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What to know about Anna Wintour’s leadership MasterClass

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  • MasterClass, an online learning platform that features topic-specific lessons from successful individuals, partnered with Anna Wintour, Vogue’s editor-in-chief, to create a class on #HowToBeABoss.
  • Business Insider spoke to five individuals who either took the course or helped in making it for their take on the class.
  • These students said that some of Wintours advice was great — like making feedback fast and direct and choosing a boss, not a job — while some of her points about taking risks didn’t feel as applicable to average people.
  • For those not willing to shell out $90 to learn from Anna Wintour, we got the scoop on what the course covers.
  • Click here for more BI Prime stories.

Anna Wintour, Vogue’s editor-in-chief and Condé Nast’s creative director, understands why viewers are tuning in to her MasterClass. 

“I know many people are curious about who I am,” Wintour says at the start of the course. And she’s certainly right about this. 

With over 30 years of experience at Vogue, the globally familiar and somehow still illusive creative — with her unchanging bob and bangs, bold print dresses, jewel-tone statement necklaces, and bug-eye designer sunglasses — has commanded the admiration and attention of not only the fashion designers, models, photographers, and journalists whose careers she has launched, but also the world at large. 

So it’s no wonder MasterClass, an online learning platform that features topic-specific lessons from the likes of multi-billionaire businessman Howard Schultz and Olympic gold medalist Simone Biles, has teamed up with Wintour to create the forum’s first ad-campaign course, which promises viewers the opportunity to learn creativity and leadership, or better yet, #HowToBeABoss — the official hashtag of the course. 

If you’re not in the mood to shell out $90 for the class, don’t fret. We spoke to five individuals who signed up for the course to get their take. Here’s what you need to know, as well as the big lessons anyone can take away and apply to their career.

Following a scenic opening of framed black and white Vogue photographs and vases of bright blooms that populate her office, Wintour takes her seat in front of the camera and describes her early introduction to the world of print journalism. This career launch involves an upbringing in ’60s London, a respected newspaper-editor father, and an eventual role at New York Magazine as the publication’s fashion editor, all of which paved the way to her becoming the eventual editor-in-chief of American Vogue in the late ’80s. 

For all her MasterClass’ meaningful wisdom and advice, the course and its accompanying PDF workbook do tend to hyper-focus on the fashion and journalism industries. There’s even a whole section on planning the Met Gala and judging a fashion-designer competition, which is honestly more amusing to watch than educational. 

The course also lingers on some of the more obvious tools to successful leadership, such as avoiding micromanagement, taking creative risks, and building effective teams, but throughout the 12-part course there are lessons that lend themselves well to leaders, executives, and creative professionals alike. 

Here are some of the useful reflections Wintour offers her MasterClass pupils. 

In one section, Wintour reflects on how numerous interviewees have sought to impress her by saying what they think she wants to hear instead of being true to who they are. As a self-professed tennis enthusiast and theater-arts aficionado, she’s caught Vogue interviewees professing their love of her favorite sport or Broadway plays before she quickly assesses they don’t have a clue as to what they’re talking about. Instead, she praises those who are bold enough to own their identities without apologizing for them. 

Christine Kirk, a PR executive who has represented brands like Four Seasons Hotels and Resorts, The Ritz-Carlton, and Pinkberry, told Business Insider that this portion of Wintour’s course hit home with her. Kirk believes that one of the main reasons Wintour is so captivating to individuals is that her behavior isn’t something typically associated with female leaders. 

“I think female leadership is still an anomaly in a way. We’re used to seeing big powerful men like Bill Gates, Steve Jobs, and Mark Zuckerberg, but when you see someone like Anna Wintour or Martha Stewart even, who behave the same as these men, they often get branded as bitches,” she explained.

Kirk said in a former position she was often labeled as difficult or cold when she focused on deadlines and assignments instead of socializing with her peers during breakroom get-togethers. After taking Wintour’s MasterClass, however, Kirk said she feels more confident in her identity as a hard worker who is committed to crossing off her checklist instead of giving into pressure to please those around her.

“Anna is unapologetically herself, and it doesn’t matter what anyone says about her, it doesn’t matter what names she is called, she just goes for her,” Kirk said. “It makes you feel better about your place in the world. You can say, ‘I have my eye on the prize and I am focused.'” 

Unsurprisingly, Wintour doesn’t leave work at work. At the end of each day, she brings home a bag full of items that need her input or approval so that she can bring back feedback to the office the next day. 

Wintour explains to viewers that she doesn’t believe in leaving anyone waiting on her and that giving quick feedback inspires a confident and energetic workplace. 

“People work so much better when the feedback is fast, it’s direct, it’s honest, and they know where they are. I think that nobody works well when the atmosphere feels slow or it feels lazy. I think people lose confidence. They lose energy. They lose that sense of anything can be possible,” Wintour says in the MasterClass.   

Jasmeet Sidhu, a MasterClass senior creative producer who worked on the course with Wintour, said Wintour’s advice of being direct with your peers validated Sidhu’s own approach to being a young leader in the workplace. 

“Sometimes I had to hedge around giving feedback or I’ve tried to maintain this idea that I need to be likable and not necessarily critical,” Sidhu said. “Anna’s advice was a great validation that sometimes people just need to know what [to] do. That saves a lot of time if you’re not worried about being likable in the workplace … it’s easier to be direct about what needs to be done and what’s working or not working.”

Greg Hahn, chief creative officer at BBDO New York, an agency that has produced content for Snickers, Fed-Ex, and most recently the much-discussed Back-To-School Essentials PSA from Sandy Hook Promise, has taken MasterClasses by the likes of comedian Steve Martin and best-selling author James Patterson, but Wintour’s class on leadership drew him in as a fellow creative mind. 

“I saw ‘The September Issue’ years ago, and I could tell from watching it that she is an incredibly strong leader with a formative vision,” he said. 

Hahn said he found value in Wintour’s tips on building an effective team and not micromanaging people’s work, but that he was also taken with Wintour’s advice to be comfortable making “wrong” choices. He points to Wintour’s unexpected decision to put Kanye West and Kim Kardashian on the cover of Vogue in 2014, which was met with an onslaught of deep criticism and concern from audiences. 

Wintour says that because West and Kardashian were so culturally relevant at the time it would have been a mistake not to put them on the cover. Hahn understands how business decisions like these made in creative settings are incredibly challenging, and appreciates Wintour’s commitment to staying edgy instead of giving in to criticism. 

“When you mix business decisions with creative decisions, it makes it hard to remain creatively brave,” Hahn said. “But the risks that she has taken, even the Kayne West and Kim Kardashian cover, clearly paid off. People couldn’t stop talking about it, and it sold well.” 

Anne Carullo, formerly the senior vice president of global product development for Estée Lauder Companies, who now works as a creative educator, said she took the Wintour MasterClass to prepare herself for teaching a creative leadership course at Estée Lauder. She argued that although Wintour does touch on owning mistakes, she struggled with the editor’s seemingly unapologetic nature. 

Carullo believes students who are watching this MasterClass might not be in the same secure career position as Wintour when making critical decisions. 

“It’s very easy to [be] unapologetic when you’re Anna Wintour. But if I put myself in the shoes of someone who is up and coming, say a young person or someone in middle management, who has to be somewhat apologetic for their errors or misguided decisions, [that advice] was not necessarily grounded in their reality,” Carullo explained. “I look at [this MasterClass] as something a younger person might have saved up their money to do, so we need to stay deeply rooted in reality about who would want to watch these things, and I think there is an art to apologizing and there is an art to admitting you made the wrong choice without appearing as if you are non-apologetic.”

One fact that Wintour makes clear in the course is that she likes to keep her meetings to the point and then move to the next task at hand. So if you’re hoping to settle into her chic office and wax poetic, Wintour is not likely to oblige. 

Kristin Morlino, a costume supervisor who has worked on projects like “13 Reasons Why” and “The Young and the Restless,” empathized with this approach to keeping an effective pace at work.  

“Time is money, and there’s only so much time in the work day, so I say let’s get it done and move on,” Morlino said.

In addition to staying the course at work, Morlino also agreed with Wintour’s advice to focus on choosing a boss you’d like to work with instead of the job you’d like to have. Morlino said that in her own experience, she could have saved herself some grief if she’d evaluated her potential bosses on the projects she’s worked on. 

“I work with a lot of costume designers, and sometimes you get along and you mesh, and sometimes you don’t,” Morlino said. “[Anna] said to remember that sometimes it’s just not the right fit, and I think that’s true. We have to stop thinking of it as failing, and instead think of it as just not the right fit for you and for them.”

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