Jim Bartolomea, SVP and Global Head of People and Places at ClickUp, talks about his "softie", Broadway-loving, military father, creating a benefits program that drives retention, why letting people go in a beautiful way is hugely important to remaining employees, why people leave managers, not jobs, conducting "stay" rather than "exit" interviews, having confidence in NOT knowing everything, the value of new AI tools like Bard and ChatGPT in the HR world, leadership lessons from Ted Lasso, and how you’ll ALWAYS make the right choice if you just ask yourself "Is it the RIGHT thing to do?"

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Welcome, Action Catalyst listeners! Today we

have Jim Bartolomea as our guest. Jim has worked at some

of the biggest tech companies in California, including Qualcomm,

ServiceNow, and currently, Jim is SVP and Global Head of People

and Places at ClickUp, the “one productivity app to replace them

all”, leading all aspects of Human Resources for the software

company. Jim, welcome to the show. Where are you zooming in

from?

San Diego, California.

Did you grew up in San Diego or did you relocate

there?

I relocated, but funny enough, all my siblings,

I'm the youngest of four. All my siblings were born here. My

father was a Marine Corps Colonel. So he was stationed out

in San Diego at the time. So I have roots here. And in fact,

when I graduated college, both my sister and my brother lived

out here.

But where did you grow up then? If not San Diego?

Virginia and Pennsylvania, Virginia Beach,

which again, actually we were in DC first because he was at the

Pentagon and then Virginia Beach is a huge Norfolk's a big

military town. So kind of, you know, wherever, wherever the the

Marine Corps takes you is what you live by. Oh, yeah. Yeah. And

then actually, his final stop was really interestingly, was to

run the ROTC at Penn State University. And so we ended up

in the middle of Pennsylvania. That is where I graduated high

school and went to college.

Wow. Yeah. So you're, I mean, you're among the

pastures and the fields before you arrive at this massive

school in the middle of nowhere, right?

It really is an oasis in the middle of nothing.

One thing I was curious about with your

upbringing is if sometimes they jump around a lot, and schools,

you're forced to have to create new friendships over and over

and over again, and you feel like part of your development as

an individual and your ability to communicate and relate and

empathize when you feel like that was part of that for you.

And your journey was creating these new relationships every

time you guys moved.

1,000% I actually have said, As hard as

it is on kids to move like we did. And by the way, my siblings

had it worse than me, the flexibility and adaptability

and, you know, kind of my what I say my ability to roll with the

punches in my career. I think really, I can attribute a lot of

that to like, yeah, new situations, new people, you've

just got to roll with it. It became a little bit innate at

some point.

Yeah, for sure. Yeah, that makes sense. And so

growing up with a dad in the military, what was it like

growing up in a household is just very discipline strict? Was

it like more creative?

You're gonna hear a lot about my father on

this podcast. I'm not gonna lie to you. He's, he's my North

Star. He was a softy and my mom the CPA chemistry teacher, you

know, chemistry teacher, then a CPA. She was the disciplinarian.

She is the one I couldn't get away with anything on. My father

was, yeah, just a, a study in contrasts. Listened to Phantom

of the Opera. If you got in his car, you hear quite a bit of

Broadway and things of that nature.

Awesome. Yeah. I love that. That's great. So you

still got both sides, just counter to what you would have

thought from the outside.

I tell people all the time like my mom, don't

cross her. But my dad was a softie.

It's so interesting, because now your

title is Global Head of people in places, right? So growing up

in high school and State College? I mean, were you

thinking man, I can't wait to be head of people for a company?

What was going through your head as what you wanted to do

directionally?

Absolutely not, actually had a long time where I

wanted to be a meteorologist. When you're on the East Coast,

you watch the weather all the time. I don't even watch the

weather here. So I had this dream of becoming a

meteorologist. But actually, I tore my ACL playing football, my

senior year of high school. And I fell in love with the physical

therapy process to the point where I went to college and

started as a biology major, but could not hack the chemistry.

And I was like, Oh, I'm not going to get into PT school, am

I and all of a sudden, just like probably everybody else, you

stumble into your career, I went over to the College of Business,

took on a management major. And eventually through the job I was

doing, I had all these interest in the HR parts of my job, and I

took on a human resources minor, you kind of rechart the pivots

in your life. And that was an interesting one. And it was

coupled with a cousin of my best friend who was a corporate

recruiter at a semiconductor company. He made the comment I

remember I was a junior in college, I was out visiting, and

he's like, You should be a recruiter. You can make great

money and it's a fun career. And you do well talking to people.

Yeah, I've done a lot of the other like HR admin stuff like

scheduling and payroll and stuff like that through the recruiting

part. Yeah, you kind of do that. But I was like, Wait, there's a

whole career where you just recruit for companies. So I came

out of college packed up the car arrive the day after the Super

Bowl in San Diego, the last Super Bowl in San Diego, found a

recruiting agency recruiting traveling nurses Believe it or

not, yeah, ultimately ended at a tech recruiting firm. Remember

that same recruiter I referenced back when I met in college, he

made an intro to a hiring director, recruiting director at

quality comp, which at the time was the place to work in San

Diego and it's still the largest public company in San Diego by

some some measure. And probably before I was even ready, I

started my my kind of corporate life non agency recruitment life

as a corporate recruiter.

And then ServiceNow and then Click Up.

Yea, it was my tech after ServiceNow where I

let I lead people and then ServiceNow was an unbelievable

four year run, also a San Diego founded company. And now click

up and the big thread you can pull through all of that, as

I've tried very hard to stay in San Diego.

Okay, I found that to be a common trait in San

Diegans. They like to stay put if they can, right. So yeah, in

my exposure to your current role has actually been as an

executive coach, we work with HR, sometimes they'll bring us

in to do leadership trainings. And also a lot of my clients

tend to be in the benefits industry on the benefit side. So

right ADL absence life disability, and I'm sure that

you end up in that decision making process pretty often.

I do. Leave of absences might be the most

complicated thing in all of what I do.

We have a lot of business owners that dial into

this podcast of all sizes, benefits, that's a big part of

hrs job. It's a big differentiating factor when

someone's looking for employment. And so how do you

what's your take on benefits? What's tended to matter more in

this generation right now, since you work with so many people?

Yeah, I actually, you hit it on that on

the head there, Adam. I've actually said many times, like,

you know, people will start with focus on what do you pay, but

ultimately, for most people at a certain stage of their life or

their career, it's going to come back to what kind of benefits do

you offer. And that's a real signal of the type of care and

investment you make in your people. And I will say that

pendulum goes up tilts towards as you go up in age, because

generally people start having families and have more things to

care for, on the newer grads side, or the more junior side,

that's aren't always as important just because they

probably don't know the importance of having a great

benefit program. So the evolution I have seen here,

though, and the evolution I really want to be a part of

building at this company is this idea of choice. So I talked

about, like, different people have different needs, when it

comes to benefits? And how do you create programs where people

can actually select the things that mean the most to them. So

if you're a family of four, having a program where you know,

there's minimal content, employee contributions to cover

your entire family, that's probably the most important

thing to you. But if you're a young single person, you might

index to things like professional development, money,

or things of that nature. So how do you and I haven't cracked the

code on this? But how do you look at it holistically, and

say, We want to invest X in all of our employees kind of

equally, but they have a menu they can choose from in terms of

the benefits, it's really hard to operationalize. But I think

that is where we're going to head. And I think, especially

with this, this current generation is coming out of

school, professional development and personal development. And

even travel is like a very important thing to them, I don't

see why we can't include that and benefits, where we're at now

is actually offering up programs that everyone can have a little

more choice in terms of how they apply that benefit. So for

instance, we just have a general wellness benefit for our

employees, it's just $500 per year. But Adam, if you're a

golfer, you could actually use that for a golf club. But if

you're a yogi, you can use that for yoga classes. And we keep

the definition of what wellness is pretty broad. And so our

employees are able to choose what works for them. And so

we're doing programs like that, or professional development

budget and things of that nature. And what I really do

want to get to, though, is that this idea that there's a certain

amount, we're going to invest in our employees from a benefits

perspective, and they're going to have a way to actually almost

spend that in a way that works best for them.

Yeah, okay. I love that. So zoom out for me for

just because we just went really deep on one side of your job,

but if we talk about global head of people, for people that don't

really know, what does that job even mean and look like?

Every day, it means something different. But

let me let me start at the highest level, which is this

thing I've said for a long time, in terms of the seat, I said it

is my job is to align the people strategy to the business

strategy, right? And so how are we doing things that accelerate

and support what we want to ultimately achieve from a

business perspective? So when I talk about benefits, really,

what are you trying to achieve? There? You're trying to achieve

care and feeding of your employees so you can retain

them, right? So that's the business strategy is you want to

retain good people. So that's why you spend time on benefits.

But my job is so varied. And probably the reason I gravitated

to this every day can look very different. So for instance,

let's say today, a senior leader gave notice, yeah, my whole day

is going to be figuring out how and when are we going to change

manage this with the organization? Who are we letting

know now when are we messaging it? What's the message itself?

Is this a good thing or a bad thing? Like that would be my day

and days probably. So there's an example of how it could go that

way. You know, and of course, there's days where I'm just

doing Like the core aspects of the job, like, what's our

strategy? Are people technology people systems? Are we

attracting the right candidates? You know, there's core parts of

the job, the toughest part of the job when you're letting

people go, how do you do that in a really humane and beautiful

way so that the reality of this situation is, every company's

gonna have people who aren't a great fit. But I always say how

you treat those people on the way out with the exception to

that like point 5%, I can count on one hand, it's just like they

deserve what is coming to them. 99.5% of people, those are

people with a family, people who have a mortgage, people who have

relationships and connections with your other employees,

treating them well, and humanely or beautifully, whatever you

want to call it is actually a really important consideration

to my job. I spend time there too. So I'm saying a lot of

words to say that I love my job because it's so varied. But the

last piece I would say spend most of my time on is making

sure our executive team is aligned. And we are all rowing

in the same direction. Yeah, you're a bit of a consigliere

very certainly to the CEO, who's my boss, but just as much to

your peers as well, because they have you thought about this, you

really do sit in a seat that change management is a big part

of what you do. And sometimes you can offer a lot of advice

there, take it or leave it right. I do view HR is like

great legal counsel, like here's my counsel, do what you want to

do, you're still the business leader, unless, of course,

they're going to do something to get us in trouble.

And you've stopped them. But you know, you don't

build a company, you build people, and people build the

business. And so the education that you infuse, having a plan

and a program in place, I think it ends up being a critical part

of how businesses keep and retain people and grow and

develop those people into being successful. Just regular

conversations about career progression won't necessarily

send your talent elsewhere, that will help you retain it. This is

something that you talk about.

It sounds so simple, because it is it's human

nature, right, which is like people want to stay somewhere

where they feel like they're being invested in and they're

growing. And so helping our managers understand that that's

an important part of their job is something that we are always

preaching here. And we've we've operationalized it right. So we

have what we call quarterly growth conversations. So that

we're, you know, there's a mechanism that both employees

and managers know these conversations should be

happening. But yeah, I mean, it really does come down to people

generally leave managers, right? And so how do you make sure that

those managers are showing those people, they're invested in

their growth invested in their development, and you'll hang on

to people for longer. And that's our goal.

Yeah, someone will come in, especially a young

person will come and join your company. Maybe they're you're

not as competitive on the dollar rate today, but they can see a

pathway to leadership, a pathway to more responsibility, and that

can override competitive pay, right.

And actually, the other thing that we preach

to managers is find out what motivates your employees, right.

So you might have an employee who you know, is independently

wealthy but chooses to work anyway. They might not care

about the money, they might just care about the promotion, or

that they're learning a new thing or so really personalizing

it, and individualizing leadership, that's an important

thing we preach as well.

Yeah. Understand your people and what what makes

them tick. That's huge. Something you said earlier that

I feel like you'd have some perspective on as well. And you

could speak to this more as the age of quiet quitting. And what

that means.

Can I tell you, my, this isn't a hot take. I

think I've heard a bunch of people say this, but they used

to call quiet, quitting resting investing, right, which to me is

pretty much the same thing, which is, you've got an employee

who's disengaged, why are they disengaged? Probably because

you're not invested in their growth and development. Right?

Or, perhaps it's that your work environment is not one that you

know, is resonating with that particular individual. And so

for me, it's like, Look, if you've got someone who's quite

quitting, it should be pretty easy to figure out why that is,

right. So if you're sensing an employee is withdrawn, and maybe

not giving the effort that they used to, because at some point,

almost every employee is joining an organization and is giving

their all but if you sense that have those interviews, we call

them stay interviews. I'm sure you've heard the book, love them

or lose them. No, you know, one of the core things in that book

is like this idea of a stay interview, which is what do we

need to do to keep you here? How are you motivated? You know,

where do you want to grow? Kind of go back to the conversation

we were having before. And I think if you're having those

types of conversations, you're gonna avoid a lot of quiet

quitting.

Simple, great advice and I think, you know,

something I'm hearing that might be a principle of yours is

having an investigative attitude. I mean, I feel like

every time we've talked about something in this interview,

you've come back to ask better questions of your employees know

them better. Be curious. I mean, it seems to be a general theme.

Did you just drop a Ted Lasso reference?

It's all in my head now. It's just baked in

after watching the episode.

So the be curious episode. And by the way,

Ted lasso is a show about leadership and how to treat

people it's not a show about football or soccer or whatever

you want to call it. But yeah, I mean, yes, ultimately, and you

know, I have a team I lead to right ultimately it comes down

to like Asking the right questions, understanding

people's motivations and trying to align their wants and needs

with what you need in your business. That's not always

possible, by the way. So some of the harder conversations I

probably had in my career are, it's probably isn't the place

you want to be then Right? Because I don't I don't know

that I can give you what you're looking for. Yeah. But you know,

being investigative, like you said, and asking the questions

and really understanding your people. Let's quarter

leadership. Now be curious. Again, I could watch, I'm gonna

go watch that scene right after this, because it is just a

brilliant, brilliant scene.

Yeah. It's amazing how those things get stuck in

your head after watching TV. Right now you oversee roughly

about 1000 or so employees? Right? There's got to be some of

the challenges that you faced growing into this position.

Personally, you know, what would have been some of those those

pivot points for you?

Yeah, I'll start with like the transition into

management, which I think is going to resonate with almost

everybody is this idea that you need to empower others to get

things done, rather than doing them yourself is actually a

really hard transition, especially for high achievers.

Right. So you know, I think back to that inflection point, and

the stumbles I had, they're staying out of people's way

helping helping where they need help, but staying out of their

way and granting autonomy. Like that was bumpy time. Like, you

know, you I think leadership is innate to some people. And that

transition happens quicker. But anybody who is a great performer

heading into management, that's a tougher transition than

probably we remember the biggest transition for me and going back

to your question, you know, when I left ServiceNow, there was

about 11,000 employees and organizations I had to remit on,

it was an enormous job with so many stakeholders and things

like that. And you get impostor syndrome, which I'm sure a lot

of people talk about on this podcast, it's a it's a real

thing. It's like, do I belong? At this level? These people are

brilliant, you ask yourself those questions. And it takes

time to grow past that, what I think my biggest learning there

was, was this idea of, I don't have to know everything, Mike, I

remember, you know, making a conscious decision to saying in

front of the CEO president, like, you know, I don't know

that answer. Let me get back to you. And let me talk to my team

and get you a good answer. Right. Whereas probably earlier

in my career, I would have been like stumbling over my words,

but like having confidence and not knowing everything, as a

leader who has such a broad remit now with our 1000

employees where I am not like, there are plenty of times where

I don't have the answer for my CEO. And it's like, Hey, let me

get get back to you with a really good answer. But in in

the same way, I do feel like I also learned how to know enough

to be dangerous in all the areas I oversaw. So it was this idea

of going a mile wide, and an inch deep became a really

important part of my job as well. And how I spent my time

and where I spent my time helped me, but I will tell you for for

some amount of time going into that job every day is so much

and again, coming back to the imposter things like no one else

in this role probably feels that way. And they're no but then you

talk to them. Like the nice part about our job, Adam is we talk

to leaders, and like the people who you would think have zero

doubts about themselves, just zero cats, right? They're the

most self assured person in a meeting. They're always saying

brilliant things, they have those same insecurities and

doubts, and if they don't the probably narcissists, and stay

away.

Yeah. Understood. No, I think that's really what

you said, as well about knowing just enough information to be

able to communicate with that department within the

department, right? Like you need to know enough to speak the

language. You're not expected to go super deep and be the expert

on everything is it's, it's impossible.

Well, that's why you have an organization, right?

Because there are subject matter experts that know everything.

And yeah, you got to be knowledgeable enough to have an

opinion or say, Hey, I don't know. So anyway, I that's a long

winded learning, but it is truly been my biggest leadership

learning.

That's great. You know, in this pathway, I guess

what, what would you give 21 year old? What kind of advice

Jim, would you provide yourself around that age? Now, having

made this journey?

You know, part of me wants to say you are who

you are, because you acted the way you did. But if I had to go

back there, honestly, it would it would truly be adopting some

of my father's life lessons earlier. I think I referenced

earlier, you know, he passed away about five years ago. And

he always had this decision making framework he placed on

everything, which is it ended with, is that the right thing to

do? Right. And I felt like that it served me so well in my

career. And now that I've just adopted it as like, we have a

lot of legal and compliance and so many things in my job where

it's like God, you can can paralyze yourself with Oh, are

we going to get in trouble? But then I apply the simple lens of

especially when it comes to the people we deal with, is it the

right thing to do and that usually solves all problems and

I think 21 year old Jim should You've heard that message

earlier, because it allows you to operate with probably a

better compass. It's great. I heard it from him all those

years, but it probably didn't hurt analyze it until I got a

little older.

That's right. Well, it was probably also on an

episode of Ted Lasso. And I think we overcomplicate

decisions sometimes. And something that's a simple

filter, which is Yeah, is the right thing can take a lot of

the complexity out and make it what it should be, which is a

simple a simple decision, even if it's one that hurts a little

bit in the short term. 100%. Yep. Yeah, this is really great

conversation, I guess, kind of quick lightning round questions

that we'd like to ask. Any like functional app that you've used

on your phone lately, that's been helpful for you or others?

I mean, doesn't have to be on my phone. I mean,

I truly have dove into Bard and GPT. I use them quite

frequently. They are incredible productivity tools. And I think

as long as we continue to remind ourselves that the outputs of

those things are imperfect, and it needs a human to make it

good. They are great things for us. And for our teams. You hear

GPT all the time, but I'm actually really impressed with

Bard, it's really good from like an answering question

perspective.

And for listeners Bard is...

Yeah, Google's large language model, better in

some ways, different in some ways, you know, for answers, I

go to Bard. And I think that's no surprise given that Google's

been indexing the world's information for 20 plus years,

right? For creativity, which is actually a big part of my job

and a starting point on how to frame a message. I enjoy GPT.

Here's another quick one, and take a minute if

you need to think about this, but define what success means to

you, because everybody has a little bit of a different

definition of what a successful life means or what success means

in general. And how do you know when you've achieved it?

Success for me is to be respected. My job is

one where I am sometimes sometimes having to make

decisions that are going to be unpopular, but am I doing them

fairly and consistently? And, you know, again, kind of putting

the human first and asking that, is it the right thing to do

question? If people can at least respect my decisions, then I'm

okay with them not agreeing.

Incredibly difficult for many of us to

change the our intake of that and say, okay, I'm okay, if I'm

not liked by everybody, because no one can be right. But you can

earn people's respect, right? And being respected versus

always being liked is probably a little bit more of an effective

way of showing up.

And especially if you're a StrengthsFinder

person as I am, I have who in there. So it's hard for me not

to be liked. But I have finally gotten to the point where it's

like, to be respected is is better than like, although I

want to be like to I'm not gonna lie.

Everybody does. Yeah, I think to a degree most

people do. But yeah, but that's a great, that's a great

definition for success. So one habit or practice that saves you

the most time each day?

I block my calendar to do actual work and

eat, by the way, because I really do need to reach arch.

But I actually blocked my calendar conscientiously, to

make sure that I have space and time to give thoughtful replies

to people, not three letter thanks, right? That's been a big

thing for me, or I always feel like I'm behind.

And you literally block it? So the assistant or

someone can't look at your outlook and go, Oh, I'm just

gonna squeeze this in there.

Well, they know that that's a really important

time for me. So I have an hour that says focus every day. And

unless there's a really big, you know, an executive leaving

coming back to that, like, unless there's a fire drill, I'm

going to get that time and I'm going to use it to hopefully,

get back to people too. And I do think it's important as a leader

to be available and responsive. And I pride myself on that.

Absolutely. But I think there's value also be able

to close your door for a minute and then be able to focus so

that's good. This has been great in any direction you want to

send people?

Actually they should come to the ClickUp

website. I think people will be surprised that no matter what

business you are in how big or small your company is, a cup is

an incredibly powerful tool to unlock productivity. That's what

we do.

Well, thanks for joining us, Jim. This has been

great.

This has been awesome. Thank you so much for