How to be a great boss: the most loved and lauded female bosses share their wisdom

Sophia amoruso

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How to be a great boss: the most loved and lauded female bosses share their wisdom

By Sejal Kapadia Pocha

7 years ago

“Instead of creating rules, we asked: what rules can we get rid of?”

What makes a brilliant boss? While female bosses on TV shows such as Scandal’s Olivia Pope or House of Card’s Claire Underwood have charm, authority and enviable wardrobes, being a manager in real life goes beyond that. It’s about reaching targets, setting goals and above all inspiring and motivating your team.

When we researched the managerial tips some of the most successful female CEOs, founders and directors abide by, we found that most (if not on all) recommend a better way of collaborating and uniting teams.

Here we collate our findings into the five key rules for being a great boss in any industry. 

1. Treat your staff as you would your friends

Eleanor Roosevelt, politician and First Lady of America for 12 years (from 1933 and 1945) once said: “To handle yourself, use your head; to handle others, use your heart.”

Research shows that empathy is key to leadership and has a positive effect on job performance. In a study of almost 7,000 managers across 38 countries found that those who showed more empathy were viewed as better performers in their job by their bosses.

Jenna Lyons, Creative Director at J Crew, is known for her compassion and warmth towards her staff. “Jenna really loves people who are themselves, flaws and all,” said employee in an interview with Fast Company last year. “If you mess up or totally do the wrong thing, you have to look her in the eye and say ‘I messed this up,’ and she will always say, ‘Okay, we’ll fix it.’”

Another staff member added: “She knows how to make you feel appreciated, even if you need to be redirected.”

Jenna Lyons, Creative Director at J Crew

“If you don’t love the company and the people – really love them – you can’t do a job like this,” says Moya Greene, chief executive of Royal Mail and one of only four women to head a FTSE 100 company.

When Sarah Tremellen, founder of Bravissimo – one of The Sunday Times’ 100 best companies to work for – was looking for a location for her head office, it was dependent on what her staff would need. “We really liked the offices in Leamington because we have predominantly female staff and the girls on the phone work until 8.30 at night, so we wanted it to have a safe feel, and also to be somewhere where they could go shopping in their lunch break. It might not sound like a normal business rationale but it was important to us,” she said

Meanwhile, Natalie Massenet says empathy is one of the key things she looks for in an employee, alongside confidence, intelligence and humour.

2. Learn to be yourself, and not channel male behaviours intentionally

When you’re in a managerial position, you may think you have to be tough, impersonal and authoritative much like the classic male boss. Alternatively, as Sheryl Sandberg (chief operating officer of Facebook and founder of Leanin.org) points out, women who tell others what to do are branded “bossy”, a term that is rarely applied to men.

“Here’s the thing: you can tailor your behavior to a certain degree, but how feminine you are – or aren’t – has to do with your body language and personal style and speech tone and patterns, and you shouldn’t have to change those things for the workplace,” says Margaret Wheeler Johnson, Senior Lifestyle Editor at Huffington Post. 

“Ultimately you’re going to be you.”

Bobbi Brown, Founder and COO of Bobbi Brown Cosmetics

Bobbi Brown, founder and CCO of eponymous cosmetics brand says, “I used to be into the whole power-suit thing. But I long ago learned to grow into a management style that is closer to my character.” She is renowned for her informal hiring style, where she has interviewed candidates for two-minutes at her SoHo office: “You look into someone’s eyes and see if the connection is there.”

“I learned to own it. Own being a woman in charge and everything that comes with it – tears included,” says Louise Hung, a Japanese Theatre director. “Own that I will never be “one of the boys” and that I can’t aspire to be. Own the scrutiny of being the Boss and that if the ship goes down, the fault will be on me. I was never one to hide behind others, but I realized that I couldn’t hide behind my own sex either.”

CEO of Imperial Tobacco and one of the five women on the FTSE 100 list, Alison Cooper recalls: “I had canapés at Buckingham Palace the other night and still had my pasty at Paddington on the way home.”

Essentially, being a boss does not require changing your personality. Chances are, it’s your natural behaviour that got you the job in the first place.

3. Banish a sense of hierarchy

Research shows that when people secure even a little power over others, they are prone to treat them in more distant, cold and insensitive (even though it may be rational) ways. One study found that people who feel powerful become less upset and feel less compassionate when talking to someone who has suffered a trauma (for example, a close friend diagnosed with a terminal illness). Other studies show that power turns people into hypocrites. 

“I’m not into hierarchy,” says Ruby McGregor-Smith, CEO of Mitie and the first female Asian FTSE-250 CEO. She tore down her office walls, quite literally, as soon as she got her top job. “I don’t want to be defined by being a CEO. I have to be able to relate to all of those people in Mitie, so I have to understand it, live it and breathe it. And you can’t do that in an office behind lots of glass, can you? You wouldn’t come to head office and ask: ‘Where’s the CEO?’ You’d ask: ‘Is Ruby around?’ You’ll even find me on reception occasionally.”

In the 2013 book The Fall of the Alphas, author and American entrepreneur Dana Ardi says the traditional top-down, male dominated authoritarian leader is being replaced by a more collaborative and connected manager. She says that the best managers are learning to lead through the influence that comes from building collaboration rather than straight force or all out competition.

Ruby McGregor-Smith, CEO of Mitie

Co-founder of independent media agency the7stars, Jenny Biggam, says that when she launched the company, “Instead of thinking of all the rules we needed to follow, we asked what rules can we get rid of?” They banished all job titles and created a new “completely flat company structure so everybody’s voice has equal merit.”

“We find that people work much more flexibly when they are not tied down by a title describing what they do, or worried about where they are in the pecking order. Hierarchies can be a real distraction in that they make companies very inward looking, focused on internal structures, company politics and competing with each other. We want the team to pull together so that we can deliver the best work for clients and compete better with outside companies that are often bigger than we are.”

They also got rid of the bureaucracy around holiday forms and allowed staff to take as much time off as they want without seeking permission. “In all that time we’ve not had one single case of people abusing the system. In fact we’ve discovered that if you trust the people you work with to behave like grown-ups, they generally do.”

The company upheld a staff retention rate of 96% since they launched in 2005, profits are up 40% year on year and it came third in this year’s Sunday Times Best Small Companies to Work For survey.

4. Share information with your team

“Communication is really important. Being proactive with communicating out, but also creating an expectation that your team will communicate back, and making it clear how that should happen,” says CEO of Girlboss Sophia Amoruso.

“Explaining not just what you want to do, but why you want to do it is really important, because people want meaning. They want meaning in their – and this is something that I would want to be better at cause I just want to get sh** done. I’m like, ‘Let’s do this.’ But it’s so much better when everyone understands why we’re doing it, and they can buy into it. And it takes more time to explain that, and have a conversation about it, and get everyone excited about it, but the work that people create when they’re inspired is a thousand times better than when they’re just doing work because they were told to.”

Sophia Amoruso, founder of e-retailer Nasty Gal

At Square, a digital payment company, CEO and COO Sarah Friar encourages an open and transparent culture: “For example, notes from every meeting are emailed to the entire company. This even includes our board meetings. We are transparent because everyone is an owner of this company and we also believe that great ideas can come from anywhere. Those ideas are often sparked by being knowledgeable about everything happening at Square.”

Jenny Biggam also says her company business plans and profit targets are shared with all team members. The business also runs regular job swaps so employees know what their colleagues do day-to-day.

5. Coach instead of control

Staff who are coached and supported are more likely to excel to higher levels than those in heavily controlled environments or when dictated to.

Research shows growing organisations are those with empowering, trusting management styles whereas “command and control” styles are linked with decline, says Ann Francke, chief executive of the Chartered Management Institute and author of How to Make a Difference and Get Results.

Nicola Elliot, co-founder of Neom cosmetics, says: “We try keeping everyone enthusiastic and perhaps, most importantly, getting the best out of our staff, who obviously are far better in their own individual fields than we are.”

“It’s about energy, passion and encouragement,” recommends Sarah Wood, co-founder and COO of  Unruly. “At the company, our secret weapon is our team. We have awesome technology, unique data, but the real competitive advantage comes from having a winning team. As the leader, it’s all about encouraging that team, making sure they feel energised and that they feel passionate about what they’re doing.”

Sarah Wood, co-founder and COO of Unruly

Artistic director Taylor Tomasi Hill at Moda Operandi (an online designer boutique shop), says her time working as an accessories director at American Teen Vogue was invaluable because “Amy Astley, the editor-in-chief of Teen Vogue, taught me accountability and has continued to be so generous with advice and guidance throughout the years. Fashion is extremely competitive, and Amy taught me to embrace my fellow women in the industry and create a team that is indestructible."


This article was originally published in 2014.

Image: Getty

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