A Key AI Challenge: How Do We Automate What Is Routine And Humanize What Is Exceptional?

Subhashish Sengupta, Chief People Officer at Assurant, discusses leveraging AI in HR solutions, predicting leadership attrition, and other critical HR lessons in this Strategic CHRO interview with The ExCo Group CEO David Reimer and Senior Managing Director and Partner Adam Bryant. 

Reimer: What challenges for HR are at the top of your mind these days?

Sengupta: There are several, but two are at the top of my mind here. One is that we live in an increasingly uncertain world. It’s volatile, unpredictable, and polarized. There is geopolitical stress and economic worries, and many people feel exhausted. As I talk to our people worldwide, I get a similar pulse everywhere.

So, how do we continue to support them and strengthen our organization, which truly, deeply cares about them? It’s important for our people to know and feel that we’ve got their back and are further strengthening that relationship of trust as part of our organization’s DNA.

I also spend a lot of time thinking about how people use technologies, particularly AI. A big priority for us is understanding how to use AI and other technologies to solve problems in a whole different way. Essentially, AI can be a force multiplier, something that augments our abilities to do more, better, faster. How do we automate what is routine and humanize what is exceptional? And how do we help our people establish that crucial trust with the technologies and leverage them to advance their own journeys?

Bryant: Trust is a big word. Can you unpack what that means to you in this context?

Sengupta: In my view, a big enabler of trust is the “say-do” ratio. Increasingly and consistently, we hear our people say that there are a few things that are really important to them. First, they want us to help them grow and advance through learning, skills, and career opportunities. Second, they want their company to help them better connect to their communities and have a greater purpose.

The third part, which has become a priority over the last few years, is well-being—not just physical well-being, but mental and financial well-being. When we put effort behind each of these, listen carefully, and act thoughtfully, with sincerity of purpose, we move the needle on trust.

Reimer: What in your background helped prepare you for your role, with so much uncertainty and new problems rolling up to your doorstep daily?

Sengupta: There are two very important influences in my life. One is my parents. People get different gifts in life, and I am grateful to have my parents as my gift. Growing up, I had unconditional love and support, and that taught me to have care and compassion as a fundamental way to live. They were both bankers; they worked for one of the largest nationalized banks in India and held positions of leadership responsibilities in very challenging environments, and they were transferred very often.

Their grit, work ethic, commitment, and dedication were unwavering. And I often saw them having to respond to difficult situations and tough and unknown environments where they never had all the information or the resources. That was passed on to us through osmosis.

The other significant influence was GE. GE helped me form a disciplined approach to navigating challenges. Jack Welch strongly believed in HR and finance as two key drivers of leadership and business success. From the very formative years of your career, you had to build the mindset of a business leader because knowledge of the business, including financial acumen, was non-negotiable.

The company believed very strongly in investing in people and developing leaders. I was exposed to different cultures around the world at an early stage of my career and had opportunities to take on roles outside of HR. Those methodical and disciplined fundamentals shaped how I think and operate.

Bryant: Can you share an example of how you used that disciplined approach to tackle an HR issue?

Sengupta: Leadership attrition is a crucial challenge for any organization and any industry. When a key leader walks out, you lose precious power. And often, despite your best efforts, you get surprises. Our goal was not just to retain talent but also to better predict any risk and get ahead of it.

So, we looked at the data for the past several years of leadership departures, ran regression analyses, and broke them down into various factors that drove their decisions to leave. That helped us create a data-driven framework that provides us with potential warning signals so that we can address problems before they become problems. The approach helped us bring leadership attrition below one percent.

Reimer: What is your framework for the X-factors of leadership that set the best leaders apart?

Sengupta: There are four things that I see in the very best. Number one is the distinct ability to create clarity of purpose. A common trait of all successful leaders is that they can create clarity of purpose without equivocation. We live in a world where we’re drowning with information, yet we are starved for insights. So, clarity of purpose is a precious gift.

Second, they bring a wave of positive energy. People want to be around them. They are like superchargers, and they help lift people up. Third is an element of physical and mental stamina—just the sheer power and grit to carry on. They can deal with headwinds, failures, and disappointments. It doesn’t matter because they have this ability to move forward. Take a few minutes, and they’re back to the supercharger mode.

The fourth one is a sincere dedication to helping people thrive. They are invested in their people and have a genuine interest in making them a better version of themselves.

Bryant: What themes come up most often when you are coaching and mentoring senior executives?

Sengupta: Number one is that when you are in a senior role, your position of power and authority allows you to ask a lot of questions. I’ve seen many leaders make the mistake of asking a random question too quickly. My advice—and I try to practice it myself—is to take the time to frame the right questions up front and then be open to a perspective that you’re not familiar with. That’s the other problem. You may ask a smart question, but you’re expecting an answer you want to like. The point of asking good questions is getting answers you’re not expecting, which takes practice.

Second, very successful leaders may want to surround themselves with people who are just like them. But they run the risk of creating an echo chamber. My advice is to surround yourself with people who care about the same things at the core but who think a bit differently, have the courage to push back, challenge, ask questions, and drive better outcomes. It takes time and energy, but it drives better outcomes. It’s easy to say but hard to do because when you’re trying to run 100 miles an hour, you often want to reach decisions quickly and move on.

Third, I always tell them to look after themselves—be intentional about their own health and well-being.

Reimer: What is the best lesson you learned from one of your worst managers?

Sengupta: There was a certain manager who was very good at recruiting talent. We had an incredible team of very gifted individuals. But they had the character trait of needing to tell you they were better than you. It didn’t matter how good your work was or how great your idea was. They had to do one better. It was disenfranchising for the team, and things went downhill quickly. It was a bit of a head-scratcher because this was a smart person with a phenomenal track record. The lesson I took away from that was a gift. Being smart and having smart people around you is obviously very good, but being a force multiplier and helping smart people go even further is truly the needle-mover.