Leveraging Leadership
Leadership is messy. Most advice isn't built for the reality of competing priorities, difficult stakeholders, limited time, and imperfect information.
Leveraging Leadership is a practical leadership podcast for Chiefs of Staff, executives, founders, and senior operators who want to lead more effectively and navigate complexity with confidence.
Hosted by Emily Sander, former Chief of Staff and executive advisor, each episode delivers real-world lessons, practical frameworks, and candid conversations with leaders across business and beyond.
Topics include executive communication, leadership presence, decision-making, delegation, organizational influence, operating rhythms, team effectiveness, and the often-unspoken challenges leaders face behind the scenes.
If you're looking for thoughtful conversations, practical takeaways, and leadership advice you can actually use on Monday morning, you're in the right place.
Leveraging Leadership
The Principal’s Perspective: How Chiefs of Staff Shape Organizational Impact
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Executives and Chiefs of Staff share practical stories about how the Chief of Staff role shapes company culture, trust, and growth. Tim Moore explains how his Chief of Staff acts as his proxy to scale leadership, while Jessica Gonzalez highlights how having Ivan as her Chief of Staff lets her spend more time with her kids and trust things will get done. Guests discuss hiring from within, the unique qualities needed for the role, and the importance of loyalty, communication, and partnership.
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Who Am I?
If we haven’t met before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.
Time Stamps:
00:42 Tim Moore
05:04 Jessica Gonzalez
09:38 Perry Knoppert
18:27 Tracy Van Grack
24:50 Erika Aquino
Welcome back to Leveraging Leadership, where we unpack the art of business leadership. I'm your host, Emily Sander, chief of staff to an executive leadership coach. This show is all about finding your points of greatest influence and leveraging them to better serve those around you. So Tim, if you were describing to another executive, "Hey, you know, here's what a chief of staff is. Here's why I think one would be valuable," what types of-- w- what would you say to convey what a chief of staff is and the benefit that you've had from having one?
Tim Moore
Well, I would say that In many ways, the chief of staff is the key partner to the CEO to communicate the vision across the company and align all the departments to work together. And in many ways, um, they are the proxy that, that is the, the vision. And so, you know, what, what I feel, uh, defines what Natalie does, uh, many times is, you know, uh, she is me in the room when I'm not there. And, um, when you have that kind of relationship, it really allows you to scale what you do as a CEO. Mm-hmm. And so, uh, you know, it's, it is a vital position. Most people don't realize they need it till it's almost a little bit too late. You know, they, they burned a couple bridges or they, uh, you know, weren't as organized as they need to be, and so they are scrambling to find that, that helper. And what I would encourage people to do is if you don't have an executive assistant already, um, but you find yourself that you don't, you don't have all the bandwidth to do the things you need to do, is start off with someone part-time just to see how the help gives you leverage to do the things that are, that are the most important. And, and a lot of times the first thing is just administrative. You know? They're just, like, uh, answering emails, doing, um, uh, calendar invites, helping with the admin side. But, uh, once, once you start to see the value of that, it becomes very obvious the value of, of what the chief of staff role would be, um, in a much more, uh, higher, uh, form, uh, of a, uh, CEO partner. It sounds like, Tim, you're a great leader in the sense that you are pretty transparent. You're like, "Natalie, jump in there. I'm not gonna hold any access back for you, from you," or, "You can't be in this conversation. This has to run through me," that type of thing. How do you work out the different roles and responsibility in your communication with Natalie? So I, I think for me, what the result is, is in the beginning, a startup CEO has to tackle every problem. You pull up your sleeves, you go in there, and, and then it becomes a part of the business where you have enough people around that if you stick there too long, you are the problem. You know? Yeah. And I've, I've certainly had that. And so the chief of staff can tell you the blind spots, to be like, "Hey, let's, let's get a level above this." And I think when you get to an organization where things are moving really well, you, you wanna be above the problems that you don't even know they happen, and that's where the chief of staff is the shield, and they're like, "You know what? I'm gonna, I'm gonna, uh, tackle this, and Tim's not even gonna know about it." And then, and then now the whole organization is just really autonomous. Going back to the, the perspective of the CEO, the, the, um, when, when you get into those moments where you're like, "Okay, this is, uh, you know, this could be a culture-breaking moment or this could be a big mistake by the CEO," and the chief of staff comes in and points out the blind spot that is a big moment of trust, right? Oh, yeah. Because there's a vulnerability for them to communicate the, what the staff is trying to say in a way that wouldn't reveal that, um, you know, uh, to compromise that. And so, you know, you start to think about the, the level of, like, algorithmic thinking- to go, "Okay, here is, uh, you know, what's been done. Here's how people are reacting to it. Here is the outcome, and then, and then here's all the things I need to do to make sure they're happy, he's happy, the board's happy." Um, so that there, there's a thing that Alan Watts wrote on this. He's a, uh, like English, old English philosopher, and he said, "There once was a man who said, 'So it seems that I know that I know, but I'd sure like to see the eye who sees me so I know that I know that I know.'" Hmm. Wow. And a chief of staff helps you know that you know that you know. Wow. And I think that it's, it's hard to understand it until you see it, but it's like when you're so convinced you're right and then you realize there's another perspective, it's like, oh, wow, that's... I'll, I'll never not wanna have that in the room now. Wow. Because it's now that I know that I know that I know. Jess, so how did you identify the fact that you and the company needed a chief of staff, and that Ivan was the right person to
Jessica Gonzalez
fill that role? So the role happened organically, meaning, um, Ivan started as employee number one, and he, his just attitude and demeanor about just everything is like, "Yes, let's do this. Let's get it done." I know if I give something to Ivan, it's gonna happen, it's gonna get done correctly, it's gonna get done on time. You know, like, yeah, I, I've, I, I gave him the kind of from the beginning almost like the number two position in the organization, which to me is like the number one position because I'm, you know, off doing all these other things. So he really kind of has helped, you know, bridge everyone together. And initially his title was head of sales and operations, but for what he did, I felt that like chief of staff is really a role that encompasses, you know, a lot of what he's doing. Um, so w- one night I was like- One night "What do you think about this role?" And he was like, "Yeah, it makes sense." Um, and he just kind of went into it. He was already doing it, so it just made sense to have an appropriate title. And Jessica, if you're talking to other presidents, CEOs, executives who are looking for a chief of staff or have a chief of staff, what is one of the main benefits that you've gained from having Ivan on your team, having a chief of staff on your team? So the benefits are far beyond anything you can imagine. So, and, and the thing is it takes a very unique person to fill that role. There has to be trust, there has to be, um, you know, dedication, um, there has to be a lot involved. And w- you know, the, the, the, the qualities that Ivan possesses, you know, have allowed me to be able to spend more time with my kids and be able to just stop and know that I, I could send him something, he'll take care of it, no matter what it is, what department, what's going on, which is... There's no value you could put to that, to having time. Um, so that's a, a massive, you know, value add. Um, having it- Me and Ivan have sessions where we just vent what's stuff going on which is great. We're able to like be human together, you know? And, and, you know, on a personal and professional level, like we're both human beings, you know, we could, you know, shoot the shit and, and, and whatnot. Um, you know, and trust, you know, Ivan knows everything about everything with the company, and I trust him impeccably. And, you know, in, as a, as a result of that, you know, um, you know, my commitment, the same commitment he has to me is the same commitment I have back to him. You know, he is part of the core team, he's part of building this. If we're gonna... If I'm gonna retire, he's gonna retire. If I'm gonna buy my parents a house, he's gonna buy his parents a house when we come out of this. Um, you know, and, uh, again, it's not an easy role to fill. It, uh, you have to find the right person that is kind of like your yin to your yang, and that takes a lot of time. I always... I try to look from within the company, you know, um, whenever I'm trying to bring up and, and change roles. So I would start there first because you already know where the culture fit is and, and all of that. Yeah. And the, the last thing that I have to say about this that's very important, um, if someone on your team is gonna become chief of staff, and they're gonna help you with all these things within the company that are very valuable, very important, very... It's a, it's an, it's an insane role. Y- the commitment that they give, you have to match. And that's the, I, I feel, the best way, where it's mutual loyalty and trust and, you know, we're building this together. This is not a, you know, Jessica's not building Happen Ventures. This is the team that's building it. I am just keeping the pieces together, but I'm gonna give the team everything that they need in terms of stability, you know, uh, growth, you know, financials, everything to feel safe and empowered here to really make a difference and like it's their own. And that's important because you can't expect someone to give you loyalty if you're not giving it back to them. So that's, I think, one of the key things that I would hope Ivan als- I- feels, like, you know, the mutual respect and, and loyalty there that like we're taking this home together. It's not just, you know, just me. It's we're a team. All right. So as we wrap up here, uh, my listener would be, would be remiss if I didn't ask, Perry, if you were giving one piece of advice to another executive who has a chief of staff about how to work well together, about some traits to look for, um, qualities that are important to have in a chief of staff, what would you say to that executive?
Perry Knoppert
Forget about everything. Um, th- I think that's, that's the most im- you know, when you're searching for a s- a chief of staff, you're not gonna find the perfect one. It's, it's probably the run right in front of you and, and you're not seeing it. It's that connection. I strongly believe in the hum- human mycelium. We're all connected, and these connections are there already. You don't even have to create a new c- connection. So it's, it's a bit woo-woo to say it like that. Let it all go. No, don't look for your chief of staff. But it's, it's something I really believe in because the beauty of a chief of staff is that it doesn't exist. Uh, uh, you know, there is no... You know, you become an accountant, you com- become a brain surgeon, you become a lawyer. A chief of staff is someone Who can feel and see everything. It's, it, it's not a job. It's, it's who someone is. And probably- Mm in your direct area around you, you already have people that are close to you that way. And, and that's what I wanted to share, is that don't look for a chief of staff. The, the, the chief of staff is probably right in front of you. Or, you know, you need, you need to let it go a little bit to, to make sure that that happens. And again, sorry for this woo-woo answer, but I can't, I can't put it any other way. A chief of staff- What do you think, Watson? is not a job. It's- It's someone, it's what someone is. Yeah. Yeah. It's not a job. Yeah. What do you think, Watson? What would you say? I would agree. Yeah. Of course. No. Um, yeah, I think- It's a way of being that seeing not only everything, but seeing the vision and the detail at the same time. Um, who's doing that in your organization? And I... And if you don't see that person directly, I would say, just as Perry had a contact that said, "Hey, I'm looking for this," they had someone that they knew fit that bill. Um, so I would say talk to your network and, um, explain what a chief of staff is for you. They probably already can help you identify that person if you can't identify them yourselves. Seems to be in alignment with your overall culture and, and mantra, so the team structure is, is kind of like an octopus too, in a way. Of course. Um, I'm curious, what led you to decide you needed or wanted a chief of staff on your team? Balance. Balance. You know, I'm, I'm a bit crazy, and, and there is a lot of focus on nonlinear thinking. And in nature, everything is in balance, so I could see the whole movement globally with the nonprofit and my nonlinear approach to many things, which really frustrated some people from time to time. "Perry, you need rules. You need a system. You need to do this. You need to do that." No, I don't need to do anything. But it's, at, at one point, when it was growing and growing and growing and growing, I was like, "Now there needs to be balance. I cannot handle this by myself, and I'm not doing a good job if the main focus is that nonlinear approach." It doesn't mean that I, I don't use linear thinking. I love structure. I love databases. Oh my God, Karen, all the air tables and all the things and all the- things that are connected. Of course I'm very linear as well, but my drive is very nonlinear, and it's, it's so nice to have Karen and bring that into balance, where we both... We play chess together, you know? And, and the chess game is the octopus move. Yeah. And it's like, "Okay, what if we do this and then do that?" I needed that, because to start something alone is wonderful. You're not wasting any time in any meetings and, and debates and, well, you know, convincing people- I don't like to convince people. I just wanna flow and make things happen. Um, so for the start, doing it all by myself was wonderful, but then you need a team. Then, you know, you're growing, and, and it's more fun to do it together than doing everything by myself. Sorry, but I do think that a perfect chief of staff is, is like an octopus, is like a non-linear thinker. You have to- Oh, yeah see everything, you have to understand everything, and you have to have a, a tremendous amount of experience in recognizing things, and people, and behavior, and energy, and, and flows that it all comes together in this role. And, and so she's using everything. She's using everything that she has as, uh, as Karen and with her skills, and that all comes together and makes it just wonderful to, to work with Karen as a chief of staff because there's so much more to it than just organizing things, right, and helping to create strategy. Yeah. It's so much more because this is the human business. We're constantly It's only about humans. And I'm assuming that there's a certain level of trust in that because you're not there to maybe check in on every little thing. You're, you're saying, "I have to understand the overall goals and drivers, and then be able to kind of speak Perry a little bit and interpret what's happening, and then do my full day of work and move, and move things forward." Oh, yeah, absolutely. I would say trust is, is a big factor, and, um, something that came quite naturally for us, quite frankly, to have not known each other for very long. Um, I mean, really not known each other at all before we started working together. Um, so it's, it's been a great relationship. I've been quite pleased with it. But I, I think, yeah, that's very important. If the trust isn't there, uh, things aren't gonna go forward very well. And, and we have never seen each other, huh? And- This, so we have never met each other, just only online. Oh. Isn't that remarkable? So just- Wow on Zoom. That's it, right? And we're really working, and there is a lot of trust, and, and we share everything and, and it, it's, it's so organic. It's so natural. And then, and I think this is also has to do with the fact that it's- For my opinion, it's, it's not about the skills, it's about the humans. And, and this sounds very, you know, logical, duh, but when I look around me, I see a lot of organizations and leadership positions where it's based on skills and background and expertise. That's, that's not the case for me. It's, it's about Karen, you know? And, and Karen is the chief of staff. It's not about the chief of staff, and the chief of staff is Karen. It's the other way around, and that's why it works so well, that our personalities fit very well together. We understand each other. She can look at my f- if we, if we have meetings, as, and we're in a Zoom, and then she looks at my face and she sends a WhatsApp message, "Perry's not happy." Uh, other people can't tell, but Karen says, "Oh, okay, I can see, you know, how he moves his hands or whatever, what's going on." That's really priceless. That's so cool to work together like that So I wanna get to where the handoff comes in with Mike and some medium and larger stage companies, but just for, for the chiefs of staff listening, oftentimes they're employee number one or employee number five at this startup, and they are doing everything from head of operations, and sales, and marketing, and product, and compliance, and head of janitorial services, and throw in communications. So- Right I think what you said about building a culture of communications is really good. Is more- And setting that foundation, and then you had m- also mentioned when you can bring on a full-time resource or even, like, an official part-time resource. So maybe just touch on if, if you're talking to a chief of staff who's like, "I, I, I have everything. I have to do everything." Yeah. Um, how they build that solid culture of communication, and then when that inflection point comes, when, "We can hire someone part-time," or, "We can hire someone full-time," what that looks like.
Tracy Van Grack
Yeah. So, you know, it's interesting. I think the first time I generally have this conversation with a founder, um, or a chief of staff, whoever is kind of leading the charge with how to maximize or take communications to the next level, tends to be around a milestone. So they have a funding announcement, they have a product launch, they have a big hire, and typically you will hire an outside resource before you have an internal hire, and I'm gonna leave it to Mike to talk about the pros and cons of that. But that's generally the way in the s- in startup world you, people will engage, um, with the communications function. And there are all different routes you can go when you hire external support. I think people don't realize, they very often think hiring outside, um, consultancies involves, you know, a five-figure, 12-month retainer, and that's not the case. The communications landscape is so varied. In particular in, you know, for tech startups, there are firms that specialize in helping companies of all different stages of growth. I even work with, um, consultants that have kind of packaged various milestones, so they will say like, "Okay, you have a funding announcement. Here are the five things you need. Here is the fee. Here is the length of time in which we are going to work with you." So that, that's the first point. The second, and I, I, I know I mentioned this earlier, is making sure you have the internal resources to manage the external resources. So a lot of times companies think, "Okay, I'm gonna hire a consultant. You handle it." But that consultant is not in your company every day, and we'll get to that when we talk about the benefits of internal hires, right? They, they do not know what's going on. They don't have a sense of the internal politics. They don't know what was discussed or canceled, you know, at a meeting three hours ago. So unless you have the capability to manage them effectively, think you're wasting a lot of time and money 'cause they're not gonna produce the results that you need them to. Um, and there are various reasons where you might escalate this or feel ready to, you know, bring it u- bring on, um, external resources again, whether it's one of these announcements or whether you have a high-profile founder, whether you're in a highly competitive industry. Sometimes there are reasons where companies will kind of, I, I think accelerate getting some resources where you might think like, "Oh, they're a pretty small company. Like, do they really need external support for communications?" And, and they do. It's been that long. Time flies, man. Like, time really does. Um, but great. So thank you both for making me feel like a slacker compared to what you all do. Uh, appreciate that. But Tracy, you know, 200 Port Cos, you work alongside a chief of staff. So just because we have- I do a number of chiefs of staff listening, and principals, and fellow colleagues of chiefs of staff, can you just give us a little flavor of how that is set up and what your interactions are like with the chief of staff? Yeah, absolutely. And I'm, I'm gonna say something before I even get to that, which is I've worked with a number of chiefs of staff over- Mm-hmm the course of my career, and I have to say they are, without a doubt, the smartest people I have ever worked with. I take... I think it takes a real unique skill set, such a high level of operational rigor, and really, um, almost a sixth sense for external and internal storytelling, and I was very excited when you brought up this topic because I have worked with the same chief of staff here for the 10 years that I have been here, and- Oh, wow I think our relationship is really foundational. I mean, she's a fantastic professional. She's had a number of really interesting experiences both in the public and private sector, and I think our relationship is the reason that so much of our communications is successful, in particular our executive communications platform, because we have a high profile founder both in the DC area and within the broader tech community. And I couldn't do my job well in particularly, in particular in that space if I didn't have a bigger, broader understanding of what was impacting him, how it was connected to the rest of the organization, our organizational goals. Um, so you know, we, we meet regularly, we communicate so often. Um, it's just such a successful partnership, and I really respect, um, everything that she has brought to the table. Successful is an interesting term to use, right? Right. 'Cause we've worked with, we've worked with CEOs who have had multiple exits. That, that is a measure of success. I have nothing to, to, to argue with that. But all of a sudden they're in something that, that isn't going to be sold, that is now all of a sudden reaching different benchmarks that they've never reached before as a CEO, that they've never experienced before, and their ability to turn around and look to the rest of their leadership team and say, "I need, I need guidance from you in certain aspects of this because we're n- I'm personally now hitting uncharted space," right? And the chief of staff plays a critical role in both kind of nudging the CEO as appropriate because they are really trusted by the CEO to, to kind of be that, that, that, you know, yang to their yin, um, and to say, "Look, hey, you know, I think we're, I think we're getting to un- uh, uncharted waters around the brand. Like, you were never tested, you were never scrutinized in this way- Mm over the last three companies 'cause you got to couple hundred million, you sold it, and, and pretty much nobody outside of the Valley knew who you were, and that was great. You're now on a bigger stage, right? Mm. And part of that is based on where we are from a digital and social media perspective today, but part of that might be where the business is as well. Yeah. Yeah. I would say, too, you know, tech founders in particular tend to be an optimistic bunch- And sometimes that optimism, whi- which I, I would attribute probably to some of the most successful innovations of the last, you know, decade or two decades, can be blinding. So it does fall often on the communications officer, on the chief of staff, because they are, at the end of the day, like head of principal management to, to offer those reality checks. Yeah. That sometimes things aren't always going, you know, perfectly. Erica, how did you go from, "Do I need a chief of staff? What is a chief of staff?" To, "This is a lifesaver. This is a savior"?
Erika Aquino
No. Well, I also realized what my day-to-day was. I analyzed... I, I looked at my calendar. I looked at what I needed to do, and I'm... And with the tr- with the amount of travel that I do, I also tend to be... Things get inefficient when you're in different time zones, right? And I thought, I need somebody who can not just help me out, but multiply the workload. Um, and at the same time, um- learn from me and I can learn from them as well. And when Patricia, so Patricia and I f- so the event was online, right? And she said, "Hey, what's up?" She sent me a private message after, and I, of course, I, you know, it was, I guess I would, you'd say she... I really admired her guts, her, her willingness to just put herself out there and approach a speaker, somebody that she didn't know. And, you know, she, she narrated what she used to do. She told me what she, what she could bring, and I said, "Hey, you know what? Let's meet up." I, I tend to hire based on not just skills, but the vibe- Yeah our alignment in, in, in morals, in work ethic, et cetera, and what we believe in, in terms of mission. So we met up in LA when I was there, and yeah, I think we just got along and I really like what Patricia was doing. And I guess I was looking for something, I just didn't know how to define it, and Patricia de- defined it for me. Ah, okay. Wow. Gotcha. Yeah. And then how did, how does the chief of staff fit within your e- your existing team or your larger team? Right. So, well, this is a very small team, um, particularly when we analyze deal flow. All right, so it's not necessary... I, I do a lot of projects, and Patricia pretty much helps out in almost all of them, but she primarily helps out in analyzing deal flow. So I do get a lot of pitches. Um, s- at one point, I think we were at, oh, God, so many at the time, and Patricia is the initial filter. Ah. Um, without her, I was just a little like, okay, things would fall to the wayside and, you know. Um, but with Patricia, she streamlined things. Um, together with our CFO, my fractional CFO, we... They live in the data room, we live in the data room, and we say yes, no, maybe, whether it's a fund, whether it's a, um, a, any type of investment, whether it's, um, you know, a CPG brand or a platform, et cetera. Patricia really kind of acts as my, um, my eyes and ears as well, um, on things. So yeah, um, that's how she kind of fits into the team. Yeah. Yes. I, I often say, uh, being chief of staff is many things. Boring is not one of them. So I've, I've yet to come across a chief of staff who says, "I'm bored at work." Mm-hmm. But, um, Erika, you mentioned something, mentorship, and it's so funny because a lot of chiefs of staff going into a role are craving mentorship. I want to work for a principal who I'm aligned with on values, but will invest in me and, and help me grow. I'll be supportive and tee them up for success and work with my principal, but they are looking for that reciprocity in a sense, and principals are buzzing, flying all over the place. You are literally flying all over the place, figuratively, literally. Literally, yeah. Literally. Um, how do you balance the, the, I need to get stuff done, I need to be front-facing, but also take care of my people and really have that partnership- Mm-hmm and relationship with them? Well, it's, it's, again, it's taking care of everybody, whether it's a decent salary, whether it's a salary that they need, whether it, health care benefits, um, those things I, I really want to take care of. Another thing is making sure that they're okay. I, uh, Patricia, I don't know if you notice this, but I do ask you- Yeah, just like yesterday how are you doing? Um, yeah. How are you doing with things? I, I ha- sorry I haven't touched base with you. How are you? How are you? I think no, when I was, you know, in my career, deep into my career and getting, getting up, going out, going up there, um, no one really ever asked me that. Mm. Um, other than, you know, let's say it was the quarterly evaluation, that's the only time people would ask me, "Oh, how are you?" I'm like, you didn't ask, you haven't asked me about this times. It's fine, which is fine. I get it. People are busy. But I think it's, it's also about... And, and I've been taught this, um, by a lot of, um, by, by my dad, by, um, my parents really, um, take care of people, they'll take care of you. Mm. Yeah. Whether it's your friends, your family, um, your coworkers, um, yeah, say be nice, be kind to everybody and they'll be kind to you. Yes. Yes. All right. And Patricia, similar question for you. For chiefs of staff listening, aspiring chiefs of staff, new chiefs of staff, multi-time chiefs of staff like you are, what advice would you give about the role or working with your principal or anything else? So for me, it's similar to what Erika was saying, but just like, uh, what I've mentioned before, um, the chief of staff is loyal to your principal, whereas, you know, let's say a COO is loyal to your company. So your relationship and your alignment with your principal is extremely important. I think that's the cornerstone of this whole thing, because sometimes you spend more time with your principal than some of your family members. That happens because you do shadow his, her schedule or his schedule or whatever the goals are. And for me, I think when I first met Erika, I told her, "I'm here to amplify your role." And I think she, that really resonated with her, and I think that would resonate to a lot of principals as well. And sometimes, you know, it can get lonely if you're just alone, and I feel like that's something that Erika also felt. And you know, if you have someone- Mm-hmm that's, you know, in the same path, you know, same direction as you- Mm-hmm things will really be easier. And again, things will be magnified in terms of impact. Please give this episode some love by liking and sharing. It's like sprinkling digital fairy dust on the algorithms and it is scientifically proven to make unicorn smile.