Leadership

This Successful Media Executive Shares a Surprising Truth About What You Must Do to Secure Your Place at the Top

Dawn Ostroff, the former president of the CW and president of Condé Nast Entertainment, says you must always be ready to embrace change.
This Successful Media Executive Shares a Surprising Truth About What You Must Do to Secure Your Place at the Top
Image credit: Courtesy of Dawn Ostroff
Entrepreneur Staff
Staff Writer. Covers leadership, media, technology and culture.
6 min read

In this series, Open Every Door, Entrepreneur staff writer Nina Zipkin shares her conversations with leaders about understanding what you have to offer, navigating the obstacles that will block your path, identifying opportunity and creating it for yourself and for others.

Dawn Ostroff has experience giving consumers what they want, even before they know they want it. As the president of the CW, her M.O. was to give the new network a reputation for being a home to zeitgeist-defining series, helping to develop beloved hits including Gossip Girl, Vampire Diaries, Veronica Mars and America's Next Top Model.

Ostroff started out as reporter for several network affiliates in Miami before heading to Lifetime, where as head of programming she helped make the network the number one cable channel in the country. From there she served as the president of UPN, and then with the merger of UPN and the WB, lead the CW. In 2011, Ostroff left the CW to pursue her next opportunity: to build a new brand as president of Cond? Nast Entertainment (CNE).

Under that umbrella, she has worked to develop content across digital, social media, film, TV and VR and grow a distribution network with nearly 60 partners, 20 digital video channels and about 2,300 websites. The film and TV divisions of CNE currently have 65 active projects in stages of development and production, one film on track to come out in 2018, as well as eight TV series that are ordered or renewed in 2018, and five scripted programs that were picked up for development and one pilot ordered by ABC.

Under Ostroff, CNE has been nominated for an Academy Award and a Peabody Award.

Entrepreneur.com spoke with Ostroff about why you must always be ready to embrace change in order to make a real impact.

This interview has been edited for length and clarity.

Related: The Surest Way to Build Your Confidence Is by Not Fearing Change

Can you tell me about a time you needed to create opportunity for yourself or others?

Launching the CW, knowing that we were going to formulate a new network to target 18- to 34-year-olds. And then of course when I started Conde Nast Entertainment. We really went from just an idea to having a full fledged company where you have hundreds and hundreds of employees. We've been able to create an opportunity for people not only on the traditional media business side but also the people who are young and really changing the way that we watch content. It's been really incredible to be able to build something with people who have a different vision and are changing the industry.

What personal traits or strategies do you rely on to create opportunity for yourself and others?

As a leader it's important to encourage your team to take a few steps back and look at where the world is headed. We're living in a world where things are changing so rapidly, you have to be nimble enough to make a calculated decision to change and also be bold enough to experiment and try new things. If you don't try you just will never know. Sometimes you stumble across things that you never would have expected.

When you experience a setback, what do you do to keep going? How do you get unstuck?

For me it's always about being able to see what was the original goal. What is the game plan? What is the roadmap? Where do we need to get to? It goes back to my mom always saying you just brush yourself off, pick yourself up and start over. When you're doing a startup, it's over and over and over again that you're going to get knocked down. How fast can you say OK, let's try another direction. Let's try this way. Always saying there's got to be a way and really persevering and not giving up.

Related: You Need to Meet Your Challenges With Pathological Optimism at Every Turn

People who want to advocate for themselves don't know always know how. What are actionable steps they can take to make themselves heard? What steps do you take?

If it's an idea that I can bring facts to the table, [I'll look at] either something that is trending, something that's worked somewhere else or a business model that makes sense. I always find that if you present an idea that's based on actual research or fact, it tends to resonate a little bit more because you've done your homework and it also illustrates that there might be an opportunity for your company to explore. Even if it's not a good idea, people respect you for thinking that way. I really encourage people to come forth with their ideas and concepts because that's a whole other skill set set that any management team would really respond to in a favorable way.

Related: Need to Negotiate? Here's the Best Way to Advocate for Yourself for Maximum Impact.

Has there been a counterintuitive or surprising way you've opened doors for yourself?

Speaking to business leaders from different business sectors is always so interesting because you can take things from that conversation and apply them to your business. You're able to hear their challenges or accomplishments or ways that they approach business. It's a company town in L.A., but going outside of that comfort zone is so advantageous because you get to really hear what what's worked elsewhere.

Was there a blindspot that you had about leadership and opportunity you worked to change within yourself?

When there is a business model that really works, you're in a sweet spot where you know that your business is humming and you're sort of sitting back and resting on your laurels. It is really important during this time to look forward and say, what do we need to be doing to protect my growth and my company for the future? The guy below you on that mountain has nothing to lose. That really creates different ways of thinking and groundbreaking concepts that you wouldn't think about. So the big challenge is how do you balance that? How do you balance a place where your company is thriving and successful and really hitting it on all levels while preparing for the future?

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