How this CEO of a 167-year-old company keeps it young

It's impossible to be in business forthe better part of two centuries without doing a lot of things right, includingkeeping up with the times.

At167-years-old, MassMutual Life Insurance Company is doing just that under thedirection of its chairman and CEO, Roger Crandall.

Crandall, 53,has moved to digitize the business to offer a streamlined application andunderwriting process for getting a life insurance policy. That's helpingMassMutual reach younger customers.

He's expandedemployee benefits and made them much more inclusive to better reflect the needsof today's workforce. The company estimates Millennials make up about a thirdof its employees.

And Crandall haschanged the Fortune 100 company's once-stiff dress code to two words:"Dress appropriately." He says he can count on two hands the numberof 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 companyhis entire career, before getting the top job in 2010.

His uncle,former chairman and CEO of American AirlinesRobert Crandall, was his role model for how tobe an effective CEO, because of the airline chief's detailed understanding ofhis company and industry.

He also looks tohis predecessors at MassMutual. "We stand on the shoulders of those whocame before us, who made good decisions and have left the company with ahistory of doing the right things for customers."

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

What's yourbiggest pet peeve about your job?

I like mostparts 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 youreach people who learn differently than you do?

I think storiesare very powerful. I tell them at basically every employee meeting, everyleadership 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 youngtechnologist at Haven Life[Mass Mutual's online subsidiary]it'sthe first time this stuff got real. We paid the claim in three days. The10-year-old doesn't even know it yet but that will change the rest of his lifecompared to if his mom hadn't had that policy.

So I tell thatstory to remind everybody that our $730 billion in assets under management, $32billion in premiums collected, our 5 million customers ... those aren'tpertinent statistics. What matters is actually helping a family.

What was yourbiggest failure at work?

I was chiefinvestment officer in 2007. Our exposure to subprimes and Alt-A mortgage-backedsecurities was not good. I was publicly nervous about the housing market and Icompletely underestimated how bad it would be.

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

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

What do you doto relax?

I really like toexercise. I love to ski. I play a little golf. I like to fish. I try tomeditate every day.

It is reallyhelpful to be able to disengage. In February I'm going to a retreat inCalifornia for a digital detox.

How many weeksof vacation do you take a year?

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

I got marriedthis summer and went on a three-week honeymoon. I ended up on the phone a bunchbecause we were working on the Oppenheimer deal.[Invesco FundsboughtOppenheimerFunds,a Mass Mutual affiliate.]

That's why I'mexcited 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 fullysure how our brains are getting rewired by the constant access to informationand stimulation. I'm pretty sure it's not good.

How many hoursof sleep do you get?

I've become abig 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 madean 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-dosemelatonin.

Whether it'sactually working or not I have no idea.

What I do knowis when I get more sleep I feel better.