Be Curious, with Jim Bartolomea – Episode 441 of The Action Catalyst Podcast

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?”

About Jim:

Jim Bartolomea is SVP and Global Head of People and Places at ClickUp. In his role, Jim is responsible for leading Clickup’s overall people strategy including global talent acquisition, people development, DEI, organizational design, total rewards, people operations and technology, employee experience, and facilities. Jim and his team’s work support ClickUp’s business goals, culture, and strategies as well as the needs of its nearly 1,000 employees around the world. In his previous role as VP of People at ServiceNow during a period of hyper growth, Jim led the people strategy for 11,000+ of the company’s solutions, I.T., engineering, product, and design professionals. In addition, he had oversight of the company’s global ER function and HR compliance team. Prior to ServiceNow, Jim was Head of People at Mitek Systems (Nasdaq: MITK), and spent 10 years at Qualcomm in a variety of HR roles. Jim holds a Bachelor’s in Science from Penn State University in Management HR and Strategic HR certification from Cornell.

Learn more at Clickup.com.

The Action Catalyst is presented by the Southwestern Family of Companies. With each episode, the podcast features some of the nation’s top thought leaders and experts, sharing meaningful tips and advice. Learn more at TheActionCatalyst.com, subscribe below or wherever you listen to podcasts, and be sure to leave a rating and review!

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(Transcribed using A.I. / May include errors):

Adam Outland
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?

Jim Bartolomea
San Diego, California.

Adam Outland
Did you grew up in San Diego or did you relocate there?

Jim Bartolomea
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.

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

Jim Bartolomea
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.

Adam Outland
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?

Jim Bartolomea
It really is an oasis in the middle of nothing.

Adam Outland
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.

Jim Bartolomea
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.

Adam Outland
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?

Jim Bartolomea
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.

Adam Outland
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.

Jim Bartolomea
I tell people all the time like my mom, don’t cross her. But my dad was a softie.

Adam Outland
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?

Jim Bartolomea
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.

Adam Outland
And then ServiceNow and then Click Up.

Jim Bartolomea
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.

Adam Outland
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.

Jim Bartolomea
I do. Leave of absences might be the most complicated thing in all of what I do.

Adam Outland
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?

Jim Bartolomea
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.

Adam Outland
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?

Jim Bartolomea
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.

Adam Outland
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.

Jim Bartolomea
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.

Adam Outland
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.

Jim Bartolomea
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.

Adam Outland
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.

Jim Bartolomea
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.

Adam Outland
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.

Jim Bartolomea
Did you just drop a Ted Lasso reference?

Adam Outland
It’s all in my head now. It’s just baked in after watching the episode.

Jim Bartolomea
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.

Adam Outland
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?

Jim Bartolomea
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.

Adam Outland
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.

Jim Bartolomea
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.

Adam Outland
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?

Jim Bartolomea
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.

Adam Outland
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?

Jim Bartolomea
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.

Adam Outland
And for listeners Bard is…

Jim Bartolomea
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.

Adam Outland
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?

Jim Bartolomea
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.

Adam Outland
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.

Jim Bartolomea
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.

Adam Outland
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?

Jim Bartolomea
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.

Adam Outland
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.

Jim Bartolomea
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.

Adam Outland
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?

Jim Bartolomea
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.

Adam Outland
Well, thanks for joining us, Jim. This has been great.

Jim Bartolomea
This has been awesome. Thank you so much for having me.