Anaplan CEO Frank Calderoni: Making a difference with character-led culture

Anaplan is a planning software company with almost 2,000 employees – and CEO Frank Calderoni has leaned into building a character-led culture.  Every single one of its employees goes through a Tilt assessment, so they can “be very self-aware as to who they are, and to allow them to have a view of others, knowing that not everybody comes from the same Tilt.”

On today’s episode, find out how Tilt has helped shape culture at Anaplan, and how it can help your culture as well.

Upstanding: How Company Character Catalyzes Loyalty, Agility, and Hypergrowth, by Frank Calderoni

Get 50% off your Tilt personality assessment with the coupon code “podcast”.


Voiceover: Welcome to What’s your Tilt?, a podcast series where we’ve invited some of our favorite leaders to share best practices and wisdoms for building a culture where people love to work.

On this show, host Pam Boney, founder and CEO of Tilt 365, a tech startup that offers a new kind of personality assessment and development platform that helps people break out of the box of type and grow more AGILE & generative teams. Tilt won’t confine you to a single, unchanging type. Instead, it identifies your favorite patterns, then maps out a path to develop your other capabilities and character strengths.

Today’s guest is Frank Calderoni, CEO of Anaplan, a cloud-based business-planning software that provides companies data for decision-making purposes. Frank has integrated Tilt with his teams, and he even wrote a chapter on the assessment in his latest book “Upstanding: How Company Character Catalyzes Loyalty, Agility, and Hypergrowth.”

Frank: So yeah, it’s great when you’ve been able to build a character led culture. Where it could go awry is, as you just mentioned, bring other people in. And so, what we do is we go through, I would say a fairly comprehensive orientation of people coming into the organization. It’s not just, we make them aware of what Anaplan is all about product and stuff, but we spend time on a character led culture.

We use Tilt across Anaplan, so every Anaplan employee has been through a Tilt assessment, and that Tilt assessment allows them, first of all, to be very self-aware as to who they are, and also what makes them up and what their behaviors can really be. It also allows them to have a view of others, knowing that not everybody comes from the same Tilt, so that you can understand and appreciate what other people with, where they tend to lean and then how you can best interact with them to get to a win-win, right. So, you lean in, they lean in.

When we bring new people into Anaplan, we start them on Tilt from day one, as part of this orientation. We bring them through a Tilt assessment. We educate them on Tilt and thank you to you and your team. We have, you know, sponsors, trained sponsors within Anaplan that understand Tilt. and then we model that in this session and we get them to really buy in, you know, one thing I’ve always said about Tilt and I learned this the first time I went through the assessment, they’ll say, because most people go in, they say, they’re a little bit skeptical, right?

Oh, this is just another assessment, they won’t know who I am. And I think you can go to this, right? What I’ve got the ratio, but it’s well, over 90%, 95% people that go through the assessment, they step back and they go, this is really neat. 

Pam: Yeah. We have, we have great comments. Like how did you see inside me like that?

Frank: When you start understanding who you are and you understand that there are three other types of Tilt and you start thinking about how best, it allows you then to integrate into our culture in the right way. We also use reality-based leadership as another part of our orientation, you know, to make sure that we understand, hey, drama is not welcome here, egos are not welcome here, right? 

We’re here to make sure we’re focused on what Anaplan needs to do to be successful, and also how we, part of Anaplan, can contribute to that and be fulfilled and energized by what we’re doing. So those are just some examples I can go on and on, on this, but just some examples of bringing people in.

And then you asked about holding them accountable when you, when you have, and this is what I learned at, at Red Hat. When you have an open culture where, where you allow people, empower people, that they can speak up and they can challenge in a constructive professional way. It allows them to check others and people should not take it personal, they should take it as, oh, that’s acceptable. And it’s worthy of a dialogue back and forth so that I would accept the feedback and then alter my behavior to make sure it aligns. 

Pam: Yeah. You’re, you’re actually making it a safe place to be honest. And a safe place to make mistakes and, you know, not worry that you’re going to get attacked by it, you know, by somebody else.

Yeah. I often say that the two of the Tilts kind of attack externally and two of them attack themselves internally, but what we want to do is stop everybody from doing any of those attacks and create that, you know, the popular term today is psychological safety. I’ve been, you know like you saying, it is a character-based culture that really matters and it frees people up to be focused on their work and their creative contribution and the things they love doing.

So, I’m delighted, like I know that the culture, you know, was, you know, when you got there, I remember you did a tremendous amount of work, at least the consultant that I know did the work there with you know, did a lot of work and I knew about the reality bit. 

We’re, you know, we’re very focused on reality as well. Character is reality. you know, focusing on responsibility and, you know, being honest with yourself, self as well as others. Anyway, I’m delighted to hear all of that. I know our listeners would probably love to know what is your Tilt and it has it stayed the same?

Frank: So, I I’m an impact. So, a changed catalyst. And, you know, I also found out that and I haven’t always been a CEO. I’ve been now four and a half years with Anaplan, but I understand that a majority of CEOs tend to be impact or change catalyst. And I can understand why. I mean, I like seeing the bigger picture. I liked the, the strategic element of things. I tend to look more longer term. I don’t like negativity. it sort of, so some of the things I do, and this is what I learned, both through Tilt, as well as through reality-based leadership is when people around me, and they tend to be very pessimistic or very negative, is how do I bring them, you know, bring them up to, okay, I understand that but let’s, let’s, let’s kind of look at it a different way, right. 

And then it’s interesting when you can kind of position it somewhat differently, how they rise to the occasion and say, oh, it really is not that bad, or I could look at it this way. And I think that also is a way of, you know, this whole thing. You mentioned diversity, and it’s, you know, diversity of thoughts or ideas and things like that that allow that to open up rather than if there’s people tend to be very closed, right. 

So, there’s so many things that I think come from that, but a catalyst, you know, as far as impact and the change catalyst, I’m always looking to change things. I’ve been a change agent in probably every organization, and initially people go like, oh, what is he doing? I’ve also learned in reality-based leadership with change, you’ve got to work with the willing, right? So, I can really resonate with people who are as passionate about looking at things differently and looking at things new and getting them to help bring some of the others along which is an important aspect of leadership 

Pam: Yeah. So, you mentioned a change catalyst and impact Tilt being CEOs. We actually see CEOs of all four of the Tilt patterns, believe it or not. But in a high growth fast moving organization, often it’s impact. and cause you know, we, I’m impact too. So, we have a need for speed. 

Frank: And there’s always a lot of people they’re probably saying Pam slow down, slow down, right?

Pam: Absolutely. I have to have like three or four people ever in the clarity corner, kind of holding, you know, holding me back a little bit. and I, as you have, I’ve had to learn to slow down and reach in and ask them, what are you worried about that I’m not seeing? You know, and they, and they, you know, are worriers about risks, some of the other Tilt patterns. And so, they’re going to tell me, and sometimes prevent me from making some big mistakes. 

Frank: You know, Pam, you bring up a good point, which I want to, I wanted to talk about. We did this as the leadership team at Red Hat, and we also did this as Anaplan, and I think you can stress this. The importance on a team is to have the balance, because exactly what you just said so that you don’t Tilt completely in one direction that you have the right, you know, contention and or debate, and or the balance of what needs to get done, right. And so, we did that assessment and we found an imbalance and we tried to, I’ve been working on trying to get it more balanced because you need that diversity of perspective.

Pam: Yeah. And we’ve also seen people move around to different Tilts as they learn about other Tilts and shift into context in a different role than what they’ve been in before. And in a different Tilt kind of seems to be the right one for the situation. so have you seen that at all? Have you seen some people shift around?

Frank: Yes. I mean, yeah. I tend to, you know, prior to being a CEO, I was the CFO, right. So, CFO tends to be much more structured, right. And so, I do have that element in me from so many years, and I see myself sometimes, you know, moving into more of a structured approach, you know, let’s talk about the process, the steps that need to kind of take place from that. And so that’s an example of where I’ve had to, you know, go from one to another. 

Pam: So, I’m thinking about last year and I, and I know on your Mad Money interview you said that Anaplan performed really well, which is a nice testament to the fact that having the information, the right information in your hands helps you to perform better. Tell us about how you did that. 

Frank: So, we’re a strong user of Anaplan. We call it Anaplan on Anaplan, and it kind of fits in with our culture. I mean, if, if you think about our platform, it does align to openness and transparency and accountability. And I think all those go hand in hand, because it allows people to have access to information.

It allows for processes and organizations to be aligned. It allows for collaboration because when you’re in the platform, it’s not like, you know, you and I are just looking at information, other people can see it as well. And so, it covers a lot of the elements and it kind of ties a lot into, you know, the values that I was mentioning before, openness, collaboration, transparency, being authentic. 

When you have information, there’s also reasons to really diffuse drama, right? Because the facts are the facts. Right, and if you can focus people on, let’s look at the information and let’s have a discussion and maybe a debate on the information rather than something that really is not there.

So, we’ve been able to leverage Anaplan in the different organizations, connecting those organizations. You know, we call these models. We have well over a hundred models that, that are really used in all different organizations and kind of brought together. So, it’s helped in managing our business.

We also use, and I talk about this in the book too, we align that to a VSEM, and I learned this in my days at Cisco, which is our Vision, our Strategy, our Execution, and our Metrics. So, Anaplan becomes the metrics, right, but they’re tied to initiatives that are aligned to both our strategy, as well as our vision.

Right? So, there’s that connecting point, and the importance of VSCM is that everyone in the organization should have clarity as to what it is so they can then understand how they align and fit in and also feel good about what the purpose is.

Pam: So, what, what is the purpose at Anaplan? How do you articulate that? 

Frank: Again, this is something that will be evolving because, you know, the purpose that we have right now is for people to do their best work. That aligns to our customers, because if we can do our best work, our customers win. If we can do our best work, Anaplan wins. If we can do our best work, our people win because they feel fulfilled. They feel like they’re developing their career. They feel like they’re doing something that they enjoy doing. 

And so that, that’s the purpose that we’ve kind of resonated with right now, and allows people to be authentic and be themselves and understand that when you are yourself, other people acknowledge and recognize you for that. And it brings that whole ecosystem of really true diversity, right. So that, and by the way, Pam, I’m talking, but nothing’s ever perfect. We all have to; I have to say this. We’re all working at this. I don’t want to say Anaplan is the, be all end all. I just, I think we have a framework that has worked for us and that we’re going to continue to evolve and work at which I’m pleased and proud of. 

Pam: Yeah. I love the idea of having a framework and I see Tilt as a framework of organizing principles in a way to try to help people kind of see what does it mean to have character, you know, like how do you define it? What is the development, you know, play on for that? Yeah. So, you mentioned agility, tell me a little bit about your, how you think about agility, especially in the context of last year. 

Frank: So, agility kind of ties back into my Tilt, right, change catalyst. I think the makeup of most humans is to resist change, right? We like to do things that we’re comfortable doing. I guess I learned early on and I I’ve said this in other conversations I’ve had, I’ve always felt a level of kind of butterflies in the stomach, right, always feeling on the edge, which allows you, you know, being nervous it allows you to maybe bring your, increases your adrenaline. It allows you to kind of be on your game, right.

And I think as a result of that I’ve been more able to accept change and lead change. And in a company like Anaplan, where the opportunity is so great in the marketplace for what we have to offer, there’s a tremendous amount of opportunity, right? So, there’s rapid change like, you know, always hiring, bringing new people in. Our initiatives do evolve quite frequently, we’ve get different requests that come from customers, we’ve got to deal with that. 

And so, change is a big part of what we need to deal with in order to be successful. And so, the way to do that change is, is to be agile, right? So as a person and as an organization so that you can be receptive of it, work through it, deal with the anxiety that comes from it and make sure that people are aligned to what needs to happen in order to be successful.

Pam: Well, Frank, I’ve heard you say one of my favorite words and I think everybody’s using this word quite a lot now authentic, and it’s, it strikes me like how authentic you feel to me. which is lovely. but I don’t think people really know what that means. Sometimes I’ll ask them. What, how do you define that? What is your thought about, what does it mean to be authentic, and how do you help someone when you think they’re not being authentic?

Frank: I think people tend to want to put out an image of themselves. And I think whether it’s society or whether its organizations have required them to do that. And I think as a result, it’s not allowed people to really bring the best to the organization or really to whatever engagement that that’s out there, because there’s that veneer, right. And when you can remove that veneer and people don’t feel like they have to perform in any way or follow a specific model or image, it allows them to really be more comfortable in their skin and who they are and bring their best selves too.

And when they’re doing that, they they’re going to, again, goes back to what I said before. They’re going to be more excited. They’re going to be more engaged and that’s going to kind of build on itself with working with others. And so that’s, when I think about authentic, I think of it that way, right. Bring your best self and not worry. We do want, it goes back to what we said before, have the right checks and balances, as it relates to the values. If we’re grounded in the values and we’re grounded in behaviors, when people bring their authentic self to it, there may be a little bit of adjusting, but it’s not like it let’s say it was in the past.

And I think organizations, I see that more and again, we’re evolving within Anaplan on that, on people that we bring in, when you’re authentic, you’re going to also be more apt to welcome differences, right. And your biases then start to disappear. so that that’s, I guess that’s what I would say as far as authentic.

And then it relates to the organization, right? It goes back to the character. It starts to build a character. And then when you, if you work with customers, the biggest thing I love about Anaplan is what I hear from customers when they talk about a product, yes, but the experience they have with Anaplan, which is the product, which is the people, which is the engagement, and see a smile on people’s face when they talk about it. 

One customer said to me, I’ve worked in doing what I do for like 20 something years and vendors that I’ve worked with have been vendors. Anaplan has not been a vendor. It’s been an engagement, a, you know, personal engagement. And that that goes a long way. 

Pam: Yeah. Sometimes I think that kind of culture of character starts with the CEO, and also with all the senior team. and you know, so when you have a top leader who’s demonstrating character, everybody else gets to see what that feels like.

And then yes, they get to be their best self. but sometimes it’s hard when you have people at the top that might not be, you know, they’re performing, they have the veneer, the things you’re talking about. I tend to think that all of that kind of happens when they’re, when we’re fearful.

And we’re humans, right? So, we’re all fearful in some ways. And fear can be really good but, you know, it’s how do we help our senior teams, especially to notice when they get into fear. I don’t mean fear, real danger, fear. I mean, you know, fear, ego fear, which is kind of false fear, you know, it’s not, we don’t really have to be afraid of those things, you know, like losing status or power or approval or, you know, attention. So, what are your thoughts as I say that? 

Frank: I think that’s very critical. I mean, it goes to a couple of concepts. I mean, as it goes back to this whole thing, and this is why, you know, I’ve been working also with Cy Wakeman and reality-based leadership and she has her latest, her last book was No Ego, right. And when you can diffuse ego especially among the leadership team, you, you eliminate politics, you eliminate all that other negative vibe that happens. And then that becomes a great example that then starts to permeate down through the organization. And, and so there’s so much that goes with it, but the interaction of a leadership team, it’s not only important for the interaction of that team, but it’s the model that it sets for the rest of the organization.

And also, you know, the effectiveness that those leaders individually and collectively, you know, have as far as the impact that they can make in that organization to drive certain initiatives and various things like that. And also, you know, they’re the models of the character led culture, right?

So, they have to really demonstrate the, those, those right values and those right people. 

Pam: Well, I’m really hoping that your book is a big hit

Frank: books. I think just, and, and, and Pam it’s, it’s just, I wrote this book just collecting. Experiences I’ve had, but also a lot of experiences that I’ve, I’ve learned and heard from others, peers, people that I’ve engaged with. Again, I’ve been fortunate to be part of some good organizations and work with some really great people.

And you learn from that, right? You learn from other people. So, this is not just me. This is kind of sharing that. And this past year with all the change, unrest, everything else that we’ve had to deal with, it allowed me to kind of step back and reflect and say, oh, maybe there’s some really nuggets here that others can leverage.

And that’s what I see their nuggets of leverage that maybe someone can pick up, learn from, maybe share theirs in in certain conversations that may come from reading the book, which is what I’m hoping for. 

Pam: Yeah, I’m wondering if during the time, last year where everybody was, seemed to be kind of in a panic, a lot of change was happening and especially the first few months, while everyone was adapting. Did you, did your team feel a sense of more stability than the norm because of the character-based leadership?

Frank: So, one of the things I think is really important on this is, is really the empathy, because in the early days of COVID I think empathy, showing empathy to one another allows you to better appreciate what that person may be going through, and how you can offer whether it’s a listening ear or whether there’s something else that you can do to kind of assist, right. I tried to, we, we, we in an Anaplan.

Uh, tried to open that sense of empathy with each other, because we were dealing with business disruption, we were dealing with personal change. Interaction, right, that we were just so used to, that was changing and so forth, but somewhat empathetic to each other, allowed us to kind of work through it. And that’s a big part of it, this character led culture. 

It also allowed us to show empathy to customers, right. Understand what they were doing. And as a result of that, we developed a, an offering. It was a free offering at the time that we made available to companies that said, by the way, we know that, you’re dealing with this huge issue. Why don’t you use Anaplan’s product, especially around healthcare, right, and in some of the things that were going on with hospitalizations, things like that. We, we, we volunteered our product to kind of help in those situations. 

And it’s amazing, the kind of will Goodwill that, that, that creates over a longer period of time. So, I would say it allowed us to really kind of move both inside the company and outside the company and being much more empathetic and dealing with the situation and then finding ways to work through. 

Pam: I’m hearing a lot of humility too, you know, just humble, connected with empathy that we don’t always know what’s going on in someone else’s life. so, although everything may seem fun on the surface, we just don’t know. 

Frank: And I think we all saw that this past year, right. There was so many things, and when you’re, when, especially when you’re on a video, right. All things, kids, dogs, cats, various things. I mean, situations where there was challenges in the home. All those things become reality. Yeah. 

Pam: Talk about reality based, right. We got real this past year. Definitely, definitely. Well, I love the conversation about empathy, especially on style bias. I think honestly, you know, there are so many personality assessments that sort of puts you in a box and then you start thinking that’s all I am.

And you know, my, my great desire for the world and especially for young leaders is to get out of that box, and that’s the only where you begin. It’s actually your character that shapes your destiny so much more than just your innate tendencies and preferences. What, what is it that you would love to say to all of the leaders that are going to be leading the world next beyond us, Frank? 

Frank: I would, the first thing I would say and I know over the years, culture has always been out there, but I think there’s been a sense that culture is fluff. It’s something that’s nice to have. And I, and I think again, with all that’s happened in the world of late, I think this is a call here that leaders have to be much more aware that you know, a character led culture is necessary, it’s not a nice to have. 

And you know, it goes back to that saying about culture eats strategy for breakfast, right. And you can’t succeed unless you do have a strong sense of who you are and the organization is, and all the studies show that, right? So, my message is to acknowledge that a character led culture is important as a leader, there are things that you can do to make it there, make it alive and, and, and make it evolve.

And as a result, you’re going to be able to attract better people, more people. They’re going to be much more energized and, and you’re going to succeed much more then you did without. And it, it also is probably the right thing to do just in society and also in the communities that we’re, that we live in as well, because it encompasses the whole point of diversity in all different ways.

Pam: So, I just have one final question for you, that I’m curious about. I’m actually dying to ask you this because it’s been my experience that when I feel good about who I’m being, I’m happier. And I’m just a better person to be around. And so, I look back over my life and I would say in my twenties and thirties, you know, maybe I didn’t have as much character,

And I realized that and I learned that I wanted to improve it, and spent a lot of time, you know, doing that. Of course, that’s my life’s work is that, and as I probably did it because I needed to do it, but I can say that, you know, 30 years later, like I’m happy there there’s a definite link between choosing to be a person that you can look at in the mirror every day and feel good about who you’re being, even in the midst of a crazy year, like last year just choosing the right thing to do, you know, in every moment links to happiness. What, what are your thoughts about it?

Frank: I agree fully with that. I mean, it goes back to the whole thing we were talking about with as far as being authentic, right. You can bring your authentic self and then as a result, you’re feeling better about it. And I think, you know, society again has changed over the years and I think it’s much more acceptable, right, and needed. 

The other thing here too is, when you think about organizations the world is much more competitive too, right? So, you want to have something that’s going to attract people to be part of what you’re trying to accomplish, an organization, a mission, right. That’s a strong attraction right now, especially with some of the younger generations. I mean, that’s where this change is evolving, right.

So, I think if we all step up and approach that, it works out to, to truly be a winner, for the person as well as for the organization. 

Pam: Definitely. So where are we going to find your book? 

Frank: As I mentioned at the beginning, it’s up for pre-order. It’s on Amazon. It’s on Barnes and Noble, anywhere where books are available online through pre-order it goes it’s going to be shipped out on the ninth.

And so, I just encourage everyone to take a read and see what you think and send me back any feedback that you may have. 

Pam: The book is Upstanding by Frank Calderoni, CEO of Anna plan and you can find So, I’m going there. You have a new customer. And I’m excited about having some good metrics and a balanced scorecard.

that’s. That was a very helpful in the hospitality industry, but we had to make our own, so I’m glad you made this, a SAS platform and I’m going to go check it out. 

Frank: Thank you, Pam. 

Full Episode Transcript

What’s Your Tilt? is hosted by Tilt 365 CEO Pam Boney, and produced by Earfluence.

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