How these women at the top manage the scrutiny of being CEO


Recognising that running businesses used to be considered “a man’s world,” three female CEOs have offered their experiences of life at the top of their companies, handling criticism and staying focused on the road ahead

Zen Terrelonge
Content Manager

I recently attended Women Rising: HM Treasury in conversation with women at the top, an event hosted by Direct Line Group and HM Treasury. It brought together panellists including Direct Line CEO Penny James, Brooks Macdonald CEO Caroline Connellan and TSB CEO Debbie Crosbie, with John Glen, economic secretary to the Treasury, chairing. I’ve always been mindful of equality – an outlook that’s been accelerated by becoming father to a daughter – so the event was as much of personal interest as it was professional.

The Women in Finance Charter – designed in a bid to produce better gender balance and senior-level opportunities across the financial services sector – was a topic of conversation at the event. Indeed, it was recently signed by FieldHouse client Funding Options, the marketplace for business finance.

Discussing the topic, Jacquie Williamson, people director at Funding Options detailed that company diversity objectives should be something for everyone. “Diversity shouldn’t be left to one individual,” she told Executive Grapevine. “If that happens, it’s always going to be an uphill struggle for that person, and the company as a whole, to implement because, without a collaborative vision, business and mindset change won’t happen.”

Speaking of which, vision and mindset were key parts of the discussion at Women Rising, particularly when the panellists were asked how they cope with the scrutiny of being in the public eye as CEO. With International Women’s Day upon us, here’s how they get the job done:

Stay grounded

For Crosbie, the fact of the matter is that her peers aren’t really who she needs to worry about. “It’s really easy for me because I know everyone thinks that as a CEO I work for the board, but I actually work for my 17-year-old, Charlotte,” she laughed. “She manages me and I get plenty of feedback ranging from fashion advice right through to ‘Are you kidding mum, you’re not doing that’ and that brings you down to earth and keeps you focused on what’s important.”

Expect judgement 

Like any job, no matter how much effort you put into something, you can’t please everyone all of the time. “You have to expect that, in the role, you’ll sometimes be criticised,” Crosbie offered. “It’s about having the stamina and energy to decide that you’ve done the right thing and be comfortable with your choices. And you just have to accept some days will be better than others.”

Don’t lie to yourself

Taking the top job means there’s a danger of staff members suddenly becoming yes people, worrying that they need to agree to stay on your right side. “Rely on people you trust to tell you what they really think,” said Crosbie, “because when you become CEO, people start saying very nice things to you quite a lot. You have to be very honest with yourself and very aware that sometimes you make mistakes – and may need harsh feedback from your 17-year-old.”

Remember who you are

Regardless of what level you’re at in a business, everyone wants to fit in. But when you’re at the top of the company, it may seem like a given that’s easy – it’s not always the case though, especially as a woman, detailed Connellan. “Being authentic is really important because it’s exhausting if you’re not,” she said. “For women that are trying to progress their careers in what’s traditionally been thought of as ‘a man’s world’, things are changing. I learnt very early on not to try bother talking about football. Rather than trying to engage that way, [I thought] ‘Could I find something we have in common?’ That could be what’s on Netflix or where you’ve been on holiday.”

Keep looking ahead

Despite how much positivity one exudes, not every day is going to be sunshine and rainbows. “You’re going to have bad days – sometimes things don’t go to plan, you don’t do things as well as you could have done or somebody else does something not as well as they could have and you need to pick up the pieces, but that’s life,” Connellan opined.

Resilience is key when those challenges crop up and you need to look at the bigger picture and keep your eyes on the prize. “You have to learn from that [problem] and then leave it behind,” she continued. “If a CEO isn’t looking forward to where they’re going and articulating why they’re going there and why people should come with them on that journey, then everybody else will look backwards as well and not come with you. It’s a really important part of being a CEO to pick yourself when something doesn’t go well, learn from it as much as you can and move on.”

Standing in the spotlight

While you may have once been able to go about your business in your local town previously, that changes when you lead the C-suite. “It’s a strange thing,” James started. “I live in a village in Hampshire and, all my career, nobody has given any interest in what I do, why I do it or whether I’m any good at it. All they know is my husband is at home and I go to the city. The moment you become CEO, it’s public property. It’s not just who you are and what you do, but the way you do it.”

Building on Connellan’s point about authenticity, James was in full agreement and said it’s key for a couple of reasons. “Firstly, it’s really exhausting to pretend to be something you’re not,” she said. “But also, on the agenda of today, if I want to create an environment that’s inclusive, where people can bring all of themselves to work, then the first thing I need to do is bring all of me to work. So, it’s very important they know who I am, what I stand for and what my life’s like, so that in reality whatever their life is bringing, they can bring that into work.”

Prepare for the worst

Being in charge means making tough choices, so you need to stand behind them no matter what. “It sounds dreadful, but you have to be prepared to be fired,” James said frankly. “That’s the thing when you get here [to this level], it’s a point where I’m going to do what I think is right. And I’ll take advice and listen, but you have to do what you think is right, even if it has consequences.”

But the good outweighs the bad

While everyone’s experiences will be different and the job of CEO will undoubtedly come with many challenges, Connellan also added that any issues are more than evened out – calling the post “a real privilege”. “There aren’t many roles that really allow you to create an environment where others can flourish and have the opportunity to shape the broader agenda,” she noted. “So, when you put all of that together, the benefits of being in these roles far outweigh the challenges of being in the spotlight.”

By Zen Terrelonge@Zen Terrelonge