I would like to see a properly digitised profession, because we’ve shown we can be productive and some firms have announced incredible returns, so it’s clearly possible to work flexibly, from home, in a way that accommodates peoples’ lives. I’d like not to return to the days of having a dual identity – the idea that you have to be one person at work and a different person at home, or where you have to hide your children away, or not admit to being pregnant or not admit the fear that you’ve been laid off because you’ve had a child. I’d like to think that the digital transformation we’ve suffered would create an opportunity to unite these dual identities and allow women to be whole people and not have to cave in to presenteeism. I also think it’s a great example that encourages children to see a different way of working that doesn’t inhibit them. I’m hoping that we stick with it because flexible working should not be a luxury anymore.

It comes back to this idea of diversity. I speak to CEOs in the legal tech world where I am often the only woman in the room, and it’s extraordinary how many of these men are still unaware of some of these challenges because they were not the primary carer. As long as the decision makers are those that have not experienced being the primary carer, they don’t understand. This is because they can opt out, which is not an option for many women. So, I’m not sure they’ve internalised the need to take on the responsibility to enable people to continue to work, that wouldn’t work otherwise. In a way, it brings us back to the original message of Obelisk, which was to question why it was impossible for people to work in a different way. I think there will be a battle between these two ideas because there are some people that want to go into the office and separate themselves from their family, and women will be the ones that carry the burden. If you don’t have the diversity within an organisation that drives the flexible working agenda, you go back to the same old pattern. It’s easy and convenient to manage everyone in one location, but it comes at the expense of leaving talent behind. I’d like to see a revolution in the way that people work, that is lasting. We’re working on it. We’ve got our own technology that’s trying to address this, which will hopefully help to avoid different levels of engagement, different visibility, basically eliminating opportunities to discriminate. Can you see how I always go back to employment law?! Must avoid discriminating against people and unlawfully disengaging them from work!

I think the key is to be a lifelong learner, to maintain curiosity and to ask yourself what excites you. When I made decisions to switch careers, it was an informed decision. I could have gone on to the Bar, or to a smaller boutique employment firm. You have to have a 5-year plan, set goals that you want to achieve and the steps you need to take to achieve them. Ask yourself how you remain interesting and have a different story to tell. A lot of people tend to stick to a safe path because they think that will guarantee them results but then sometimes life turns out unexpectedly and they get the shock of their lives! You don’t have to be fixated, especially at the beginning of a career, or stick to a single path. There’s so much to learn! In the last 3 months, we hired 2 people who joined us wanting to be paralegals. An internal role came up that involved helping me and the sales team with client marketing. Our Head of Marketing noted that one of them had a natural flair for marketing but was unaware of it herself. The other joined us as an internal contract paralegal. It may not have been the original experience he envisaged, but he was open minded enough to recognise that it was a great opportunity to work in a slightly different legal business. Sometimes other professionals will talent-spot you for roles and opportunities that you may never have considered. I’ve always listened to people who have identified skills and talents in me.

I recognised that there were certain obstacles to becoming a partner at a law firm, especially if I wanted to have children, so it occurred to me that I could reach the same place by running my own business and selling it. It was a no-brainer!

Q. What key skills or characteristics enable you to be successful?

One of the things that helped me was that I didn’t measure my life by how others measured my life – that makes you courageous in your decisions. If you constantly think about status and how you’re perceived, it can be paralysing. You have to learn to see mistakes as opportunities to learn. That’s what I did when I started out in journalism. I went to a newspaper straight out of high school, with no experience, and persuaded them to allow me to show them what I could do. Who wouldn’t want someone who was willing to work hard and develop?

Because so many people going into the legal profession are high achievers, it can be difficult for some to adjust. For me, every pushback has been an opportunity. When I was refused a scholarship, I recalibrated, problem-solved, went back in and got it. Fight for yourself because you know you have something to offer, but don’t be arrogant. In business, you won’t last if you can’t take rejection. If you give up, you don’t build anything. When I started the First 100 years project, my own board director advised me not to do it because of the time commitment, but I persisted, and then it became everybody’s project!

Dana will be speaking at our Celebrating Women Leaders in Tech Law Event on 8th March. To attend, please sign up for a free ticket here.