The Power Of Negotiation: Transforming Careers And Lives With Kathryn Valentine

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Negotiation isn't just about asking; it's about asking in a way that transforms possibilities into realities, reshaping the world of work, one empowering conversation at a time. In this episode, we have Kathryn Valentine, the CEO of Worthmore Strategies, discuss all things negotiation. She explains the gender-specific challenges faced by women in the workforce and how she discovered the strategies to negotiate her way to thrive. She discusses the power of asking and the art of negotiation beyond monetary gains. Through her work, Kathryn has reshaped the dynamics of negotiation, providing a full list of 75 negotiable aspects and breaking stereotypes about women in the workforce. Tune in now and learn how to negotiate your way through life.


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The Power Of Negotiation: Transforming Careers And Lives With Kathryn Valentine  

It is my honor to introduce you to my guest for this episode, Kathryn Valentine. Kathryn was raised by a single working mother. She has recognized early the challenges that women encounter in the workforce. Starting at McKinsey, she honed in on female-specific negotiation strategies during her academic pursuits. As the CEO of Worthmore Strategies, Kathryn uses her insights to assist giants like JPMorgan, KPMG, and Cox Communications in nurturing and retaining female talent. A respected figure, she has spoken at elite institutions and has been spotlighted in HBR, Wall Street Journal, Forbes, and other notable publications. She's based in Atlanta. She finds balance with family, reading, running, and moments of quiet reflection. Kathryn, it's truly an honor to welcome you.

Tony, I'm so excited to be here. I also can't stop laughing because the way that my life was described is, "She found balance." I wish I could show you what it looks like. It looks like chaos. It looks like a hurricane all day long. I'm sitting on a pair of children's socks.

You keep your composure in that balance too. You keep your composure in the chaos. I always talk about chaos, and we have to embrace chaos in the moments that we are navigating and still find ways to make an impact, which we do.

I was listening to one of your previous episodes where you were talking about embracing chaos and it was one of those things where it's like, "That is exactly what I need to hear." I don't know if it's the phase of life or if it's the moment in time that we're all in potentially but it's feeling particularly chaotic.

I'm so thrilled to have you here. We're going to have such a great time exploring all of the things that have gotten you to where you're making such an impact. I love the work you're doing. I'm looking to explore and share the work you're doing with the people who are reading. The way we roll on the show is we explore people's stories through what's called flashpoints, these points that have ignited your gifts into the world.

What we're going to do with that framework is explore your journey and look at the flashpoints that revealed who you are. You can share what you're called to share and start wherever you like. Along the way, we will pause and see what themes are showing up. Before we get started with that, are there any questions or anything you would like to share?

Let's do it.

This is going to be great. Please, take it away. Get started wherever you would like.

I was raised by a single mom. She is an incredible person. She used her savings and went to school with a toddler. I was two years old when she went back to school and that changed our lives simply because of what she was able as the primary earner to provide. I also remember watching what she had to do versus what in my idealistic mind I would have wanted.

The workplace wasn't built for her and there were all kinds of tiny moments that made that true. Her employer would have 7:00 AM meetings, which is fine unless you have a kid. She would carry me in my pajamas downstairs to the apartment underneath us where this wonderful woman, Katie, lived. She would leave me there asleep. I would wake up there. Katie would help me get dressed and then take me to school. She made it work with this incredible community of people that she had but so much of the way it's expected to go is built on this idea that there is someone behind the worker that is doing all the things.

It wasn't true with my mom and it's so much less true now than it was years ago. Somehow, we still haven't solved that part. The ideal worker still just works, does not have children who get sick, does not have parents to care for, and does not have a house where something is going wrong. Somehow that experience highlighted this gap we have and a place to go to try and make a mark.

I love it because here's the thing. A lot of children grew up in that environment and it's true, we haven't solved that yet but your attunement to that is interesting because you saw the unfairness and what it is that these single mothers especially have to deal with and what they struggle with. It's not an easy path. Oftentimes, there is this expectation that you have to do it all and be it all, all the time.

Meanwhile, while you're doing it all and being it all, you're going to be paid 20% less. When my mom retired, we found out that over the course of her career, she was paid about $1 million less than the men in comparable roles. When you're a retired person, $1 million is a game-changing amount of money. If the roles had been reversed, and she had been a single dad, what would that have looked like? What would that have been like? We will never know but it's something that rolls around in my mind.

VCP 233 | Negotiation


Were you a single child?

I was an only kid.

I was trying to find the words. Thank you. You're going to have to assist me along in this journey.

If any of your audiences are like, "I didn't realize until I went to college that there were sometimes negative connotations with that."

Tell me about what happens as you have this childhood moment and then you start to think, "Something is not right in the way that the world is wired." You start thinking, "I want to do something about this," but you don't immediately jump into this mission that you have. Tell me more about the events that started to transpire as you moved through the world.

The next one is to flash forward twenty years. I worked at McKinsey and an apparel company. We did the growth strategy and then it sold for $100 million, which was a super fun job with incredible people. I went to business school. When I was in business school, I was doing my summer internship, which was a three-month job interview. There was a ton of pressure on this. In that internship, I finished my project early. It was supposed to take all ten weeks. I finished it in four.

I went to negotiate to be placed on another team and spent the whole weekend getting ready for this conversation. I went to Barnes & Noble, bought all the books, highlighted them, and underlined them. This is telling you both a lot about how I work and also how old I am. I wrote the script of what I was going to say and went into the meeting on Monday. At 10:00, the meeting started. I was asking to be moved to another team because I finished my project. I did it in a very assertive way because that's what the books told me to do.

What ended up happening is that I ticked off the person that I was negotiating with and she told me that I was no longer a culture fit. Your eyes are saying it. That is death. I was not going to be getting that job interview. "I finished the whole project you gave me in four weeks." I was over-performing but I was no longer going to be given that job. This is where it gets interesting. If I wasn't going to get the job, then finishing the internship no longer made sense. I needed to find a job. I had six weeks.

I ended up no longer going forward with the internship and she said, "I understand," and immediately called security. The protocol was if you quit, you were escorted out of this Fortune 20 company by security. I started my conversation with her at 10:00 AM asking to simply be placed on another team. The negotiation went so poorly that by 10:15, a security guard was walking me out of the building.

In less time than it takes to get a latte, I derailed my career because I tried to negotiate like a man. That became the guiding principle, "We're giving women incorrect tools in this situation and then almost making them feel bad when the tools that we're creating for them don't work." That became the new calling. There's great research on how to do this well. How can I take that research to women who can use it so that no one else has to go through my giant failure? This happened years ago. I am shaking telling you about it.

It's such a powerful moment. First of all, that was my initial curiosity. All those books were written for men. I can almost guarantee it. They don't take in the nuance of what it means to negotiate as a woman. You can't paint the picture all the same way.

Isn't that incredible? I believe the gap between the information that is publicly available and what research shows us works is largest in negotiation but we also see that gap in networking. We also see it in saying no. Historically, much as I was telling the story of how the workplace wasn't built for women, business skills are still being taught through a male lens. In some places, it's similar but in a lot of places, research is showing it is not the same.

We're giving women these tools that weren't built for them and then expecting them to do great things. I live two hours down the road from Augusta. I always picture what would happen if we went to the masters, gave all of these men golf clubs that were made for the average 5'2 woman, and then told them to play a great game. What would happen? We do that to women in the workplace every single day.

This is a tangent from what you're sharing. One of the things that came up was the concept of tall poppies. It comes from Southeast Asia, predominantly Australia. When you stand out, you have to get put back down. You strike me as someone who started to stand out and the workplace that you were in wanted to put you back down because you were someone who was disruptive or was creating disruption. That is something challenging to face. Realizing that you don't want to stand in, you want to stand out.

You want to do it in a way where you don't get hammered back down. To your point, what happened is that because I present as a woman, society expects me to be others-focused. In that conversation, I took advice that was not others-focused. I remember getting ready to go in the room and feeling, "This is so uncomfortable. This isn't me but it's what the books tell me to do."

How many times have we convinced ourselves to do this thing even if it feels uncomfortable? Sometimes it works. Sometimes the right thing to do is to push through the discomfort. In this particular case, that was not the right thing to do. Not understanding the nuances around negotiating specifically as a woman derailed my career at that moment.

At the same time, it's the moment that pushes you in the right direction.

It birthed a new career. Thank God.

Let's honor that. That's why I say the flashpoints are powerful because although they can change us entirely and sometimes feel uncomfortable, they also put us in line with what we're meant for. That's a beautiful way to think about this. Tell me what happens next. What did you do with this moment? Now that you've had this realization that you're not going to be working here any longer or you're not going to be working with them, what did you do with this new insight that you had harnessed?

For seven years, I didn't do anything with it. I found a job because I needed one of those. I was a management consultant again. I worked in an apparel company and I didn't do much. I coached some friends on the side but it was always a fun conversation to have. COVID hit. In a single afternoon in March, our nanny quit, our daycare closed, and my mother left town. My childcare and backup childcare were all gone. I had a 3-month-old and a 2-year-old.

I remember my husband and I sitting down to dinner that night. Everyone has their story of what happened at that time. They're all different. In my particular story, everyone was talking about online schooling, which frankly seems like its version of hell when you have to also figure out how to be a teacher. I have a baby who's crying all the time. I have a two-year-old who's tearing things off bookcases and trying to accidentally hurt himself. There's no pause.

We sat down the dinner that night. It was very clear that one of us was going to have to leave their job. There was no way through for us. I preferred it to be me at that point in time. That's what we did. Daycare was great but very strict. For the next almost eight months, I was home with both of them. In an attempt to connect with my pre-COVID self, when they were napping, I would write. I acted as if I were writing articles. Keep in mind, I had published nothing ever. It was a little bit like playing house as a child. We're like, "I'll write an article. I'll pretend I'm this thing."

I happened to be talking with some friends from HR who were saying that all these women were leaving much as I had but if they had asked for what they needed, the company was much more willing to negotiate than they ever had been before. That triggered in my mind what I had learned. After the last failure, I spent an entire year studying how to negotiate specifically as a woman at Kellogg, Northwestern. That research was always in the back of my mind. It was what I coached people on occasionally when I had those conversations but it was never my full-time thing.

I ended up writing this article called Before You Go and it was about the research behind how women can ask and what they can ask for. We have this list of 75 things that you can negotiate, which we have been building over the past few years. I wrote this article and put it out there in the world. A friend of a friend saw it and was like, "I work at Adweek. This is good. We should publish it. It blew my mind."

That article went viral, which is a weird thing to say about yourself and something that you wrote. As a result, I ended up being connected with the Head of Women at JPMorgan who said, "We're hemorrhaging women and we will try anything. Let's try this. Can you spin up training on this to give our women?" I was like, "I can." It ended up being the most popular module that they offered, and it has been the most popular module every time they offer it and they have been offering it for years, which is how to negotiate successfully as a woman.

The reason why I love what you shared so far is all the little breadcrumbs along the way have led you to this from your childhood to the moments that you've experienced in the workforce to your COVID moment. The pandemic was a flashpoint for so many people. Many people on the show have shared that was a moment for them. Everything led you to this and you can see if you look back how much those things all fit together perfectly. I don't know if you realized how much they fit well together.

Not at all. It's funny getting to sit in this chair with you because when you draw it out that way, even this idea of flashpoints, that does make sense. When you're living in it, it does feel like chaos. There was no storyline there.

When you are going through the journey, it's the ups, the downs, and what have you. The challenging part is to make sense and make meaning. It's a daunting journey. I also want to recognize this idea that when women take breaks to raise children and take care of loved ones who are sick, it can feel like the end of a career or something but the reality is it doesn't have to be.

It can be a pause point. It can be a point where you can say, "This is the end of a chapter but it's the beginning of something new. I can reemerge and do other things." I would love to hear your thoughts about that idea. I'm always thinking about Climbing The Right Mountain, which is my first book, and this idea that it doesn't mean the end of an ascent. It could mean that it's a brief respite on the path to something else.VCP 233 | Negotiation

I have a very strange agree-and-disagree response to that. On my side, I agree that taking time off clarifies where you want to go. Not to mention, frankly, you get to reignite your whole network, meet people, and think outside the box. I've talked to one woman who I adore who took a couple of years off to be with her young children. When she did, she realized that her friends were shopping online, and wasn't that interesting. She went back to her former employer and was like, "We should try this eCommerce thing." eCommerce does the majority of the business for this company that she's at. Thank goodness that she happened to leave for a little while.

It allows you to pull your head out and see what's happening. However, the flip side of that is it only works if you can find someone in the workplace who is open-minded enough to see it that way. Her magic happened because she already worked for the CEO. He believed in her, would sponsor her, and was willing to take that risk with her but for so many of us, we don't have that inherent sponsor before we take time off and then it becomes difficult to get back in.

I love this nuance that you put in here because it's this sense that we need other people as part of our journey along this path. You can have the best ideas and insights when you take that pause but you need people who believe in you and who will support you on that path of reemerging or coming back in and bringing what you've learned into the workplace.

Now that you're saying it, outside of even caregiving, I do wish that we had more of a society of taking breaks. You think of Europe and their six weeks. Germany has eight weeks of required paytime off every year. They are naturally building times of rest and reflection, and we are not. I have to believe that it seems like it helped us for a while but we're at that turning point where it might not help us as much in the future as it did in the past.

We have opened up another thread, which is fantastic. We need to make sure we avoid the hustle culture that we have built over time and not get back into that. We have to wire ourselves for that place of having rest and also make sure that it's common among everyone so that we're not having a one-way judgment on people who take rests and come back. You started Worthmore. What are the things that have been the biggest challenges as you've taken this journey into starting your business? It's a tough question because there are a lot of challenges but what has been the biggest a-ha moment that you've experienced?

When this started, I was like, "Companies are not going to pay me to teach women to negotiate." I'm amazed by how willing companies are to think broadly about this. At the end of the day, it's to their benefit because women who can negotiate, as research has shown, are more likely to stay than women who can't negotiate and who haven't been able to taught to negotiate in a gender-specific way, which is what I do.


Women who can negotiate are more likely to stay than women who can't negotiate and who haven't been taught to negotiate in a gender-specific way.


Originally, when I started it, I figured it would be one kind of company because I didn't think that companies would pay me. The corporate business is where a lot of the action is happening because companies are realizing that if they want to be successful moving forward, they have to be able to nurture the talent that they already have and be able to advance them. To do that, they need to be able to hand women gender-specific skills. How do you negotiate specifically as a woman? What does the research show on how you network specifically as a woman? Men need one network to be successful in business. Women need two.

Understanding that changes everything. How do you say no as a woman? Women are at a much higher risk of backlash than men when they say no. Learning how to do it in a way that you can sidestep that risk frees up a lot of time and energy to put toward what you're being paid to do as opposed to all the other things you're being asked to do. This flip that I didn't expect of companies of pushing the boundaries on how we think about this has been so phenomenal but I didn't see it coming.

I love that it's the realization that you had. This is what you need to lean into.

The realization was like, "This is a corporate business." I thought it was going to be a B2C business, coaching, or online courses. We do have an online course because we want those resources available to women who need them but it's become much more of a corporate business.

That's what often happens when people start a business or some endeavor. They think, "Are you going to solve the problem where it's most visible?" The reality is you have to go upstream and figure out how to solve it where it starts. You realize that the problem is bigger and can be solved in a much bigger way by going to the right point to solve it.

JPMorgan is introducing negotiating training for managers because if you think about it, this is such an important conversation for managers to have with their reports. We don't train people at all on how to do this. We can impact both sides of the conversation and therefore the culture. I believe that there is untapped potential all over our organizations because we're not talking about, "What are your strengths? What do you need to reach that? You need something different than this person's needs." We can make all those modifications if we free up the conversation to happen.

There are so many directions we could take this but I want to get back to you specifically. I would like to ask what of the particular learnings about yourself that you would like to share.

The biggest one is that it felt to me in the position that I am in that there were two options, stay-at-home mom or work 40-plus hours a week. This is how that goes and what it looks like. I am trying to figure out a different path because I very much enjoy what I do but also, my mom couldn't have summers and afternoons with me. That was not an option.

I'm in this place where I would like to try and craft something that works. Maybe we will have this conversation in five years and the next flashpoint is that my oldest son started kindergarten. I looked at the calendar and there are sixteen weeks that he's not at school. I realized that everyone reading this with children is like, "Duh." Am I supposed to not work?

There's this crazy spreadsheet that floats around Atlanta of all the camps you can put your kids in and the hours they run, "Don't do this camp because if it rains, they cancel it. Don't do that camp because they end at 2:00 PM." Like the logistics puzzle of this, I wish I paid more attention in operations class when I was getting my MBA because this is a whole thing.

I love what you shared because there's something about this that has me thinking about how we live life on our terms. People hear that. That's great for people who don't have a job, who aren't leading a company, or who have a trust fund. I want to challenge that mentality. I want to challenge people to say, "I can have it all to an extent. I can run a company but I have to choose what I do and how I design my time around the things that are important to me. If I want to take time off, I need to make sure that I have the right people on board to help me along that path." I would love to hear the reaction to that.

I'm so in this bowl of spaghetti. I have not figured out this one but it does feel a little bit like I cannot have it all. Where I am sitting, to try and have it all would be to set myself up for failure. However, I do think there's so much truth in taking the time to figure it out. I find knowing that I cannot have it all to be very freeing. If I cannot have it all, what are the 2 or 3 things that matter the most? It's trying to figure out how to protect those. It's all a work in progress. If you have any insight, lay it on me. To any other parent out there who is like, "This is how this works," I feel very in the blender on this one.


There's so much truth in taking the time to figure out


What you shared is a good refinement of what I was trying to say. All is very nebulous. It's big. You can't have it all per se but you can have a life, lead a company, and do some of the things that are important to you but you have to make sure that you have some boundaries that you create around those things, understand what are the important things, and make sure that you create space for the important things.

I worked with a woman who works at a top-three consulting firm, not known for its lifestyle. That's how I would say that. She had been a lifelong swimmer. She realized that since she joined the firm, she had not stepped into a pool in years. She's one of the bravest people I know. I find her incredibly inspiring. She ended up negotiating to be offline between 11:00 AM and 2:00 PM three days a week so that she could join the master swim team in Chapel Hill, North Carolina.

This was also pre-COVID when people did not negotiate to be offline. It's during the workday. She has been doing that for several years. She was able to have it all in the way that mattered to her so she's still a top performer in a career that she loves and also was able to carve out enough time to take care of herself so that she could take care of her kids and family because she has that energy.

That's a beautiful story. I love that. Sharing that gives people some hope that if they're willing to push back against what's expected of them and say, "This is what's important to me," they can create that path.

I watched hundreds of negotiations over the past few years. The thing that has been interesting to me is it's usually not what you ask for that people respond to but how you ask. You can create that space to figure out what it is that would be your greatest dream or even frankly relieve stress for you. I worked with a woman who needed to negotiate a different chair. This doesn't have to be a big thing. Somebody wanted to negotiate to not work on Wednesday afternoons because she's training for a marathon and that is a life goal. Whatever that thing is, as crazy as it may seem, you can ask for almost anything if you ask well.


Whatever that thing is, as crazy as it may seem, you can ask for almost anything if you ask well.


This is amazing. I could talk to you all day. You're giving me so many ideas about what I want to bring into the conversations with the people I work with because a lot of them struggle with this. It's not just the females. It's the males too. It's the men who struggle with asking in the right way.

One of the things that I've wondered about is the pendulum swing here of we have more women in the workforce than we have ever had before, which means there are more, to an extent, heterosexual relationships where that invisible labor has disappeared. The pendulum is swinging a little bit to more of the traditionally male side of men negotiating flexibility. Men are starting to think out of the box more because the culture is requiring it.

I don't think that our workforce is as good at thinking creatively frankly on either side of the equation but even less good on the male side. When I used to do coaching work, one of my favorite questions to ask was, "If I gave you my magic wand, what would your life look like in five years?" From there, you can pick it apart. "You want to have that degree. Let's think about how to negotiate that. You want to run an Ironman. Let's think about how to negotiate." That was always the funnest question for me.

The magic wand question is great. When you hear people say, "I can't do that," I'm like, "Why?" I have to shift gears because I don't want to keep you too long here but I have one last question that I ask every guest and I'm dying to find out. What are 1 or 2 books that have had an impact on you and why?

The first one has to be Women Don't Ask, which is by Linda Babcock and Sara Laschever. It came out years ago but it was the first time where I was like, "It isn't that I did this wrong. It's that I was trying to do something that wasn't built for me." That very much changed my life. I don't know what the other one is.VCP 233 | Negotiation

There's no pressure.

I adore reading. Fair Play by Eve Rodsky was a game-changer. That's a good one.

I've never read that before and I meant to put that on my list.

It's fun.

Thank you for sharing that. I love when people share books that are especially related to topics that are front and center for them because this is where people can take a topic and dig deeper into it. I'm so grateful and honored to have you on the show. This has been so much fun. Your stories and insights have been brilliant.

We have been talking about this. I'm so excited that we had the time. It was wonderful to get to chat with you.

Same here. Before I let you go, I want to make sure that audiences know how to find out more about you, reach out, and learn more about your work. Where is the best place?

The best place is our website. It's One thing that we do offer there is for anyone who wants to think more broadly about negotiation, we have a list of 75 things you can negotiate. Any of your audiences can go to our website and click on the top bar to download that. We also have additional resources on networking and negotiating as a woman and how to support women for corporations.

Thank you again for coming on the show. This has been so amazing. Thanks to the audience for coming on the journey with us. I know you're leaving so inspired and hopeful that we can go out and make a difference in the world. Please do reach out to Kathryn. It will be worth your money and time. Take care.


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