It’s impossible to be in business for the better part of two centuries without doing a lot of things right, including keeping up with the times.

At 167-years-old, MassMutual Life Insurance Company is doing just that under the direction of its chairman and CEO, Roger Crandall.

Crandall, 53, has moved to digitize the business to offer a streamlined application and underwriting process for getting a life insurance policy. That’s helping MassMutual reach younger customers.

He’s expanded employee benefits and made them much more inclusive to better reflect the needs of today’s workforce. The company estimates Millennials make up about a third of its employees.

And Crandall has changed the Fortune 100 company’s once-stiff dress code to two words: “Dress appropriately.” He says he can count on two hands the number of times he’s worn a suit in the past six months.

Like his dad, who was a Mass Mutual salesman for 30 years, Crandall has been at the company his entire career, before getting the top job in 2010.

His uncle, former chairman and CEO of American Airlines Robert Crandall, was his role model for how to be an effective CEO, because of the airline chief’s detailed understanding of his company and industry.

One of the biggest lessons MassMutual CEO Roger Crandall has learned over the years is that people think and learn differently. Stories, he's found, are a powerful way to convey your message.
Courtesy of MassMutual
One of the biggest lessons MassMutual CEO Roger Crandall has learned over the years is that people think and learn differently. Stories, he's found, are a powerful way to convey your message.

He also looks to his predecessors at MassMutual. “We stand on the shoulders of those who came before us, who made good decisions and have left the company with a history of doing the right things for customers.”

Crandall spoke with CNN about how he’s evolved as an executive and a person. Here’s an edited, condensed version of that conversation.

What’s your biggest pet peeve about your job?

I like most parts of my job.

There are times that constantly being ‘on’ is a little wearing. That probably means I’m more of an introvert than an extrovert.

Also, I can be abrupt. I had to work at getting better in dealing with people. It’s not a pet peeve but an area where I’ve had to change.

What have marriage and parenthood taught you about business?

Both are incredibly humbling. I used to think the skill sets you needed to be successful at home were completely different than the skill sets you needed to be successful at work.

I’ve come to believe the skills that make you good in your relationships are very valuable to being good in business as well.

Like what?

One is the ability to listen, and not just listen but hear. Also, the ability to put yourself into the other side of a conversation. To understand that people think differently, learn differently. That the same situation and data can be interpreted very differently by different people.

When I became CEO I felt all I needed to do was let my employees see the data. “It’s obvious,” I’d think. “Look at our cost structure compared to the industry!”

It took me a while to learn it’s not quite that simple.

So, how do you reach people who learn differently than you do?

I think stories are very powerful. I tell them at basically every employee meeting, every leadership call I have and I didn’t do that earlier in my career.

[Crandall recounts the case of a 30-year-old woman with three children who bought a $250,000 life insurance policy. She and two of her kids died in a car crash. Her 10-year-old son survived.]

For the young technologist at Haven Life [Mass Mutual’s online subsidiary] it’s the first time this stuff got real. We paid the claim in three days. The 10-year-old doesn’t even know it yet but that will change the rest of his life compared to if his mom hadn’t had that policy.

So I tell that story to remind everybody that our $730 billion in assets under management, $32 billion in premiums collected, our 5 million customers … those aren’t pertinent statistics. What matters is actually helping a family.

What was your biggest failure at work?

I was chief investment officer in 2007. Our exposure to subprimes and Alt-A mortgage-backed securities was not good. I was publicly nervous about the housing market and I completely underestimated how bad it would be.

I view it as one of my single biggest failures having those exposures, and not realizing how bad it could get and losing what we did.

[That said] we actually outperformed the insurance industry through the crisis and after.

What do you do to relax?

I really like to exercise. I love to ski. I play a little golf. I like to fish. I try to meditate every day.

It is really helpful to be able to disengage. In February I’m going to a retreat in California for a digital detox.

How many weeks of vacation do you take a year?

I would guess six weeks, but I rarely go four hours without working in some capacity.

I got married this summer and went on a three-week honeymoon. I ended up on the phone a bunch because we were working on the Oppenheimer deal. [Invesco Funds bought OppenheimerFunds, a Mass Mutual affiliate.]

That’s why I’m excited to take a dedicated eight days for the digital detox.

I think time, reflection, and deep thinking are powerful things. And we’re not even fully sure how our brains are getting rewired by the constant access to information and stimulation. I’m pretty sure it’s not good.

How many hours of sleep do you get?

I’ve become a big tracker of sleep. I average about 6.5 hours of actual sleep time.

I try, though, to give myself 7.5 to 8 hours of sleep opportunity.

I’ve really made an effort to change my approach to sleeping in the past 18 months.

I’ll wear masks. I’ll listen to a sleep meditation tape. I’ve gone on and off trying low-dose melatonin.

Whether it’s actually working or not I have no idea.

What I do know is when I get more sleep I feel better.