Jamie Kalamarides of Prudential Group Insurance

    We Spoke to Jamie Kalamarides of Prudential Group Insurance on Being an Effective Leader During Turbulent Times

    As part of my series about the “Five Things You Need To Be A Highly Effective Leader During Turbulent Times,” I had the pleasure of interviewing Jamie Kalamarides.

    Jamie Kalamarides is president of Prudential Group Insurance, a business unit of Prudential Financial, Inc. Kalamarides writes and speaks frequently on the role of employers in supporting employee Financial Wellness; the critical need for a broad and consistent paid family and medical leave (PFML) solution for American workers; the connection between #WorkandWealth and providing effective lifetime income solutions for all. Through consultation with Washington policymakers, in public forums and in collaboration with partners including Prosperity Now and The Aspen Institute, he advocates for legislation that will provide both traditional and independent workers with access to income protection and other financial planning solutions.

    Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

    My wife and I have five children — three are adults, two are in high school. I started in this industry like everyone else does, by mistake. I was working in a management consulting firm and I was traveling 50 weeks a year. We decided it was time for me to leave consulting and pursue something else. The president of an asset management company called me about a role. After turning down a meeting with him twice, I finally said, “Well, okay, I’ll come up and talk to you.” And from there, I realized he needed the specific background I had. So I took the job and worked for an asset management company within an insurance company, and then I worked in the 401K side of that insurance company. And then Prudential bought that business in 2004. And I’ve worked on almost every single job in the 401K business and several other businesses within Prudential’s retirement business. Three years ago I was asked to come over and run Prudential’s group benefits business, which is called Prudential Group Insurance. Whenever you get asked to do something completely different, there’s always a little bit of hesitation. But in this case, it really piqued my interest and I was really excited about it because I get to expand my focus helping individuals with financial wellness, but in a different capacity. There’s a newness and a freshness to this job. And there are interesting business and customer problems to solve in employee benefits. And I love solving business problems.

    Can you share a story about the funniest mistake you made when you were first starting out? And could you tell us what lessons or takeaways you might have learned from it?

    Earlier in my career when I was at asset management company, I was in charge of a group of clients that included not-for-profit hospitals, governments, and unions. I wanted to get out and meet our clients. So I asked one of our client managers for an introduction. We wore suits all the time But I realized that this union client I was going to meet probably wouldn’t be in a suit because of the nature of that sector. So I asked a colleague, “What do people normally wear around there?” And he said, “They typically wear nice slacks, a button down and a leather jacket.” So that’s what I wore to this client meeting. And I get there and the client who always wears slacks, a button down and a leather jacket was in a three-piece suit — because I was coming to meet him. And we had a good laugh. It reminds me of a couple things. First, it really is important to go talk to clients. The second, it’s important to be yourself when you do it. But the other thing I learned was that I needed to develop trust and respect with this client so that he could be authentic himself, show up dressed the way he normally dresses, and tell me the straight truth. And by the end of that conversation, we had had enough laughs that that was the case. Relationships take time, trust and respect.

    None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards for helping you get to where you are?

    It’s my wife, Diana. She knows me better than anybody else. She cares about me, wants me to be successful and impactful in the world. But she also has shares in a loving way the traits and characteristics or attitudes that I need to change. There’s nothing like hearing from someone who really cares about your best interests that helps you when you need to change. For example, early in my career I was very analytical. I was the best at financial and analytical problem solving. And the feedback I’d get from folks was that I needed to do a better job listening. And I thought, “I do a great job listening. You say something to me and I can memorize it pretty quickly.” I came home and talked to Diana about that feedback. She said, “Yes, dear. But you don’t always let the other person know that you’re listening and being able to say their points back in the moment.” Certainly, I got all of what they were saying, but I wasn’t digesting it and letting the other person know that I was listening, that I could repeat back what they said right away and get the essence of what they said instead of just the memorization of what they said. And she’s helped me with lots of things besides that along the way.

    Extensive research suggests that purpose-driven businesses are more successful in many areas. When your company started what was its vision? And what was its purpose?

    John Dryden [the founder of Prudential Financial] in 1875 brought back from England a concept called industrial insurance. And he applied it to the largest social problem of the day in Newark, New Jersey and its surrounding areas. And that is working class families’ primary breadwinners were dying and they were leaving their families destitute. The families couldn’t afford to pay for their loved ones’ funerals, much less pay off some of the debts and be able to get through this great tragedy. And so he created an agency and a distribution group that would go out with coupon books and collect premiums every week, sometimes as few as a penny or ten cents a week, so that the family could have enough insurance to cover against unexpected loss and risk of financial destitution. And that simple method of focusing on what the social need of the day was and coming up with innovation in a way that’s affordable and really protects against unexpected risks is exactly the same mission that Prudential has today. We solve the challenges of our changing world. And we do that by focusing on people’s financial wellness. That purpose guides us and drives us all the time.

    So now let’s turn to the main focus of the discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?

    It’s important to have already laid the groundwork. What I mean by that is to have a purpose, to have clear values, to have chosen strong leaders. And to have a business strategy that is certain enough that everyone knows where they’re going, but also flexible enough to react to uncertainties. In 2007 and 2008 during the Great Recession, the world seemed to be falling apart faster than we could understand it. We went into a weekend wondering if the banks were going to open on Monday and whether or not we could get cash out of them. For the vast majority of our employees, even in the industry we participated in — I was working in the retirement side of our business at the moment — they really didn’t understand why an investment bank failing was a challenge and was threatening them so much. The critical issue here about leading was first set the foundation, and then second, provide context. Use storytelling to help people understand — our employees first and then our clients, and then their employees because we’re in a business-to-business consumer environment. Tell each of the stakeholder groups what was actually happening, what was likely going to happen going forward, what might happen, what the risks are and what was definitely not going to happen. Giving them that framework was the critical solution to allow people to realize that they don’t need to worry about feeding their family. “We’re a strong company, we can get through this.” The Great Recession not only provided challenges for our clients; it provided opportunities for us to be able to serve those clients better. As soon as we provided that context and shared that story and dialogue, our employees stopped worrying about themselves to the greatest degree and started acting and thinking about the clients and how we could help them through their challenges going forward.

    And that same framework can be applied to today’s COVID pandemic. The challenge of today is that many companies are facing the challenge of a pandemic, the challenge of seeing racial inequities in wealth and injustice and trying to deal with that. The political environment, the economic environment, plus whatever’s going on in people’s personal lives and work lives. Those are a lot of challenges. And giving people context for what to focus on is the only way you will get back to the basics of, “What’s your purpose?,” What’s your business strategy?,” “What’s the task ahead?,” and “What should we be focusing on?”

    Have you considered giving up? And where did you get the motivation to continue through your challenges? And what sustains your drive overall?

    About three times a day.

    Having an understanding of myself and what motivates me is really critical to getting through challenges. When you get thrown challenges, the first reaction in a hostile environment is fight or flight. And that’s giving up. That’s just what your brain wants to do. And it’s only by thinking about the higher purpose and whatever motivates you, can you get beyond that and start thinking rationally and acting. So now I know when my body’s going into fight or flight. And I quickly say, “Okay, but what’s my motivation? What do I want this to be like when it’s done?” And I use that motivation. For me, the motivation is transforming a business to serve clients better and creating a legacy, and doing it in a way that has stewardship for the company. That’s what motivates me. That’s what drives me. For other people it might be relationships, money, science or inventiveness. Lots of things motivate people. And you just have to be aware of what those things are and use them for your own good.

    What would you say is the most critical role of a leader during challenging times?

    I think the most critical role of a leader during challenging times is listening. Listening with empathy and discernment, and filtering out the critical issues from the noise. And focusing on those critical issues, and letting the noise go. So it’s active listening.

    One really important example of listening with empathy occurred this past spring when George Floyd was killed. And Ahmad Arbury soon after that, and the Chris Cooper incident. And the Breonna Taylor incident. Each of those events caused my colleagues to go through grief, anxiety, fear and worry. And they were bringing that fear and uncertainty from outside of work inside of work. And unless I was actively listening to, “How are you doing? How are you feeling?” and people saying, “Fine” — unless I pushed on it, I would have missed it. And I realized that weekend of George Floyd’s death that I needed to really start getting back to basics with employees. Saying, “You’re safe here. You belong here. You’re loved. You’re worthwhile.” Because they were having fundamental questions about whether or not other people believed that. And by starting to listen and respond to the underlying needs briefly and in a very personal one-to-one approach, but then more broadly, we created an environment where we realized at Prudential that we needed to listen to everybody. So we set up a series of hundreds of listening sessions among thousands of our employees. And based on the input of over 7,000 employees, we identified nine racial equity commitments: five to support our employees, two to support clients in the marketplace, and two to support our communities and social justice efforts. And we’ve shared those publicly and said to the world, our employees, our clients, our communities, “Hold us accountable for these. These are our aspirations. These are our goals. These are our commitments.” And this is not going to be an instantaneous switch, but we’ve got to keep striving and moving toward these commitments. And they came out of the fact that in times of crisis, we first listened.

    And as a leader, how can one make plans when the future is so unpredictable?

    The future feels really unpredictable right now because we’ve had so many surprises. Every week feels like a month and every month feels like years. But it doesn’t mean that our business purpose isn’t solid, that our values change, that our leaders can’t handle it. They can. So I’m going to go back to what I talked about before: purpose. Choosing good leaders, developing them, giving them tough opportunities so that they can grow, and guiding them. And then having a clear business strategy — clear enough that everyone’s heading in the same direction, but flexible enough so that you can adapt and change when the unexpected occurs. And it is the duty of leaders to think about what risks could happen. Not just the minor risks that are important, like making sure you’re passing the audit or keeping track of the money. But the major risks too, like a pandemic, technology leapfrogging or a dramatic societal change that might change the demand or the supply of your business. It’s important to be prepared and think about those risks.

    Is there a number one principle that can help guide a company through the ups and downs of turbulent times?

    It’s very simple. Be purpose-driven and follow your purpose.

    And can you share three of four of the most common mistakes you have seen other businesses make during difficult times, and also things to keep in mind to avoid that?

    I think the most common one is forgetting the basics, like forgetting that your clients have needs and serving them. Failing to recognize that your employees need to have their needs met before they can serve clients. And I think those are the first two. If you have a business where your employees are required to serve your clients, you’d better focus on your employees first so that they can serve the clients. And you’d better reorient them away from the turbulent times to focusing on clients if that’s appropriate. And then focus on the client’s needs. And then I think the third one is not telling the truth. And telling the truth sometimes means saying, “I don’t know.” Or, “This is likely going to happen, but may not. And these are the risks. I hope they don’t happen, but they could.”

    Generating new business, increasing your profits or at least maintaining your financial stability can be challenging during even good times. Even more so during turbulent times. Can you share some of the strategies that you use to keep forging ahead and not lose growth traction during a difficult economy?

    The first thing is you have to have a customer and market-facing business. You have to have one that’s focused on meeting customers’ needs. And you have to be out there listening in the marketplace. Because during a difficult economy, customers — whether or not they’re consumers or businesses or both — have a different set of needs. And so if you’re listening to your customers, they will express a new set of needs in these challenges, and it’s your job to respond quickly. A really simple example that we all saw is alcohol manufacturers switched from manufacturing their preferred drink, beer or other spirits, and started producing disinfectant gel. Why? Because that’s what consumers had a shortage of. And it turns out that if you have the machines going and you’ve got the pure alcohol to start, you’re in the best position to manufacture that and get it out on the shelves. So we saw a lot of microbreweries and a lot of micro-distilleries shift their production toward producing sanitizing gel. Great example of someone saying, “My job is to serve my customers, and I’m going to develop the solution to do it.” So the quick difference there is that purpose can’t be in a product. It’s got to be in fulfilling a need for a target set of customers because products will change, but customers won’t. Their needs may change, and if you keep listening to their needs, your purpose will last a very long time.

    Here is the primary question of our discussion: based on your experience and success, what are the five most important things a business leader should do to lead effectively during uncertain and turbulent times? And please share a story or an example of each.

    The first one is, have a purpose. John Dryden had a purpose. He was serving working families to stop them from becoming destitute. Prudential’s current purpose is to solve the financial challenges of a changing world. And that leads us far and wide. It’s focused on a set of customers and their broad set of needs — not about pushing any product.

    The second is choosing a set of leaders that are diverse and complementary, not clones, that have different traits, but can work together as a team. And assembling them as a team and understanding what motivates them, and challenging them to work together as a team. Because what might challenge one person might be very unique and different from what challenges another person on the team. When I became president of Prudential Group Insurance, my team was ten white men and two women. And now our team is 14 people: eight women and five people of color.. And that team aspect is one that brings a much more diverse set of thinking and approaches and attitudes toward the business.

    The third is having a clear strategy, one where everyone can focus on where to go together, instead of going in different directions, but be flexible enough to deal with today’s challenges. Solving financial challenges of a changing world is our purpose, but our strategy is to focus on our target markets. We want to continue to grow and remain very competitive in our large client base, which we call the national markets. And that means understanding our clients’ needs and challenges. Their needs are growing not only in life insurance, but in disability and absence management and paid leave, and supplemental health products — ones that help people when they don’t have enough savings to handle unexpected financial events or afford their out-of-pocket medical expenses. And then we’ve learned to supplement that further with products we don’t manufacture or provide, but that our clients need, like debt management, student loan management, financial counseling, education. And sometimes we can source that from another business in our company, and sometimes we have to go out and find an outside partner.

    We can change our strategy while still fulfilling our purpose if times and circumstances change. For example, we didn’t write out in detail what we should do in the case of a pandemic. We had a strategy that worked during a pandemic. Our business has always been tech-enabled, so our whole business went virtual over a weekend without any disruptions. Our employees met the clients’ demands — including the tons of calls that came in as a result of COVID for both paid family leave and short-term disability and long-term disability claims. And unfortunately, when people lost family members and we had to both console them and help them through the process of filing a life insurance claim. And we continued our business model and do continue our business model virtually. We’ve continued to participate in the sales season and onboard new clients. We are helping educate our clients’ employees about financial wellness in this new world through virtual methods. And we’ve instituted new online capabilities this summer just to allow people to more easily apply for paid leave. And that’s all because our employees are resourceful and we gave them the framework through which to act and be creative — all consistent with our strategy.

    And then the fourth thing is providing context and telling stories and making sure we’re meeting the needs of our various stakeholder groups: employees, clients and distribution partners. And I’ve done during the Great Recession in 2007 and 2008, and now during this pandemic.

    And then the fifth thing is active listening. It’s listening to the changing needs of clients. It’s listening with empathy and understanding. It’s that skill my wife Diana taught me. And it’s that active listening that makes all the difference. Because as a leader, if you’re not listening five times more than you’re talking, the world is passing you by.

    Can you give us your favorite life lesson quote? And can you share how that was relevant to you in your life?

    The quote is, “Be prepared,” which is the motto of the Boy Scouts. I am an Eagle Scout. I originally thought it meant be prepared for every circumstance while you’re camping. Be prepared to provide first aid. I then learned in life that it meant be prepared as a leader. Be prepared to help out other people. Focus on the basics. Be prepared in business. Be prepared for the question. Anticipate risks. Be prepared. As I’ve gotten older, another life lesson that’s quite ancient has gotten into my life. And it’s a phrase in Latin called “memento mori.” And it means remember you must die. I know it sounds morbid, but it’s not at all about being morbid. It’s about remembering to live life the way you want to. And “Be prepared” is the same way of saying it, but memento mori is at a much grander scale. So be prepared now means to me, live every day as you want to. Be prepared, because eventually your life will change and move on. Am I focusing my energy on the things that matter most? Or am I letting situations control me? And that life lesson quote of being prepared has stuck with me my entire life. And it now lets me prioritize on the things that really matter to me, like helping, coaching, and mentoring young leaders. Transforming not just a business, but an industry so that customers — not just today, but in the future — can have much better financial wellness. Making sure my family and my kids are growing up to be responsible adults. And making sure that I’m focusing on the right priorities in life on a day to day basis.

    How can our readers further follow your work?

    They can follow me on Twitter at @kalamarides and at