Company Culture & Values

How To Develop and Infuse Generosity Into Your Company Culture

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We talked with Bob about:

  • His personal and professional experiences with generosity
  • What generosity and collaboration mean and how they impact your team
  • Real tips that can improve your company culture overnight
  • How to authentically communicate what your culture looks and feels like

About Bob DePasquale

Bob DePasquale, aka “The Generosity Guy,” is a broadcaster turned financial planner and passionate advocate for the power of generosity in building strong company cultures. He advocates for the implementation of programs and systems that empower individuals to use their skills and talents for the collective good. Bob believes fulfillment comes from contributing meaningfully to a shared cause. With his commitment to promoting generosity, he inspires individuals and organizations to unleash their full potential and create a ripple effect that positively impacts the world. 


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Full Audio Transcript

Lauren (00:05):

Thanks for being here.

Bob (00:07):

Glad to, Lauren. How are you today?

Lauren (00:09):

Yeah, I'm good. It's really fun. I know we chatted before, and of course LinkedIn is this awesome place, so it's been fun to chat with you there. And I think I'm not just here about your passion with this idea of generosity — we'll get into that more — but I really appreciate all the content you put out. You're not just kind of preaching to the choir but you're hoping to educate people about what it actually means to be generous, and how that impacts company culture in your day to day. And we'll get into more of that. But just for folks who aren't familiar, I'll let you do an intro. I mean, you are a keynote speaker. You talk a lot on this topic, give a variety of presentations. I know you've got a rich experience in financial services and it's more of your day to day. But before we get into it, I don't want to steal away your thunder but why don't you share a little bit of background about yourself, and then I’d also love to hear more about how it's taken a bend to be a bit more on the generosity focus. So over to you.

Bob (01:09):

Sure. Thanks for giving me the floor. I'm going to try something new on you and the guests because someone asked me on LinkedIn actually the other day, how we connected, and they said, so what do you do with your life? The way they worded the question was kind of intense. I mean, not insulting by any means, but I was like, oh, I never really heard it proposed that way, if you will. And I said, all right, well, I had a minute to think about it because it wasn't a live conversation. It was on LinkedIn. So how am I going to respond to this? So I came up with this: I'm a broadcaster by education, I'm a financial planner by profession but I am a generosity guy or The Generosity Guy by passion. And so when you talk about the things I do, and I appreciate the compliment, by the way, with the actionable items on the content, because I believe that's really, really important with what I'm doing, and maybe I'm biased but I would argue the most important content producers and people thought leaders in the space these days are the ones who are doing good things and empowering people to use their gifts and skills for good in the world.

And that's what I believe part of my mission is. So I think it's imperative that I give people steps and things they can do to actually implement, because otherwise, if it's just thoughts and ideas and dreams, it'll never get implemented. In fact, I was just writing content about this today. I had a gentleman by the name of Brian Kluth on my podcast, and he calls himself The Generosity Mobilizer.

Lauren (02:35):

Oh my goodness. So you share that parallel. Yes. Tell me more.

Bob (02:39):

Yeah, and he's all about mobilizing. I mean, actually doing it, not just talking about it. So that's what I do on a daily basis. Now, like I said, I am a financial planner by profession. I own an RIA firm but I think the main reason why I do my work is so people can be as generous as possible. And I don't just mean with their money, I mean with their lifestyle and mindset.

Lauren (03:00):

I love that. When you think about generosity, you do sometimes think about what you are giving away from a charity perspective or what have you. But let's talk more about the mindset thing and how did you come into this? Was it just something you kind of saw as a part of your own experience with work? Is it something you kind of started to coach others with? How did you — I don't know if I should even use the word — stumble into it, but yeah, tell me more.

Bob (03:23):

Yeah, stumble is probably the right word. So I'm going to confess here. Live recording with Lauren. Thank you for asking the question. By nature, I'm not an extremely caring and generous person. I'm a spoiled only child who my parents like to say they gave up after having one child. I think my dad wanted five, and my mom said, oh no when I was like, about a year old.

Lauren (03:54):

Maybe. It is a lot.

Bob (03:57):

And I didn't get any easier. Was I a bad kid? No. But I had a lot of opinions and expressions I needed to make. And so I've grown up most of my life really feeling this need to express myself. And I think that's why I studied broadcasting, because I thought that was the way I was going to do that. And so you asked about how I came upon generosity, and it really was a life shift, and I'm not going to be one of these people who says, I went through one specific event and it completely changed my world. I can tell you a story, I will, I'm sure I'll share it here in just a moment about how generosity changed my life but it's really been a lifelong journey. It's not something that a switch just flipped and I said, you know what? I'm going to talk about generosity. It's been a lifelong shift, really. It's been a change over time in my life mindset.

Lauren (04:52):

Okay, so let's talk about how it goes in company culture, right? Because I think sometimes it's easy to check the boxes of like, well, we have this benefit. We've got 401(k) benefits, and we've got these holiday days off. And by the way, we've got a great kitchen stacked with tons of food and coffee and donuts and everything you'd want but it doesn't necessarily impact the heart to heart stuff. And how you helped empower people. And I was alluding earlier about some of the content you're creating — you're giving the real stuff away, it's not just about other on the wall things or even values on the wall, why those are important but how do you live that out, right? You've given examples before your time and helping to coach people and even the language you're using. Can you share a little bit more about that and how do you actually live that out, and how does generosity unfold within the workplace, if you will? So I'd love to hear a little bit more about some of those examples you often share.

Bob (05:49):

Sure. I'm one of those people who's attracted to a good story, and I think a lot of people, in fact, I think storytelling is probably the most powerful form of communication we have in the world but I'm one of those people who I used to do business with organizations or at least consider doing business if I needed their services if I felt they were a giving, generous organization. And when I realized about a decade ago now — it's hard to believe it's been that long — but about a decade ago, my wife and I had an opportunity to do some more traveling and some flexibility in our schedule, maybe some more in the budget to be able to do this. And I started looking into needing to do research on other things like hotels and travel and eating out more and all these different things, luxuries we have in today's world. And I was drawn to organizations that said they were giving back. And then I realized just about all of them said they gave back in one fashion or another. And the example I have is, have you ever flown Delta before? Have you been on a Delta flight?

Lauren (06:57):

Yes, yes.

Bob (06:58):

Okay. Delta happens to be a great airline for my wife and I because we live in South Florida and she's from Michigan, and that's the easiest for us to fly through Detroit and connect to the small town where her mom still lives. And so we fly Delta a lot. I noticed in the jetway to get on the plane for Delta flights they're all the same ads. One of them is a picture of people, presumably, I guess you would consider them to be Delta employees but they're volunteering with an organization called Habitat for Humanity. Some people may be familiar with them. Their mission is essentially to make sure just about everyone on the planet has adequate housing. And although they've made quite a dent in that over the years, it's still quite an issue in many places in the world. In fact, the company I used to work for at one point, I'm not sure if they still are, but they were the world's largest donor and financial partner with that organization. So I actually went on some trips myself. So I knew the experience with Habitat for Humanity and the program called the Global Village, where you travel to another country on a mission and you build a home regardless of your skills; believe me, I have no construction skills. I can barely use a screwdriver.

Lauren (08:10):

So they take you how you are ready to help.

Bob (08:15):

Get people involved. And so this is not my criticism of Delta by any means but I got the feeling just in talking with a couple people and then also looking at the ads that was kind of checking the box. They thought, well, we need to show the consumer like Bob, who's going to be flying us, that we care about the world and that will ultimately be good for business. I don't think they have been doing it for the past decade since I noticed it. I noticed it that day. And it's probably the same picture. Here we are 10 years later.

They're doing it, and I'm sure it's helping business one way or another, otherwise they wouldn't be doing it. But I got the feeling it was just checking a box to use the language you mentioned a little bit earlier. And I don't believe that's actually how you build a culture of generosity in your organization. That may be a marketing tactic or a branding skill but it's not the way that you truly get people involved. Because generosity, in my opinion, Lauren, is not an event. Generosity is a mindset. Generosity is something built over time. I mentioned Brian Kluth a couple minutes ago when I was talking, and he also said generosity must be trained. It's not something you just do. There's a natural inclination for humans, as scientifically proven, to support others but that doesn't mean you'll actually take action.

And so I strongly, strongly believe the best leaders and the best organizations have programs and systems and language — you mentioned that earlier — in place that empower and encourage their employees to do their best work and use our gifts and skills to contribute to the cause of the company, which is a cause that's bigger than just themselves. And this is in stark contrast to many organizations, specifically sales-heavy organizations, that give incentives to their employees to win a contest or take down the person in the cubicle next to them, to come in first for the quarter or the year and do things to get recognized as opposed to doing things to get the company or the mission or the purpose and the cause of what they do recognized, and I always say this, instead of trying to work toward being recognized, what if you work toward making an impact with the gifts and skills you have? And that's the reason why you were hired, right?

Lauren (10:37):

That's right. Yep.

Bob (10:40):

And the parallel in my financial practice and working in that world is that I've counseled thousands of business owners over the years. And without fail, I could probably count on one hand the amount of them who really only cared about the bottom line of their business. The ones who were the most generous and the most caring of their employees were the most successful and the most fulfilled because their culture was enjoyable. They enjoyed their work, they retained the top talent. People didn't want to leave. And it wasn't just because of the donuts in the break room, like you said.

Lauren (11:15):

That's right. That's right. Yes.

Bob (11:16):

And customers are really loyal, and maybe I'm speaking out of both sides of my face. I've been a loyal customer of Delta, regardless of my criticism I just gave. But for the most part, people want to know and want to see that what you're doing is truthful and that there's meaning behind it. And I believe truly and deeply in my heart that the most loyal customers are attracted to generous organizations.

Lauren (11:41):

I love that. I think that's so true. And it's something you can't, I don't know, it's not putting any lipstick on a pig sort of thing, right? It's real. It's the real thing. One model I saw recently was this idea of culture champions. They're the people you can train to this stuff but part of it is also some people just are embodying it, and they help to reinforce either, like you mentioned earlier, the language or the support or the time or what have you, as kind of a methodology, especially for large organizations, to be able to have those culture champions to help keep that culture alive and help it waterfall down. Are there other things you're seeing that really help to hold culture over time? Because over time, there's people who leave and come and you grow, especially businesses that are focused on growth. How do you maintain that culture so it isn't frail, it doesn't kind of unravel over time? I love to hear more on that side of things too.

Bob (12:50):

Well, I'll give you an example from my wife who's actually a kindergarten teacher and kids are geniuses on their own. I think there's something to be said for innocence and connection with other people. And so my wife tells this story — I had written about this in my book — she talked about having a class one year that was terribly misbehaved, and this is a few years into her teaching career. She's in her, I believe it's her 17th year now, so she's got way more experience but this was deep enough into her career where she didn't; it wasn't like an imposter syndrome type of thing. I mean, she was like, there is something wrong with this class. It's not me being a lousy teacher.

And every industry, including the financial industry, and anyone out there who's listening, I'm sure if you have a designation or some kind of professional degree, there's some kind of continuing education you need to do. So my wife tells a story about her and her aide going to one of those professional continuing education types of courses to get the credits they need. And it was one of those things where they're like, well, I don't know if I really want to go here. I'm just going to go to get the credits. I have to.

Lauren (14:00):


Bob (14:01):

Little did they know at that session, they learned a classroom-changing for the rest of the year technique that I believe, and I have seen worked tremendously in organizations, whether it's a Fortune 100 company or a kindergarten classroom. And that is simply this: catch people in the act of doing something good. And so when you talk about language and processes, I can give you a million programs and systems for goal setting, how to run an effective meeting, how to motivate salespeople…

Lauren (14:36):

All of it.

Bob (14:37):

Yes, I can show you all that stuff but the simple act of making it a habit of catching people in the act of doing something effective when they're around other people is such a powerful force. And so what my wife did was she immediately got back to the classroom after that. It was during break. It was actually during the holiday break they went to this continuing education. They came back in January and immediately she told herself, she made a rule. I have to correct children or stop them from doing things that are wrong, whether that's speaking out of turn or doing something wrong or being mean to your classmate, whatever, I have to do that. But no matter how many times I catch them in the act of doing something wrong, I'm going to catch them in the act of doing three times as many good things as wrong things they've done.

Lauren (15:29):

So positive. It's so true. Yeah. I love that, and I think also what you said too is to give them praise in front of others. And so praising in public I think is something really, really key too, to be able to reinforce that.

Bob (15:45):

Yep. Great.

Lauren (15:46):

You'd be surprised what a big difference that makes.

Bob (15:48):

You'd be absolutely surprised. I mean, yeah, sure. Someone asked me this the other day, actually, Lauren, I had to bring this up because this one hit me hard. They asked the other day, she said, what has a boss done? Or what can a boss do that's ineffective and effective for making someone feel valued? And it reminded me that I was put in this situation of, well, more than a handful of times in my previous role as I was given gifts and awards and recognition for specific things I did. And how many times did one of my superiors come up to me and ask me how much I liked the trip or the television or the whatever.

Lauren (16:33):

Yeah, the stock? The thing?

Bob (16:36):

Yeah. I didn't realize it at the time. I was nice. I thought it was a nice question. It wasn't mean or anything, so I don't want to overblow it. But what I realized yesterday, or was it yesterday, a couple of days ago when someone said this to me, I realized it was their own way of validating their own actions. That person wanted to know I like the gift they gave me. And you don't want that of your boss.

Lauren (17:02):

That's not the purpose of it, boss. Yeah.

Bob (17:03):

No, you don't want your employees to think, man, I have to tell them, what was I supposed to say? No, the trip was terrible and don't ever give me another, I mean, come on. You can't do that. No, it's got to be consistent. And you would be absolutely surprised how much more important, simple, subtle, hey, great job. I'm glad you did that. That's it. Do that three times. As many times as you tell them you probably should have done this instead. I bet you within just a couple weeks, the culture of your organization will turn around.

Lauren (17:35):

So powerful. Okay, so I think we could talk for a really long time having really fun with this. I'm going to slide in one more question here if I can. So one of the challenges, arguably the biggest challenge right now in financial services is talent, right? Attracting talent, especially in the wealth management world, finding really good talent that's a company culture fit. We've had clients we've worked with that are like, okay, we've hired executive search firms, we've done this and that. It's not working. And so part of it is how do you showcase that culture outright, externally? But it's a tricky balance as you were alluding to earlier. It's not just a check in the box. It's not just this and that. Any thoughts on this idea of authentic marketing and getting the message out there of being generous, of having that? How do you take that internal company culture that's like, yeah, if it is, yeah, authentically putting it out there to be able to attract, that's going to help to fuel that company culture?

Bob (18:45):

Well, if you're specifically in a recruiting type of role, I think it's a little bit different than maybe the company's branding aspects. And I can speak to both briefly if you are truly in that recruiting role. Surprisingly, I think it's less about the actions you take and more about the questions you ask potential people. So instead of saying, hey, if you do something good at our job, you're going to get a nice pat on the back instead of a bonus. I mean, that's not how to address it. But if you ask questions like, well, what's important to you? Or what's your most valuable thing in a relationship with a colleague you can find? Or how do you accept praise? Those types of things are great questions, and it almost doesn't even matter the answer unless they tell you something off the wall that totally disqualifies them.

But what it does is it gets them thinking and making them realize these are things you actually care about. So that's for the person specifically in a recruiting role or a leader. If you're trying to hire your first VA or you're on your 75th advisor, ask good questions. And then for the company in a branding aspect, I think the number one thing you have to do is talk about it. And what I mean by that is, once again, not specifically, hey, today we celebrated our employee of the month. That's good. Do that. And if you can work that into your marketing and you think that's worth it in the budget, tremendous. Put that stuff in your content. But when I say talk about it, I mean talk about the things you see happening, relationship-wise in your business. For example, one of the big things I learned in my previous role, my employer, is that it made a lot more sense for me to work together with the people, even though a lot of times I was pitted against them in sales contests and leaderboards, and we were kind of all fighting for our own thing.

But the more I collaborated with them, the better. So when you have language on your website or in a social media post for example, that says, let's say you're an investment organization and you have a CFA, or you have a couple of different investment analysts on your staff, instead of having you say, well, we're going to bring on Bill to talk about commodities, or whatever it is, you might say something like this. You might say, well, in our next webinar we're going to highlight an article that was written by Bill and Jenny, who have been collaborating on this project for the past six months. And then when you bring them on the show, when you bring them on or you write about it, wherever it is, you just display that collaboration between the two of them.

Lauren (21:31):

Yes, yes. It's the positioning and the messaging of that too.

Bob (21:35):

Absolutely key.

Lauren (21:36):

Oh my gosh, this is so fun. Like I said, I think we could go on for a long time, and I appreciate the time and also the thought you give to this. Sometimes I think there's some folks who, for lack of better words, generosity might come easy, and for others it might not. But I really appreciate you've taken the time to also think about what that means and break it down for all different audiences to kind of understand how you can be more generous. How can you create that throughout your organization and reinforce it as folks grow? So thank you again for your time.

Bob (22:11):

Oh, absolutely. You're welcome. I wish people a generous day and the simplest things. It's all about simplicity and just making people feel like they're capable of contributing to something great.

Lauren (22:22):

So well said. Thank you.

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