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Life Lessons: Carolyn Jameson on navigating the workplace as a woman

THIS IS NOT GOING TO BE A NORMAL ARTICLE. This is a tactical handbook based on real, lived experiences from a role model in the legal profession, specifically Carolyn Jameson, Chief Legal Officer at Trustpilot. Carolyn is a badass, powerful, female executive who does things in an under stated way. The fact she doesn’t do everything perfectly and struggles at times makes her about a thousand times better than any unrealistic female role models. Yes, I am looking at you, the female professional, who supposedly woke up at 5am, drank a cup of hot water with some slices of lemon, worked out, kissed her five perfect children goodbye and was at her desk at 7am, with not even a hair out of place!


Culture Wars

This is often a man’s world at work, but its cultures are Fifty Shades of Grey.

Not THAT fifty shades but the fact that cultures, even ones which are not that healthy, are never just black and white. They don’t generally come with a health warning or helpful signposting to alert unwary women as to what they might be walking in to. A workplace culture might seem great at first, but actually be full of hidden micro-aggressions and traps to make even the most, savvy female executive fall victim to gaslighting.

It’s been interesting for me to observe that you can bring the same attributes to different organisations and be viewed in completely different ways depending on the subtle cocktail of cultural ingredients. I wondered how Carolyn viewed the different cultures she has worked in since going in-house in 2002 and what have been the attributes that helped her the most?

Carolyn has worked in a number of engineering, software and internet companies, not cultures which have traditionally been that diverse and inclusive. A key factor in making her way in these different cultures is, she thinks, sheer bloody mindedness.

“I’ve always been a stubborn (according to my mother – I prefer to say determined) sort of person. I think that’s really helped, albeit it’s definitely something I need to watch out for as well at times. When I first started, I was in software, which really threw me in the deep end, but probably helped me ultimately. There was lots of heavy, time-pressured negotiations with quite difficult situations at times. The company supplied their product on a disk, and people could download as many copies form the disk as they wanted.

I’d get sent into companies to demand payment, sometimes for amounts they hadn’t budgeted for. I was put in these sorts of intense situations, firstly in my legal role, and then subsequently when I went to work in sales myself for a year. That gave me a real appreciation of the commercial side of things, but also how to handle a certain level of aggressiveness or even predatory behaviour. That world was quite old fashioned, and I would sometimes get propositions along the lines of: ‘Well, I’ll certainly buy this if you come for dinner.’ I found it, I suppose, easier to deal with then than now. The fact it was so upfront helped, and I was probably even more gutsy in my youth, meant it would be much more like water off a duck’s back. I’ll get more agitated about inappropriate behaviour now than I did then.”

I understand what she means: is it age and an accumulation of factors like not feeling we need to please others as much as we did when we were young women? Does it also take on a different lens when we look back on what was the norm through the lens of more recent movements such as #MeToo and #TimesUp and realise what was normal then, wasn’t ever acceptable.

Carolyn eventually went as an in-house lawyer to a semiconductor manufacturer in Scotland, which was even more male dominated, “to the point where, there were hardly any other women there. As you walked along the engineering floor, you could sense the nervous eyes looking over the screens.”

Her career then took her to Skyscanner for a number of years, followed by the Danish company, Trustpilot, where she currently works as Chief Legal Officer. “The Danish culture has been really fascinating to see. It’s certainly the environment where I have felt least aware of being a female in the workplace, and I think that’s because as a country they do so well at integrating gender equality into societal norms”.

Over the years I have known Carolyn I have always been impressed with how assured and understated a leader she is. She always recalls to me Michelle Obama with her ethos of “when they go low, we go high.” She’s also a lawyer who is not afraid of being a business thinker and feels that embracing a more strategic role is what modern general counsel need to do to fulfil the remit in a senior in-house role in the 21st Century.

But it’s certainly not all been plain sailing. Carolyn and I discussed some of the challenges she has faced, many of which are commonplace still for women, and how she has handled them.


Workplace Hacks for Women

Problem One

They don’t think you’re up to the job.

For ’tis the sport to have the engineer Hoist with his own petard; and ’t shall go hard But I will delve one yard below their mines And blow them at the moon. O, ’tis most sweet When in one line two crafts directly meet. —  Hamlet, in Hamlet, Act 3, Scene 4

There is fantastic phrase which is not used enough but perfectly describes what women or indeed any group that may be de-valued in a workplace can do: “Hoist with his own petard.” The phrase was first seen used in Shakespeare’s Hamlet in the speech when Hamlet becomes aware of his Uncle Claudius’s plot against him.

A petard is a small bomb and the bombmaker is hoist (lifted up into the air) in other words, being blown up by his own bomb. It essentially describes an ironic role reversal or moment of poetic justice.

It’s something many women and diverse individuals need to use in their careers. How it works is playing along with someone’s misconception that you’re not fit for the role/negotiation/court case etc. and then obliterating them with your brilliance.

Carolyn has had to do a fair few ‘mad things’ as she describes them in her career from her early days delivering bad news about uses of unlicensed software onwards, to leading the sale of Skyscanner to Ctrip. Or being in a David and Goliath situation, when she was at the semi-conductor company as general counsel and had to visit a large, Multinational Conglomerate, to inform the all-male group at the meeting that they were infringing her employer’s IP. She remembers being in all male negotiations throughout her career, and in some of these instances, she was being actively undermined or seen as not up to the job by others, “But it could actually be powerful knowing that the other side doesn’t think you’re up to it and I always tried to use it to my advantage.”

Lesson one: Be strategic. If you’re being devalued in a situation where that can be to your advantage – use it. You don’t have to do really do anything, the other side’s tired stereotypes and lazy thinking will be enough to trip them up while you do your job to your best ability.


But this can lead to Problem Two

Beware Ambitious Woman at Work.

“You know you that bitch when you cause all this conversation. Always stay gracious, best revenge is your paper.” Formation – Beyonce

There’s long been a double standard for women at work. Ambition is often a dirty word when applied to women. There’s a number of interlinked factors that contribute to this. Firstly, the fact that those throwing that accusation at you are likely scared that you are overtaking them at work. Secondly it stems from the outdated view, but one which can still permeate attitudes, that women shouldn’t focus on their career when they have all these other fabulous things to do such as, being wives and mothers!

Carolyn remembers this raising its head in her career and in a particularly insidious way: “There was one chap who I worked with, who on the face of it was very supportive of women progressing in their career. But that only went so far. I remember there was a project he wanted to run, and it was given to me; so outside the room he said to me, in total seriousness, “You know, Carolyn, people don’t like women that are too ambitious.” She still kept the project and did it really well, spurred on by that discussion …

Lesson two – if you have been asked to do the job, you’re the best person. It’s all semantics: ambition is not a dirty word for men so it shouldn’t be for women. By being ambitious we’re opening doors for the next generation of professional women.


Problem Three: The problem that isn't there, or is it....?


“More insidious than those moments of outright hostility, though, and maybe more powerful, are the constant, low-level reminders that you’re different. Many of us feel different in some way, but it’s really jarring when one of your differences is obvious at a glance—other people can tell you’re different simply by looking at you … Even when you feel like you belong, other people’s reactions—even stares and offhand remarks—can make you feel that you don’t, startlingly often.” — Celeste Ng, “Everything I Never Told You.”

Whist there are obviously sexist behaviours still at play in the workplace, a challenge is that many of these biases are quite subtle, and may be getting even more so. Many of those displaying these behaviours may also be quite familiar with the practice of gaslighting, named after the 1940s film with Ingrid Bergman where she is being driven slowly insane by her perfidious husband.

I experienced this a few years ago. I was imaging things when I complained that I felt senior meetings were not hospitable to me as the only woman in the them – there may even have been a ‘dear’ added to the end of the phrase “It’s all in your head.”

I did spend 48 hours wondering if I was delusional but thankfully a few conversations with other current and former female employees confirmed that I wasn’t. I say thankfully but that meant that workplace had a culture issue that it was burying its head firmly in the sand about. It’s now obviously a former workplace …

Carolyn agrees that there are still negative behaviours in the workplace for women, all too frequently. The advantage for women who entered the workplace when things were not so seemingly advanced, (those of us who are more J-Lo vintage than the Dua Lipa vintage), is, she feels, that issues could at least be spotted more easily.

What can be harder now in the workplace is the disconnect between statements and values which pronounce the importance of diversity and inclusion, and everyday behaviours that do not support it.

“When something is obvious you can complain, whereas when it’s said quietly to you in the corner or is implied rather than explicit. I think that makes it very hard to deal with. I think you get worried about saying something; would they believe you, or would they just think that can’t possibly be true – look at all the things they say over here about the company’s commitment to diversity.”

When it’s possible, calling out the micro-aggressions can be helpful, particularly when you have a one on one situation. In some instances, those who display that behaviour may not realise they are doing it. Carolyn remembers one of her new bosses (who hadn’t had a female in his team before) saying:

‘What I really want to know is, are you like some raving feminist.’ They were the words, so I asked what he meant, and he said ‘Well, you’ve got to this sort of level. Is that how you’ve done it?’ So, my only question was, do you have this conversation with the men that work for you?” He just stopped and he never did it again, but he was always quite wary of me after that, which was a shame.”

This follows the advice given by Ella Washington, Alison Hall Birch and Laura Morgan Roberts in a recent article in Harvard Business Review. In the article the authors cite the best tactics for confronting micro-aggressions to be Disarm; defy and decide. Disarming is when you confront the micro-aggressions and what’s important “Explain that the conversation might get uncomfortable for them but that what they just said or did was uncomfortable for you. Invite them to sit alongside you in the awkwardness of their words or deeds while you get to the root of their behaviour together.” 1

Defying is when you use a probing question to unpick the situation. As Washington, Hall Birch and Morgan Roberts explain this tactic gives you an opportunity to better gauge the perpetrator’s intent. “One of the greatest privileges is the freedom not to notice you have privilege; so microaggressions are often inadvertently offensive. Acknowledge that you accept their intentions to be as they stated but reframe the conversation around the impact of the microaggression. Explain how you initially interpreted it and why. If they continue to assert that they “didn’t mean it like that,” remind them that you appreciate their willingness to clarify their intent and hope they appreciate your willingness to clarify their impact.” 2

Finally, the article advises those who are in the minority in a workplace to make a conscious decision in deciding what the incident will mean. It can be hard to do that as such aggressions can have ways of getting under your skin. Carolyn thinks this has been something that’s easier to do as she has become more experienced. “I certainly haven’t let it upset me in a way that I would ever let someone see. It actually makes me more determined to prove them wrong. I think it says more about the other person than it does about you, so that’s the approach I try and take to deal with it.”

Lesson three as Washington, Hall Birch and Morgan Roberts put it: “Let protecting your joy be your greatest and most persistent act of resistance.” 3 

Problem Four

How to deal with the ultimate professional betrayal – don’t get mad, get even.

“Revenge is a dish best served cold.” — Old French Proverb or Klingon proverb.

The phrase “revenge is a dish best served cold’ has a varied etymology but seems to have originated in France around the 18th century. In more recent years it was cited as Klingon proverb in the film Star Trek: The Wrath of Khan, (1982.) It was also more recently cited as the epigraph to Quentin Tarentino’s Kill Bill Vol 1 (2003). In that film, which is a story of female revenge its use might be most analogous to how many women can get payback in a professional situation. Sometimes waiting for the right moment can be everything.

When working in one particular role, Carolyn found out that she was pregnant with her 2nd child. Her boss at the time, said to her “If I’d known you were going to get pregnant, I wouldn’t have given you that promotion”.

That was a particularly hard moment for Carolyn, who had worked really hard to get that promotion, particularly when the company then went on to create a new role to sit above her during her maternity leave, and take her off the company emails, so she didn’t find out until she went in to visit with the baby. “ But I decided to play them at their own game. Rather than put myself through an upsetting legal action when I’d just had a baby, I just said that I was still coming back. They were so relieved, but also nervous, that they paid me a significant bonus that quarter. On the day it hit my bank account, I said I wouldn’t be back after all! My boss didn’t speak to me again …”

Lesson four: find the most effective way in business to make your feelings felt – good and bad. It’s easy to get caught up in the heat of the moment but keep your cool to give you the chance to collect your thoughts. You can’t change the situation, but you can work towards an outcome that suits you.


Problem Five

Because she’s worth it.

“Ask for the highest number you can say without bursting out laughing” — Cindy Gallop

Former ad executive and tech entrepreneur, Cindy Gallop, has become famous for outspoken opinions on the need for greater diversity in business. She has also been an active sponsor of women and minorities, particularly in her former industry of advertising. What she passionately advocates is that all employers pay diverse talent “a shit load of money” to retain their creativity which is the life blood for business in the 21st century.

The reason, Cindy Gallop has cited for exhorting women to constantly ask for as much as they can is because money is the yardstick. As she explained in a 2016 interview in Ad Age “When senior management goes into budget-planning meetings, and they look down the spreadsheet of employee salaries, and if they see all the women are making less, the assumption is they are not as good. Money is the shorthand for who is successful, who is contributing, who is worth it. Parity in pay checks will hopefully lead to parity in how men and women are viewed as being capable and valuable.”4

But what’s often cited as a challenge for many women in trying to achieve their potential is their capacity to not put themselves forwards for promotions or pay rises.

There’s an oft quoted statistic that men will put themselves forward for a new job or promotion if they meet 60% of the criteria and women only if they meet 100% of the criteria. That finding came from a Hewlett Packard internal report and has been quoted in other sources such as Sheryl Sandberg’s Lean In.

But a study by McKinsey has also shown that men are more likely to be hired on their potential and women on what they have already achieved. Therefore, it’s not a problem that just women need to fix.

I do think what is true in corporate settings is that many men are better about talking about what they have achieved and therefore asking for what they feel they are worth. I feel I’ve had to train myself to show management that this is what I’ve done, even though it may feel like stating the obvious. I found a lot of male colleagues would be very good at that; sometimes it seemed to me they overdid it, and they would almost spend more time telling management about what they had done than actually doing it, but I was also surprised at the results that got for them. I wondered how Carolyn, who is also somewhat understated, has also managed to achieve the career successes she has. Does she feel we women have to be more strategic about it?

Carolyn agrees that she thinks most women do underplay their achievements: “I certainly feel I’ve done that through a lot of my career.” What she feels helped her the most was working at Skyscanner. “As a start-up, everybody was striving to show what they had done and I thought ‘Oh my god, if I don’t do that too we’ll be left behind.’ And that was the key; The thing that made me do it was for my team. I quickly realised that if I didn’t start shouting about what we were doing, then they were never going to get the recognition they deserved.”

It’s true that fighting for someone else can often seem easier than fighting for yourself. Being more proactive in shouting about what you have done is definitely a learned ability feels Carolyn; you feel uncomfortable the first few times but then it becomes easier.

“Now I very much take the view if I don’t feel scared about something I’m doing, then it’s probably not worth doing, because it’s not going to make me develop. I just tilt myself into doing it and when you’ve done it enough times then you just get used to the potential for failure, and kind of get on with it.”

But also having reliable sources to share ideas with before you go public is a great way to get easier with doing so: “I think, to give you that confidence in what you’re doing, it’s really important to find those people that you can talk to or just run ideas past, and probably not friends because friends get bored of all this work talk, so it’s got to be people that know enough about it or have enough insight to be able to help. I’ve had some wonderful support and advice through my career from others, including a number of men.”

Lesson Five: speak up, think about the bigger picture if that helps – your team; other women in the organisation; other women generally! It also helps to run your asks past objective sources who can help your practice before you go for it. The role of male allies is crucial to female success. So, men, be one of the good guys!


Problem Six

The Token Woman.

“I love to see a young girl go out and grab the world by the lapels. Life’s a bitch. You’ve got to go out and kick ass.” — Maya Angelou

For successful women, like Carolyn, being a role model is a now given not an option. As discussed earlier, perhaps, for all of us progress is about getting uncomfortable with being uncomfortable. But the fact remains that many professional structures still remain much more uncomfortable for some than others. I asked Carolyn what she feels needs to change within how the professional world does things.

“I think if we could get to a point where the driver of career success is outcome and delivery, which is often where women are particularly strong, then we’d be in a much better place. A more outcome-based focus would also help with the fact that women sometimes still carry the brunt of work in the home as well, and it would enable them to find the right balance. But the truth is, quite often what gets in the way of that is office politics around issues like presenteeism, and cronyism, those sorts of things which I think are really damaging to women.”

In the Glass Wall Sue Unerman and Kathyrn Jacobs write compellingly about how it’s not so much a glass ceiling for senior women but a glass wall, where informal and social bonds between men can exclude senior women colleagues. 5

It’s something Carolyn has seen in action:

“On one occasion I was attending a board meeting, when I heard all the men talking about the previous evening’s entertainment – all the men gone off to watch football together the night before, and they had assumed I wouldn’t want to go. But that isn’t really the point. When you think about that from an office politics view: for a woman trying to get ahead how do you build those relationships with senior colleagues if you are being excluded from social events and your male colleagues aren’t? It’s very tricky.”

One of the things Carolyn finds interesting at the moment is that there’s more recognition of the need for women in senior positions, which is leading to more opportunities. For Carolyn, as she advances in her career, she has also realised that being the ‘token’ woman is an important step as it opens the door.

“Sometimes opportunities present themselves, and a phrase that has been said to me is ‘we really need a woman’. Clearly, that rankles because it should it be about the skills I can bring, but I’m starting to feel that maybe it’s my responsibility to just ignore that clumsiness and go for it’. because then you’re playing a part in establishing that new norm and getting into the position to influence the change. If you start to get offended and then don’t take the opportunities, we’re not going to change what we have.”

Lesson Six: You’re not the token woman – you’re the pioneer changing structural inequalities!


End Notes

  1. Ella F. Washington, Alison Hall Birch and Laura Morgan Roberts “When and How to Respond to Microaggressions.” Harvard Business Review July 3rd 2020

  2. Ella F. Washington, Alison Hall Birch and Laura Morgan Roberts “When and How to Respond to Microaggressions.” Harvard Business Review July 3rd 2020

  3. Ella F. Washington, Alison Hall Birch and Laura Morgan Roberts “When and How to Respond to Microaggressions.” Harvard Business Review July 3rd 2020

  4. Ann Marie Kerwin “Cindy Gallop Doesn’t Care What You Think.” AdAge August 22nd 2016

  5. Sue Unerman & Kathryn Jacobs The Glass Wall ( Profile Books 2016)


Credit to Author - Interviewer: Catherine McGregor; Interviewee: Carolyn Jameson, Chief Legal Officer, Trust Pilot

Original article can be found here: