Managing Former Peers with Jen Dary

Jen DaryJen Dary is the founder of Plucky, an organization that works with companies and individuals to create healthy dynamics at work. She is a leadership coach and speaker; she travels across the US teaching workshops, including her popular course, So Now You’re a Manager, which trains new managers across the country for the complex work of herding humans. Jen lives in Berkeley, CA with her husband and two young sons.

On today’s episode we discuss one of the tricky challenges of being a first time manager – managing your former peers and friends. We also discuss Plucky Cards? What are those? Stay tuned to find out!

Contact Links:

twitter: @jenniferdary, @beplucky
IG: @bepluckster
Show Notes:
Brene Brown Ted Talk: The Power of Vulnerability 
Read Full Transcript

Christian Mccarrick:
[0:00] Good morning Jen welcome to the show.Jen Dary:
[0:05] Christian thanks for having me.Christian Mccarrick:
[0:07] Absolutely it’s always my pleasure and I where you calling from today Jen.Jen Dary:
[0:10] I’m in Berkeley California so right across the bridge I think from you right are you there.Christian Mccarrick:
[0:16] Yeah I actually if I look out my window I can kind of see the the hour from the University of Berkeley so I can probably see you it’s a little Misty this morning but I.Jen Dary:
[0:24] You said you see me waving but.

Christian Mccarrick:
[0:26] I did always that you know.

Jen Dary:
[0:27] Nano that’s me yesterday.

Christian Mccarrick:
[0:28] Okay.
Excellent thank you for being my neighbor across the bay I actually lived I tournament the Far East Bay cuz I kind of live over the Berkeley Hills and commuted to the city so.
Ijen let’s get started little bit can you give me a little background kind of where you got you where you are today.

Jen Dary:
[0:51] Yeah that’s a good question so today we just,
start for a little bit backwards where I am is I I run a company called Plucky and I actually read it from home I I have an office in our house,
and with Plucky about half my time I spend leadership coaching,
so that’s coaching people who are either currently managers and leaders or emerging managers and leaders,
the other half my time I spend teaching professional development workshops sometimes in the house sometimes not and so they like 4 times a year I teach something called so now you’re a manager at like a two-day workshop training and I sell tickets to that so that’s to an external audience,
and generally the way that I got here is that I really like people,
and that is something you know you cancer Trace very far back but I’m the oldest of three kids and I grew up in a house where I was,
you know helping to plan and and helping to move people around and Corral the cats into the minivan and those sorts of things.
And you know you probably know this about humans too but I think we.
We reserved take one of two paths at any given moment with her guitar career we either it look for things were really good at or we look for things that we think we should be doing.
And hopefully at some point you start listening to what you’re good at more than the shoulds,
and you find your way towards a really fulfilling scenario and so you know the long story short is that I tried to escape being a lit major because I was a little worried about the viability of careers of what.

[2:25] Could not do it ended up with a master’s in French Lick.
Yep yep very marketable and then ended up working on project for a while and then my first job in check was in New York which is where I’m from,
where I,
started copywriting and then dance around that company in a lot of different roles that ended up is the director of employee development it was there that I really started to observe that this Affinity that I have four people and the facility that I have a sore,
Rowling humans and moving them around and helpful ways finally was able to be leveraged by what I was paid to do,
and so moving from there it is about the time I had my first son and I was doing a lot of those big thinking questions like why am I on the planet.
Thing and how can I erase I can just a little and.
And I realize that what I was doing and house there felt like there was space in the market to address that in other companies and so I started lucky and so Bucky will be 5 years old in September.

Christian Mccarrick:
[3:25] And you know I notice a lot of your clients maybe that I’ve seen tend to be on the set of Technology focus is that is that something you started with Richard kind of evolved that way and there was a need or how did you come to get into the text side of of the managers.

Jen Dary:
[3:39] I think that because I I had that director of employee development role at a digital agency in New York,
I was already swimming a bit in that population and so that the only reason I felt like I could step out on a limb and start Plucky was because I had a group like a network of sorts of people that were.
Decision makers so whether they were owners of digital agencies or they were other managers that I had tried to hire or hurt you notice at least new in the market they all happens to be in that vertical but,
like,
a good example is this Workshop that I teach to know your manager next week is the one in Oakland and I’m looking at this attendee list I invite 20 people or 20 people allowed to come and like I have people coming from a butcher people coming from people coming from Chocolate Factory people coming from super large tech companies and,
prophets of the human work Underneath It All is very.
Is is the link right like it doesn’t really matter where you manage there are going to be for sure differences but there’s a lot of things in common and so text is sort of just where I grew up,
in my career and certainly a really good starting point,
not the extent you know there’s there’s like a lot of other places I think I can go but I also let you know I’m married to somebody.
I’m freezing here in that role and so I’ve been around the block with him to serve here his point of view too so it’s fun to pick up these vocab words even though I have never developed any.

Christian Mccarrick:
[5:07] Sure yeah I think it’s interesting that you get people together from Tekken on time because I think sometimes Austin technology can be very isolated Nunnally,
physically in Silicon Valley but even just in our new concept of what’s out there at the outside of you know developing its next to do a foursome game or something right is a whole the rest of the world basically is a technology.
Getting into partner lies but they’re not actually building.

Jen Dary:
[5:34] I love that you said that Christian cuz it is one of the things I think about the most when I,
develop that Workshop is like I care a lot about who is in that room and I sell tickets accordingly and Pace you know based on gender and diversity and vertical and all those things someone told me a story the other day that they were having coffee with a friend who works at Google and I need it like weekly for a few months and,
I know a couple months in this woman who was talking to me said that they were about to leave the coffee shop.
You need to pay did you pay for your coffee yet to the friend who works at Google and the friend who works at Google was like oh my gosh.
They have been going out for coffee for several months and Netflix the woman who works at Google had never realized oh you need to pay for coffee in this coffee shop because she assumed that,
I don’t know the company funded it I guess or whatever and yeah sometimes I feel the need to get everybody in a room with people who are in very different verticals who did not have the stability of budget or some of the luxuries that come with,
some of what our industry of tack is is known to kind of just take for granted email.

Christian Mccarrick:
[6:44] Yeah that’s it that’s a funny funny story cuz I have an anecdote I use Uber so much and I pay but I took a cab so the first time in a while and I got out and I didn’t pay and then I was like.
I actually thought it was automatic.
Concepts which is hard I mean I actually I grew up in New York to into a cab and then suddenly to not pay one is like but I don’t think when I grabbed it and pay somebody that’s in my parents.

Jen Dary:
[7:11] Totally and it’s at you know what it’s not to demonize that moment because I think there’s reasons logical reasons why we get used to those sorts of things but I also think every once in awhile particularly are you if you are signing up for learning setting it’s really good for you to remember how other people in the world live and function,
and helps I noticed underscore the gratitude that you might feel for what has become so you know normal.

Christian Mccarrick:
[7:34] No absolutely no the.
You obviously you coach you do classroom trainings and whether it’s for Tech or not as you say it is a lot of an overlap.
With just managing humans right so what do you see as some of the biggest mistakes that you’ll managers are or companies have been trying to lead teams.

Jen Dary:
[7:58] Well I think a few things first I will say that.
One of the things I call out in any room that I’m teaching managers in is what I called Creator grief.
And what I mean by that is it often the people who are managing or leading used to be the makers,
used to be the creators it’s the weather that’s that they used to be in code and pixels or they used to be in the weeds whatever the version of the weeds is for your company you know,
for your industry and now they’re not doing that anymore,
and that is really hard and there’s some grieving that needs to happen because the new currency of course as a manager or leader that you inherit is humans and a human currency is really different than something you can chew Ave or a B test or in those sorts of things and I,
find that I don’t know if I’m called a mistake but a challenge that people have is figuring out will was it a good day to like.
Was it a good day just have nobody quit like what what the hell is the metric you know and people have a really hard time with that and so so one of the things that I kind of,
I do not want to wait I got my guy there is to say when you are on your way home from work I think you can ask yourself did I move something forward today.
And if you move something forward today then call it a win because you will never be able to get through your whole to-do list of moving things forward and yet that doesn’t mean it wasn’t a successful day and.

[9:33] And I think that sort of like really identification process that needs to happen I am a Creator but I’m not a creator of things I’m a creator of teams and Dynamics and successes and you know how human.
I don’t know pass when you when you can sort of like.
Evolve that in your mind you’re going to be in a much better place not only will you be more successful but you’ll be more fulfilled in the work of leading,
another thing that comes just quickly to mind also about mistakes is,
the ability to forgive yourself and be real about who you are ready maybe think that as soon as they get promoted into a layer of management or certainly on an exact team that you’re supposed to be the like trip PhD Super Black Diamond expert in like all things,
and that busted and that’s not real and you will get way further with your humans if you can admit that there are some things that you really really are very strong at,
and there’s other stuff that you’re kind of new at ever learning and the ability to make space for that and be vulnerable.
If you can’t do it people think you’re full of shit people think you’re not being authentic.

Christian Mccarrick:
[10:39] Yes but I am in those are two great points in the first one and we often hear people talk about you that the the feedback cycle for seeing a change or what your doing becomes longer is a manager.
Right if you’re if you’re waiting tables are your building something right that might be tangible you can hold it.
With the people it might take 3 months to know that you’ve made a difference or positive impact on someone’s lives or seen efficiency of your team bro.
It’s about patience to I found in and people who to work with their hands at they like that to get that feedback and it said to rush for them.

Jen Dary:
[11:13] Totally and also just to add the wrinkle to it just switching to a human currency the work really becomes.
I don’t know just the understanding that it’s it’s going to be heavy lifting that you can’t just put your headphones on,
and your music on for 3 hours that maybe every once awhile you get a stretch of that but pretty often it’s going to be meetings and you know hard conversations and giving feedback in hearing feedback all that kind of stuff and that will mean.
Particularly for a population who is more introverted which some verticals find that to be true that that’s going to be really,
like Harder by the end of today by 5 you’re going to be a lot more tired than maybe you were before and so that the self-care component become super relevant then to was as you move into this levels of leadership.

Christian Mccarrick:
[12:05] Absolutely absolutely the energy the energy demands are are are high dealing with people I like to hear you should have cautiously tiptoed around the certain verticals.

Jen Dary:
[12:20] Yeah it’s it’s funny because I I just did some work and advertising for the first time and the whole year do I sound like a survey ahead of time to sort of.
Have people self-identify in Fredericksburg.
And such a high percentage of introverts there and I was really shocked I don’t know why I just thought like all the Madmen space they’re all created you know I don’t know I just assumed.

Christian Mccarrick:
[12:46] Different going to like a sales conference where you can no one can stop talking.

Jen Dary:
[12:50] Where was also thinking I haven’t done this yet but like if I was invited to to go do this for room of teachers like I think my inherent.
What is a bias or Siri type would be that,
teachers must be extroverts if you’re interviewing your teacher like what you doing this is like you know from day one like you’re going be with humans all day long but maybe that’s not true you know I’m actually curious to see that.
My life one time to get in the room with teachers.

Christian Mccarrick:
[13:16] Yeah I know that that’s that’s the definition you think about know what do you.
You talk also about not only current managers but people that maybe are on the.
On the transition or they’re going to become a manager what kind of tips do you have to help people that you give to help prepare them to step into that manager role maybe before they’ve actually you know.

Jen Dary:
[13:39] I think there is a conflation that happens with.
Making progress in your career and managing so first I would call that out that by and large we believe that like the way to get forward and equally the way to make more money or you know,
present yourself as someone who has earned your career is to someday become a manager and that is not I think that’s pretty busted and that’s not.
True I think you can decide to Progressive,
way other ways that don’t involve managing humans like you can become a deep expert you can become a speaker who makes does the speaking circuit on certain things you know especially in something like check the facility to have like open source project,
side hustles already know whatever people want to talk about those sorts of things also deepen your career and experience and,
many companies are starting to realize that like oh the only way we move people forward should not be towards management cuz something is really that’s not there damn that’s not you’re not cut out for it and they won’t take joy from it,
so the first thing I would ask yourself is are you doing this because you’re really curious about the the work of management or are you doing this because you think somehow that sending the right social cues to your LinkedIn followers are like your mom you know.
But after that I would say just the same guidance that I would give to any other person who just started a new job your job for the first three weeks in a new situation is to listen.

[15:09] So you show up and you’re going to get way further again whether you’re,
it’s your first day as an Icee or an individual contributor or your first day as a new manager you’re going to listen and you want to listen to see what people are bringing up and what they’re not saying and you want to have.
Good in individual conversations with all the people on the team to show that I’m a person who’s here to listen to you and then act accordingly,
I’m not saying you cannot have a backbone to your plan or a Strategic Mission or anything like that but wherever you’re trying to go,
you need the buying of the people who are involved and and the only way you’re going to get that is if you can hear directly from them here’s the kind of person I am here’s what motivates me here’s what I’m.
I don’t know Jon to buy here’s what I’m skeptical of like all those things will come about in your first few weeks of one-on-ones with your team and soda start by listening and you know I often joke that like if you go into new job and you start.
I don’t know sidelining yourself with the loudest person in the room and really trying to get on their good side you have no idea whether that’s the person that everybody wants to be fired or not and so you’re kind of like I don’t know attach yourself to someone that you have not yet,
notice what the political situation is there or just a social situation so I can make sure you can read the room before you you know drive home.
Real fast with any any solid point.

Christian Mccarrick:
[16:36] Yeah and kind of answer to that what what would you describe as a manager’s role or is he had to go to narrow it down to what is a managers jobs in a company.

Jen Dary:
[16:51] That’s a good question cuz no one’s ever asked me that you went good job good job.

[17:01] Well I think I have two slightly different answers the first is to.
Guide and Coach people.
But that is a naive answer if it is not also somehow combined with the fact that the business must also survive.

[17:25] Feel like God coach people like cheers you should go be a coach then.
You have to do that work in service of keeping a business successful and a float and hopefully more than a float so to maybe also succeed in.

[17:43] Whatever the metrics are given to you as in terms of like your discipline or your department or or helping the company to exist and then within that goal.
Do you know.
Coaching and guiding the people because the people will tell you what they’re hungry to do and at a certain point you might say what you’re hungry to do is no longer what we need to do here so I’m going to help you gracefully depart right but.
But making sure that you have the resources lined up to enact the kind of success that the company wants at a higher level that feels very relevant.

Christian Mccarrick:
[18:15] And I really like the second part of that that answer because so many times I see.
In companies where it’s supposed to do a software engineering sometimes they get so far removed from the business and the.
The you know the consumers of the other product that it kind of a lose sight of why why they’re even there and they’re not there to get the free lunch or to work on an awesome piece of Coda low and I can give them the satisfaction but right if it companies not.
Doing well or doing business or being successful right you’re not helping anybody.

Jen Dary:
[18:49] Yeah and you’re a ticking time bomb and so is the rest of the thing I mean.

Christian Mccarrick:
[18:55] So far I thinking in this Ernest you with so much venture-capital everything around that a lot of UniFirst line and Engineers might be like well just get a new job but this one doesn’t work out and.
I think you over all these managers right we should also try to do a really good job is not better of.
Really showing and combining the mission in the value of the company and.
What we’re trying to accomplish with the employee’s tasks and like you say you know make sure they’re lying.

Jen Dary:
[19:26] Totally I I mean I was just talking to someone the other day who has just taken a new gig and is more senior in her leadership role and,
you know someone ask her if she’s daunted by some of the stuff she’s hearing about what’s going on internally wasn’t too bad but just like some you know classic to functions going on,
and I was like trying to reassure that person I was like if you have been around the block like you have worked somewhere,
like more than two or three somewheres you know that every place is going to have it stuff,
sometimes it’s really really really dysfunctional and you should never go work for those kinds of places but every place is going to have a certain percentage of I don’t know just like imperfection and,
person taking a senior role who is going to pretend that none of that exist that’s not your right fit you know there they had there going to be mature enough to show up and say yeah okay I know I know we got to work on X Y and Z where I hear you,
but that doesn’t mean that it’s not a job worth taking and the ability to discern that.
Of like is this Mission what I believe in and do I believe the leadership here are really trying their best and they need me to get us over the hump towards major success great or is this place.
You know really not on Rails and really not ethically where I need to be because when you think about it,
where kids all day there at school where are Delta all day they’re at work okay so like you get like 40 sometimes Plus hours of a place that you get to spend your energy every week.

[21:01] Make sure they deserve it make sure you are at a place that you feel.
Good and you can sleep well at night knowing that that’s where you’re giving your energy and if you can’t then go find a place that will and that will sell the hell out of you in the interview you know it’s like,
really start speaking to the end as a manager make short because especially managers who are not on the c-suite.
Does that excite you are in the middle right you’re like the messenger all the damn time you got a message stuff down streaming I messaged up,
Upstream just make sure that you know there’s enough support system in place for that to be worth it cuz the work is going to be wearing and and heavy,
so fulfilling when done well.

Christian Mccarrick:
[21:43] Yeah and I really again like to the point you make about.
Trusting kind of your gut Your Instinct about the values of your getting a tooth because I interview a lot of people on this podcast and I talked to a lot of people and frankly there are.
There’s more should shows out there then people think right to the grass isn’t always greener right but.
The important thing is it’s always going to be hard right and you shouldn’t try way from that hard work and you know might not even potentially be you don’t know it’s going to be successful or not.
The difference that you point out is.
Are they aligned ethically with you are they aligned with your values and that makes all the difference about you know going in and and feeling good about giving it all and really trying to help a company be successful.

Jen Dary:
[22:26] Absolutely and I also don’t think that everybody needs to like go quit and start nonprofits like that’s fine you don’t and I promise there’s sometimes mission-driven work that’s really fantastic but you don’t have to be like a sew-in Soul love with where you are but make sure it’s not,
bruising to your ethics to be there and then equally I think,
this is just sort of a large statement about careers but everywhere that you work will be a learning experience like,
again that’s your grown-up school right so you can ask yourself what do I want to learn while I’m at this place and sometimes the answer is oh my gosh it’s so small here that I’ll get to wear so many hats and other times the answer is holy cow it’s so big here that will only get to wear one hat and I’ll get to go deep on that hat you know and it just to be aware,
of what you’re setting yourself up for what you want to get out of this experience it will bring you very alive to work everyday because you will realize that,
you’re not just like clocking hours you are showing up,
to meet curriculum that’s going to be lost that you in every direction all day long and every moment every challenge for success is the opportunity to take something away from that and learn something and all of that you know when you zoom out is the,
building of a lifelong career.

Christian Mccarrick:
[23:37] And you’re not sick with little bit into something I’ve ever read about on your website when you talk about adult development what does that mean.

Jen Dary:
[23:47] So I was walking my car I was walking back from dropping my son off a few years ago at his daycare and I was thinking as I was walking back home like you know and,
when you’re a kid you are in the face of this thing called childhood development which at every age your parent or teacher is sort of checking you against a matrix behind you like okay is there this age can they skip their this age can they say 3-word sentences you know these are two things and then all of a sudden the strange thing happened where you turn 18 in,
dang Alright you’re done fully baked good luck out there you’re perfect now,
I think that’s pretty not true although I will say of course there’s no Matrix behind us we’re not on a,
age driven situation anymore it’s not like by the time you’re 25 you should have had this many breakups or eat or whatever in your life and I I started thinking about,
yeah plenty already existed but I was still stabbing in the dark a little bit about what the mission was underneath lucky like I was serving to hitting it but I didn’t have words for it and I,
I really thought okay I want to make this,
concept of adult development which is that you will be learning in and out of work doesn’t matter but after you are 18 years old and that all the experiences in your life that occur whether that’s having a baby or having triplets or having a medical situations in your life or divorce or married or whatever it happens to be,
that will affect you you will learn from that and.
And because my work happens to be in workplaces my adaptation for adult development then becomes something called employee development which is his concept of empowering adult development and workplaces say.

[25:23] Okay we all screwed up that push to prod what do we learn from it right the ability to extract learning from all these things and to make it okay to learn,
again not at the expense of taking the company but you know along the way finding micro lessons there and making space for it because I always sort of mention this as a tiny anecdote but.
Very early in my career you know before I was married have kids nothing I realize that the IT guy in our nonprofit office was about to his wife is about to have triplets from one day to the next.
Julian is going to be really tired,
next week when he comes to work but he still supposed to fix the printer and he still supposed to get this Richie’s good are you still supposed to do all the same stuff how unfair and strange that nobody has accounted for that right and.
Know what logistic Lee needs to be accounted but even if it’s just in the moment of giving Julian a little bit of a pass for a while because he’s probably really freaking tired that felt like,
the kind of workplace I wanted to work in and Empower with with my work with lucky.

Christian Mccarrick:
[26:24] Okay I think that’s one of the things that.
I kind of found online again was it brought a blog post you had written about managing Serta former friends and.
This is a topic comes up a lot especially when talking with new managers I haven’t surprising I should have talked about on my podcast before so I want to spend some time the rest of the show here discussing that right in.
You know what kind of Google is there some situation that you encountered where that cause you to sort of write that article.

Jen Dary:
[27:00] I think there was one but I I think.
I sometimes work with companies like something worthwhile to do something called an employee experience audit,
and that means I talk to everybody at the company for half an hour and then write a document afterwards for talent strategy going forward and what I would notice is some of the more.
I wasn’t even at Junior people that people who were a little bit past Junior would starts to be like a little bit flirting with this idea of maybe,
one day managing but there was a lot of like social pressure they were feeling to not.
Sometimes they would verbalize it as such but often they were kind of just venting feelings about it of this feeling of like selling out that oh you weren’t.
You weren’t you know on the on the sea or part of the team anymore you were at like you were the man now you know and I.
I understand that because I was early in my career for a while to but I also understand that like,
well every once in awhile it’s time to be a grown up you put your grown-up pants on and you come to work and you act as such and that you have no control over the emotional growth of other people around you,
so given that that in the moment when you feel compelled to leave,
or learn or evolved you should not be held back by whoever your social group happens to be in that moment and I would give that damn advice to people in high school or middle school or college or well beyond.

[28:31] Until I wrote yeah I wrote that article called how to manage your friends I think because,
I wanted to be reassuring for the people who knew there was a cost to pay who knew that there would be some people in their lives be the teammates or other people that company or sometimes honestly like family or friends outside of work who are skeptical of you changing Who You Are,
it’s like yeah man don’t worry let me know or Molasses for you it’s going to be hard but here are the reasons that you should do it if you’re compelled and how to stay sane you know continue in that vein,
any less you back question what do you think is hard about that.

[29:07] What would it what would your.

Christian Mccarrick:
[29:08] On the spot.

Jen Dary:
[29:08] Yeah Hey listen looks looks really do this podcast.
What’s Your Gut tell you.

Christian Mccarrick:
[29:14] What are the hardest things is always about the Friendship thing right and I think one of the things that I often see and it increases as you go higher and higher and companies.
It’s I think the first part when you become a manager when you first you first get the inkling of wow this is a little lonely.
Where you know I don’t I can’t.
Maybe go out to beers with these people and maybe have that camaraderie and maybe bitch about the manager anymore because no that’s me.
And I can’t talk about.
Salmonella I’m struggling because I know there’s an employee on the team that I just don’t know how to handle I can’t talk about that with my former friends like to talk about everything with right and those things.
And as all the other crap that goes along with like you know the passive aggression animosity the jealousy and you know all that stuff that people.
Unfortunately I said it does remind me of junior high or high school with how some of the Motions play out there.

Jen Dary:
[30:15] If I can just rip on that a little bit to me it is not unlike other transitions we making life so for example,
like I was one of the first ones of my group of friends to have a baby and all of a sudden.
What time are you starting to Birthday Party 9 p.m. go away I’m not going to your birthday party like come on man and that sort of again also morning sugar in on some level of like I’m not,
able to do those things man that is a real I don’t know spin cycle,
and so that you know it sometimes shows up when you when you go through some has nothing to do with work there there’s a parenting example or you know it’s other,
poison people’s lives taking taking care of their parents or taking care of family members who are unable to live on their own like those sort of things that are realities that show up responsibilities that are now on your plate and if the people,
previously new you are not able to sort of absorb you in a new way then,
too bad for them right like you you are still very valuable and sometimes life will give you the unexpected,
and you’re going to have to swim anyway so,
you know the ability to sort of side now this is something I’m really curious about I would like to move into management or Parenthood or whatever it is but it will mean that you and I talk differently I think the ability to hold two roles simultaneously,
is challenging but it is grown.

[31:45] And I ice it again like I have two little boys and you don’t my husband night we have to simultaneously be married people who are super into each other and also parents together and sometimes that is not the same,
you don’t think there’s there’s like a conflict there and we also want to be like,
business people who like totally Riff on cool brainstorm some stuff right and end in in those moments we need to serve brie clarify like hang out is this a conversation where you want to vent or you want feedback right like those sorts of things seem really explicit about what this conversation is can be helpful it’s awkward but guess what welcome to planet Earth.

Christian Mccarrick:
[32:20] Do it in your writing and sometimes you talk with his life changes and sometimes there by choice and sometimes they’re not and it could be illness health or financial situation changing and so they can’t go out to that expensive dinner that all your friends are going out to and it makes you feel bad as well.

Jen Dary:
[32:35] Great Point yes absolutely.

Christian Mccarrick:
[32:37] In that we kind of go through some of the different steps you have in an article I think the first thing you talk about is you call out you know call a spade a spade right.
Don’t beat around the bush.
Address of head on so what are some of the steps you would coach someone in this situation they get this promotion they come in on your the first day of the first week what should I do.

Jen Dary:
[33:01] Yeah so don’t like bringing a mug that says world’s best boss.
Okay my first rental guidance there.
I think I’m going to go in and depending on the climate of the in which you got promotion it is also possible that the hairiest version of this happened which is that you were up against several friends.
And you got it and then it’s like congratulations now you’re screwed socially right I think similar to the guidance I give a few minutes ago your first job is just sort of.
Listen in a way so I would pull aside who whoever your feels relevant to you in this situation so it looks like a close friend I pulled her aside and I would say Hey listen,
I I would I just to call the awkward here and say that I know this is going to get tricky right that I’m now somebody who is responsible for,
you know parts of your career and and you know just lay out a little bit of the job and to say I still really want us to be friends and there will be stuff that I won’t,
be on the table for me and you to talk through but as often as possible I just want you to know that I’m.
I really want us to evolve our relationship so that we can continue working together and great ways and also be friends outside of work and we will mess it up sometimes,
and we will need to like keep,
like editing it along the way but I just want you to know that I really like you and I I’m super like excited for this opportunity but also very self aware that this is you don’t going to get a little bit dicey so.

[34:37] I just want to say that now the recipient of that conversation your friend in the moment.
We don’t know how they’re going to receive it right they might be like oh my gosh you’re such a Class Act that’s amazing cool yes where at let’s have lunch on Friday will process your whole first week I’m going to buy you a glass of champagne,
and you know will it you’ll be off and running,
that’s the best-case scenario right where you also have many other scenarios where they like literally roll their eyes at you or they are just like okay cool like not glad to see you’re starting to read your management books or just some passive aggressive shit that comes out.
Because of other stuff that’s going on for them and in that moment you have to be the bigger person and you have to just say okay well,
again just reiterate I’m here like and I hope that we can navigate this and then let them go like don’t keep them in the conference room for like an hour.

[35:28] But what side this is a side conversation and let them go and what’s going on is that they are doing some level of morning as well and processing and.
Might be a little more immature about it than you are and you know your best bet there is then to give them you know a healthy leash of processing.

Christian Mccarrick:
[35:44] And like you said don’t keep them there because this conversation isn’t about you it’s about right so don’t do it at some way to just sit there and like ass ways your guilt because you got something in your there like you shut up now and just get me the hell out of his room.
And you’re like blah blah blah blah.

Jen Dary:
[35:59] Yes exactly I think you that you are there to communicate a message and then underscore the message and then let them leave you know.

Christian Mccarrick:
[36:06] Now there’s that there’s another interesting piece that potentially can happen to which I think needs to be dressed which is you might have a friend who’s.
Maybe you’re closer to one person on that team who was a Peter you get promoted and everyone knows you really good friends with them and they’re cool with it.
But now you have to watch that sort of nepotism saying right that yeah I know you know.
Christian and Johnny are really good friends and know how old is Johnny getting the good thing to do is you getting the promotion X-ray and navigating around that too is something that you have to realize that I think just call out specific.

Jen Dary:
[36:43] Absolutely I find the situation where so it’s sometimes in my coach and gigs I coach like,
three members of C sweet tea more or four members of leadership team or whatever that is right.
And in each of those conversations I may be hearing.
Problems or drama or dysfunctions or description about another person I coach right and I just always tell them from day one and then reminders as needed like.
Just so you know you can tell me all the all the stuff about what happened with you know this person I am a grown up,
and I still like them and I’m still going to coach them and I’m but like you are allowed to tell me all your stuff about them and then I’m going to help you Wade through it and equally if anything ever came up about you I would I would take that same,
track and so communicating like by the way I’m a grown up I’m able to see several perspectives on the same problem at the same time and to say you know that,
say that in in a meeting or in a one-on-one with the people that may be so skeptical of your ability to do that and then also.
Act accordingly so make sure you are not only calling on your best friend make sure you are not only giving the prize work to that person like you know make sure that you are being fair and hold yourself accountable to that.

Christian Mccarrick:
[37:59] And the next thing you should have call out to is identifying a role model for you know why is that important as you can step into that role from managing Staffing of the manager role sent for managing.

Jen Dary:
[38:13] So sometimes in the beginning of a workshop with me especially if I’m in a room with meters I have them go around and either see their name in a little bit about how many reports they have it went. But I also asked him to share a leader that they admire,
and I have heard many different answers his question question some people are dead some people are well alive some people are from Lord of the Rings,
sometimes I get a Jesus like I got a lot of different things including like my grandfather my mother my,
great aunt you know like those are two things and the important part of that question is not who they name but then I say oh interesting say more things and I wanted to explain why they chose that person and my belief Christian is that they are communicating to you a blueprint,
of the kind of human that they are and what they value and my secret theory is that that person whether it’s Jesus or their grandma that’s who they’re measuring their boss up against.
Everyday all day it’s not conscious but I think there’s parts of that so if somebody says you know I just really admire Obama because of his ability to,
you know share vision and speak inspiring words and that kind of stuff then you know somehow in their minds that they’re holding their boss against that and wondering why doesn’t my boss ever hold fission why doesn’t my boss ever inspire me like those are two things now,
as a boss of the manager you’re going to have less a five people on your team they all have different answers and that might feel slightly schizophrenic that you have to be both cheeses and Mother Teresa and Steve Jobs at the same time right,
but what I would say is that you just have to maybe like.

[39:46] Be aware of that when managing each of those individuals look like of this person this person wants me to talk to them about where the company is going,
versus this person just wants me to be nice and say hello and remember my kids name and just as a manager to be very self-aware about that.
Feels really relevant.
I did the other reason that’s helpful to you when you name that person is that whatever sticky situation you find yourself in as a manager you can ask yourself,
okay with my Uncle Bob do here.
Okay what Michelle Obama do here you know these sorts of moments because it helps you reframe the situation it takes the personal out of it and helps you sir and bring your why is this part of your brain to the answer.

Christian Mccarrick:
[40:31] No good great.
After that and I think you had a group appears you get promoted we talked about maybe you can’t do everything the same together again it’s something you talk about finding new peers right now how important is that in that Journey.

Jen Dary:
[40:47] I think it’s vital cuz,
teaser word from earlier it’s lonely it’s very lonely especially when you used to be part of like the NIT in group and now you are not and I find the higher up the chain you get in unless people are really doing a good job.
I don’t even know like quarterly offsides or whatever to create Team Dynamics on leadership team all you people are real busy and you got a lot of moving pieces and you don’t have a lot of time to build relationships with each other so,
I think you need to build a peer Network.
In an ideal sense some of which is internally where you are and that can be as simple as just going to somebody who also is a manager and say hey do you have time to grab a coffee next week,
I think you know now that I’m in this new role I think it’s I don’t know it’s just be good and help keep my sanity and check to talk to somebody who who is also a manager here.
And see who’s open for that right that you you are allowed to just go invite somebody to Coffee whenever you want to and so to start making inroads in that way but another reason that I.

[41:52] Think I don’t know if he was outside of work or helpful to which is a big part of this tonight your manager. I do is it helps to normalize it like you won’t get to,
in your own brain about like oh yeah this company I work for it’s just so hard here it’s so political and that’s the reason why managing is hard it’s like,
no you should also have someone ideally that you can have coffee with her lunch with her just see socially from time to time who’s the manager in some other place we can be like dude you think that’s a hard conversation let me tell you about.
I had to tell someone they got to wear deodorant the other day like you know like it’s funny and it makes it alive and human and and really.
Normalizing about whatever the heck is on your plate today.

Christian Mccarrick:
[42:31] Sure. Yeah that is true and you know .02.
In this happens I think in technology companies that person doesn’t necessarily also have to be a tech manager but I think.
Go to marketing you go to cells going to something else you could have again not a new people is not a new people right and don’t just look and be focused and I’ll pick in your in your possibly techmatic expand the boundaries.

Jen Dary:
[42:58] I think you don’t often people be like oh I just got promoted to manager what leadership books do you recommend and I’m like,
I don’t know man you should walk around a library and see what literally falls off the shelf at you then that’s the book you should read I’m not saying that there aren’t like.
I don’t know more healthy versions versus I don’t know why we’re not as well written things but generally you should be following what makes you curious and I don’t care what department that comes from and I don’t even care what industry that person wears for I,
I almost never read business books honestly I read memoirs,
which I really edifying to read very complicated hard thing some other human being did and then it gives you a lot of grounding on sort of where your your thing is that your path is that I have this random book I actually have it right here next my desk that I bring,
to all this anger management workshops and it’s going to be crazy maybe we can include the link in the show does but it’s called It’s called The Illuminator and.
It’s a kids book sort of it’s this giant book where they have overlaid like the,
was that called like RGB like all the three colors right like blue and red and purple,
blue red and yellow and on each page it’s like the like a different area of the worlds like the Andes mountains or another one is like the rainforest in any way they give you these little glasses to wear and the glasses one one,
pain when peeing is red one is green and then the third one is blue and.
Anyway what I’m driving out here is when you open this crazy looking page where you really can’t make heads or tails of anything if you look through the red it shows the animals that are awake during the day.

[44:36] If you look through the green it shows you all the plans and if you look to the blue it shows you the animals that are awake at night than nocturnal once and I bring this to manager trainings because I say,
this is your new world you got to move from the red pain,
to the green pain and that means that you can be looking at the same exact situation document meeting invite whatever it is as one of your individual contributors and you are seeing very different things,
and part of that is just to remind you that you used to be in their scenario and interpret things differently in another part of that is just like a welcome to a new level of.
You know ability to see further transparency without numbers how much stuff really costs like all that kind of thing and I don’t know that’s a really strange I don’t know what recommendation to give for leadership books or people in management,
but I think the metaphor is strong and just to have it around every once while I was really help.

Christian Mccarrick:
[45:28] No I think it’s it’s incredibly helpful and the seeing from a different perspectives as a manager becomes incredibly more important and it’s why I recommend people to read.
A ton and not necessarily just a nonfiction I think the whole.
Ability to resection in this week. And I was actually one of my Majors was English literature chewing tobacco later but it was.
You know it’s really about what they found that once people people who read a lot of special about fiction can just become more empathetic right it helps you to see into other people’s viewpoints on the people’s eyes and as a manager.
Thought about you have to do that right to put things in perspective probably yes awesome that’s an awesome book you know send it over to me and I’ll look it up and we’ll put in the show notes for I’m going to look at and I need to buy for my kids cuz it sounds pretty cool.

Jen Dary:
[46:19] Boom it’s great my kids are like why is this book I was in your room I like quiet I need it for my work.

Christian Mccarrick:
[46:24] So the last thing you talk about history of that article was stay in your lane and what is that mean you know it’s your manager now stay in your lane why did you do that.

Jen Dary:
[46:35] Well I think that I think that if you get moved into management odds are that you’re pretty smart.
And that you have the ability to see a lot of.
I know a lot of places to grow places to get feedback but I think it is really.

[46:58] Vital that you even though you may see what somebody else is department needs and what is messing up over there it is not in your best interest to go try to solve that for them cuz it’s not your job,
and all that’s going to happen is you’re going to create a fracture between you and the person who is leading that department,
now is there a spectrum here yeah for sure if it if there are literally running the thing into the ground then share that feedback upwards and and sideways to them as well,
but to know that keep your eyes on your lane keep your eyes on the the work that is in front of you and try to do the best you can with that,
and even though you might have great ideas about other departments you are not living the life over there you do not know if it’s the same thing as like walk Miles when she was right,
don’t know the challenges and victories that they have in front of them and so.
That feels important from a manager to manager stay in your own lane on a more like soul I don’t know human-level stay in your own lane,
you have no idea what happens during that person’s commute this morning what kind of text they got from their dad and you don’t know what your friend I think it’s in that context it was your friend,
what your friend is navigating or what’s triggering them or any of that kind of stuff and so just focus on how you are showing up to the conversation and.
That’s the best you have control over I want to teach workshops I often have this one slide and I slow that were shot down in that moment and I say if you take nothing else from this Workshop please take this.

[48:35] You are the energy sorry please cut this out in the show I want to be.

Christian Mccarrick:
[48:41] Okay okay.

Jen Dary:
[48:42] You are responsible for the energy you bring into a room and if you just set your brain on straight.
Then that’s the best that you can do and you show up to the room ready to go curious about the work you take care of yourself enough that you’re not.
I don’t know over waiting room with tragic regrets that you once had or whatever it is you just show up confident enough in your own lane and you go from there and if everybody did that I’m telling you question we would be like 88% more efficient in this world.

Christian Mccarrick:
[49:15] Call grid definitely see that you point out you’re all smart people and smart people like to self challenges but not every challenges yourself.
Is that can cause more problems than it did his Works absolutely one thing and I found this on you I said a while ago too and intrigue me.
And it’s it’s his card you have business lucky cards like.
Tell me about those like what are the what is the purpose of this plug-in card Spider-Man I haven’t seen them you know kind of what they are.

Jen Dary:
[49:46] Yeah so you know I’d like I said he’s almost 5 years old and I’ve done a lot of coaching last five years and sometimes,
a question with her just naturally come up in a conversation I was having with someone in a coaching call and it would really push the conversation to a point where somebody was starting to admit things that they hadn’t before or they were starting to see new I don’t know new opportunities,
and I be like oh my gosh still a question that said that ended up being such a good one steal. Take that to your one-on-ones this week with your reports,
and they would like get really quiet and shy and like I don’t know like here’s a good example of what is the hardest thing you’ve ever done in or out of work.
So that was a question that came up one time and I was like holy cow that was a good one like steal that guy and then take it next week so you’re what I want and people it’s like I mean I’m not Oprah Jen like what am I going to show up in the question.
Especially.
In like a vertical where as we’ve decided there’s a decent amount of introverts and you know people are certain navigating that identity problem anyway of just like how I get supposed to be more human oriented when it’s very draining for me,
anywho.
It started this happen all the time I believe you’re still a question be like I like kind of shy away from it sounds like okay this is really interesting we have a question that we know has proven out a good amount of self-awareness and growth we also.
Have the scenario that they are going to need to have that kind of conversation with five of their reports this week and yet there’s this Gap in it in the behavior and we can’t somehow overcome that and so I.

[51:25] Ice I thought a lot about that and I realized that what was missing was some sort of social proof,
wake me up Billy Dee to say that question without being like without worrying that somebody’s interpretation of that was like.

Christian Mccarrick:
[51:40] YouTube Jerry Springer what’s going on.

Jen Dary:
[51:42] Yeah. Like if I show up and I’m just like asses hard question would normally I’m saying like how’s the budget has a deadline then then then the the prison.
Did you just like Rita business.
Right like they’re going to.

Christian Mccarrick:
[51:56] Autumn eagle.

Jen Dary:
[51:56] Exactly they’re going to cut through it and so I thought okay cuz sometimes it’s able just just blame me just like I had his lady Jenna was just talking to ask me a question and I kind of want to try with you that seems to get over it but I wanted them to have some candles so anyway,
I took 48 of the questions that I felt like we’re the most,
interesting and I had my designer design a pack of cards they’re like big.
Surly flash card size cards and I need questions or needs card is a question and still in this way what you can do as you can walk into the room you’ve fan out a few of the cars and say okay pull the card and that’s the question we’ll talk about it and suddenly,
it’s the cards fault you’re talking about it it’s not yours right and.
So if you pull that card and it says you know what the hardest thing you’ve ever done in or out of work and I think you would like oh that’s a good one alright when you go first what’s your answer and then I’ll go right and it creates this space this like third party this neutral.
Entity of sorts that allows the question to be asked in the room and they wanted to ask,
you’re good you going to go and have that conversation and my belief is that once you do it like four or five or six times people then start to associate you with the kind of person that could ask that sort of question and then you know maybe that’s like a much easier battle but regardless.
It’s called a one-on-one starter pack and I sell it on my website and it has been so amazing Christian I like a very personal level to imagine how many conversations are being possible,
because of these cards right now all around the world that people buy them all around the world and I think it’s so great I think it sends a cutie reports that.

[53:30] I’m a person who doesn’t know it all and I’m still looking for Cool Tools to mess around with so let’s get some Plucky cars let’s see what that does for us you know.

Christian Mccarrick:
[53:38] Well awesome I’ve been tempted to pull the trigger on the myself for myself my managers and I just go ahead and do that because I really do think it’s.
Sing idea so great.
Final kind of coming around here I asked my gas so I know you don’t miss a record you mention before you mentioned one book specifically that you put in the show notes anything else any kind of other resources you might recommend managers out there.
Or talks workshops blog Ted to anything that that you might you know or or even just that something interesting that you’ve read recently that hey that made an impact on me.

Jen Dary:
[54:12] Well I’m always a huge fan of brene brown and her work and her TED Talks.

[54:17] Rising strong as one of her books daring greatly I also.

[54:24] Pipe it enters like podcast and stuff I mean I really do think you should listen to the stuff that is fascinating for you so late,
it’s not a podcast but it’s making me think I would like I read a book to have it right here but it’s a memoir of this guy Mike Massimo I think it’s the name he was astronaut you work for NASA like,
mad Memoir did big things for my career you last year when I reddix today I start thinking like Jesus will everything that feels hard for me right now well it’s not like Landing of Rover,
somewhere.
Yeah I’m perfect exactly and a podcast that I listen to every once in a while which is helpful in the business context I think of something else how I built this.
And it’s more from an entrepreneurial spin but I think.
Maybe I’ll show that every once in awhile when I’m at a Crossroads in Plucky work and I’m trying to think about what to do next and it is like kind of challenging,
I always think oh one day when the interview me on how I built this this will be the moment when I say like you know nothing way back in the early days this was happening,
you know and so I try to think of whatever my problem is today is something that will be the well Sally you’ll never believe this you don’t like in a podcast 10 years from now or whatever when things have really taken off I think it helps to.
Provide perspective on those moments too.

Christian Mccarrick:
[55:48] Perfect and I know you have a couple workshops coming up there’s one super soon I think in Oakland and then there’s anyone be on that if you want to give me a kind of listeners Maybe.

Jen Dary:
[55:59] Yeah Oakland is pretty like two tickets left that’s pretty sold out for next week but if anyone is very fast on the trigger come on over and the next one so now your manager number 5 is going to be in Dayton Ohio in August August 16th 17,
you should definitely come for that because I feel very strongly that,
great conferences should not only exist in our assumed San Francisco New York mines but should go everywhere and when a friend of mine offered me space to hold,
one of the snow your manager where shops there I was like yeah,
sure I’ll come to Dayton Ohio let’s do this and you know getting people to move for that kind of education it provides a really good perspective in the room too so of course I’ll be some locals but it will also be some people coming from other places and I’ll do another one key for but I haven’t totally decided on which city yet.

Christian Mccarrick:
[56:44] Okay well perfect and so people can find you online and Plucky want to see if you can go ahead and just get my listeners I will put on the show newest but just going to go out and install out for my listeners the best ways to get in contact with you.

Jen Dary:
[56:57] So my website is beep lucky.com b e p l u c k y. Com and on Twitter you can look for beep lucky or you can also look for Jennifer,
Dary Dary I’m on Twitter their Instagram to I had to pick up lexter.
Because before he was taken but that is fine still valid you look you’ll see the pee with the lightning bolts that’s how you’ll know it’s me.

Christian Mccarrick:
[57:22] Okay well Jen had a great time in our conversation this morning I really appreciate you coming on the show and then thank you very much.

Jen Dary:
[57:29] Same no problem thank you so much Chris.

Christian Mccarrick:
[57:31] Okay bye.

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