Ann Silla: Journey From Magic Circle to In-House With Media And Tech Companies

Welcome to the Crafty Show, a legal podcast.

Produced by Crafty Counsel, a digital media company and community with the aim to spread joy, connection and insight to in-house lawyers. 

Join Crafty Counsel’s founder Ben White as he speaks to lawyers who have left private practice, often to join in-house legal teams, about their career journeys.

In the second episode Ben talks to Ann Silla, a senior legal counsel who trained and then qualified at Linklaters in the private equity corporate team.

Ann moved in house after four and a half years and subsequently spent several years in the publishing industry working at The Economist Group as senior counsel. She later joined Deliveroo’s legal team and is currently a senior legal consultant. 

Transcript

Copy Transcript Copied

Ann Silla:
In order to be that quick and agile in movement, you have to be comfortable taking certain amounts of risk. And it's not doing anything bad or illegal or anything like that. That's not what I'm saying at all. But you have to get more comfortable with risk. And so depending on who you are as a lawyer, and let's be honest, we're lawyers for a reason as opposed to being in the media or whatever, there's probably something in your personality that is slightly risk averse. Or I can say that speaking about myself anyway at least. You just have to get yourself comfortable in going, okay, look, I've done everything that I'm supposed to do. I've given you all of the answers. If somebody then wants to make that commercial call and go, I'm going to take the most risky option, you kind of just have to get yourself comfortable with that.

Intro:

Welcome to the Crafty Show, a legal podcast produced by Crafty Counsel, a digital media company and community with the aim to spread joy, connection, and insight to in-house lawyers. Join Crafty Counsel's founder, Ben White, as he speaks to lawyers who have left private practice, often to join in-house legal teams, about their career journeys.

Ben White:
Hi, everybody. Today I'm speaking with Ann Silla. She's currently an independent legal consultant with a super interesting background. She spent four and a half years at Linklaters as a private equity lawyer and then moved from there to another august institution, the Economist Group, where she spent several years and was a senior counsel and then moved away from venerable institutions like that and joined Deliveroo, the well known tech start-up, just before its IPO. So three really quite different organisations that she's worked for. And she's now an independent legal consultant. Super interesting career, super interesting story. I can't wait to hear what insight she has to offer us.

Ann Silla:
Now you set me up, Ben. You made me sound really interesting. I better not bore everyone.

Ben White:
Well, Ann before we dig into your career in a little more detail, I'm going to hit you with some quick fire questions.

Ann Silla:
Okay.

Ben White:
So are you a work from home or an office person work?

Ann Silla:
Work from home.

Ben White:
Why?

Ann Silla:
The commute. Everyone who knows me is like I'd much rather get more sleep than be on the commute. So yeah, yeah. Definitely work for home.

Ben White:
Nice. And if you weren't a lawyer, what would you be?

Ann Silla:
You know what? I had a bit of a crisis thinking about this. Ask me on three different days. You'll get three different answers, but it's probably either something that I think is slightly more intellectual. I like to empathise and think about and read people and therefore figure out what dynamics of personalities work well. So, maybe something in psychology, and in the alternative Formula One. I want to travel the world and get paid for it and drive fast cars. So, anything in Formula One would be amazing.

Ben White:
You already drive fast cars?

Ann Silla:
No. Obviously if the police are listening, no, obviously no. Racing days…I have done a couple and yeah, I just love fast cars, yeah.

Ben White:
What's your most used emoji?

Ann Silla:
It's the smiley face with a little sweat beat, and it's usually because either I'm being sarcastic or slightly worrying about offending somebody or just laughing at myself.

Ben White:
Okay, and are you an emoji user in a work context?

Ann Silla:
No, I find it really weird. I remember when I moved to The Economist and people would put kisses, and it was really funny because it depended on which department within The Economist it was. But when they're in the media group, they'd often end their emails with kisses and that threw me. So no, I'm still very much a lawyer in that sense.

Ben White:
For some reason it doesn't shock me that it was the media folks who were adding kisses to the end of their emails.

Ann Silla:
Exactly, exactly. Now with Slack and everything like that, yeah, sure, fine. But in emails you still get a little bit of kind regards or regards depending on how annoyed I am.

Ben White:
Right. Ann, I want to dig into your career story. I gave a little bit of an intro at the beginning, but I start with the present day. So right now you're an independent legal consultant.

Ann Silla:
Yeah.

Ben White:
What is an independent legal consultant?

Ann Silla:
Good question. I mean, I guess I'll get more experience in it because it is very new, but basically it means that I have put myself out as a senior counsel. Obviously, I've got a background in a couple of different things but mostly in the corporate and commercial space, and I will be working for different businesses who need some interim support on some short to long term, but it looks like up to about a year's worth of chunks of time each time possibly. But yeah, I'll be doing whatever takes my fancy and whatever that business really needs.

Ben White:
And how do you find clients?

Ann Silla:
Good question. Actually, it's quite interesting. So I've signed up to a couple of different things. I think people are probably more and more aware of things like Axiom, things like Peerpoint, which is like the Allen & Overy  version. Also LinkedIn. Obviously I have to go back to the mothership. So they have one called ReLink. So I've signed up to those three, and it's just a case of they will bring things to me and say, you look like you might fit this profile, and also looking and saying actually that one seems quite right. So yeah, a bit of a combination of both, but I've signed up to a couple of those kinds of businesses.

Ben White:
Do you think this is the future for how lawyers are going to be working?

Ann Silla:
I think that there's going to be a bit, definitely more of this, because I think one thing that the pandemic has done is give people more options and also emphasise people wanting to take more control of their career and things like that. I mean, I was joking before about the commute, but even little things like that, it just means if you're able to choose to work from home, if you're able to choose to whatever that thing is, whether you want to live in Manchester, but work in London and vice versa, all of these things, just that kind of consulting thing, I think gives you that flexibility. Because there's a lot of skilled people who otherwise might just leave the industry entirely because they can't seem to figure out a way to get what they're looking for out of their life with some of the work challenges. Everybody certainly, and I can say that for me, I still want the challenge of being in a big industry in the city working hard, but a couple of different things make you think about different options. So yeah.

Ben White:
Great, really interesting Ann. Well look, let's take it back a bit. Linklaters.

Ann Silla:
Yes.

Ben White:
You were a private equity lawyer.

Ann Silla:
Yep.

Ben White:
I can imagine some of that because I think at the same time I was somewhat further southeast of you at Clifford Chance doing M&A deals. What was it like?

Ann Silla:
You know, it was the best time and also some very tough times as I'm sure you know as well. But no, I loved it. I had, what, four and a half years qualified there. And I think at the time it was when I qualified, so it would've been, and I'm really old, it was around 2009, but just coming out of the initial or kind of the boom at the bust that happened to Lehman Brothers was September 2008, obviously. And then it was just hectic as everyone was trying to scramble around and doing deals. And I think that buzz just made it so exciting. And I was in, I think, a particular dynamic team. Obviously everyone uses those kinds of words these days, dynamic and agile. But it really was the two leaders of the team, if I can put it that way, they had these personalities that were just, you always wanted to be involved. And one day you'd be working on some hectic deal. One day you might get sent on the flight to go and do something else. And all of that just made it really, really interesting.

 And so you spend, I think in the usual way, you spend the first two years doing all of that, and it's just all hands to the deck. You're trying to figure out what it is that everybody wants, what is it I'm supposed to be doing about a due diligence report? Great, never done one of those before. Scramble around, call your friends, beg people to help you, and it's Saturday night and you're like, I don't know what he wants. I'm confused. All of those things. And you gradually learn your way. You start moving your way up, SPAs, and now your thing and this kind of thing. It just made it really exciting.

I think also I was lucky that I had around me a great peer group. So, both in terms of the people who were actually my peer group who were fellow trainees, not necessarily in the PE team around Linklaters, that was a really good group of people, but within the PE team as well, there was people all around the same age, give or take a couple of years. And everyone just got on really well. And the nature of the team just meant that everyone bonded together, worked it through. Everyone was like, right, this deal is on, you've got your levels of senior, junior, most junior people, everybody piles in and just gets on with it. And those kind of days and weeks in the trenches, if you don't get on, then you're going to be really unfortunate. And I was lucky enough that we all got on and made it work.

Ben White:
I mean, this all sounds great.

Ann Silla:
Yeah. And yet…

Ben White:
You end up at The Economist.

Ann Silla:
Yes, I did end up at The Economist. So how do I end up there? I guess obviously it was a great experience. And every time I look back now, at the times when I wanted to be, we have to do this and not another weekend of, oh Friday when you're like, I hope the deal dies so that I can go home. No, it didn't die in the end. Now I have to do this weekend thing that I was dreading. All of those things actually shaped who I was and gave me the skills that I needed and probably the confidence to go ahead and do the next things. So over the last two years of my Links contract, I started to do more and more portfolio work, which is what we called it, where private equity clients would buy a company. That's often referred to as a portfolio company. That portfolio company often as they're bought by private equity ends up changing something, the management structure, or something like that. So it's usually get rid of the entire C-suite, including the GC, but not always.

But anyway, I increasingly built relationships in that area, worked really hard in that space, and had just found myself doing lots of the post deal stuff. People would be like, what is it? We agreed on the management equity structure. Oh, I'm doing a bolt-on acquisition. Oh, now we're ready to sell all of those things. And I increasingly was involved in all of that. And just through that, and through the partners reshaping some of the private equity team, they wanted to focus on that and give a dedicated team to that, which I was one of the first people involved in. And what that meant was I started building up really close relationships with those portfolio company people and the C-suite. And so when there was a particular deal where I did end up doing the DD (due diligence), the SPA (sales and purchase agreement), and so I'm working on the actual deal, but then when the deal was closed, I ended up working a lot with the management team post deal. Inevitably, as I said, the C-suite team was shuffled around a bit, and this time the GC left, they needed somebody just short term. And just by the nature of how it happened, because I'd done the deal, because I'd had my head in all of the details, I knew the business quite well. So I think everybody just thought it made sense.

 So I ended up going on to secondment, and spent six months there doing two jobs. We called it part-time, but it wasn't. I ended up doing both Links (Linklaters) and this job at the same time. But the point was that I ended up really loving it because I got to, being the only lawyer in that business, I got to see what it was really like because there was nobody else. If the salesperson was about to talk to X big bank, we need your help.  That was me. If it was, we need to do the Christmas party contract, that was also me, and everything else in between. But I just like that dynamic. I like the variety. I like the freedom. And I was just in all of the different steering committees and all of these different C-suite meetings. And so actually that really cemented for me, that kind of dynamism, that dynamic, that ability to get involved in business is what I wanted. And so by the time I came back from secondment, literally within about three months, I was off to The Economist and was there for seven years. And so that was kind of how I ended up at The Economist. But yeah, I loved it. I had the best time at The Economist.

Ben White:
So seven years at The Economist.

Ann Silla:
Yeah.

Ben White:
What was that journey like?

Ann Silla:
Amazing. I mean, we went through lots of stuff. Obviously The Economist is in the publishing industry, and as I joined, everyone was just getting to grips with it. Actually this blip in advertising is not a blip. It's here to stay, and we have to make digital work and find other ways of driving revenue, and what are the other things. And The Economist actually, which I think people are quite surprised about, it is called The Economist Group because there's lots of other businesses. There's a PR agency. It has lots of information, so country reports and this kind of thing. So information and analysis for businesses as well as, obviously, the newspaper, which everybody knows. And I just was allowed through my seven years to really dig into pretty much whatever I wanted. I had a great relationship with the GC. I was effectively his number two by the end of it and thought I was his number two, by the end of it. And he allowed me the freedom to basically get involved in everything. So that was obviously the stuff that you expect, someone to be doing, which was if there was an issue with the newspaper, some kind of libel is often where we'd get involved, or if we were trademarking some new project, like the new app or the new podcasts and things like that, as they became more regular, I'd get involved in that kind of thing.

But I also would do, we change their customer journey, and I'd get involved in tech contracts. We moved further and further into China. And I find myself knowing more than I ever wanted to know about how to set up in China and how to operate and understand what the law says and what the regulators say, not necessarily the same thing, and just navigating all of that. But yeah, it was fascinating. It was great.

Ben White:
Do you ever miss private practice?

Ann Silla:
Never. I can say that with 100% certainty. Never, no. I mean, perhaps some of that was that also at the time that I left, some of that core group that I was telling you about that we all had friends and we spent our time joking and this, that, and the other in the down times at Links (Linklaters), some of them spread their wings as well, and they also left or moved on or moved up or whatever it might be. And so that core group of lunchtime crew or evening crew, whatever that was, was dissipating as well. But also just actually, I was so fascinated by everything that I was doing. And I really was given freedom to basically get involved in whatever I found interesting. And that you can't replicate that at private practice where I think in the end, you're always responding to a client on their terms.

Ben White:
But from the outside The Economist group, a fairly venerable institution if you like, you jump from there to Deliveroo.

Ann Silla:
Yes.

Ben White:
So why did you do that?

Ann Silla:
Why did I do that? I mean, I guess a couple of things, obviously most people... Let me say it another way. The first time I mentioned that I was moving to Deliveroo was the first time everyone knew what I was talking about when I said I was moving to Deliveroo. People knew Linklaters, but they're like something to do with law, can you get me out of jail? No, not that kind of law. When it was The Economist, people knew the newspaper but not realised there was the rest of the group as well. Deliveroo everybody knew this, yes of course I order food and I've used delivery. So obviously there was the pull of working in such a well-known fast building tech business. And I wanted to get involved in the tech industry as well and understand it.

 And then obviously most people had an idea that it was about that time that it was going to IPO and it was that challenge that I wanted to get involved in. So I absolutely loved The Economist, still in close contact with my former boss and several people at The Economist and really loved it. But in looking for another challenge, and I do like to do that, I like to challenge myself, I just figured the best next challenge was something outside of The Economist. And this seemed great is what I want to get involved in.

Ben White:
So Ann, from the outside, they seemed like they were probably quite different places to work, but what did that feel like? What was the difference in culture between working at Deliveroo and The Economist Group?

Ann Silla:
Yeah, massively different. The Economist 1843 legacy just is established in terms of its processes in terms of how it operates, and actually it's not listed, but it acts like a listed company in terms of how it reports. All of that permeates through how it operates in terms of when it needs to make decisions. Whilst people are agile, especially when they're doing something in the tech space, it's going through several layers of approvals and so on and so forth to get things done, which lends itself to the culture of working, which is you know what processes you're supposed to work towards. And several people have been there for 10, 15 years...that kind of a culture where everybody's been there for several years, kind of knows what they're doing, and knows what to do to get to where they need to get to.

 Whereas at Deliveroo, obviously it's a young company anyway, but it's also a tech company. They're used to just fast paced. Everything is yesterday, if not the day before that, in terms of making. And that lends itself in terms of culture as well, because that means that everybody's always on their toes. Everybody's always getting ready to react, and that can be in every single way from, this is a fake example, but for example, something sports related, if something's happening, the marketing team is immediately, how can we get involved and do some kind of marketing or something like that, some kind of social media post that will get people talking and pointing? And so everybody's reacting really quickly. Similarly, it's a tech-based business. Everybody's always shifting in terms of improving the app, in terms of improving the website, in terms of improving the experience.

And all of that just means that the people who work there are all constantly on, constantly looking for the next thing to be the top and the best and so on and so forth. And that just means they're much more comfortable. We're going to turn this on pivot, go forget it, that didn't work, move on. We're going to do something else, pivot, go and do something else. And so there is definitely a different culture shift because that's an adaptability that you need to have, which can be quite a funny switch when you are used to okay, we're going to spend three months planning this and then another three months testing it. And then if it doesn't work, then we'll take another, you know what I mean? And I'm making up the timelines versus you'll go through 10 different projects in that same time period at Deliveroo.

Ben White:
I can imagine a lot of lawyers would struggle to adapt to that change in culture. How did it feel for you?

Ann Silla:
I think the biggest challenge about it is more that all of the ideas and the things most of the time, it's like that makes sense. I get why you're trying to do it, but often in order to be that quick and agile in movement, you have to be comfortable taking certain amounts of risk, and it's not doing anything bad or illegal or anything like that. That's not what I'm seeing at all, but you have to get more comfortable with risk. And so depending on who you are as a lawyer, and let's be honest, we're lawyers for a reason as opposed to being in the media or whatever, there's probably something in your personality that is slightly risk averse, or I can say that speaking about myself anyway at least. You just have to get yourself comfortable and going okay, look, I've done everything that I'm supposed to do. I've given you all of the answers. If somebody then wants to make that commercial call and go, I'm going to take the most risky option, you kind of just have to get yourself comfortable with that and just be ready for the, I can justify this, I can explain this, I've built in all of the different fail safes and jump off points in case anything happens or doesn't quite work. But it's definitely an interesting shift in mind that you just have to get used to.

Ben White:
Can you tell us about a difficult decision that you had to make while you were there?

Ann Silla:
A difficult decision that I had to make whilst I was there? I think probably without going into too much detail, but quite early on, I was asked to work on a project for gift cards, which was really exciting. It was the first big project that I did when I joined and also it was coming up to Christmas, so it was all timeline responsive as well. And that obviously the best time to get gift cards out is, everyone's looking for those ones where, I know you, but not that well so let me just throw a gift card at you and go on and that will be your Christmas present. So it made sense to be trying to get it. And in that, obviously it's the first time that I'd done it, that Deliveroo was doing it, and we were working through those things, but you get to a point where we're working towards this date and everything's going well until you realise there's this one particular thing that it's not going to happen in the set deadline that was supposed to be launch day. And it's just that decision, which I think everybody has in every business of, okay, I'm going to have to be the person that says guys, I know that we want to try and just get there anyway and hit this deadline, but I promise you you're going to want of take the extra period of time to get this right rather than pushed through. And in any other business that extra time would've been a week or two weeks. Actually in Deliveroo, it turned out to be two days, but it was hard just knowing actually you do have to make that call, but actually it meant that it gets through, everybody scrambles to figure out what they're going to do next.

So I think those are probably the kind of things where actually, it also makes you step up. As I said, in any other business, it probably would've been a two, three week job at minimum. And it wasn't because there just wasn't time for that. So we figured it out. And so you learn about just moving quickly, just discarding things that you know aren't going to work, keep moving forward. It definitely adds to the skills.

Ben White:
I mean, that's so true as an in-house lawyer that you often have to be that bearer of bad news.

Ann Silla:
Yeah, yeah. And you definitely don't want to be the person that's saying no. And I try very hard to not be the person that's saying no, but more not like that. We have to think about X and Y. And often in the legal team, I found, because it depends on where you work, but in the jobs that I've done, you kind of end up sitting right in the middle of everything. You see how the finance team operates and what they need to get themselves comfortable and what the tech team needs to get themselves comfortable. And so you end up in a position where you see all the different projects and all different things that the individual teams don't necessarily see across. And so you find yourself in that space where you're going, actually I know that the marketing team wants to do this, but I know for a fact the tech team isn't able to, because I've experienced this problem in another area. Those guys should probably talk to each other. They haven't had the chance to. Let me just tell them both because they need to get to it quickly if they're trying to hit whatever deadline, but it definitely makes it interesting.

Ben White:
What do you think is the biggest challenge about being an in-house lawyer?

Ann Silla:
That your job is not actually to know the law. It is to facilitate the business by giving them the guidance they need. And once you get your head around that, I think that the sky's the limit in terms of what you can achieve and what you can contribute, but it might not be what you think when you first go in-house. I think a lot of people think a bit private practice style, you write a five page memo on the answer and that's great, but that's not what I want. And I find myself on the other side now, when I do instruct external counsel, it's like I really appreciate this very detailed answer and all of the different things that may or may not happen. And at some point I will need that detail, but I could have read the law myself to do that. What I'm looking for is what will the regulators do if I choose this? Or what will the fallout be if this, et cetera, et cetera. And that added commerciality I think is the thing.

Ben White:
It's a tension though, right? Because this year we've seen a couple of high profile stories of where things have gone a bit wrong, where lawyers have got involved inside businesses. I mean, people are talking about the Post Office, Royal Institute of Chartered Surveyors (RICS), and to use the Donald Trumpism, people are saying or questions are being asked about the role of the lawyers involved in some of those cases. And you take the RICS, the Royal Institute of Chartered Surveyors example, at the time that we're having this conversation was just a few weeks ago that the Leven QC delivered her report which was very critical of the general council and also the external council involved and in particular that they're perhaps over-identified with the CEO and the COO…

Ann Silla:
The business, yeah.

Ben White:
...being their client and taking their side against some of the board.

Ann Silla:
Yeah.

Ben White:
What was your reaction to that when you read about some of those stories?

Ann Silla:
I guess you have a little bit of sympathy, empathy, because you can see how but for the, what's that phrase, for the grace of God or whatever, maybe in some circumstance could I have found myself like that. But at the same time and it's certainly not for me to comment, I don't know enough of all of the detail, I wouldn't want to be there anyway, but I can certainly say for myself, my tried and tested measure for have I gone too far is always, can I stand in front of the board? And I say the board, not the CEO, the board and justify the decision I made at the time. And if I can, then you know what, it's not always going to be the right call.

It's a really silly example, but at the Formula One, just this weekend at the time we're talking, there was a minute where they came down, it was do we go for this tire or that tire? Some people got it right. Some people didn't get it. Some people got it wrong, but with the information they had at the time, it was absolutely the right decision. And that's the same thing I use. With the information I have at the time, can I stand in front of the board and say yes or no? Would I make that same decision with the information I had at that time? And if the answer is yes, then I can get myself comfortable that it was the right call to make at that time.

 And I think some people do get persuaded by in their head, they'll have a little red light going that's not the right decision. That's a bad decision, that's a bad call. But you've got the CEO, you've got the CFO, you've got whoever it is, this chief tech person saying, we must make a decision. It's going to cost us millions. And it's like I hear absolutely, and I get it. And I also appreciate all of the pressures that everybody is under, but I cannot not highlight to you that these are the risks that are running. And in my view, those risks are a bit too big right now. I think there's something else that we can and should do before we make this particular call.

But, absolutely it's attention and it's tricky. And I definitely would not want to be in those shoes. I think as a lawyer, it comes down to your own personal ability to withstand that kind of pressure and willingness, as I said, to fall on your sword and stand behind, I'm comfortable that this was the right decision with the information I had.

Ben White:
And let's zoom out a bit and talk about the legal sector.

Ann Silla:
Yeah.

Ben White:
Is there something that you wish the legal sector would do that it's not doing or something that you wish that in legal would stop doing?

Ann Silla:
What's the right answer to that question, because I think there's some things within the actual job? I think that we've been a little bit slow to embrace tech in ways that can benefit all of us, both the business and actually the lawyers doing that work, because I see situations where some of the stuff. NDA is a really easy example cause everyone knows what that is, where obviously we've just done the oneNDA project and that's great, but it's like, how did we not do that years ago, and why did it take so many big brains to get there? But, that's not so much a tech thing, but just examples of you've got a standard contract. There's no need for you to be seeing that, run it through whatever Adobe DocuSign or Salesforce or whatever other Juro or whatever other technology you have that just allows the business to just run it through, change the names, change the pricing and go as opposed to thinking that we have to be in the middle being bespoke, and just in case the salesperson go a bit rogue, I need to check it and this, that, and the other. And I think there are ways to manage tech while still allowing the processes to just make sure if anybody is doing anything slightly rogue that is going to get caught.

So, I think that's one thing that the legal team I wish as a sector we could do better at, but I think it is coming. I just think that it's quite in pockets at the minute. If you are in a tech business, more likely you are already seeing that advantage versus maybe a bit more of an older school business. But you know, there's a tipping point that we're not quite at yet, but that's one thing.

But I think in terms of being a lawyer itself, I think that I would love it if we could get away from this idea that you have to do the hard yards of all-nighters, and I did 120 hours this week, and all of those things in order to get to the point where you're able to recognise, I don't need to do that time in order to be good at my job and contribute in a really meaningful way, whether that's in house or private practice, because I think, and obviously mental health and awareness and all those kinds of things are happening. It's an increasing focus and I love that for the industry, but I just think that there is still a little bit of, you have to do your hard yards before you're able to do that. And I don't think that's necessarily the case. I think we can take a bit more time to train people in the same way that we take our time and make sure that you get the black letter law skills and then the ability to draft properly. I think if you also build in some look after yourself because you're alive for a long time, hopefully, and your career should be sustainable, and you absolutely can be a good lawyer whilst not also giving up every single weekend, et cetera, et cetera.

I just think there's a balance because some people might hear what I've just said and go, ah she's not ambitious. And actually that's not the truth. I'm the most Type A person. When I was younger, I was that person going, I'm going to be the top of this, I'm going to be the General Counsel, I'm going to be the part, everything. All of those things are true. I also really like being able to have my weekends. There's a balance.

Ben White:
I'm going to bill a hundred hours thing, that culture you described. Do you think that's a macho thing?

Ann Silla:
Is it a macho thing? I guess the lazy answer would be yes, because predominantly, perhaps, especially in the past, more recent past, like eighties, nineties, but past nonetheless, most of the time, the more senior you get, the more men you saw. But, actually now I think it's built into the culture. I often see women being the most dogged and determined and willing to do those same hours at the most senior level. And I wonder if that's something about, because you're a woman, you have to be twice as good or twice as hard, whatever that thinking is in order to succeed. But I don't know that it's macho, but I think it's an industry-wide phenomenon.

Ben White:
Ann, is there a piece of advice that you've ever received that you would like to share or something of the lesson that you'd like to share with the audience?

Ann Silla:
Yeah, I've got two actually. So one, when I was at Links, the partner I worked most closely with, Richard Youle would always be closing and be like ABC and I'd be like, okay, great, Rich ha ha, but it's three in the morning coming up, and I'm tired. But, what he meant by that I've since learned was just always be ready to execute you. Shouldn't be waffling around, and as I said, writing ten page memos when the client maybe doesn't have time, maybe doesn't have the capacity to take in what you're saying. They just need you to get to the point and say don't worry about these three things, but these two things can I have your input on because it's really important. This is the thing that you should really be caring about. So, I think that's what he meant by always closing. He might hear this one day and say, no, that's not what I meant. You misunderstood, but that's my interpretation of what he meant.

And the other thing actually is something that I watched my boss at The Economist, Oscar, do a lot which was really invite and give people the freedom, everybody, the freedom in the room to have a voice. Well actually I assume that he knows does it, but I wonder how much he knows he does it because I really recognised it being often, especially when I first joined, one of the youngest people in the room, often one of the few women in the room. Sometimes you have to have a confidence about yourself to be willing to step out, even if it's just “I didn't understand”, or to actually contribute: “I think about this or I'm aware of so, and so, did you think about this?”, and what he would always do is look around the room and be like, Ann did you have something you wanted to contribute there or whichever junior person. And he just gives them that room.

And I think that's a thing that people might not appreciate but actually really gives people the freedom to grow, to know that actually they have a space where they're allowed to make mistakes because someone is watching and listening and they're going to give you room to really contribute in a safe way. It gives you that psychological safety to know that I can make a suggestion. No one's going to be laughing at this. So some of them will be rubbish. We all make rubbish ones, and some of them will be great, but everybody's got that freedom. So yeah, I think those two things are probably the key.

Ben White:
Ann, that's a lovely perspective to share. Before we finish, I want to ask you one final question. How do you find joy in your work?

Ann Silla:
How do I find joy in my work? The challenge, I think, as you've said, I like to switch industries and switch challenges. So at The Economist I was there for about seven years, and the way I found that joy was actually, I started out on first. It was mostly contracts, and then it would be more strategic stuff, and I'd get involved in the podcast, and I loved the media space. And then I got involved in GDPR and people might say, did you love that? And I was like, I loved the challenge of learning it. So that kind of joy and actually really watching junior people really succeed and giving them the freedom to succeed is something that I really, really love. I love that I'm now in a position to engage in shape teams and give people like: “No you are on the right track. Okay, maybe you missed this point, but don't worry about it. I would've missed it at your stage, too, with the information I had, but have a think about this” and just letting them go away and come back and giving them that freedom. I love that. I love that kind of thing.

Ben White:
Absolute joy speaking with you.

Ann Silla:
Thank you, thank you, likewise. No, this was really fun. I've not been on this side before, but yeah, I loved it.

Ben White:
For those who've come this far in the podcast, Ann was interviewing me for her podcast a few weeks ago. So I got to turn the tables today a very few times.

Ann Silla:
Yes, exactly. But no, it's been easy. It's been a great experience. So thanks a lot, Ben.

Ben White:
Thank you.

Outro:
If you like this conversation, please subscribe to the podcast, The Crafty Show, and we'd love to hear your feedback and suggestions about lawyers you would like to hear interviewed in future episodes.