Jane Saccaro

Jane Saccaro, Executive Coach, Consultant, and Speaker, explains the power of consciously creating ripples that positively impact the communities you are a part of.

Jane Saccaro believes we all have the chance to be positive ripples and beneficially impact the organizations, communities, and families we are part of. Learn more about Jane's philosophies on "ripples" and "splashes" at janesaccaro.com.

About the Guest

For the last 25 years, Jane has helped individuals and organizations formulate, effectively communicate, and mobilize to achieve a shared vision. She has been fortunate to serve in leadership roles with a top-tier consulting firm (Bain & Company), an entrepreneurial start-up (eToys.com), a Fortune 500 corporation (Princess Cruises), and a dynamic non-profit organization (Kesem.org).

As CEO of Kesem, Jane regularly gave speeches to hundreds of supporters, adapting her style to connect with sophisticated corporate partners, foundations, donors, families, and college students. During her nine-year tenure, the organization increased its service base from 1,200 to 10,000 children served annually, with donations growing from $1M to $13M.

Jane is passionate about helping individuals unlock their unique gifts and vision, understand their strengths and areas of growth, make choices aligned with their values, and create steps toward the life they were meant to live. She believes in elevating voices and presence, not only to allow for greater individual fulfillment, but to benefit the world with more inclusive and expansive perspectives, skills, and collaboration. She is an enthusiastic champion of others, and enjoys connecting, laughing, and celebrating the victories (both big and small) we have every day. Jane earned a MS in Engineering-Economic Systems, and a BA in Economics and Psychology, from Stanford University. She is a Certified Professional Co-Active Coach (CPCC), which is recognized as the most rigorous and respected coach training and certification in the industry. Jane resides outside of Chicago with her husband, three children, and her favorite hiking companion (her dog).

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Alison Dean (00:09):

This is the Breakthrough Podcast, an ongoing series where we interview game changing leaders in technology, business, government, and entertainment about their experiences and perspectives in life and leadership, learn about their latest breakthroughs and hopefully inspire you to have some of your own.

Alison Dean (00:32):

Welcome to The Breakthrough. I'm Alison Dean, and today we are talking with Jane Saccaro, former CEO of Kesem National, a nonprofit that supports children who are affected by appearance cancer, and currently she is a certified professional coactive coach and consultant. Jane sent me this quote from Mary Oliver, which I love. "What is it you plan to do with your one wild and precious life?" Love that. Hi, Jane.

Jane Saccaro (00:58):

Hi, Allison. Thank you for having me.

Alison Dean (01:00):

Yes, I'm happy to have you. I want to know what that quote means to you.

Jane Saccaro (01:04):

Oh, there's so much in that. I think at the essence, it means to me that each day is a gift that we've been given and it's our choice of how we are going to use that as a perennial planner. I love that she's included, "What do you plan to do with this?" Because that gives some sense of intention and planning, which has been a big part of my life and just reminds me that each day I get the opportunity to show up and do it all over again, and that is the greatest gift of all.

Alison Dean (01:38):

I love that. Okay, so this is the breakthrough. Curious about what you recall as the first breakthrough that set you on your career path, like that inciting moment?

Jane Saccaro (01:51):

Yeah. I think for me it happened in a startup that I was working at. It was called etoys.com. It was at the height of the very first internet bubble, and I had previously been working at a consulting firm and everyone was jumping into this .com excitement. And so, I left the consulting firm and jumped into a job at eToys knowing nothing about what I was doing, but just having a desire to be part of it. And so, since I knew very little, I took a big pay cut, I took a big title cut and I showed up and I was the associate product manager in charge of shipping.

Jane Saccaro (02:37):

And so, my job was literally, "What does the shipping page look like in your checkout?" It was a lot to stomach like. Oh wow, I went from this big important job where I was advising Fortune 500 companies to, I'm now responsible for shipping. But I thought about, Hey, I chose this for a reason. I chose this because I wanted to learn. I chose this because I really wanted to dive in. And that's what I did. And an incredible opportunity presented itself to me. Three months later after I joined, we went into peak season, so holiday season 1999 and demand far, far exceeded our systems and our expectations. And while that's really exciting for most companies, if you are a toy company and you are responsible for delivering on Christmas and you are failing miserably, it is really, really challenging. And so, we all got plucked out of our day jobs and put into all hands on deck, we need everybody to help out in the warehouse. We need everybody to help out in customer service. And so, lo and behold, I was put in charge of the escalations desk, which is basically the last place you want to be in the weeks leading up to Christmas because you only get to talk to the people that you are not going to be able to deliver on their Christmas joy. And what I learned through that process is I had the ability, even though I'd never been in this space, to quickly figure out, okay, here's the systems and processes that we needed in place to be able to manage a really, really difficult situation, and here's how I can bring all sorts of different people with different backgrounds along on this journey so that we can do our very best to try to placate some very, very upset customers.

Jane Saccaro (04:29):

Flash forward, why this was a breakthrough for me is I then got plucked permanently out of product management and for the next year worked across the company, bringing together people from every part of the organization to redesign the customer service on the backend. It taught me a few things. It taught me that it's okay at times to take a step backwards and pay or responsibility if you really do need to learn. It also taught me that the skills of being able to go in and figure out the right systems, the right processes to get done are very valuable. But the most important skill, and the thing I've tried to use in every role since then is this ability to bring together lots of different people from lots of different backgrounds. Often when I don't have direct reporting relationships over them and together achieve a common mission.

Alison Dean (05:22):

I love It. This goes back to your favorite quote and intentions and things. Do you have a morning routine?

Jane Saccaro (05:29):

I do.

Alison Dean (05:30):

I'd love to learn about Jane's morning routine.

Jane Saccaro (05:34):

As context, I'm also a mom of three work and I have a very devoted dog. The morning routine, for it to be a true morning routine starts quite early. I get up usually between 5:15, 5:30 in the morning. First thing that happens is I grab a big cup of coffee in the silent house and I sit down and I meditate. I do the Calm app, the Daily Calm, every day. It is how I start my day. I wish I could say I had the discipline to sit in Lotus position on the floor, but I'm on a comfy couch with my warm cup of coffee, and that's my meditation. From there, I write down three things that I'm grateful for, and then I shift into getting ready. And for me, that involves exercise. Usually I'm on our Peloton tread, doing a class with one of the really inspirational teachers that get me motivated, and then once I finish that, then I'm waking everyone up, getting them ready, getting them out of the door, and hopefully at my desk after getting everybody to school, and that by about 8:00.

Alison Dean (06:40):

It's a lot going on between 5:00 and 8:00. It's busy like it. You talked a bit about the career trajectory from Fein to E Toys. What was it that prompted the move from eToys to Princess and then from Princess to Kassam?

Jane Saccaro (06:57):

Yeah. So, eToys was an amazing experience for the highs and lows of that internet ride, but sadly, at the end of that ride, the organization no longer cease to exist. It was a decision made for me. I was one of five employees that stayed on to help the organization through bankruptcy and sell off all of our assets. And what that experience taught me is that I loved operations. I just had a yearning and I toyed for a bit of, "Do I go back to Bain?" And what I knew in my heart was I wanted to be the person who was doing the operations. I wanted to be the person who was leading implementation and managing teams. And Princess had been one of my clients before when I had worked at Bain. The head of Human Resources gave me a call and said, "Hey, we're looking for someone to come in and create a new department here."

Jane Saccaro (07:50):

And it's in operations, it's a department that has not existed. We're looking for someone to come in and really build out our onboard revenue group. And I don't know, Alison, have you ever taken a cruise?

Alison Dean (08:02):

I have.

Jane Saccaro (08:02):

Okay. All right. you're familiar with this. Onboard revenue is basically everything we ask you to pay for once you come on the ship. It felt like an amazing opportunity to get to work in travel and leisure, an industry I am really passionate about. And I got to think about, "Ooh, how are we going to make people's experience shopping and in the spas and in photography and in the casinos even more exciting and more enriching?" And to date, Princess had not had one organized group doing that. It was living in lots of different areas and outsourcing a lot of that work to concessionaires, and we really wanted to bring all that in-house. I got the opportunity to design the strategy and then really build out our team to execute on that.

Alison Dean (08:48):

That sounds like a really fun project. Okay. What took you then from Princess to Kesem?

Jane Saccaro (08:55):

Princess to Kesem, again, what caused me to leave Princess was actually a personal reason. My husband got an opportunity to be transferred overseas to Switzerland, and I quickly did the time zone math and discovered that I was not that super excited about having calls with a nine-hour difference. I winded down, I continued to do some consulting work for Princess, and then we moved overseas. And while we were there, I had the opportunity to really reflect on, "Okay, what do I want to do next?" It was the first pause I'd really ever had in my working career. And what kept calling to me was I really wanted to do something that gave back. I really wanted to do something with a purpose beyond what I was doing.

Jane Saccaro (09:37):

I spent our time over there really getting smarter about the social sector, understanding what it took to be successful in the nonprofit sector. I did a lot of reading. I Read fundraising for Dummies, Board Development for Dummies, and I had this path that I said, when we come back from living overseas, I really want to find a nonprofit and get involved and really bring some of these skills that I'd honed in the corporate sector into this space.

Jane Saccaro (10:07):

And I was so fortunate, we moved back and literally within probably a month, I really hadn't even started my job search yet, I learned about the opportunity at Kesem from a board member, and I was just so compelled by the mission. I'm sure we'll talk about it a little bit, but just as context, the way Kesem supports families impacted by parents cancer is by recruiting and training and mobilizing thousands of college students across the country. And so, as I read about it, I was just so inspired. I was like, "Wow, this is an opportunity to work with some of the most incredible dynamic young people who are making a difference while helping a population that had..." Obviously as a parent, I could relate. If I was ever diagnosed or I'd watched many friends and family go through this experience, your first thought is, "What's happening to your kids?" And so, it had a lot of appeal from the work we were doing, but how we got to do it and working with college students was ultimately what drew me in.

Alison Dean (11:13):

That's so amazing. Another fun fact about you, you have a master's degree in Engineering economic systems, which my producer and I both were like, "What is that exactly?" Maybe tell us what that is. I'm curious what called you to that master's degree and curious how that degree supported these various transitions that you had, if it did at all. I mean, I'm assuming it helps you.

Jane Saccaro (11:40):

I'll start with what it is. the closest proxy in other schools is industrial engineering or operations engineering. And really at a high level, it's looking at business problems from a quantitative mathematical perspective. And so, why I did it. As an undergrad, I studied economics and psychology and I was-

Jane Saccaro (12:03):

As an undergrad, I studied economics and psychology, and I was fascinated by the interplay of business and how organizations worked. And I felt like if there was something in my background that I wanted to really strengthen, it was my quantitative skills and my ability to come in and really bring that perspective to the work. And I was studying at Stanford, and they had a really cool program where you could start to take those graduate courses as a junior and senior. And so I started dabbling into that and really fell in love with it. A big part of EES, as it's called, is decision analysis. And so you literally learn how to take really complicated decisions. And instead of just being like, "Here's the pros, here's the cons, here's why I should do this." Put numbers behind expected outcomes and probabilities and help that guide individuals and organizations to make better decisions.

Jane Saccaro (13:02):

So it really played into the econ, the psych for me, but then also brought it home with, okay, we can actually put some numbers behind this and some data. Flash forward into my roles, I think it's had a huge impact. I'll just talk about the practical nature. When I enrolled in EES, I think at the time it was 90% male, 10% female, and the vast majority of people who were getting that master's degree came from engineering or science backgrounds. Very rare to see the econ and psych major role in there. So I think the practical skill that it gave me, which I've used literally in every role I've had, is you're showing up. You're definitely in the minority, you're coming at this from a really different angle and a really different lens than most people around you. How are you going to do that?

Jane Saccaro (13:56):

How are you going to figure out how to be successful? And so that practical experience, I think, was probably the most formative that I've used in so many different jobs since then. And then I think the analytics have helped me immensely because I can think about decisions from the emotional side of things. I can think about it from a rational side of things, and then this just brings data to it too, which allows, I think, you to reach lots of different audiences of what is ultimately going to move the needle in making that decision.

Alison Dean (14:26):

Right. I feel like I need to start learning about EES more and stuff. It's fascinating. Okay.

Jane Saccaro (14:32):

You do not want to know how many personal decisions I've created an Excel spreadsheet for it to be like, oh, turns out we should move to Chicago.

Alison Dean (14:39):

There you go. Or Switzerland or what have you, right? Yeah, I love that. Okay, so in the world of technology consulting, we use the phrase transformation quite a lot, and the word digital transformation, I feel like there's now new debates on whether that should be archived entirely because is it just transformation? But I'm curious for you, what does transformation mean in the Jane Saccro world of today, and how do you see it play out with your clients?

Jane Saccaro (15:05):

I think about transformation in two different areas. One is what it can look like in an organization, and what it can look like in an individual. So for the purpose of thinking about clients, I'll talk about just individual transformation, and I'm happy to talk about organization, too. For an individual, for me, I think what's so exciting about coaching and the work I get to do is often the people I'm working with have a pretty good sense of their goals and where they want to get to. And we do some work to articulate that and maybe bring some clarity. But what is so hard often is getting to those goals, and that's where real transformation comes in. That's the meaty stuff that we get to do, which is explore what's getting in the way of going for that goal? Is it limiting beliefs you have about yourself?

Jane Saccaro (15:58):

Is it the way you're approaching this goal? Is it that this goal isn't actually in service of you and what you're trying to achieve? And so where I see real transformation happen is when together working with a coach, a client can really uncover, this is what I want to go for, and I'm going to finally unlock the path that's going to allow me to get there, to get to see them to do that. In the coaching world, there's sort of this theory that there's an imaginary line, and a lot of different organizations have talked about this line, and we sort of live either above the line or below the line. And when we're above the line, it's all the good stuff.

Jane Saccaro (16:43):

We're creative, we're coming at life from a theory of abundance and there's enough, and this is the sweet spot of where we do all of our great work. And then there's where we spend 95% of our time, which is below the line, and it's where we're reactive and where we're not showing up as our best self. And we often have behaviors and thoughts, and feelings that are really generated by fear and generated by scarcity. So transformation for me happens when, with a client, you can create that awareness, and you can just get more and more of life above that line and in that space where they're doing their best work, where they're having a really positive impact on those around them.

Alison Dean (17:30):

I love that. Okay, so speaking of transformations, you've mentioned quite a few things where I think it could be in the category of transformation, but what comes to mind for you as the most memorable project or transformation that you've been part of and why?

Jane Saccaro (17:45):

Working at Kesem, for sure. So a little bit of context. So I started in 2010. At that point, we had 23 college chapters running across the country. What I quickly realized is these 23 chapters were pretty much running independently. We had sort of set up the organization, that we were not able or not giving a lot of centralized support. And so we gave a good training toolkit, good resources, and then they were on their own to go. So when I came into the organization and started talking about, "Wow, we're only serving 800 kids, and there's three million kids out there that we should be serving, how are we going to do this?" It was really clear, the only way we were going to do this is if we all started working together really closely and really supporting each other. And the first thing I did is I went on a little meet and greet and a listening tour with all of our college chapters.

Jane Saccaro (18:44):

And what I learned is, yeah, no, I have no interest in doing that. I have no interest in really collaborating because I got a good thing going here. I'm running my chapter, it's successful, and we're good. And so I got really curious and just started to listen about, well, why? What would it take for you to grow, and what do you really need in terms of support? And what I was able to figure out is there were so many opportunities, and there were so many things that each individual chapter was doing phenomenally, and a great opportunity to pull those all together into best practices and start sharing those with other chapters and start investing in the systems and tools that would really, really allow them to scale. And so together, once we started to do that, and once we constantly put it in mission first of our one desire is to serve more of those three million kids, and just started every day, every meeting, every time together with that.

Jane Saccaro (19:49):

Over the period of two to three years, it shifted really, really quickly, and suddenly the chapters were very interested in sharing information with each other, very interested in helping each other, very interested in taking new chapters under their wing. And probably my favorite thing that we did with the chapters is we launched something called Kesem it Forward, sort of under the pay it forward model. And basically, the concept was if a chapter at the end of the year had excess funds from their fundraising efforts, they could help fund the creation of new chapters. It went from something that was like, "Wow, that's really cool," to raising millions of dollars every year and funding a hundred chapters. So it was, to me, the best sign that we'd really moved from, okay, I'm operating here in a silo, to I'm part of this national movement and I'm part of this national organization.

Alison Dean (20:45):

That's so awesome. Now, in terms of the most difficult project that you've been part of, you've also said a few things in terms of things that you've had to do at Etoys, Princess. I mean, launching a new revenue model for a company seems like it could be difficult, or it could maybe be something you did at Bain. So I don't know, what do you think was the most difficult?

Jane Saccaro (21:10):

So many difficulties. I think the hardest I've ever done probably was at Bain, just because I was so new. And the model of a consulting firm is you're plopped on the client's site, and typically you're 20 to 30 years younger than the clients you're supporting. They're often, when you get to a line level, and folks that I was working with, they're not really that thrilled that you're there asking a lot of questions, and it's sort of like, is this just going to be a colossal waste of time on their part?

Jane Saccaro (21:44):

When I think back to really difficult formative moments, it was showing up in those client sites and being like, yes, I can quickly demonstrate that I will add some value. I will be very respectful of your time. I will develop really strong relationships with you so that, at the end of the day, I can get access to that. And many of those situations were sort of sweaty palms moments as someone who's 23, 24 years old walking into some pretty tense situations. So I think those were probably the most difficult experiences, but also the learning curve was so formative to being able to walk into other situations, and be like, all right, I got to figure this out really quickly.

Alison Dean (22:30):

The gear shifting, you were gear shifting really well. Okay. What do you think in terms of most innovative project that you've been part of?

Jane Saccaro (22:36):

I actually think some of the stuff we were doing at Kesem was really innovative. I was there for nine years, and so we were in the thick of it and often not even pausing to step back and really looking from a meta level at what we were doing. But now that I'm away from it, the innovation is really, really hitting home for me. And what I'm struck by is we had this model that, literally, with the right investment and the right support, it could just grow and flourish on an exponential level quite quickly. And the innovative part of it. So this is a combination of the work we did and just how humans are wired. There are many, many volunteer experiences that you can do where either you're doing hard work throughout the year or you're doing a really amazing hands-on experience.

Jane Saccaro (23:36):

And Kesem was this amazing blend of it. And so our student leaders would work their tails off throughout the school year. I mean, on average, they were putting in 500 hours of volunteer service throughout the year. But what was the magic and the innovation? Is after they worked so hard on fundraising, on outreach, on recruitment, on getting all the safety protocols in place, and all the operations, they were the ones then that got to go deliver the service. They were the camp counselors. They were the ones experiencing this firsthand. And so what it did is when they came back after that summer, they were motivated. They did not need any rallying cry. They're like, "Oh, I'm in because I had this firsthand experience and that is going to motivate me even more." So that model I think was incredibly innovative.

Jane Saccaro (24:29):

And then the other thing that I've stepped back and thought about is we were a virtual organization before virtual and hybrid was cool. Almost by necessity. We have been a remote organization and we were able to grow and scale and never have an office and never have a point of presence. But what I think we did that was really innovative is we were super thoughtful about meaningful in-person time.

Jane Saccaro (24:56):

So I've counted, I think eight times a year we were together for really important in-person time. And when we were together, we were really thoughtful about building relationships, establishing trust, all the cornerstones. So then it allowed us to then go back into our world and operate effectively in Zoom because we'd done all the hard work of the relationship building. And so as I'm watching organizations sort of struggle of what does hybrid look like? How do we do this? I think there's things in the in-person time and the relationship building and that culture building that was really innovative at the time.

Alison Dean (25:37):

Amen to that. Yes, to in-person time and understanding what that looks like if you are a remote first company. It is, I think, very necessary. Although I will say it's interesting how many people that have been on my teams that I've never met in person, that I feel like I've met in person just because of. I'm sure it'd be that much better in person, but it is interesting for me to reflect on that too. Okay. Part of me really wants to hear more about the Princess Cruise project because I find that fascinating. And also I'm like now very curious if all other cruise lines operate in an external vendor situation for all the onboard revenue stuff. I'm hyper curious, but I also feel like that could meander us into an entirely separate podcast episode.

Jane Saccaro (26:24):

I love the cruise industry. I'm always happy to talk about it. It's fascinating.

Alison Dean (26:26):

It is.

Jane Saccaro (26:27):

It is just as this city unto itself.

Alison Dean (26:30):

And it's also, I think when I was starting my career, I was also thinking I really should just enter into vacation business itself. The perks are probably epic. I mean, I guess depending on how you level up in the hierarchy of things, but yeah.

Jane Saccaro (26:46):


Alison Dean (26:47):

Right? All right, well this kind of segues into my next question. So on your website, janesaccaro.com, which all of our listeners should check out, the headline reads, Creating Positive Ripples, which at first I thought was tipping their hat at the cruise industry. But can you tell us more about these ripples as it relates to, I guess, your own career and your clients?

Jane Sacarro (27:12):

Yeah. I love the nod to the cruise industry. I hadn't even thought about that. The ripple for me is we never know the impact we are going to have on those around us. You have no idea. And in the choice of being a positive ripple, which I try to be, you have the opportunity to improve so many lives. It can be as simple as how you talk to the barista when you're picking up your coffee, to letting someone in front of you in the lane, to really looking at someone in the eye. So it starts for me with very small actions, but it goes to how you're showing up in the world. And I think the opportunity to have that positive ripple, that's sort of what gets me out of bed every day. I think I've been wired that way, and I've always believed that.

Jane Saccaro (28:04):

But watching this at Kesem is where it came to life for me. So little bit of context, 80% of the student leaders who volunteer at Kesem have had cancer impact someone in their family directly. And they're making a choice. They could say, "Woe is me. This really sucked. I lost my mom when I was 14. I lost my teenage years because my dad was in chemo throughout it." There's so many ways that you could rightfully respond in one way. And here's what I saw our student leaders do every time is, this was a really awful thing that's happened to me and I'm going to choose to respond in a positive way. I'm going to choose to respond by using this terrible thing and helping someone who's going through a similar journey and their ability to help someone because they walk the walk and they've experienced that is tenfold. It's on my website, so I'll share. My personal story was I started working at Kesem and seven weeks later, my younger sister was diagnosed with stage four colon cancer out of nowhere. So suddenly I'm in it. I'm in this job. I now have a very real connection with our mission, and she passed away within three months. It was just a really, really awful diagnosis and awful outcome. Alison, I'll tell you, I had many days at the beginning, "Can I do this work? Can I show up and talk about this subject that is so raw for me right now?"

Jane Saccaro (29:40):

And that thought of being the positive ripple was literally the only thing that got me through those first few years. I'm like, you have a choice. You can be mad at the world and you can be mad that this happened. And there were many days that that's how I felt. Or you can take this experience and do something good with it and do something that helps. And I know it helped me personally and my inspiration, I had to look no further than I had 18, 19, 20 year olds all around me doing this every day and showing me how to do that and how to live that way. And so that's what it means to me to be a positive ripple.

Alison Dean (30:21):

I love it. I need t-shirts that say it too. We all need the mantras on our wall. You can start selling those, Jane.

Jane Sacarro (30:27):

Yeah. There we go.

Alison Dean (30:29):

Another revenue stream. It's our quickfire. We call it the Break On Through segment. So basically I'm going to ask you a series of questions, just the quickest answer, just the first thing that pops in your mind, and here we go.

Jane Sacarro (30:51):


Alison Dean (30:51):

Favorite Chicago activity in January?

Jane Sacarro (30:57):


Alison Dean (30:58):

Oh, getting out of Chicago.

Jane Sacarro (31:00):

In Chicago. I'm looking outside. It's so great today. And we have no snow, which is crazy. So let's pretend we have snow, then I'll answer your question. It is going for a hike with my dog in the snow on a beautiful, sunny, cold day.

Alison Dean (31:13):

I love that. Okay. Best pizza in Chicago.

Jane Sacarro (31:16):

Oh, this gets me in so much trouble every time. Giordano's was the most faithful, incredible sponsor of Kesem, and I adore them. And one of my dearest friends ran Lou Malnati's for many years. So I'm going to give it to both of them. Giordano's and Lou Malnati's.

Alison Dean (31:33):

Okay, good. Good. That's fair. Very politically correct. Favorite item at Trader Joe's?

Jane Sacarro (31:39):

Ooh. I may call them the wrong thing, but they're salted caramel, chocolate covered, caramel, salted. I get them every year, but only for our holiday party because if they're in the house, they're gone.

Alison Dean (31:52):

I have things like that that I cannot keep in my house as well. Coffee or tea?

Jane Sacarro (31:56):


Alison Dean (31:57):

AM or PM? I think we got that one answered already. But.

Jane Sacarro (32:00):


Alison Dean (32:00):

Favorite place to travel?

Jane Sacarro (32:02):

Anywhere where I can hike and there's sunshine.

Alison Dean (32:06):

Okay. Historical figure you'd like to have dinner with?

Jane Sacarro (32:09):

Ooh, Jesus.

Alison Dean (32:12):

Favorite book.

Jane Sacarro (32:14):

Anything by Brene Brown. But if I have to pick one, Daring Greatly.

Alison Dean (32:17):

Wow. Okay. If you could have one superpower, what would it be?

Jane Sacarro (32:22):

I would love to be able to time travel.

Alison Dean (32:26):

Ooh. Good one. Love that. Last TV show that you binged.

Jane Sacarro (32:31):

White Lotus.

Alison Dean (32:33):

All right. I've heard good things. Favorite movie.

Jane Sacarro (32:36):

Something that really moves me, which has got to be a musical. So I'm going to go Greatest Showman, maybe Moulin Rouge. One of those.

Alison Dean (32:45):

Oh, I love that. Okay. And favorite podcast.

Jane Sacarro (32:49):

Again, Brene Brown. Both Daring to Lead and Unlocking Us. Those are my go-tos.

Alison Dean (32:54):

I love that. Okay, good. All right, so continuing our tradition of past guest questions, this week's Breakthrough Club question is from Dr. Ron Glickman, CIO for Trader Joe's, and author of the book, Lead for a Change. He asks you, Jane, what was the biggest leadership lesson that you learned as CEO of Kesem and how has it influenced your leadership style since leaving the organization?

Jane Sacarro (33:27):

Can I pick two?

Alison Dean (33:29):


Jane Sacarro (33:30):

Okay. So the first is never underestimate the power of being a good listener.

Jane Saccaro (33:36):

I saw this firsthand. I talked earlier about the power of listening to our student leaders and understanding what they really needed. I also saw it when it would come to maybe a tense situation with a parent or with a camper or with a family. Often there's so much going on in the lives of people that we were serving that really the opportunity to listen, to really uncover what was going on, could do profound things in diffusing tense situations, and really being able to provide the help that folks needed. And at the end of the day, Kesem was an organization that people supported and gave to and came to because of what they felt, right? That's what it was all about. And listening is a big part of that. Understanding what's important to people, what motivates them. And that was the biggest shift for me of learning how to support donors and board members, was really getting to know them and the underlying dreams and motivations and thoughts they had for supporting it. And I don't think you can do that unless you're really actively listening. So that would be one.

Jane Saccaro (34:49):

And then the second would be your integrity and what you do matters so much. And it's like what we say with our kids. You have to walk the walk. You can't talk the talk. And so examples for me at Kesem, gratitude is one of my most important values. And expressing gratitude is incredibly important to me. So it's one thing to say that to our student leaders, like, "Hey, make sure you get your thank you notes out promptly after every gift. Make sure you do this." But to walk the walk, it became very personal to me. So it meant that I probably hand wrote hundreds of thank you notes every year. It meant when I got on a stage at an event, I would have all the sponsors memorized, and I would personally thank each one of them. It meant that everyone got something customized and delivered to them after each event.

Jane Saccaro (35:49):

And that walking the walk, I think is what actually instills the values. And if you talk to our staff or you talk to our student leaders, those are now just intrinsic. And it's so different to just say those things...

Jane Sacarro (36:03):

... and it's so different to just say those things versus to actually do that and to know, "Yeah, I'm right there with you. My hand is cramped also, but we're still going to keep on writing."

Alison Dean (36:16):

Yeah. Okay. What are maybe some of the biggest lessons that you've learned from working with other leaders?

Jane Sacarro (36:22):

Talk about never underestimating the power a leader can have, good or bad, on those around them. And I've seen it in every organization I worked with through consulting and then being in the organizations. But a good manager is everything. If you have a supervisor that you have a great relationship with and you want to work for and you're excited to be there, that's like 80% of the job satisfaction right there.

Alison Dean (36:52):

You're right.

Jane Sacarro (36:53):

I think that is actually what the studies have said when folks leave, 80% of the reason is the person they work for. So how you show up and how you are there for the people that work for you, matters so much. And it's not just the employees, it's their families. It's what they do when they leave. It's the person they're going to hopefully let in on the highway and that. So I think leadership has a tremendous amount of privilege and a tremendous amount of responsibility with that, to show up in a way that is really supportive.

Jane Saccaro (37:25):

I think the other thing I'd say about leadership is we as humans are so hardwired to look for the negative. It's called a negativity bias. It's studied in psychology. And our brains, I think I read somewhere recently, like 95% of the thoughts in our head are actually negative. We're just wired that way. And for every negative comment you hear from someone, it takes five positives to kind of bring that back into balance about how you're feeling about yourself.

Jane Saccaro (37:56):

And so I think there's an opportunity, and the leaders that I really admire do this really well, which is you have an opportunity with feedback to equally shine a light on what's working and what's going well, as well as being constructive. And you need to do both. But I think as leaders what I see too often is there's a lot of feedback on what's not working and a lot of constructive feedback and what's working is usually like, "Yep, great. Great job." And so I think the leaders that I most admire are spending just as much time focusing on here's working, here's what I want to see more of, and that's how they're cultivating those incredible relationships with the people around them.

Alison Dean (38:38):

If I was in a jazz club, now would be the time for the snaps. Yes, yes, yes. Okay, now what about the most important lessons that you've learned from your mentors?

Jane Sacarro (38:50):

I think what I have learned is the best way to show up is by being really in touch with who you are as a leader. Knowing your unique strengths, your unique gifts, and then surrounding yourself with a ton of great people who compliment you in those areas that maybe aren't your strengths and maybe aren't your passions and your interests. And the best leaders that I've seen and the best mentors that I've had, do that beautifully.

Alison Dean (39:22):


Jane Sacarro (39:23):

They know their lane, they know when they're in their zone of genius or their zone of greatness, and you can see it. And then they're not afraid and they're humble and down to earth enough to say, "Yeah, in this area, I'm not the superstar and I'm going to make sure I've got great people around me to support me in these areas."

Alison Dean (39:43):

More snaps. More snaps for you, Jane. What conversations are you most looking forward to as you continue coaching?

Jane Sacarro (39:51):

There's a couple things that are really just fascinating to me. Okay, one, I'm just excited because it seems like we're at this inflection point where it's okay to talk about your emotions and feelings in a work setting.

Alison Dean (40:04):

Thank you. Right?

Jane Sacarro (40:05):

It's like the iceberg. You can see 10% of the iceberg and 90% is below the surface. That is how we are as human beings. What you see above the surface is our behaviors, our actions. But what's going on underneath are all of our thoughts and feelings. And yet we've somehow been taught you can't talk about those at work. And that is what is motivating and fueling all of those behaviors. So in general, I'm excited that that is becoming more of a norm. And I'm seeing that, especially with my executive coaching clients, that there's an interest and an aptitude to exploring what is under there. Like, "Hey, I keep on repeating the same behavior. Let's actually dig into why that's happening." I think that's really, really cool.

Jane Saccaro (40:52):

The second thing is I keep on reading that this is the year of connection. Astrologically, there's a whole bunch of reasons, apparently. I'm such a novice in that I can't speak to why. And I think it's an interesting moment for all of us going back to the remote and hybrid work to really think about how do we foster connection in this world. Because we're never going back to the way it was. This will be the reality. And so how do we really foster meaningful connection in that and thinking about meaningful in-person meetups and ways to do that. And then the last thing I'm so fascinated by is, I'm turning 50 this year, and so that's probably why, but Arthur Brooks wrote this great book called Strength To Strength, and it's really shifting from all of this doing and executing and work that you sort of do in the first chapter of your life to, "Hey, in this next chapter, how do I want to use all this accumulated knowledge and experience to really coach, mentor, develop those around me?" And I personally am really interested in that work, but I also think working with clients who are at that point and are really thinking about what does this next chapter look like for me and how can I really help lift up those around me, gives me a lot of energy and a lot of excitement.

Alison Dean (42:20):

That's awesome. Okay, what future innovations are you most excited about? And it could be personally or professionally.

Jane Sacarro (42:29):

I think we have to solve how to connect better. I think the future innovation for me is, there's all these studies that are being done that we are becoming far more and more individually focused. So people are not as involved in religious institutions like they used to be. People are not involved in community organizations like they used to be. There's not the fabric of our society, which used to keep us involved and interacting with people at different ages, different backgrounds, different stages of life, and it's just not happening naturally.

Jane Saccaro (43:05):

And so the future innovation I'm really interested in is how do we do that? How do we start to create that? And I definitely don't have the answers, but where I'm leaning in on this is like there's a lot of parallels for kessim with me in the adult world. So how do we create this sense of engagement and involvement in a way that uniquely takes each of our skills and uses those to help those around us? And I think it solves a lot of things if we can do that. I think it helps with connection. I think it helps with mental health.

Alison Dean (43:45):

Oh, yeah.

Jane Sacarro (43:45):

I think it could do wonders in terms of really lifting up communities around us. So that's my future innovation. I have no idea where it's going. When I wake up in the middle of the night and have excited thoughts, that's where my brain goes.

Alison Dean (43:59):

Maybe that's telling you, Jane, it's something that you need to be the one to champion.

Jane Sacarro (44:06):

It might.

Alison Dean (44:06):

Oh. Okay, that could tie into the next question. We talked about an early breakthrough. What about a recent breakthrough that you've had?

Jane Sacarro (44:13):

Oh, gosh, this is good. Okay, so when I went into coaching, everybody in my life was like, "This is natural. You've been coaching and advising and mentoring your whole career. Of course you should do this." Then I enrolled in my coaching classes and I learned, literally in the first week, that I have not been coaching at all for 25 years. What I've been doing is problem solving, advising, recommending, telling people what I think they should do. And that serves its purpose. It can be very helpful. It is very different than coaching.

Alison Dean (44:47):


Jane Sacarro (44:48):

And my breakthrough has been really in the last several years of going through this certification process and learning a new way to help those around me. And coaching is far more about, "Let's uncover what's going on uniquely in you, Alison," versus, "Tet me tell you, Jane Saccaro, what I think Alison should do." And that's why coaching works, by the way. If it's about telling you what to do, you can buy a bunch of books that'll tell you what to do, and yet you still don't do it. And so I am learning a whole new set of tools and techniques and ways to support my clients. And it is hard. It is hard to learn. I can literally feel the synapses in my brain having to be fired up and new pathways being formed every day. But I do really believe that it is transformational. And it's changing how I parent, it's changing how I relate to my spouse, my parents, my siblings. So it's really an interesting journey.

Alison Dean (45:56):

So it sounds like there could be a Jane Saccaro book that's going to emerge as well. We have the Ron Brickman. You can do your four word. It's perfect. Is there anything I didn't ask you that I should have?

Jane Sacarro (46:11):

No. You did such a beautiful job, Alison. I could stay on this for another three hours and give you lots of other questions, but I think you did such a beautiful job. I think we covered all the important points.

Alison Dean (46:21):

Although I really do think it's true. We could have you on for a whole other focused sesh on something, for sure. Jane, thank you so, so much. I so appreciate you being on The Breakthrough. It was a pleasure to have you, and I look forward to more stories, at some point, I definitely do.

Jane Sacarro (46:40):

Thank you, Alison. It was a pleasure. I really appreciate your time too.

Alison Dean (46:44):

And thank you for tuning into this episode of The Breakthrough. Be sure to subscribe on your favorite platform and follow us on Twitter and Instagram, @BreakthroughPod. I'm your host, Alison Dean. Until next time.

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