194 – Winning At Life With Tim Flanagan And Amanda Kramer

John Over the last two decades, I’ve been on a quest to learn everything I can about leadership obsessed with what makes the best leaders so good after running companies small and large for the last 20 years. Today, I speak on stages all across the world to audiences who are interested in that same question. My name’s John Laurito and I’m your host. I invite you to join me on this journey as we explore this topic. What makes the best leaders so good? Welcome to tomorrow’s leader. 

John Hey, they’re tomorrow’s leaders, OK, if you want to know how to build and run a winning organization, this is the episode you want to pay attention to. So I have Tim Flanagan and Amanda Kramer on. I think you’re going to love this. I love the conversation. Tim is the president and CEO of MassMutual and Charlotte. And Amanda is the director of adviser experience. And basically, the two of them work phenomenally well together. Amanda is kind of the person to bring a lot of Tim’s ideas around culture to life. 

John She’s done a phenomenal job and I love their stories. So you’re going to hear a lot about what they do. And as they’re describing the culture, I’m like, wow, this is a place I’d love to be a part of. I mean, think about all the companies and industries out there. And a lot is commodities, but the culture is really what differentiates and they make that point. So listen to some of the things that they do that’s really unique. And it’s not surprising their results ultimately reflect what they’ve done with the culture. He has won, recognized him as the most admired CEO in twenty nineteen in the Charlotte Financial Services area, which is a highly huge award in a highly competitive field. 

John And they have also attained the chairman’s award, which is really, really tough coming from the business. I know how tough that is, multiple years. So I think you’re going to really like this. So here are Tim and Amanda. All right. Welcome to today’s episode of Tomorrow’s Leaders, where we dove deep on all things leader related to leading yourself and leading others. 

John I am thrilled to be back here today with two fantastic guests. I’ve gotten a chance to know Tim Flanagan and Amanda Kramer pretty well over the recent number of weeks and very, very highly respected in their organization and in their marketplace. Tim runs the MassMutual Carolinas Organization, which is a top-performing financial services organization in the Charlotte area. Amanda has been a key ingredient of that place over the last ten years, I believe you said, right, Amanda? 

Amanda I’ve been in the industry for ten years and have been with Tim for five years. 

John OK, well, welcome to you both. Thank you for joining me today as guests.

Amanda It’s awesome. Thanks for having us. 

Tim Thanks for having us, John. It’s good to be with you. 

John Absolutely. Likewise. So, so many things I’d love to talk about and just pick your brain on because both of you have had a lot of success in an industry that’s very tough, as you know firsthand for sure. And it’s all about leadership. I think about financial advisors leading their clients and your roles in helping to lead an organization that helps advisors do that effectively. And to maybe start with you, because I know your background, you’ve over the last 18 years been commanding that ship, so to speak, and leading that organization to continue greatness and even above and beyond where it was when you started there, of course. Tell us a little bit about your experience. I know it’s a big question, but what has this what do you think has been some of the keys to your success in leading an organization like that over the course of almost two decades that you’ve been there? 

Tim Yes, good question. There’s a few key things, John, I think that jump out when I took the firm over from my predecessor, Ivan Heinrich’s, we had about a three-month transition period. And he had given a speech earlier that year that I was that entitled Leave the Campsite Better Than You Found It. And that speech, along with a conversation we had in our three-month transition around stewardship, really gave me a sense that as long as I was able to run the organization and lead the organization and in our construct, I, I am running and owning the organization, that I would be a steward to everybody around me and all the resources we had. So my mantra became, I’ll leave the campsite better. And then I found it and in the 18 years certainly learned an awful lot. But some of the key elements of doing that have really been focusing on the advisors that we serve and the clients that they serve and making sure that they’re having an outstanding experience with our organization and also making sure that the employees that are part of our firm that support those advisors and their clients are the best people they can be and that we’re giving them an environment to learn, grow and be challenged in. And we’re doing that in a way that we have shared values, shared vision, and mission of success. Ultimately, now are our tagline is helping our advisors, really everyone in the organization win at life. And, you know, that’s just been an iterative, evolutionary process of trying to respond to the market, overcome the challenges that, as you mentioned, that inevitably come our way and just keep the eye on the prize again, helping everyone win at life, making sure the organization is healthy, moving forward and relevant. 

John Well, I love that a few things that you said, a love win at life. You know, most leaders I think business leaders are so focused on their business, they forget or maybe don’t even realize that the name of the game is really it’s winning at life. It’s not just the business aspect. So I love the fact that that’s what you’re focused on. I know one aspect of that, obviously, is helping people step outside their comfort zone and do things that they haven’t done before or take chances, take risks. And that’s how you help people grow and that’s how you help an organization grow. At the same time, I know a lot of leaders struggle with that, with how to get people how to help their people and their organization do that. How do you, what are your thoughts on how you’ve done it or how other leaders that you’ve seen have done it extremely well? 

Tim Well, I think this is a classic example, John, of leading by example, putting yourself in situations where you’re vulnerable are going to be uncomfortable, putting yourself in situations where you can be authentic and share with people what you’ve learned, whether it’s from a success or failure. But I think that’s a key piece. I can’t ask anybody on my team to get uncomfortable if I’m not willing to get uncomfortable. And I can’t say you go out there and do that scary thing while I stay back here and don’t have to face that. So you know, I candidly, probably earlier in my career, ran into too many self-created challenges to stretch my comfort zone, but now really look for ways to stretch myself, challenge myself and bring other people along in the journey. And it’s not easy because, again, we’ve had a lot of success and success, I find, at least for me, can breed complacency and comfort. You know, I just finished reading a fantastic book. I actually read it twice, which says a lot called the Comfort Crisis. And it speaks to this fact of our society, which is really almost driving us to comfort. And I think we all know we don’t grow in our comfort zone. We grow outside of it. 

John Absolutely, such a great point. I love the point about leading by example. I think that’s so critical. And that’s an absolutely essential part of a leader helping people do things that they otherwise have not done before. I agree 100 percent. Amanda, I know your role as director of advisors advisor experience is also a lot about creating the right culture of the organization. How important do you feel that has been to the success of the organization? And then as a follow-up question, maybe. To share some of the things that you think go into that, for the leaders that don’t know, how do I create and kind of or change the culture? What do I do? How do I go about it? 

Amanda Yeah. So to answer your first question, extremely so from a standpoint of how you actually do that and just sharing a little bit more from what Tim just spoke to is the fact that he is a very vulnerable leader and a very good way. So one of our very first interactions is we were actually integrating two firms together was to come to a table, have a discussion on what are the core values of this organization going to be, what have they been and how are we going to blend in, put to, I think, very different mindsets and different feelings of coming together. What does that look like ultimately? And in that conversation, we were all around this table throwing words on a wall saying, OK, this is important to me, this is important to me, and really distilling that down into what ultimately became our five core values. And Tim and I always kind of joke, he had one that he was really, really strong about that needed to stay. We had a couple of other individuals at the table that had one or two they were really, really passionate about. And then the one that I consistently brought up and would not let go was balance. And Tim, in our conversation, was the first person to say, raise my hand and say I am not the poster child for balance in any way, shape, or form. 

Amanda So it actually really allowed us to have a dialog around what that actually meant for us and what it was going to look like and honestly what it wasn’t. And so to this day, we consistently have that radical candor environment where we can say, hey, listen, this is maybe maybe not somebody that I’m the poster child for the example for, but I am going to lead by example. And so I’m going to work towards that and have dialog around it. And so when I think about the importance of culture and how you build it, it’s really all in the shared experiences. And I’m a huge proponent of that. And if you have an opportunity to listen to Tim and I actually have a podcast called Winning Through Culture, we talk a lot about the shared experiences that we’re developing and then driving in the organization, because ultimately we want to make sure that it’s not just in a business realm, but that we are focused on the complete person. So we over the course of this last, I would say, 20 months, have really had an opportunity just given our environment to create some uncomfortable moments. 

Amanda So some challenges that we were able to overcome together as a leadership team, but ultimately provide that shared experience with our advisors and our associates and our staff, something that we ended up creating. And Tim has a lot of ideas on runs. So he’ll come back and he’ll say, hey, I have this crazy idea. Do you think it’ll work? And somehow it always comes to fruition and it’s a lot of fun. But our most recent was called Transformation 20 20 Challenge. We had such a great response to it that we actually just launched a transformation in twenty, twenty-one. And it was all about growth and getting uncomfortable. But in the three aspects, meeting in a professional sense, in a relational sense, and then also in a physical sense. So we created a series of challenges that people could voluntarily sign up for and figure out ways that they could step their toe into being uncomfortable in a new way and ultimately either build a different mindset around it and or get rewarded for making that choice to get uncomfortable and to be OK. 

John So what now? What were some of these challenges where they runs or races or things like that? 

Amanda So we actually have five choices in each of the categories. So in the physical space, we do have one that’s called a step up. So there’s actually a step challenge where you can join a team and actually have a step goal to go after. There’s one if you want to run a race or maybe it’s a Spartan or a 5K or whatever it is, you have the opportunity to sign up to do that as well. And then what we’re doing is actually creating teams behind the scenes where people can motivate and inspire each other based on their goals. So if we have 20 people that say, hey, I’m going to run in a 5K, that’s great. We’re actually creating a channel for them to motivate and inspire each other because they have that goal in mind. And it’s really neat because ultimately that becomes a shared experience. 

Amanda We have people that are all over the Carolinas and in other states. And so it’s amazing the relationships you’re able to build outside of the four walls that become an office, so to speak. So, you know, there are different challenges in those three categories from a business perspective. You know, it’s basically from a standpoint if they want to invest in coaching and really what does that look like and how can they go after and actually invest in something that will push their business forward? There are some that are more internally focused from a business standpoint, things that they want to focus on in their practice. And then from a relational standpoint, we have an opportunity to we’re actually going to do. Book club, this time, Tim just referenced the book that we’re going to be utilizing, which is the comfort crisis, so they can actually join a book club, they can have an opportunity. We have a race relations study group that they can join as well. So there are different offerings. Again, it’s ways for people to take that first step, make that one-degree shift, and really have an opportunity to get uncomfortable. But ultimately, what’s a goal for them to grow? 

John I love that because that’s doing a bunch of different things. One is you’re bringing everybody together. So it’s a really great team builder. You’ve got accountability among those teams. But I love the fact that you’re really you’re helping them grow personally, not just professionally. And just like you were saying earlier, with Win at Life, this speaks to it. This is exactly you executing on that desire. And I think that’s fantastic. Tim, as an organization, what are your observations when you see this and this has been rolled out and this is part of the culture, what difference has it made with people? Because you might have some leaders out there that are saying that seems like a lot to be doing, that much more focused on so much interest of what they’re doing outside of work. But how is it helped not only who they are outside of work, but how is that translated to them inside of work? 

Tim Yeah, I mean, it’s a great question, John, and I mean, maybe kind of give you the evolution of this in the financial services industry. For the most part, everybody does the same thing. And it’s very difficult in many respects to discern one firm or one adviser from the next. And about five years ago, just before I met Amanda, you know, through a series of business challenges, I was trying to figure out how do we create an organization that’s distinctive in a very commodity marketplace. And the one thing that I came to the conclusion of actually through an organization I’m involved in called C12 was culture. And, you know, people can replicate your business processes, your ideas, your products, all that stuff, but they can’t replicate your people. And to me, culture really is about the people of the organization and tending to them. So I tend to a lot of ideas, as Amanda referenced, but also don’t always have the means to execute them. So enter Amanda Cramer into the picture in this, bringing these two organizations together. And I immediately know she’s the person that can actually bring these ideas to life, which is what she’s done. And over the last five years, working together with the rest of the team, we’ve really put a heavy emphasis on culture. 

Tim And again, to Amanda’s point, that’s really the development of the people and what it’s what has evolved to John and I got this idea of Spartan racing started that almost five years ago. And one of the things that Joe Torre Center, the founder Spartan community, has done a great job of is creating a community. And that’s really what we decided again, in an industry that’s commodities where advisors might move around firms like professional athletes to teams and same thing with employees. How do we create a place that’s got some stability the people want to be a part of or here because they want to be here, not because they are compelled to be here. And that’s really the transformation. Twenty, twenty-eight now. Twenty twenty-one challenge was how do we engage people’s hearts, minds, and spirits in a way that gets back to again, helping them win at life. Yeah. I mean, to your point, John, I think some people I share this with, especially in the financial services profession that come out of my mind, you know, it’s all about making money when you waste time on that stuff for. 

Tim But, you know, Amanda, and many of the other people on the team, I’m a generation ahead of her and a lot of our folks and, you know, the employees of today, especially in the competitive marketplace, we are and want to be a part of an environment that’s beyond a paycheck and a job. They want to be a part of an environment where they know they’re making a contribution. And quite frankly, I think that that organization’s making a contribution back to them, the betterment of them as a person, not just a professional. So it’s our thing. It’s what we do. It’s definitely out of the ordinary man. And I have a vision that perhaps other organizations will either through our podcast and we just did an episode on this transformation twenty twenty-one challenge and said anybody listening once the template will be happy to give it to you as well as some advice. 

Tim It’s work, there’s no doubt about it. I remember when I first put the idea out there and in one of the other members of the team, Amy drew it out on a whiteboard and I looked at it. I’m like, well, this is too much. And they’re like, nope, we got it. And it was a lot of work. Not going to lie, Amanda did most of it. It’s a little easier this year, I think, but it’s definitely to have you know, last year we had over 70 people in the middle of covid engaging in this. And, you know, some pretty transformational things happen, quite frankly, both in the organization. To your question, John, whether it was relationally, business-wise, spiritually, we had a pretty big component on the spiritual side last year. And so some really, really fascinating things that, again, have kind of set us apart from just another financial services company. 

John Well, and it’s first of all, it’s absolutely fantastic, tremendous job with that because I think that’s it is unfortunately lost on many leaders. They don’t understand the connection between that. And you have differentiated yourself in a huge way. And I love that you would mention that differentiating in a commodities business, which it very much is. What’s also interesting and not surprising, though, is that has translated to phenomenal results. You just wonder have continually wonder many times the best places to work, which is certainly a very difficult, very challenging award to get, because it’s your organization vote and it’s not other people looking in on your organization. They’re the ones that are giving their honest, anonymous opinions. You’ve also, I know, recently been awarded with the most admired CEO a couple of years ago, which is tremendous in Charlotte in financial services, which incredibly difficult award given the competition. 

John So it says a lot about who you are and if, by the way, for the audience out there, it took me a lot to pull this out of Tim and our preinterview here, because he’s such a modest guy. We had to dig it out of them. But I love that. And congrats. First of all, let me just pause and congrats on all that that you’ve accomplished. That’s tremendous. 

Tim Thank you. 

John Amanda. Question for you is, with all this and all the things that you do to develop people in your organization and help them take chances to step outside their comfort zone, the personal development, what have you seen it do to confidence levels? I mean, I would imagine that’s a direct correlation and impact and obviously that’s a game-changer for somebody. But what have you seen? 

Amanda Yeah, no, that’s a really great question. Is interesting that you bring that up, because I was actually just reading an article, somebody that is from my former life, and she was kind of talking about this from a standpoint of just how you make decisions. And if maybe at one point in your life you feel a little overwhelmed in one arena or the other, you’re not alone. And so she actually went on to say that when we lack confidence in ourselves, even if it’s just for a moment, you really have to look around and borrow the confidence that others have in you. And so through building this culture and building the relationships and we talk a lot about relational capital in our organization, the confidence that people have not only from a standpoint of what they’re doing from a professional standpoint but really what they’re doing personally. And it just exudes like I got on stage a couple of weeks ago just to actually launch our new version. So transformation twenty, twenty-one. And the response was, I want to sign up. Why has it taken you so long to get it together? I want I’ve already I’ve been wanting to do this, I already have all these goals and now I have to you know, we actually asked them again to make a one-degree shift. 

Amanda So say, hey, you pick one thing in each category and really go after it. And they’re like, I want to do all of the challenges, which is just great. But that’s the response that we’ve gotten. But really, from a confidence standpoint, the amount of people that have come up to me and up to 10 and said, hey, you know, I lost 20 pounds because I signed up and got outside his comfort zone or, you know, now I’m so much more comfortable on the phone doing X, Y and Z because I signed up for this study group that you offer. It is just overwhelming. And it’s such a good way to have people say, you know, I actually I have the confidence in myself now to do this and then too if they need to lean on somebody, I’m here. I will absolutely let them borrow the confidence that I have in them at any point throughout the year. 

John Wow, that’s amazing. I love that, you know, and I’ve always I know organizations, a very common challenger issue. And something I get asked about a lot is how to keep and retain their top people. And it’s interesting because this really speaks to it. I mean, I’ve always talked about these three things that top people need in order to want to stay. They need to feel like they’re growing. They need to feel like they’re making an impact and the biggest impact they feel they can make. And they also need to feel valued. And they need to feel important, and that really hits on everything that’s helping them grow, and that’s not just business-wise, but personally, it’s helping them also make a bigger impact in their own lives and grow confidence and increase that which helps make an impact in other people’s life. 

John And, of course, makes them feel valued and important being part of an organization that cares about them like that, like you do. So tremendous job. I mean, that’s outstanding. What do you think? And this is really to either one of you or both of you when you see and maybe step outside of your organization and just look outside and maybe some of the other organizations and even other industries, what do you see as some of the things that make you want to jump in and say, oh, you got to do that differently? You see some mistakes that other organizations are making that, you know, are fixable, that are maybe even some of the easy ones. But you see them made a lot. What are some of the things that come to mind? 

Amanda I’ll hop in first. So from a standpoint I shared earlier about shared experiences, but more so from a standpoint of getting feedback on those experiences, a lot of people will do as we do family baseball night and getting people together to celebrate on an annual basis. Maybe it’s an awards celebration or whatever that might look like. But I think the one thing that a lot of leaders and organizations missed out on is really hearing the feedback that people have to say after those events take place because ultimately there’s somebody that’s putting it together and there’s a lot of work that goes into it. And that person really wants to make it the best experience they possibly can, but they honestly cannot change a single thing if they don’t actually hear what the individuals that attended felt like or that maybe even if it was a family event, how their family felt about it. 

Amanda And so one of the things that Tim and I do, and I do it specifically with the staff of the organization, and then he and I are both in the conversations with our advisers is what do you find value in the organization? We want to be your most valued business partner. And that goes down to the experience that you have professionally and then also personally, and that extends to your family. So any event that we’re doing, we’re constantly asking for feedback and we’re constantly actually asking for them to tell us so we can hear them. It’s not just a survey that they complete. We get on a call. We have a Zoom. We have an opportunity to actually have dialog. And that is so important and something that I think a lot of places are actually missing. You know, having that constant feedback loop that’s a little more personal than a survey that just goes out is really something that I think propels your culture forward. 

John Great point. I see leaders missing that opportunity all the time. That’s so, so valuable and so spot on. Great. Tim, anything to add?

Tim Yeah, I mean, I would I think you’ve spoken about this in your previous podcasts and your speaking engagements, but, you know, trust is the currency that makes things happen. And I think what I see is missing a lot of times is a combination of authenticity and transparency. I mean, you know, people in our society today I think want to know the truth, not the social media version or the slanted news version, but they want to be able to see, you know, transparently what’s really going on and not see leaders dodge difficult issues or try and either ignore them or explain them away. When everyone is sitting there looking at it saying, obviously, that’s not the truth. We’re not reality even more so than the truth. You can argue the truth, but you can’t argue reality. And that that’s backed by a measure of authenticity. And I think in the absence of those two things, you see organizations kind of shoot themselves in the foot and get in their own way. 

John Hmm. That’s a great point as well. And you certainly do see that, not just in organizational leaders, business leaders, but you see it all across every type of leader, from every political to individuals to parents to coaches, to everybody. And that’s a universal, universally applicable concept for sure. Excellent. I’ve loved this opportunity to talk with both of you. The time has flown here and I’m wishing we had a lot more time because there’s a lot more I’d love to ask you so we might have to do a part two. But let me just finish with giving each of you the opportunity. You’ve got a wide audience that listens to this show, all different types of leaders from mid-level to senior CEOs, business leaders. You’ve got people who are not formal leaders but just want to lead their lives better. What parting words of wisdom would you have for them? And I’d love to hear from both of you on this. 

Tim Sure, Amanda would you like to go first? 

Amanda I’ll let you go first this time. 

Tim Well, it’s a wide topic, John. I mean, I think it comes down to a couple of things. One is. You know, develop a high level of self-awareness, you are clear on who you are and how you show up around the people you know that are around you. So that’s the first one. I’d say. The second one is, you know, I have to say, I’m just a guy that had a few ideas that happen to be surrounded by an amazing group of people. And I don’t know anyone that succeeded on their own, independent of being a part of a team and having a great group of people. So I’d say the second one is you pay attention to who’s on your team, whether you intentionally or unintentionally form that. That was mentoring somebody recently. And they kind of were sharing with me some of the people that had their life. And I ended up being very direct and in my mentoring comments. And, you know, respectfully, if you want to be the person you say you want to be, you’re not going to be that person hanging out with the people you’re hanging out with. 

Tim But in a business setting, certainly, you know pay attention to who’s on your team and really cultivate that. And then third, you know, as you look at who’s on your team, look for opportunities to help people grow, understand who they are, what their strengths are, their desires, their aspirations, and find ways to help them achieve that in the context of the business so that they can continually be challenged and growing and know that, you know, you genuinely care about their well-being, something you said before as well. That’s, I think, critical. And I think it’s even more critical in today’s day and age. I mean, we’re kind of in crazy times, at least from my vantage point right now. And given some people some stability and some focus on their overall well-being, I think it’s super important. So those are my top three things. 

John A lot of excellent, great advice, thanks. Amanda?

Amanda Yeah, absolutely. I would just add two things. So you actually said this earlier in a conversation, but talking about your attraction value. And I think it’s really important that as a leader, you figure out who you are and don’t try to be anything other than that really, you know, lean into what you were. Unique gifts are Tim mentioned about, you know, who is the team that you have built around you? Every single person needs to bring something unique to the table, and it’s the blending of that. And is that shared experience to where the magic really comes to life, especially, you know, from being a leader of an organization and building a culture. And ultimately, what we’re trying to do right is to build that community that is values-based. And I think a lot honestly, the second piece that I would add to that is the opportunity to honestly lead with your heart. So there is you know, we’re all human. At the end of the day, everyone is carrying baggage that maybe, you know about or don’t know about. So in your interactions with those that are around you or whether it’s a client or an associate or a prospect or whoever, it might be, really making sure that, again, you have that self-awareness, but that you are leading first with your heart and then ultimately the results and the money and all of those fun things will come as long as you have that mutual respect and are able to build trust with the individuals that you have in your circle. 

John Absolutely. Well, I’ll tell you honestly, this has been fantastic. I’ve loved the conversation we’ve had. I know this is going to be a very popular, probably replayed episode because there are so many good nuggets, great leadership lessons for people in the. So I greatly appreciate Tim and Amanda. Thank you for joining me today, it’s been a lot of fun.

Amanda Thank you for having us. 

Tim Absolutely. John. Really appreciate the opportunity. Enjoyed getting to know you. 

John Yeah, absolutely. Excellent. And thanks for joining everybody. We’ve been here with Tim Flanagan and Amanda Cramer, Tim the president and CEO of MassMutual Carolinas, and Amanda, the director of adviser experience to very impactful leaders who have built a fantastic organization, award-winning organization. 

John If you liked today’s show, of course, go down below, give five-star reviews and give a thumbs up share. I always appreciate your comments and suggestions for future guests and also topics for now. Thanks for joining. Look forward to seeing you next time. Thanks, everybody. Thanks for joining us on today’s episode of Tomorrow’s Leader for suggestions or inquiries about having me at your next event or personal coaching, reach me at John@johnlaurito.com. Once again, that’s John@johnlaurito.com Thanks, lead on!