re shift­ing from being an indi­vid­ual con­trib­u­tor, that type of role where you’re respon­si­ble a lot or some, a lot of your work has been doing the things, right? Yeah. Very task ori­ent­ed, let’s say to, Hey, now most of my work is actu­al­ly man­ag­ing peo­ple. And it’s a very, very dif­fer­ent par­a­digm. And I think what’s real­ly inter­est­ing, and I want you to share some of this, is what are these work deter­mi­nants? And then what it looks like. Cause I think on the lead­er­ship side in par­tic­u­lar, there’s some­thing, some things that are real­ly inter­est­ing and prob­a­bly lev­el up to a degree that’s maybe a lit­tle uncom­fort­able, what our expec­ta­tions should be for any­one who’s lead­ing people.

Jor­dan (16:55):

Gosh, I have a lot to say about lead­er­ship. In a very short time, I feel like I went from an indi­vid­ual con­trib­u­tor in a role that we were both in pri­or to Fringe, pri­or to our oth­er com­pa­ny, Green­house Mon­ey, where we were com­plete­ly respon­si­ble for every sin­gle task and run­ning our little -

Jason (17:21):

Yeah, if you don’t do it, it does­n’t happen.

Jor­dan (17:22):

It just does­n’t hap­pen. And now to be CEO of a com­pa­ny, it’s incred­i­bly dif­fer­ent. And I will say it’s a lot scari­er to me at least than how so than being indi­vid­ual. Because what­ev­er emo­tion I felt in the day, if I felt like, oh, I’m not get­ting enough done, or I haven’t made enough calls, or I haven’t had enough meet­ings, or I haven’t, what­ev­er, I would just go do the thing, what­ev­er the thing was that felt that as though it were lack­ing, just more clear, I would just go do it. Myself, right? But my role now is very far removed from that. It would actu­al­ly be a great offense to peo­ple if I was stress­ing out about like, oh, well, we did­n’t get enough leads this month, or we did­n’t like what­ev­er the thing is, we did­n’t put enough ads out there.

Jason (18:16):

You’re not the one that’s sin­gle-hand­ed­ly respon­si­ble for that.

Jor­dan (18:17):

And if I just went and just start­ed doing it, peo­ple would be like, what the hell kind of lead­er­ship is that? Do you not trust that I can do it? Do you not trust that you have lead­ers under you who lead oth­ers, who lead oth­ers who write, get this stuff done? It would actu­al­ly be a big mis­take for me to just grab the reins and just do the task. So it just takes this enor­mous amount of trust. And I have to trust that the exec­u­tive lead­er­ship team is lead­ing the man­age­ment team that’s lead­ing the mid- man­age­ment team, that’s lead­ing the indi­vid­ual con­trib­u­tors to do the thing that I want, and not so far in the past did myself. And it’s ter­ri­fy­ing because I have so lit­tle direct con­trol. And so for one, that’s why it’s so impor­tant to build your orga­ni­za­tion well, and to hire peo­ple you can trust.


But for two, I have to facil­i­tate an envi­ron­ment where I am trust­ing in peo­ple, and they feel that trust, and they feel as though I have belief in them that they can do the thing that’s nec­es­sary, oth­er­wise they don’t feel safe. They feel like some­body’s just going to snatch their job away from ​‘em, or their task away from them. And they also just don’t get to feel that sense of, I have a pur­pose here. I have a thing that this is my exper­tise, this is my thing, and I’m going to do this for me, because it makes me feel like I’m a worth­while indi­vid­ual because I hus­tle and I do this thing, but also for the com­pa­ny. And I can’t steal that from peo­ple. So I have to sit in my fear and in my strug­gle to trust peo­ple that I don’t have even influ­ence over directly.

Jason (20:07):

Yeah. Well, I mean, I think some of what you are demon­strat­ing right here in this con­ver­sa­tion is what they’re describ­ing in this arti­cle that’s real­ly imper­a­tive to what lead­ers do, which is they have self- aware­ness, right? And there’s a lev­el of, I mean, I was sur­prised to see this in here. They say that your emo­tion­al intel­li­gence is real­ly crit­i­cal for lead­ers, because you need to be able to say, Hey, I under­stand the things that I’m feel­ing, right? And I under­stand that the actions that I take may have a cer­tain way that they feel to the peo­ple that I’m lead­ing. And not every­body under­stands that. And I think some of what gets dif­fi­cult too, and we have this at Fringe, and I’ve expe­ri­enced this myself again, is, you know, go through jour­neys where, Hey, maybe I’m man­ag­ing peo­ple and I have indi­vid­ual con­trib­u­tor respon­si­bil­i­ties. And that starts to get real­ly tricky.


Hey, some parts of my day. It’s like, I am respon­si­ble for doing the things. And so I got to switch that part of my mind on where it’s like, okay, if I don’t do this, it does­n’t get done. And then over here in this part of my work, it’s like, okay, I’m respon­si­ble for lead­ing through peo­ple. So now my job over here has helped them be suc­cess­ful. And it does take a lev­el of emo­tion­al intel­li­gence and self-aware­ness to be able to do that well, and even to acknowl­edge, hey, some­times I’m not going to do it well. Right? Being able to acknowl­edge that too.

Jor­dan (21:34):

Yeah, it’s been amaz­ing to me lead­ing a com­pa­ny, what is mean­ing­ful to peo­ple and what isn’t. From an indi­vid­ual con­trib­u­tor stand­point. And if that’s the major­i­ty of your career, which it’s the major­i­ty of mine, I always think, oh, well, when I was a guest on that pod­cast, or when I wrote that blog, or when I raised that mon­ey, or when the thing that I did, yeah, that’s the thing the com­pa­ny needs most. But the feed­back I get is absolute­ly not that. The feed­back is like, Hey, the most impor­tant thing you did this week is when you reached out to so-and-so and you said this. Some very vanil­la thing. Just like, Hey, you did a real­ly great job. I’m so grate­ful you’re here. Some­thing that took some vul­ner­a­bil­i­ty, but very lit­tle time. Yeah, very lit­tle intel­lect to do, which thank good­ness, right? Yeah. Thank good­ness. EQ is what’s demand­ed of me and not IQ. Cause my IQ is aver­age at best, but -

Jason (22:40):

Don’t sell your­self short.

Jor­dan (22:42):

But that’s what I keep hear­ing being demand­ed of me and asked from me is just be vul​ner​a​ble​.Be kind. Be grate­ful for your peo­ple. Express to them that you’re thank­ful for their con­tri­bu­tions, and give them clear direc­tion on what to do.

Jason (22:59):

Well, do you know, one of the things that they list as a key lead­er­ship behav­ior is?

Jor­dan (23:03):

Tell me.

Jason (23:04):


Jor­dan (23:05):


Jason (23:06):

Which is what you just described, quite literally.

Jor­dan (23:11):


Jason (23:11):

So yeah, I mean, I think it’s inter­est­ing too. The oth­er thing that they say that stuck out to me when they were talk­ing about lead­er­ship behav­iors. So there’s this self-aware­ness, emo­tion­al intel­li­gence or EQ, they talk about fos­ter­ing psy­cho­log­i­cal safe­ty, which I feel like I’d want to unpack maybe sep­a­rate­ly, because I have some ques­tions even about what do we mean when we say this and what’s going on there. But the oth­er thing that real­ly stood out to me was exhibit­ing pos­i­tive per­son­al well­be­ing behav­iors. So basi­cal­ly do as I do, not as I say, right? I mean, again, this, it’s like, duh, we all learned that. We all were told that’s what lead­er­ship is, right? And that’s like what we do with our kids even, right? We don’t like, Hey, I want to exem­pli­fy for my chil­dren, and not that employ­ees are chil­dren, but in areas of our lives that I think we just kind of take for grant­ed that we’re lead­ers of peo­ple or kids and so forth. That sort of the oper­at­ing prin­ci­ple there is the words don’t mat­ter. The actions are what mat­ters. Do as I do. And so that is what they’re call­ing out here is a real­ly crit­i­cal piece of lead­er­ship behav­ior is like, don’t just tell your peo­ple, do this or that. Demon­strate for them what you want that to look like.

Jor­dan (24:37):

Wow. Yeah. I mean, it comes right back to just open­ness and vul­ner­a­bil­i­ty. I think as a leader, if you’re not real­ly will­ing to show your­self to the peo­ple you lead, who you real­ly are and what you’re about and what moves you, why you get out of bed in the morn­ing, how are you going to expect any­body else to oper­ate from this place that we’ve preached about the last two, three episodes around pur­pose and around hav­ing a mis­sion in life and that’s just not exhib­it­ed from the top. How do you expect peo­ple to act that way, right? Because it takes a seri­ous amount of vul­ner­a­bil­i­ty to share with peo­ple, here’s what my life is about. Here’s why I do what I do. Here are the peo­ple that I love and what I’m striv­ing after for them. And it all just always, no mat­ter what top­ic we talk about on this pod­cast, it always comes back to some incred­i­bly open, vul­ner­a­ble place that the lead­ers need to be. They need to be at in order to exhib­it this ful­ly raw human thing.

Jason (25:57):

Yeah, it, it’s a human thing because so many, I don’t know, you say so many pres­sures and what we, what we real­ly love get­ting from some­body is authenticity.

Jor­dan (26:18):

The actu­al truth.

Jason (26:19):


Jor­dan (26:20):

Devoid of all the bullshit.

Jason (26:23):

And even just know­ing like, oh man, this per­son­’s not bull­shit­ting me. They’re real. And they can acknowl­edge their mis­takes and they can acknowl­edge they don’t have it all together.

Jor­dan (26:34):

Fail­ures, needs, fears.

Jason (26:35):

I’m grow­ing too. I’m doing the best I can. It may not always be awe­some. And we’re on this jour­ney togeth­er. And I think that that’s actu­al­ly, when we see that in peo­ple, it helps build trust and it helps. Maybe that’s what some of that psy­cho­log­i­cal safe­ty is. It helps build that set­ting where it’s okay to share those things and talk those things and not be perfect.

Jor­dan (26:59):

So the table that we, I think we’re going to share here after lead­er­ship, it talks about design of work, high­er orga­nized. So what it looks like, Deloitte describes this as work is designed to lim­it clut­ter, opti­mize scope, and stream­line the flow of infor­ma­tion to the work­ers, can focus on out­comes rather than task and enable more pur­pose-dri­ven work. I don’t know about the out­comes rather than tasks, but I think the stream­lined flow of infor­ma­tion has been a big les­son learned for the two of us. I think there’s so much infor­ma­tion that we start­ed the com­pa­ny that we run. We know what’s going on. We are in the board meet­ings. We know what the bank account looks like. We know what every depart­ment is doing. And so there’s just this aware­ness that’s just there from an exec­u­tive lead­er­ship stand­point because you just run the damn thing where I, I’ve dis­cov­ered that this real­ly, there’s a ton of thought that needs to be poured into the flow of infor­ma­tion. How infor­ma­tion is shared, when it is shared, whose lips is it uttered, and with what tone and what, because peo­ple, you’ve got peo­ple that I think kind of bury their head in the sand and they’re just like, I don’t know. I just do my job and what­ev­er. And you got peo­ple on that oppo­site end of the spectrum.

Jason (28:31):

What the hell’s going on here?

Jor­dan (28:32):

I want to know every last thing that’s hap­pen­ing. I want all of the content.

Jason (28:36):

It’s not even pos­si­ble. I don’t even know every­thing that’s happening.

Jor­dan (28:39):

First of all, I can’t give you that. And sec­ond­ly, are you sure? So I think that’s big though. I think it’s some­thing we real­ly learned about. We’re on this top­ic of well­be­ing. We’re on this top, on this top­ic of peo­ple feel­ing psy­cho­log­i­cal, safe­ty, et cetera. And that’s a real strug­gle I think for us, is to fig­ure out exact­ly what to com­mu­ni­cate and when to com­mu­ni­cate and how to com­mu­ni­cate it. And I think that is essential.

Jason (29:09):

That’s tied to the out­comes. And so that’s how I inter­pret some of this is that it, it’s less about, peo­ple need to know every­thing exact­ly at the right time, and it’s just going to be impos­si­ble. Cause every­one has a dif­fer­ent way that they feel about it. It’s true, as you

Jor­dan (29:24):

It’s a whole lot of dif­fer­ent desires.

Jason (29:25):

But what every­body sure­ly needs to know is, what do I need to do? What does suc­cess look like? What are we aim­ing for? And I think that, so that’s what stood out to me when I read this, was the out­comes rather than tasks. I don’t care what you’re doing day to day, as long as this is what we get.


And the this needs to be real­ly clear and every­body needs to be aligned with it from top to the bot­tom of the orga­ni­za­tion. Right? So that is very obvi­ous. This is the expec­ta­tion, this is the out­come that we’re aim­ing for. Now how you get there, there could be a whole bunch of ways that you get there, right? And I think that’s where the auton­o­my and trust comes into play. Cause peo­ple want auton­o­my. They need auton­o­my in what they do. And so we can say, Hey, this is what we need deliv­ered, right? Yes. How you get there, I can help. I’m will­ing to dive in. I’m not going to micro­man­age you in it, but this is what we need and you let me know what help you need. But you also have cre­ativ­i­ty and auton­o­my with­in that to get there. Hope­ful­ly that’s why we hired peo­ple that we believe have that abil­i­ty to prob­a­bly bet­ter than we would come up with ways in which we’re going to achieve the out­comes maybe with bet­ter designs than we would’ve come up with on our own.

Jor­dan (30:44):

Yeah. I think it is easy to think that that work is this lin­ear path where you come in as an indi­vid­ual con­trib­u­tor and you become some sort of asso­ciate man­ag­er of some kind, and then you man­age it.

Jason (31:02):

It’s the career lad­der, right?

Jor­dan (31:04):

This lad­der, and it’s just not real­ly true. Peo­ple have par­tic­u­lar gift­ings and skillsets, and some peo­ple need to be real­ly high­ly paid and beloved and appre­ci­at­ed indi­vid­ual con­trib­u­tors for 35 years and because that is how, that is just what they’re great at. It’s just get­ting stuff done. And sure, can they show oth­ers how they get it done along the way in the moment? Yeah. It’s not to say that there isn’t any lead­er­ship capac­i­ty there, but that maybe the role does­n’t fit that. Because when I think about what you just said, there are tac­tics and there’s strat­e­gy, right? Yes. What we’re con­cerned about is the strat­e­gy and the strat­e­gy is what­ev­er leads us to the out­come. And so we’re going to have this notion of like, we are going to climb the moun­tain because at the top of the moun­tain, there’s this gar­den full of fruits and veg­eta­bles and every­thing we need to sus­tain us and the beautiful -

Jason (32:09):


Jor­dan (32:10):

Just going to get up there. You and I, we don’t care whether we throw a zip line up and we climb up or we use cara­bin­ers or we don’t, or we paraglide. I don’t care. Paraglide up the moun­tain. We use giant springs like in a Mario game or some­thing. I don’t care how we get up there, but there are peo­ple that are actu­al­ly fan­tas­tic at exact­ly that, right? No, actu­al­ly the best tac­tic is this. Yeah. Cause we’re going to waste a bunch of ener­gy doing this route or that route. The oth­er thing, and I think some­times we’re so obsessed with, I got to climb the cor­po­rate lad­der. I got to get to the next stage. We should have low lev­el or mid-lev­el man­agers. That might be some of the high­est paid peo­ple in the orga­ni­za­tion because they’re so freak­ing good.

Jason (33:01):

Or not even man­agers, right?

Jor­dan (33:03):

Yeah. Or not even man­agers, maybe just indi­vid­ual con­trib­u­tors. They’re the high­est peo­ple in the com­pa­nies because they’re so good that what they do. And I think that’s one of the mis­takes of how work is designed to get back to exact­ly the info­graph­ic here. Some­times it’s designed to be a ladder.

Jason (33:24):

That’s how you esca­late and that’s how you move up. And there’s respon­si­bil­i­ty to the orga­ni­za­tion to make sure they design paths for peo­ple to find ways to con­tribute that don’t require, Hey, the only way for you to go up here is to man­age peo­ple. So I mean, I’ve gone from in my time at Fringe man­ag­ing small teams to man­ag­ing teams of 20 peo­ple to now I have lit­er­al­ly nobody that reports to me and actu­al­ly kind of love it. It’s been a real­ly great, it’s great. It’s been a great time. I’m doing some cool stuff, work­ing on projects that I’m the one doing the task stuff and exe­cut­ing, but it’s great. And so, I mean, I’d also want to encour­age peo­ple lis­ten­ing even to feel like, Hey, real­ly think deeply about what you love doing too, because there may be a path that isn’t what you always thought it need­ed to be.

Jor­dan (34:11):

This is exact­ly where the sat­is­fac­tion and well­be­ing is a joint respon­si­bil­i­ty. Yes. Because you can tell that what you just said is -

Jason (34:19):

You need the opportunity -

Jor­dan (34:19):

Indi­vid­u­als, employ­ees out there, find what you love and do it. But if your employ­er does­n’t facil­i­tate an envi­ron­ment where you can progress in, where you find your call­ing, if you will. You find exact­ly what you’re best at. And they’re just like, well, yeah, you’re best at this, so we’re just going to treat you like you’ve been here a short time and not real­ly reward your exper­tise. That’s problematic.

Jason (34:46):

A thou­sand per­cent. Yeah. So let’s hit on this last one here. So ways of work­ing, how you get work done. So I want to read the descrip­tion, but this will tie into some stuff that we’ve talked about in the pre­vi­ous episode. Tech is used in strate­gic ways to facil­i­tate automa­tion, enable more mean­ing­ful work and lim­it task switch­ing. Stream­lined tech comes with clear­ly com­mu­ni­cat­ed expec­ta­tions and sup­ports inten­tion­al­ly designed hybrid work. There’s a lot there.

Jor­dan (35:17):

There’s a lot. So many buzz­words in there.

Jason (35:20):

A lot of buzz­words. Wow. They are consultants.

Jor­dan (35:22):

Hybrid work -

Jason (35:23):

They got to sound real­ly important.

Jor­dan (35:24):

Stream­lined tech. Yeah. Yeah. You’re real­ly down on con­sul­tants tonight. No, I think, yeah. I mean, what I take away from that, if I get through all the BS of the jar­gon of, okay, mean­ing­ful work. Yes. Enable mean­ing­ful work and clear­ly com­mu­ni­cate expec­ta­tions, right? Yeah. Give peo­ple flexibility.

Jason (35:52):

I took flex­i­bil­i­ty. Yeah, because the hybrid work thing, I mean, it’s kind of a hot top­ic right now, and I think it’s a lit­tle ridicu­lous that it is a hot top­ic. I mean, I think where that plane is going to land is peo­ple are going to need hybrid work, peri­od. So let’s not even dis­cuss it fur­ther than that.

Jor­dan (36:09):

Where else could it even land? Yeah. Yeah. I agree whole­heart­ed­ly. I think, again, I mean, we said this ear­li­er, I want to beat a dead horse, but clear­ly com­mu­ni­cat­ed expec­ta­tions. Lit­er­al­ly every­thing else is a tac­tic. Every­thing else beyond, here’s your job, here’s how your job con­nects to the broad­er pur­pose of what we’re try­ing to do, and here’s how I define suc­cess for your par­tic­u­lar role. Every­thing else is a tac­tic. Oh, well, okay, I’m not real­ly sure how to do my job. Use this tool. I don’t know how to use the tool. Get trained. I don’t like this tool. Let’s get anoth­er tool. Every­thing else is a tool. Every­thing else is a tac­tic. Every­thing else is a kind of way in which the thing gets done. But that’s not where orga­ni­za­tions fail. Orga­ni­za­tions can always find the right piece of soft­ware, right?

Jason (37:00):

Well, and the dan­ger is think­ing that that’s going to fix the prob­lem. Yes. When it’s not the problem.

Jor­dan (37:06):

It’s not the prob­lem. The prob­lem is peo­ple don’t actu­al­ly know what’s expect­ed of them.

Jason (37:09):

I want the new shiny thing. Right. That’s not the problem.

Jor­dan (37:12):

That’s not the prob­lem at all. Yeah. Yeah. And some­times the expec­ta­tions are clear and some­times the tool is actu­al­ly there in place, but it’s just you just going through a peri­od of strug­gle. I kind of described, we were talk­ing about this with some oth­er peo­ple at Fringe late­ly. It’s an eco­nom­ic down­turn. It’s just a tough time for a lot of busi­ness­es right now, and we’ve actu­al­ly been real­ly for­tu­nate to not have a hor­ri­bly hard time right now. We’re doing pret­ty well, but some­times you’re just on a los­ing streak. The whole coun­try’s on a los­ing streak right now. There’s not time to freak out, change tac­tics, change strat­e­gy, change peo­ple, what­ev­er. It just, you just got to hus­tle. You just got to believe that work is good and believe in your mis­sion and pur­pose and just get after it. And things are going to turn around to, not to dimin­ish what this is say­ing about the ways of work­ing are impor­tant, the tac­tics are impor­tant, the design of work is impor­tant, but I think all the more so, the top of the chart here, if you’ve got lead­ers that peo­ple trust and a clear direc­tion that we’re head­ing, and peo­ple under­stand how their job aligns, the direc­tion that the com­pa­ny’s head­ing in, you can weath­er a whole lot of storms and switch­ing tools around might help you in small ways, but it’s not the point.

Jason (38:38):

Yeah. I mean, the thing is just achiev­ing lever­age with the tools. So I think the hot top­ic now is Chat­G­PT, what­ev­er. Peo­ple are find­ing all sorts of cre­ative ways to do it. I mean, even in my own work, I found some inter­est­ing ways to lever­age Chat­G­PT to cre­ate effi­cien­cy. And so I think those are great things, right? Because they can help peo­ple accom­plish the job faster. It can maybe offload mun­dane work that is a lit­tle bit drudgery and that kind of stuff. And then the task switch­ing is actu­al­ly real­ly inter­est­ing to me. I think we’ll come back to that in anoth­er episode because the task switch­ing, I mean, it’s some­thing we’ve been talk­ing about at Fringe with deep work days, right? Because the task switch­ing actu­al­ly gets in the way of doing real deep work, which helps the com­pa­ny from a pro­duc­tiv­i­ty stand­point. But there’s actu­al­ly a lot of sci­ence that I want to delve into around deep work. How that ties into the notion of flow, which is psy­cho­log­i­cal prin­ci­ple and how the notion of -

Jor­dan (39:36):

I’ve heard you talk about flow.

Jason (39:37):

And how the notion of flow -

Jor­dan (39:39):

Big flow guy.

Jason (39:39):

Yeah. I mean, well, flow relates very strong­ly to your sense of sat­is­fac­tion and pur­pose at work. And so to the degree that you expe­ri­ence more flow, all of those things are going to be felt more pos­i­tive­ly. And so I think that lim­it­ing task switch­ing, that’s sort of a neg­a­tive fram­ing. The pos­i­tive fram­ing would be like, well, hey, we’re actu­al­ly accom­plish­ing some­thing bet­ter by replac­ing task switch­ing time. We’re mov­ing back and forth with some­thing that’s deep­er and more mean­ing­ful in terms of the work that’s tak­en place.

Jor­dan (40:12):

That makes per­fect sense. Well, we are well into the time that we intended -

Jason (40:21):

We are. But we’ve cov­ered, and I think exhaust­ed this report

Jor­dan (40:24):

We have, I think we did well. I just real­ized too that I think we’re going to have to give you a W on the word of the week, because I just com­plete­ly fell down.

Jason (40:35):

Is this a win-loss game now?

Jor­dan (40:36):

Yeah. Yeah. I think it prob­a­bly ought to be.

Jason (40:40):

If it is, the inten­si­ty is about to increase.

Jor­dan (40:43):

Some of it. Just take the L here instead of try­ing to come up with some BS sen­tence to find a place for equiv­o­cal in our con­ver­sa­tion. I was lost in the con­ver­sa­tion itself and did­n’t think much about it, so I apol­o­gize to the audi­ence for break­ing my streak here.

Jason (40:59):

Well, I will give you the word for the next episode.

Jor­dan (41:02):

Yeah, give me the word for next week.

Jason (41:02):

Which is carouse.

Jor­dan (41:04):

Wow. You’re just get­ting bet­ter all the time, and I’m get­ting worse. Oh, we’ll see how that plays out. Thank you so much, guys, for lis­ten­ing to How Peo­ple Work. It’s been an enjoy­able time just sit­ting here with you. Jason, I appre­ci­ate, again, your prepa­ra­tion, your insights, your read­ing, your nerd­ing out, as I like to say, on dif­fer­ent arti­cles and stud­ies that you’re look­ing into. I hope this episode was enjoy­able to lis­ten to. Please do, send us feed­back, send us ques­tions. We’d love to answer any ques­tions for you guys, or just have dis­cus­sions that are par­tic­u­lar­ly inter­est­ing to what’s going on in your life and your work and the things that you’re try­ing to learn about. Thanks for lis­ten­ing. We’ll catch you next week.

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