The first day Brian Kenny started work at management consultancy Arthur D. Little, he sat in his office and wondered if he’d made a huge mistake.

Kenny, who is now the Chief Marketing and Communications Officer of the Harvard Business School, left his job doing marketing at another Boston-based school, and took a gig in the private sector. It was a space much less familiar, and on first impact, everything in the office sounded foreign.

“I can remember that my office looked out at the parking lot, and I could see my car from the office window. I just remember wishing I was getting in that car the whole day, like ‘God I just want to get back in the car and go home,'” he said.

First days are seldom easy. But, even from a moment of what Kenny called deep seated insecurity, he’s pulled out a pattern that’s proven insightful whenever he finds himself in a similar headspace.

“Every time I’ve been the most nervous or the most scared of a decision I’ve made, it’s turned out to be the best decision I could have made,” he said.

Kenny stayed at the firm for a while before leaving to work at Northeastern University, and then subsequently at the Harvard Business School, where the combination of his experience in academia, as well as his experience working with C-level executives at Arthur D. Little brought his career full circle.

When he started at HBS six years ago, Kenny was the first person to hold the position. When he first called his mother to tell her he got the job she said ‘Oh my God, that’s so great, you’re working at Harvard,” and then followed it up with ‘Wait a second, why do they need you?’

The decision to add the position (and his mom’s reaction) speaks to the difference between having brand recognition, and actively maintaining a brand.

“Somebody understood when they created this role that we too are in a competitive space, and that the longer you don’t tend to a brand, the more opportunity others have to market against you,” he said.

In Harvard’s case, they don’t have to work too hard to introduce themselves to people. They do face a challenge in influencing the way those people feel about them.

“I will admit that when I came here, my expectation was that I was going to be dealing with really smart people, sharp elbows, very opinionated. We hear people describe people here, if they haven’t been here, they might think that people are arrogant or elitist,” Kenny said.

His experience bucks his original thought, so part of his job is inciting a similar opinion-shift in others through stories similar to his.

“I want to surface those voices in a way that people can experience it on a grand scale. That’s really the challenge that we have is helping people understand the reality of Harvard Business School so that we can knock away whatever negative perceptions they might have,” he said.

One project that Harvard Business School undertook that Kenny hoped improved not only perceptions, but the school itself, came about in 2012 at the 50th anniversary of allowing women in the MBA program.

“We wanted to make sure that people understood that although we realize that this was a really important milestone, we also realize that it shouldn’t have taken us 50 years to allow women into the MBA program, and even though we were 50 years in, we still had a lot of progress that we needed to make,” he said.

Harvard Business School planned a year-long series of events, and initiated research into understanding not only the barriers that many women face in the workplace, but the barriers women face at HBS and how their experience differs from male students.

The year of research and discussion culminated with an event that brought 3,000 people, most of whom were women and graduates of the program, to campus to discuss the future of women in the workplace.

“We’ve continued to carry on the research, we’ve continued to carry on the public outreach around women in the workplace and that has now become a permanent thing for the school to focus on and to continue to improve in,” Kenny said.

Whether it’s a year of events, or something much smaller scale, Kenny said there’s almost nothing he does outside of a team. The culture is very meeting-intensive, though, that doesn’t always mean formal meetings. They do informal stand-ups called campfire meetings, and Kenny also walks around a lot to check in with folks.

“I probably hear more in those quick hallway conversations than I would get if I staged formal meetings all the time for people, and it’s less of a burden on people.” he said.

Plus, he’s learned that building trusting relationships with peers has been crucial to his success at work.

“I guess I have a philosophy for my approach to work, which is that — it’s going to sound really trite, but it’s really true — you need to have empathy, you need to treat people the way that you want to be treated, and if you engage in every interaction with people that way, whether it’s the head of the organization or the person who is delivering the mail to your office, I think it gives people a level of trust and comfort with you that allows you to be so much more effective in what you’re doing.”

In his own words…

How do you unplug?

I am a musician, I sing in a rock band. Music is definitely my way of unplugging. I love to ham it up in front of an audience, so for me that’s a lot of fun.

Tell me more about that — how did you guys get started?

We’re called The Sellouts, and you can interpret that anyway you want. It’s a six-person group. Two of the guys have been lifelong friends of mine and we’ve performed together in high school and in college, but we broke up for 25 years. We got back together 6 years ago and we only perform for charity, so we don’t take a fee, we just play of worthy causes, and we’ve helped to raise about a half million dollars in the last six years we’ve been back together. It’s a way for us to take what we do — and none of us are doing it for the income. We have real jobs, but it gets us back on stage. The way we look at it is, if we’re not charging a fee, people can’t complain if we sound bad.

If there a social media account or website you read for fun?

Somebody just turned me on last week to I don’t know how new it is, but I really like it because can basically go in and type in the keywords you’re interested in, the things that you want to follow, and it basically curates content for you and pulls it forward, and then you can actually scoop a story and write your own front end and push it out through social media. I like that because it’s definitely built around an engagement model.