47· Influential Women With Hilary Ross
Podcast show notes
Welcome to another episode. Today, I’m thrilled to have Hilary Ross, Managing Partner for DWF in the UK and Ireland, joining me today.
With years of experience at the top of the legal world, Hilary brings incredible insight into what it takes to rise to such a high level, especially as a woman.
In our chat, we explore the power of influence, the grit needed to overcome being overlooked, and the balance between resilience and perfectionism.
Hilary’s candid reflections on navigating career challenges and breaking through the glass ceiling are both inspiring and eye-opening. You won’t want to miss this insightful conversation!
Here are the highlights
(1:48) Hilary Ross's Career Journey
(3:37) Impact of Gender on Career
(7:04) Managing Emotions and Perfectionism
(13:06) Handling Setbacks and Resilience
(17:33) Operating at Board Level
(20:59) Challenges for Women in the Workplace
(24:42) Promoting Diversity and Resilience
Connect with Hilary here
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Connect with Ruth
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Ruth:
Hello and welcome to today's episode of Frustrated and Exhausted. Today, I'm absolutely delighted to be in conversation with Hilary Ross. Hilary is the UK and Ireland managing partner for DWF, which is a global law firm. It's one of the highest ranking in the world. She has a wealth of experience operating at executive board level. She's been doing that for quite a number of years now, and today we are talking about what it takes to get there as a woman, and the importance of influencing skills and resilience around that, and Hilary is sharing really how she's overcome the challenge of being heard, something many of us grapple with throughout our careers. So tune in now. Sit back, relax and have a listen. It's a great conversation,
Hilary, welcome to Frustrated and Exhausted. It's great to speak to you today. How are you doing?
Hilary
Very well. Ruth, lovely to see you. Thank you so much for inviting me along today.
Ruth
It’s an absolute pleasure. Can I ask you to introduce yourself to everybody. Could you just say a few words about kind of your career so far, kind of what the key kind of moments in it have been for you?
Hilary
I think the first sort of highlight was getting my traineeship, which was with a very well-known criminal law firm in Glasgow, then deciding that I was going to go to London and coming down and joining, you know, an international law firm, which was a huge change from being sort of Glasgow High Street. And I sort of really changed course then, and became a pharmaceutical lawyer, which was very interesting at the time, because there was lots of actions going on against drug manufacturers. And then I realized that it was, it was quite difficult to progress because I didn't have a medical degree. So I sort of very gently shifted into food law, which was really embryonic at that time. Worked for a US firm where I really got my stripes, you really, really worked hard. You know, it got to the stage where I realized I hadn't been home in a month when I did get home, literally, there was no loo paper, so I had to bring some from work, you know! And then I got Partnership, which was a really key thing, really lovely firm at the time, really interesting work there. And then eventually I came to DWF, and it was really then that my management career started, starting off from head of the retail sector, then going on to the board, then becoming the role I've got now, which is managing partner for the UK and Ireland. So sounds quick, but it's been very long,
Ruth
Sounds like you were a busy lady! I can't imagine coming to work to grab loo roll! But yeah, that's what you call flat out, you know, the long hours culture. How do you think, I mean, we've obviously had a pre conversation, but I think this is really interesting. How do you feel that being a woman has shaped that career, shape the choices that you've made?
Hilary
I think it's been fundamental. Ruth, I mean, when you're at school and university, your gender really doesn't matter, you know, you're just you're judged on your academic capabilities. But suddenly, when you go into the field of work, everything about your gender shapes what you do from, you know, just very basic things I would notice when I was a trainee that my male counterparts could just say to a secretary, can you type this? Can you do that? Whereas, if I behave like that, I'd have been seen as very uppity. You know, who does she think she is? So it started very early on, realizing as a woman you have to influence, because you may not have a direct ability to control, or if you did, you were seen as a bit of a ball breaker, and that is not a way to to run your career.
So this idea of influence really started from the day you walk in to the office you're going to work in, and that has certainly been something that has been key throughout my career. How do you influence get people to maybe do things they don't want to do? You know, get them to do what they're doing better. And I think that's very different for men. So for example, Ruth, one of my close friends, who is a man, would say, Oh, you don't need a title. You can get whatever you want just by your existing and I thought, no, you cannot if you're a five foot three woman, you know, the title is really important to help that influence, you know, and help make your mark. And I think, you know, I can look over my career where so many times whatever I look like, I know I don't look like I'm in any kind of position to do anything, you know. So there was once we brought in a very senior member of the judiciary to give a talk, and I'd written to him in my role, and, you know, I put my title then, and I went downstairs to meet him when he was coming to do the talk, took him through to the room, and he gave me his coat and his briefcase and I had to say, I'm not the receptionist. I'm going to be the person who's introducing you! So that makes you think very differently about how you behave, how you come across. And I don't think men are quite as self-conscious about their gender when they carry out their day to day work.
Ruth
Yes, I think it says something about the degree to which women have to be more self aware, and as you said, self conscious of the choices, all the little things we see and the little actions we take, and how those are going to be perceived. In that regard it's quite easy sometimes to get caught in overthinking, how do you stay out of that? And kind of eyes on the prize and kind of stay focused on the reasons that you're trying to do this?
Hilary
Oh, it's really not easy, because, you know, you really analyze absolutely everything you do, and you lie in bed staying at the ceiling with that kind of self conscious “Should I have said that? Should I have done it differently?” And I think the only thing that has made a difference is just age and experience and thinking, Okay, you're doing okay. You know, you've got this far. If you make a wrong decision, it's not the end of the world. You can undo it. You can unpick it. Because if you trust your moral compass, you know, and I think that's probably what age is, what I trust is my moral compass, and will I get it right every time? Absolutely not. But, you know, I think I've got a good track record of getting it right most of the time, which is the absolute best you can hope for, you know, and stressing over every single thing doesn’t help. And I think this is a real women thing, this drive to be perfect, you know, you need your top grades, you need to be best in class. You always need to be perfect. You can't have a flaw in your makeup. You've just always got to be perfect. And we're not, we're just human and, you know, and as soon as you start to live with that, and actually, nobody else expects you to be perfect, the only person putting pressure on yourself is you. You know, it's, it's all right to go out with two left shoes, you know, two odd shoes, one black, one blue. It's all right to have a rip in your tights. Because, you know, we all have bad days.
Ruth
That's really true. How do you think that perfectionism that women particularly, I mean, men can be perfectionists as well, but I think for women, there's that extra edge to it, because it has an impact. How does that kind of relate do you think to emotions at work? Because this is something else that women get tagged with a lot “emotional” in whatever form that might take, and it can be a real stereotype. And with perfectionism and the overthinking and that that drive to be perfect all the time, sometimes that means those emotions kind of build up behind the facade, if you like. How do you go about managing what's going on inside? You know you're operating kind of board level and above and out and you know you're leading a large organization. How do you manage that?
Hilary
Well, I think I've had different coping techniques throughout my career. So when I started as a trainee, a really fantastic associate took me one side and she said, “If you're going to cry in the toilet, try and cry with your head down, because then your mascara doesn't run and your eyes don't get red”. And I thought, what totally terrifying advice to be given that there's a technique to this, what is going on. And I think I've, you know, I've honed it as I've gone through but one thing that always strikes me is the way I think our emotions tend to come out, or where I see in other women. And certainly there's, talking from a purely personal position, when I am really, really angry, I tend to want to cry. And of course, the people around me think, Oh, she's so upset. Oh, I need to help her. And I'm like, I don't need a pat in the back. I'm absolutely furious with you, and I just I don't know how to deal with this. I don't want to show I'm just really angry. And it's so often that that certain emotion comes out just as a release, as wanting to cry. And I, you know, I rarely cry at work, but I can feel sometimes my eyes fill up with tears, you know, because I just, I'm so angry with the person, but you get better at it, because, again, you hone those emotions. So I think coming from the west coast of Scotland, you will know you don't cry, right? You know, that's just not something that's in our genes. And sort of over the years, I've learned to think, well, will getting angry achieve anything? And of course, it just doesn't. It just makes people a bit weary of you, because you look like you're out of control. And so does crying, you know, so thinking about how you influence in a way that keeps your emotions in check, because actually you're gaining nothing by being angry, or you're gaining nothing by being upset. So thinking about speaking to other people if you can't get your point across, or if you can't get what you think is a great idea across, going to speak to other people on the board offline to say, look, if I just got this wrong, you know. And having somebody explain to you sometimes that, yeah, you have got it wrong is really helpful, but other times you can get your point across in a calmer situation, you know, where maybe emotions are running less high, or there's more time to explain something, and then suddenly you've got an ally who also wants to help influence because they understand, you know, so taking those emotions and putting them to achieving something rather than just feeling ineffective and having runny mascara.
Ruth
Yes, head down - terrifying advice, but also probably quite good advice. One of the things I find interesting about anger, in particular, as an emotion, is because there's something about understanding the things that trigger that anger. There will be specific things, and it'll be different for everybody, but there'll be specific things that just get to you. It might be a particular behaviour that somebody else has, maybe just be a bit of incompetence. It might be things not being done in the way you've expected or to the standard, but in understanding that for me, for me personally, that was one of the things, I think, that self-exploration that helped me kind of get a handle on that immediate reaction and create a bit of a gap to think and catch myself before I reacted.
Hilary
That's such, such good advice. I think my trigger point, Ruth, is not being heard. And I'm not talking about not being listened to. I'm just not being heard. And I still have this situation where you say something, kind of people go right, and they kind of move on, and then maybe 15 minutes later, a guy says it, and everyone goes, oh, right, yes, that's a really good point. I'm invisible, and that feeling of invisibility triggers me instead of, you know, and I think over the last few years, I've honed it, rather than being triggered, I thought, well, at least the point has gone in. Yeah, good, you know. And that's the main point, you know, that's the main issue here. Yeah, it's that focus, keeping that focus on the outcome, and trying not to do it personally. It’s not always easy. Sometimes I do feel like I'm an actor in the Fast Show sketch, you know, where the woman was always giving the advice and the men completely annoyed, and I'm like, hello.
Ruth
How do you handle it when you feel like there's been a setback?
Hilary
Oh, I mean, it is absolutely inevitable. You do not go through your career and you don't become a manager without facing lots and lots of setbacks. And a lot of management is you do two steps forward, three back. You know, it's like you have to be really resilient. And I'm not sure we train our people enough to be resilient, because you have to just keep going. And instead of beating yourself up for what you haven't achieved, because you'll have a goal in mind, think about what you have achieved, and that's really difficult. Because, you know, high performers think this is what I wanted to achieve, and I've achieved, you know, 2% of that I failed. And you just can't let yourself think like that. You've got to think we're 2% forward. Next year, we could be another 2% forward, and we'll get to where we want to get to. Because the thing about managing lawyers is they're high performing, highly intelligent, and it is just much more difficult to get to where you need to be, because they all have their own ideas. They've all read up on management. They all think they have the answer. And what I realized by coming into management is there's such a bigger picture you've got to take account of, and it's difficult, because it's like a spider's web. Everything you touch touches something else. So sometimes you don't have the ideal solution, but you've got something that's better than what you have at the moment. Yeah? So again, it's moving away from that perfectionism.
Ruth
It definitely seems to be coming back to that, doesn't it, allowing yourself to kind of change and change the goalpost a little bit as you go. And I think the pace of change in the world, full stop, is so high now that we need to be able to allow ourselves to work more in that way, because the goal posts are shifting constantly, and if we don't allow our plans and goals to shift in the same way, then we get stuck.
Hilary
Yes, and also, Ruth, I think what I'm learning now post-covid is you have to give people some control. You know, you can't just say, right, this is what it's going to be. Everybody back to the office. We're going to mandate, this is how we're going to behave. Because it's, it's very damaging, specifically to women, I think, or people with caring duties, or, you know, duties outside their own day to day profession. It's really important that people feel they've got some degree of control somewhere, and especially with that degree of change, where nothing feels the same and everything's new. You know, it's like giving people back that little bit of control. Treating people like adults, is really, really important.
Ruth
I couldn't agree more with that. We all need to feel a bit safe. And when we don't feel we've got any control, then you lose that sense, and that just puts us into, like, well, certainly not a productive place anyway.
Hilary
That’s for sure, it’s anxiety, isn't it? People just can't do anything. Yeah, I can't do anything, right? And that's, you know, that's not a good place to be.
Ruth
No, it’s not. Well, that's where the burnout rates come from these days, isn't it? What's it been like learning to operate at board level in a large law firm?
Hilary
It has been really interesting. It's taught me to moderate when I speak. Because, as you can probably tell, I’m a bit of a blether, you know! So I had to learn when not to speak and make it impactful when I did, it's made me be far, far more interested in the character of the people around the board, because I recognize, for a lot of people, they won't think in the same way as I do. And I'm not saying that's unique. It's just I'm not a board level thinking person, and I've had to adapt to that. And quite a lot of our people on our board are, for example, corporate lawyers. And corporate lawyers are very, very methodical. You know, they've got a spreadsheet. They've got 100 day plan, and, you know, so recognizing you have to kind of fit into that. You have to kind of adapt your style so you can be effective. And I think that probably the most important thing I learned was when I first got onto the board, I thought, Oh, my God, I'm innumerate. You know, I would sit for hours and hours before board meetings and read through all the figures and work it all out, and I'd have little sums everywhere working it out. And then we'd go into the board and everybody's going, figures, figures, figures, and they could do it in their head. And I was going, like, Where the hell's that figure? What's that come from? And I suddenly realized what they didn't need in the board was another accountant, another mathematician. What I brought was something very different, and to embrace that so thinking right? Trust, trust the people who can do the numbers. Because it doesn't matter how hard you sit and look at it, you're never going to be that, you know, sort of on the ball, but learn what's the important bit of the figures, and then also bring what you can contribute which they can't. So that did, because I think I first went on the board in 2016 so for the first few years, I felt like a complete imposter. You know. I thought, why am I here? And that made me nervous and probably less effective, but understanding you all bring something different matters.
And also, the one other thing I've learned is not to be afraid to challenge, you know, because I really felt, you know, I said this to my husband, I have to be able to look myself in the mirror and know that I've done the best for the partnership. So if it's asking those difficult questions, or the questions that partners ask me, that I don't really feel I've got a full answer to you have to be that voice on the board. Because even if it's just to explain it to them, you have to be able to do that, but if you feel like an imposter, it really dumps your confidence, and it's very difficult to ask those questions. So it took me quite a few years to get brave enough to be able to say it, because I thought if I ask it, they're going to think I'm stupid, and why am I on the board and things like that.
Every time you change your role, you go through a lot of self reflection and straight back to that imposter syndrome. And I think is what you said earlier Ruth, I think women of my generation, and above or and just below as well, think we have no right to be in the workplace that it's, you know, or if it's something which is, you know, it's, we've just got that right, and we have to hold on to it. And then things come along, like you get pregnant, then you get the menopause, you know, it's like everything seems to be to undermine our positions in the workplace, and that we seek. We still feel lucky to be here. And I hope that future generations never think that they think it's their right to be here, you know, and I can see that coming along. But I think for many generations, it was like you were in the minority, you know, you start to look up and see somebody that looked like you, you know, things like that. And so that has, I think, made it gives people a different perspective, and hopefully we'll be able to change that.
Ruth
I think that's so important. How have you managed that? That sense of maybe not being the only one, but being one of the very, very few at your level?
Hilary
It's quite lonely, and so I think, you know, I've got a trusted circle of friends who are women and men, and I've really tried to seek out people I can look up to, you know, but they're not a lot of people. But when we were a PLC, we had some really great NEDs [non-executive directors], and they were great to watch and learn from, and, you know, they were really helpful. But I can see people coming through as leaders within our organization, and God, they're really good. And sometimes I think “she dealt with that that way. Maybe I should deal with it this way.” So, you know, we've got absolutely phenomenal office managing partners in Scotland and Belfast, and they have taught me a lot. They've got such utterly different styles. I thought, Oh, that's really good. I'll take a bit of that, and I'll try that, you know? So it's not just looking up, it's looking at people that are coming through that you can admire.
Ruth
One of the challenges for women, and one of the places I mean, women drop off at different points, sort of through the career trajectory. But one of the key points is kind of those early roles when men will put their hands up and go straight for that promotion, and won't even think about whether they should or they shouldn't, they'll just do it. And women often hold back kind of thinking they need to tick every box. How do we break that? And what would you say to sort of women coming through sort of early careers, kind of into mid-career now?
Hilary
Well, first of all, I don't, I really don't hold with just promoting somebody because they're women and you need to get your stats right. Equally, I get absolutely furious when I've heard people in the past say things like, “Oh, we only promote merit”, so you've got a white-dominated C suite, and you've got a lot of women looking up saying, so the message to all of us are, none of us have any merit, which is infuriating. I've never liked that either. So how do you get the balance right? And I think as much as you can say to people, put your hand up. You know, don't be shy, because you want to tick every box. Try and just go for it, I think we need to try and create systems that help diversity.
So one of the things we've been working on is we have key account programs for a lot of our clients, and what we've tried to do is diversify who is on that account, and by trying to bring women and also quiet men who don't put their hand up, you know, trying to bring them through, to give them a role in that account, get exposure to the client. And you know, if they have the skill sets, which we think they do, they'll thrive and flourish, and then they'll start meeting the metrics to, you know that you need for partnership, or you need for promotion, and it gives them a feeling of self-worth. It gives them a feeling of confidence, if you, if you somebody saying you can do this, but just kind of going have a go, you know, just saying we need to meet these metrics and promoting them. If they don't actually know they’ve earned it, they're always going to feel like an imposter. They're always going to think, well, I shouldn't be here because I'm up against somebody who's got this type of practice or have achieved these metrics. So I don't think that does any good at all, but giving them an opportunity to go away and thrive and prove their worth. I think is really, really important. But for the kids, what I would say is just put your hand up. Just be curious. Put your hand up and give it a go. You know, the worst that can happen is you fail, you know and but when you're when you're young and starting off, there's nothing worse than failure is there. But if you think about that sort of the old Edison light bulb, you know, it took him 10,000 times to fail and once to get it right, you know. And he turned that into its 10,000 times to get it right, and again, it's back to that resilience Ruth. We need people to be brave enough to fail, because so many people I see just don't even try because they're scared of failure, but you're never going to get anywhere if you do that. You stop learning when you stop trying.
Ruth
Absolutely. Just to kind of wrap us up, what's the best piece of advice you've ever been given?
Hilary
That's a good question. Ruth, I think the best piece of advice I've ever been given is just give it a go. And what was the context of that? It was the initial board that I went forward for in 2016, it was one where the partners had to vote you on. So that was a huge thing, because I was dependent on 2000 people liking me enough to vote, and it scared the bejesus out of me, because I thought, Oh, my God, this could be every worst nightmare of me lying, looking at the ceiling, going, does everybody hate me? Am I not good enough? Because if you didn't get voted in, it was definitely personal, because you were putting yourself on the line. And it was a really wonderful HR director at the time who just said, “Just give it a go. I believe in you just give it a go.” And because I admired her, you know she was an older woman who had gone through everything, but it was far more difficult. I thought, all right, I'll give a go, but honestly, if I'm not voted in, I'm going to be sitting in a in a corner crying with a bottle of wine and taking it very personally.
Ruth
But that that speaks against that point about the moments where you need that bravery. You need to kind of find it within yourself to sort of step forward and take the risk.
Hilary
And that's it, I suppose, actually, when you catalyze it like that, you know, be brave, take the risk and just try it. Just give it a go and see what you can do.
Ruth
Brilliant. Hilary, thank you so much for your time today. There's, there's tons in this conversation, and I know we could talk for hours. Thanks so much for your time again and for sharing your thoughts with us today.
Hilary
Absolute pleasure. Thank you, Ruth,
Ruth
What a great conversation that was! I really hope you enjoyed it.
A few things for me that really stood out from that. I think Hilary's emphasis on the importance of influencing skills for women, really stands out. It's easy to be underestimated, to feel underestimated, to feel unseen, unheard and a bit invisible at times. I think what Hilary said about actually, maybe sometimes stepping back from your own ego in that and actually just making sure that the outcome is what's most important doesn't matter really at a certain point, if somebody else said it, but actually just being happy that it's been said at all can really take the sting out and the stress out of that concept. Being not heard. And I think that's great advice, and I think also that recognition that actually, because we are not seen and heard in the same way that potentially a man, some men, not all men, might be women, have to rely much more heavily on influencing skills, and have to approach things often in a different way. And while that might not be fair, it is the reality that we live in at the moment. So, if we want to progress and we want to be heard, we kind of have to find other ways to do that.
The importance of having a trusted circle, having people to look up to, and, you know, look side to side, and you know, all around you to learn from, I think, really came across in that conversation as well, and the fact that you can learn from everyone. It's not only, you know, Hilary said it can be quite lonely when there aren't other people like you, at your level or above you to look to, but actually you can still learn from other people, and there will be other women in other places, in your organization, potentially, that you can look to and learn from, and that that's really important to do as well, and as well as having a circle of people that you can turn to for advice when you when you need it.
Finally, I think that last point there really about just finding the bravery, finding it inside yourself, to try to push forward, to take a step forward, to have a go. To just give it a go, even if you know it might not work out, take the chance and go for the promotion or do the uncomfortable thing, if it helps you to learn and move forward, even when it’s not easy and not comfortable. Of course, we all know that, but so, so important for women to just push that little bit past the fear.
I really hope you enjoyed that. I certainly did, and kind of I'm going to be taking those things away to think about a bit a little bit more. Have a great week, and we'll see you back here next week. Take care.
