Christine Osekoski on the importance of being decisive

Christine Osekoski has been Publisher at Fast Company for eight years where she is responsible for driving the brand management and leadership of advertising sales, marketing and promotions. During her tenure the brand has undergone an incredible reinvention and holds many accolades. Last year it won Magazine of the Year at the National Magazine Awards. Christine is progressive, incredibly dynamic and has enjoyed a 25-year career spanning sales, advertising, media and publishing. I had the great pleasure of spending an afternoon with her in February where she shared her lessons on career moves and seizing every opportunity.

What did you want to be when you grew up?
As you can see from my office here, I like animals. (Upon entering Christine's office you are immediately greeted with a life size toy Cheetah). I grew up on 24-acres of land with 5 cats and dogs, a brother and two parents, all this land and endless wildlife. I went horseback riding from a very young age and it was a natural choice that I wanted to be a Veterinarian.

At the time, my Mom was a careers specialist and she organized for me to do some work experience with a local vet. I walked into the clinic and almost passed out. The smell of formaldehyde, drugs and blood completely turned me off and I never wanted to be a vet again.

Who would you invite to your dream dinner party?
I'm lucky enough to host my own ‘Salon Dinners’ on behalf of Fast Company where I invite really interesting people featured in the magazine and other friends, entrepreneurs and creative people I admire. I've been hosting a few women-only ‘Salon Dinners’ for the last couple years so I've had the privilege of being able to truly curate my own girls’ dinner party.

I've met amazing people but what I would ultimately love to do is combine iconic women who have changed, are changing, the face of the planet like the likes of Gloria Steinem, Hillary Clinton, Elizabeth Warren and Kirsten Gillibrand and mash them up with women I admire in the business space like Wendy Clark, Anna Maria Chávez, Lisa Cochrane, Susan Credle, Eileen Fisher and Joanne Wilson.

It would be a fun combination and I’d love to watch the dynamic unfold.

What single book had the greatest impact on you?
There are two books for me.

Firstly, The Fountainhead by Ayn Rand. I loved reading about the architectural space of New York, but more importantly her concepts of individualism and objectivism.  Happiness should be one’s highest goal. The women in the book were kind of crazy and also very powerful so it was a wake up call to me to say, it's all on you. 

Secondly, about 20 years ago Julia Cameron (the first wife of Martin Scorsese) came out with a series of books called The Artist’s Way. The books look at how to unlock all your creativity even in work situations that may not seem creative. Regardless of one’s artistic talent, I think everybody has creativity in them and should be empowered to bring that to the party. That's been critical in my entire career.

When do you go to bed and when do you get up?
I'm such an “early to bed, early to rise” type of person unless I have a work function in the evening.  Sleep is so luxurious to me. I've been known to crawl into bed at 8 o'clock and just read. If I'm not in bed by 9:30/10:00pm I feel totally off-kilter. In the summer time I'm up at 5am and keep farmers hours.

What is your favorite time of the working week?
7am to Noon.  I just find that morning is my most productive time. My head’s clearer and I feel that I can actually think. It's my best time for creative writing. If I need to write a really important email to a client that isn't pressing, I wait until the following morning because I know I'll be “on”.

Can you briefly explain your career path to date?
I made a mistake in the very beginning when I graduated from college. I went after what I thought was bigger money, instead of going after what I really wanted to do. At the time I wanted to work for an advertising agency. I loved marketing.  I loved everything about brand building. I loved advertisements. I would watch shows for the ads, interpret them and translate them.

I graduated from University of Dayton and I had been doing technical writing for NCR Corporation as an intern and they offered me a place on their sales program. It offered $38,000 a year and I was like WOW. I thought it was so much money.  I could select whichever city I wanted to live and they offered to put me through a sales training program. The prospects sounded great but in reality I hated it. I survived for two and a half years. AT&T bought them out and they offered an early-out option, which I took. I called up my father one day, who was in the military, and said "Guess what? I'm leaving Atlanta, and I'm taking everything and moving to Chicago" and he asked "Do you have a job?" and I said " No but I'm going to get one!"

I knew I wanted to go back to what I'd wanted all along and sure enough I landed a job with the advertising firm DDB Needham. I loved advertising but after several years was burned out.

A very good friend of mine and amazing Media Director, David Handelman suggested that I should go into publishing as a Media Rep. I had no idea what was involved but he said that my mind worked so fast I would love working on several different client's businesses, vs. just one. 

Sure enough I interviewed and ended up working for Parade Magazine. At the time it was a huge subsidiary of Condé Nast. I was like buying network TV because you were buying 80million pairs of eyeballs.  I just clicked with it. My background in advertising, writing strategy and understanding creative, put me in good stead for convincing clients to use Parade.

Jack Griffin, formerly the CEO of Meredith and at the time with Parade, proposed that I move to New York. This was in 2001 and he wanted to create a whole new department that I would lead. It was to be a bridge between Sales and Marketing. He called it Integrated Sales and Marketing and believed because I was a marketing and sales person, I would be able to do big things with different media and clients. At the time it was earth shattering. He was prescient.

I had the best time. For my first deal, we worked with Share our Strength and we executed this concept called The Great American Bake Sale. We partnered with Betty Crocker, Reynolds of Reynolds Wrap and tied in ABC to execute Great American Bake Sales across the country. It was groundbreaking at the time to have an integrated media mix.

I went through publishing and ended up going to work for Hachette Filipacchi Media on Road, Track, Car and Driver. I was there for three years. I was in charge of all the non-endemic business so I forged partnerships with Rolex, Breitling and accounts that were non-car.

The opportunity at Fast Company arose when the company was bought by Joe Mansueto in Chicago and they were looking for a Head of Sales. I walked into the CEOs office and told him what I had to offer. I said: I've managed people but I've never done the hiring and firing but I can manage marketing and I can manage sales. He questioned whether I felt comfortable joining a start up to which I responded, “the only way is up." He offered me the job.

That was over 7 years ago and it's been amazing to watch the company grow to where it is today. I was onboard for about a year before Bob Safian joined. Together with the editorial and the business side we were able to create an incredible brand.

What is the biggest obstacle you’ve overcome, as it relates to your industry?
The obstacle as it relates to Fast Company is how to convert creativity into something that you can monetize. It's a huge obstacle because how do you take a media property and re-brand, re-package, and recreate it so that people want to buy it.

The media environment that we're in … there’s so much content out there and there are so many companies that are not monetizing their content. How do you stay afloat? That's the hardest obstacle that we've overcome. How do you keep creativity fresh and grow, without being in the red?

What motivates you?
Building and Creating. The funniest thing is when we re-started the brand 7 years ago we had to work hard at being innovative and always keeping things fresh. I look back now and realize that that's what motivated me all along. How can I do something that nobody else has done before? Many things have been done before but how can we do things in a different way?

What advice would you give to someone at the start of their career?
Take anything. Volunteer for any project anybody gives you because you're going to learn from it. You will be that can-do person and even if it's the most ridiculous thing you will still learn from it. You will meet new people, you will learn new things and it gives you a much more well-rounded space. I remember biting off more than I could chew at DDB Needham but I was that girl that the Managing Partner would come to with the opportunities to work on different projects - that opened so many doors for me. 

What do you consider your greatest achievement?
I struggle with this question because I've always found it hard to stop and smell the roses and recognize my accomplishments. I'm slowly learning that I need to slow down and stop going after that next thing and just process what I've done so far. When I think about it I have achieved so much with Fast Company. It was funny because last year when Fast Company won Magazine of the Year, our editor asked me "Have you even stopped to think about this?" and I really hadn't. Actually we've had a lot of great things happen with the brand, between the Adweek and Ad Age accolades, I've led a team that has quadrupled the business in the last 7 years. I'm really proud of Fast Company, of where it's come from and where it's going. 

What do you believe has been the key to your success?
Fearlessness. One of my mentors, Jack Griffin, when he was talking me into coming to New York said, "I've never met a salesperson like you. You are fearless. You will take every risk out there. It will be calculated but you'll go for it." I realize he was right. It's funny because it's also a part of the DNA of the Fast Company brand.  

What is the most important lesson life has taught you?
Confidence is critical. Even faking your confidence is critical. The big question is where to get your confidence from and sometimes it's just putting on a really hot pair of shoes and I feel like wonder-woman. Trust me it works! Whatever your armor, do what you need to, to fake it till you make it. Then you get in a space where, coupled with knowing what you're talking about, you can achieve anything.

What do you believe are the personality traits of people in leadership positions within your line of work?
Leadership is everything. Companies succeed because of the leaders that are driving them. 

Great leaders learn from everywhere and everyone. Great leaders recognize they don't have every single answer but know that ideas, opinions and "a-ha" moments can come from a lot of people on their teams. 

But the most incredible trait is that you have to be decisive as a leader. You have to be decisive in a way that's tempered with knowledge. I have watched it so many times when someone is all over the place and won't make a decision over the course of months and it slows your growth and makes people feel like you don't know what you're doing.

Do you believe there's a secret to rising to the top?
There's two ways to becoming really successful.

One is so simple. Hard Work. You're smart, you apply yourself, and you work really hard. I remember my first years at Parade Magazine, everyone was amazed at how relentless I was. It wasn't like I had to prove myself and be the best, it's that it does take a lot of hard work, it does take a lot of hours.

I also believe that networking will get you there faster. I didn't have that quality. There are people who are supernatural; and they succeed quicker than the rest. 

Who do you turn to when the going gets tough?
I am very lucky to have some great people in my life who I can go to with anything. I have an amazing cousin who's a creative director who's been in the business for a long time. 

One thing that Sheryl Sandberg said in her "Lean In" book that I thought was smart was how important our choice of life partner is. Things happen, but if you are in a strong, fulfilling relationship, that's a really important partnership. I’m extremely fortunate; Matt is a go-to person for me. 

I'm thrilled I have an executive coach, a small network of best friends and 2-3 women business friends that I trust implicitly who understand marketing/media. Once you reach a certain level it's harder to find people within the business to talk to and it's important to have an outside network to use as your outlet and that you mentor each other.

What's next?
2015 is the 20th Anniversary of Fast Company so it's a really big year for us and also affords us to look within and ask ourselves, how can we be more innovative and creative than ever?

As told to Caroline Hugall at Fast Company Headquarters, New York on Thursday 19th February 2015.