Fostering female leaders
Caroline Whaley spent 17 years managing teams at Nike, which saw her projects vary from training athletes to working in Africa with teenage girls determined to eradicate global poverty.
Setting out to economically empower women, both personally and professionally, she co-founded Shine for Women with developmental coach Anna Baréz-Brown in 2013. The organisation now trains over 10,000 women globally to reach the top of their field, with a focus on gender parity and seeing women as their whole selves. Edit Her sits down with the leadership advocate, who shares her insight and words of wisdom.
“There’s very really little point in doing work around women’s leadership if you don’t actually look at the whole person,” Caroline affirms. Her work at Shine is all about humanising businesses and paying attention to women as individuals within organisations. “We [women] define success very differently and much more holistically than men usually do; we don’t compartmentalise our lives,” she says. “If you ask a man about what makes him successful, he will talk about his career and work. If a woman says her business or work’s going well, she’ll normally come back and say, ‘Well, I’ve been a terrible mother and a useless friend’ or ‘an awful mother, wife…’” she says. This leads to her recalling “a lovely stat that [says] if a girl earns money, she’ll reinvest about 95% of what she earns into her family; if a boy earns money, he’ll reinvest about 35%.”
Caroline, who strongly recognises the value women bring in poor countries, soon references micro financing for young female entrepreneurs. “The payback rate is something like 99.9%; it’s just phenomenal when women get involved in things like that,” she enthuses.
Explaining that Shine has been mainly working with emerging female leaders, she says, “Young women are without doubt the worst off from this pandemic. If I got paid a pound for every woman who’d said to me she wants to be more confident, I’d be a very wealthy woman, seriously.” And academic research proves just how self-deprecating women are. The Harvard Gazette reported on a study from the National Bureau of Economic Research which suggests men find it easier to self-promote than women. The women examined rated their performance lower than men, despite having the same average score.
Caroline explains that Shine has changed “quite a lot” since the beginning. “When we first started, we were mainly convincing white male CEOs why we needed more women at the top. That changed to how do we do it, and how do we do it fast?” She notes a further shift to “How do we take men with us? We need male allies.”
On confidence and imposter syndrome
“Less than 5% of women we work with have ever done real work around their personal values. So, until you know what absolutely drives you, what you’re passionate about and what you can’t live without, it’s very difficult to go out there and be really confident in who you are. You have to just stop and take stock: ‘Who am I? Who do I want to be?’, rather than ‘What do I want to do?’ When you work out how you want to live [and] show up, that’s the bit that gives you confidence. It’s really critical that you know yourself, that’s the number one thing and, by the way, that’s a life’s work. So don’t kid yourself that you can do it and then go ‘I’ve done that’, because as we’re human, we tend to be messy and a permanent work in progress.”
Caroline, who refers to imposter syndrome as ‘gremlins’ says, “I’ve never met anyone who doesn’t have some kind of gremlin running around telling them they’re not good enough, or they’re a fraud. Whatever your gremlin is, it’s super important you get to know these destructive voices. We [at Shine] work with women on strategies to learn to live with them because they’re not going away.”
“Do one thing and do it brilliantly”
On knowing the right time to leave a full-time role to start a business
Caroline has seen many people do a “really nice job” of going part-time (e.g. “work four days and spend one day setting up the business”), if they haven’t got the financial freedom to do otherwise. “You don’t always have to be in it or out of it; there can be a hybrid version of that.”
On standing out as a business in a saturated market
“The sharper your proposition, the better. There is such a temptation to get into mission creep, to try and be all things to all people, and that never works; you just get lost with everything else. Do one thing and do it brilliantly.”
On facing big challenges in business
“I’m actually a big optimist about recessions and creativity, I think it absolutely brings out the best in young people. The answer is to focus on what you can control, not on what you can’t.”
On finance
“Cash flow [not having enough] is what kills companies. So, building a business model that’s robust is really important.”
Caroline brings up a point about expenditure leaving businesses without pay for a long time: “You have to be able to cover that. So, I’m a great believer in building teams of people who are far better than me at the bits that I can’t do. The trouble is that, at the moment, people are extending payment terms and not paying on time; it’s the first thing that happens in a recession. Just because you say, ‘pay on demand’, that’s not going to [necessarily] happen, so have someone working on the capital in the business. If you’re going to get investors in, get people who you really trust.”
On working with investors, specifically
“What’s dangerous is that if investors are only in it for the money, they’ll always be breathing down your neck, and the one thing you will need when you start up is space. So, you need to work with people who trust you, who believe in you and are in it for a longer term, rather than a fast buck, otherwise you’re really in trouble again. Don’t be tempted by the shiny thing [which] is all about ‘great, as long as we get paid back in nine months, or 12 months…’. It always takes longer to make money than you think.”
On business survival
“Often businesses fail the three-year mark, and it’s because [they’re] very diligent and careful in the beginning. Between two and three years is when you start to get your confidence, and it’s often the case that after you start to expand, maybe you overstretch yourself,” Caroline explains. She reaffirms her earlier point: “Find people that are better than you to come on the journey.”
On personal style and self-presentation, particularly in the fashion industry
“If you want to put yourself at the forefront of fashion, by God, you better be at the forefront of fashion,” Caroline jokes. She touches on tailoring your style to your surroundings. “If you feel good, that’s by far the best way to decide whether or not you’re in the right space. Feel confident and you’ll shine.”
On whether all leaders are influencers
“Influence is not about age or seniority; the more confident you are on the inside, the more influential you’ll be on the outside,” Caroline asserts. She says it’s also about the “art of empathy”, which is “a real biggie”. “The most influential people just have a really good ability to read the other person, to know what makes them tick, [so they can] start pressing buttons on that person really well. It’s super dangerous if you’re arrogant enough to think that just because you’re older or more senior, you are influential.”
She also reflects on reverse mentoring: “I coach more senior people, and the fear of being left behind from a digital point of view is really high. [It’s a] really scary thing for older people who just haven’t grown up as digitally-savvy as the next generation.”
“Find them, stalk them, track them – it’s not like it’s difficult. If you want to meet Richard Branson, go out and find him – stick your neck out”
On making yourself visible for a promotion
“That is really tricky at the moment. If there’s a high-profile project on the go, put your hand up to be part of things – even if you know you’re [already] working hard – because waiting to be asked (a bit of a female trait) never works. If I’m honest, I see it quite a lot: ‘I work hard, keep my head down and I will get noticed’ – but it doesn’t work like that. You have to make sure that you are connected to the right people and nurture those relationships.”
Caroline soon recalls a client’s experience of working in advertising. “She’d only been there for a month, and she had sent an email to every member of the executive committee, asking if she could have a coffee with them. Every single person responded and she had coffee with every member. All the other women in the room were like, ‘You have to be kidding, OMG I couldn’t do that’. But guess how well she did, guess how successful she was? She built her network like that.”
On networking
“We [at Shine] do a session we refer to as ‘allies’, which is [around] really becoming conscious about building your network – an important thing to do; you cannot leave that on chance. It’s funny, at home we’re really good at asking for help, personally. Somehow when we get to work, we’re just not as good at doing it, whereas men are the other way. They’ll go out and find out who they need to know from a work point of view, and that’s the bit we need to get really good at.” And despite the likelihood of it giving “you a bit of sweaty palms”, Caroline says “Find them, stalk them, track them – it’s not like it’s difficult. If you want to meet Richard Branson, go out and find him – stick your neck out. Most of the really successful women we work with [like CEOs] are very intentional about their support network.”
Caroline advises introducing yourself to potential allies early on. “You have to be a bit brave on that one,” she insists. “I think people are actually more open to an informal cup of coffee, even if it’s on Zoom, than they would’ve been before [the pandemic], when everyone’s chanting around at 100 miles an hour. Don’t underplay that.” Alongside highlighting that networking with influential people is “probably the most critical thing”, she’s also clear on it being a two-way street: “It’s very lonely at the top of an organisation – people underestimate that. The more senior you are, the less friends you have,” she says.
On what separates the good, effective leaders from the bad, ineffective leaders?
“I think the more human you are, the better leader [you are]. The need for us to be as inclusive as we’ve ever been is vital right now. There is a need to be able to have really honest and open conversations with each other.”
Caroline brings up a very valid point about conversations being driven underground as of late, highlighting race as one of those taboo topics: “It’s like, ‘I’m scared of saying the wrong thing, so I either won’t say anything or talk about it over here with somebody I know’”, she says, referring to a typical conversation. “It’s stopped people going, ‘I’m really sorry, but I actually don’t know how to talk about this, and can you help me, or tell me what your experience is…’”. Caroline is sure that it’s only by being human – in other words “compassionate and kind, but also messy and flawed” – that people can engage and open up in such difficult conversations. “That way we look after people, but we don’t sweep necessary conversations under the carpet, either,” she explains.
On how she envisions organisations in the future
“I think the future is entirely hybrid,” she says, pointing out that connections and creative collaboration will still thrive. “I think flexibility is here to stay and that will require a very different kind of leadership; I think it will breed higher levels of trust. Everybody agrees that productivity is not suffered, so we know this works. Now we can actually do what’s best for individuals as well as organisations.”