Why Negotiating Feels Risky: What Successful Negotiators Do Differently with Kathryn Valentine

Kathryn Valentine:
The research that is making me really nervous right now came out about six months ago showing that if women use AI to guide their negotiation, AI will recommend that they ask for 21% less than if you tell AI you are a man. We’re only going to perpetuate the cycle that already exists if we keep doing it that way.

Blake Schofield:
Real leadership, real life, real impact. No more choosing between your career and your life. Here you’ll find honest conversations, science-backed strategies, and inspiring stories to help you thrive at work and truly enjoy your life outside of it. I’m your host, Blake Schofield, and I’m honored to help you create more impact with ease.

Blake Schofield (00:29.774)
Kathryn Valentine is an executive coach and nationally recognized expert on women’s leadership whose work has been featured in Harvard Business Review, The Wall Street Journal, and Fortune. Her TEDx talk on negotiation was the number one most trending talk on TED.com, and she’s spoken at companies like JPMorgan, Bain, and KPMG. Kathryn lives in Atlanta with her husband and two sons who keep her leadership skills sharp and her coffee consumption high. We had such a phenomenal conversation. I feel like I could have talked to her for hours. Kathryn shares real facts and data and important information around why learning how to negotiate matters so much, not just to your career trajectory, but to your own personal balance and happiness. And what really shocked me is some of the stats she shared about AI and how leveraging AI actually can put you at a massive disadvantage. I’m honored to have her on the show, and I hope you enjoy this conversation as much as I did.

Blake Schofield (00:01.651)
Kathryn, thank you so much for joining me today. It’s amazing. We’ve had maybe five minutes or so of discussion, literally just met face to face. And you are, as I said to you, the very first guest I’ve ever had on the podcast that I found just by being actively involved in LinkedIn. I saw your post about your TEDx talk, watched some of it, and said I need to bring this woman on the podcast. And just in the first five minutes of connecting with you, your energy is amazing. I’m so excited for this conversation. I feel like I just got introduced to a kindred spirit. We get to sit around and hang out and chat, and people get to be a part of the process with us.

Kathryn Valentine (00:53.358)
I’m about it. I’m also excited because when you mentioned the LinkedIn thing, I haven’t talked to many people on LinkedIn, and I don’t do much on LinkedIn, so the fact that it works this way makes me really excited. You’re also the first live conversation I’ve had off of a LinkedIn connection, so thank you so much for inviting me on.

Blake Schofield (01:13.315)
Absolutely. So why don’t we get started? Can you share a little bit about your background, your life, and who you are? Because I always think that’s so important for us to really connect to your story and what you have to share today.

Kathryn Valentine (01:30.904)
Sure. So the quick background on me is I was raised across many states. I worked at McKinsey as a strategy consultant a couple of times. I’ve actually worked there three times over the course of my career. I spent some time in apparel, like you did, which is always fun. And then when COVID hit, I had my infant and my two-year-old at home. There was this one conversation where my husband and I looked at each other one night and said this is not going to work—one of us is going to need to shut it down for a little while. So I raised my hand to take that because I was excited to just step back for a bit and see what that felt like.

One day when they were napping, a friend of mine in HR said their company was losing a lot of women and that there had never been a time before when women had as much leverage as they did, but we weren’t using it. So I sat down and wrote an email that said, “Hey, maybe pass this to the other women at your company. Maybe this will encourage them to speak up for themselves.” It was based on research I had done in business school about how to negotiate as a woman. That email ended up being forwarded thousands and thousands of times. A couple of publications picked it up, and then the head of JPMorgan’s women’s division called me and said, “Can you spin up a workshop on this?” I did, and it became the most popular workshop they’d ever offered to women.

From there, I got invited to speak at other corporations that were trying to figure out how to retain the female talent they had attracted and developed. From there, it became a broader focus on understanding the common obstacles women face in the workforce and what research we can apply to solve them. There’s a lot of strong research around negotiating, networking, and time management. The gap is that researchers are incentivized to publish academic papers, not to translate those findings into practical tools for women in the workforce. That’s the gap I try to fill.

Blake Schofield (03:40.435)
I love that so much, and we’re definitely kindred spirits in that. I have three kids and spent 18 years in corporate retail. I was a top performer in every company I was in, but that struggle is really real when you are trying to balance showing up as a successful mom and being successful at work while managing the majority of the household. It’s an interesting thing. Like you, I ended up at Target Corporation, and there weren’t a lot of people from outside the Minneapolis area when I went to work there.

Kathryn Valentine (04:30.144)
I have two people that I’m coaching who are at Target right now, so I’m very familiar with that dynamic.

Blake Schofield (04:34.427)
Yep, yep. I love my Target people—some of the best people I’ve ever worked with. What I was told consistently was, “You know how to sell yourself. Can you help us do that?” And I was like, what? It was very interesting to me that there was such a gap in that skill set. Like you, I ended up doing that because people were saying, “You seem to have figured out how to have balance. You seem to have figured out how to position yourself.” And I think some of that was true—I had learned how to position and communicate those things and continued to build on those skills. And some of that was sheer grit. I looked like the successful working mom who had it all together, and yet I was internally struggling with the balance between ambition and having the energy and ability to be present with my kids in the way I really wanted, and to have space and time to cultivate community and friendships the way I wanted to.

When I left corporate in 2017, I really felt like my experience was just my own. But the last nine years has shown me that what I struggled with—the same things that were really challenging for me—are consistently challenging across the board, especially for women. So I’m really excited to hear your perspective and what you’ve learned and how you approach this.

Blake Schofield (06:18.215)
There is so much research, but often the researchers aren’t living it. They don’t have the practical experience. They don’t know how to navigate it. For me, at least in the last nine years, I’m somebody who goes down rabbit holes—I tend to go five levels deeper than most people. And I also go much broader and connect things that people don’t.

So like you, I’ve seen and understood these principles that are being taught in colleges or research, but actually, how is that showing up in real life? Why is that connected? Why is it happening? And what do we do about it? I think the more voices that share what we’ve learned through experience and how to connect that, the more we can bring practical tools to the people who really need them.

Kathryn Valentine (07:15.342)
Agreed. And also, when you were chatting, the one thing that I’ve been flipping over in my head that I’ve never talked to anybody about before is the generational nuance in where women in the workplace are right now. Because what I’ve been hearing pretty consistently across coaching clients is that, let’s call it people in their 40s to 50s, that level right now is getting additional pressure.

The women entering the workforce are saying, “No, no, no—here are my boundaries. You will not stomp on them,” which I credit them for. I think that’s amazing. The problem is the C-suite is not honoring those boundaries, and the women in middle and upper management are having to play that in-between role. They’re not getting the same level of hustle from analyst roles as before, but CEOs still have the same expectations. So I’m seeing that layer get doubly impacted right now.

When I felt those dynamics, the incoming generation was still hustling. Now the incoming generation is asserting boundaries, which is great, but it creates this additional layer of pressure. Have you seen that? What are your thoughts?

Blake Schofield (08:34.355)
Yeah, this is such a good conversation. I have so many opinions on this, and I’m thinking about the most effective way to share them. I’ll start by saying I spent 18 years in corporate retail, and for 10 of those years, I felt like I should be doing more meaningful work. I kept going through cycles of hoping that the next job or company would make it better.

I made a lot of money and carried a lot of responsibility for my family, so I couldn’t find a way to use my skills and replace my income in a way that felt responsible. A lot of that frustration came from beliefs about what it looks like to be at that level—the level of sacrifice required. I was also very used to solving problems on my own.

Over the last nine years, working with leaders from senior manager to C-suite, I’ve seen that about 75% of the things creating stress, burnout, misalignment, and lack of fulfillment are actually solvable without changing your circumstances.

Kathryn Valentine (10:14.158)
Okay. Can you give me a couple of examples?

Blake Schofield (10:15.281)
Yes. I had a recent podcast episode where Corey shared her story, and she said that 75% of the things that were creating friction, stress, and misalignment in her career 90 days ago have now been resolved.

What I started to understand is that people go through cycles of fulfillment and burnout, thinking that the next change will fix things. But burnout isn’t what most people think. People believe it’s about working too hard or being misaligned with values, but that’s just the peak. Most people are actually in burnout cycles the majority of the time—they just don’t recognize it until they hit a breaking point.

That’s when they might end up on a performance plan, get laid off, or experience serious physical or emotional burnout. Then they try to make a change, but the same patterns follow them. I saw this in myself when I moved into entrepreneurship. I thought the problem was my boss or industry, but eventually I realized—it was me.

And what I came to understand is that what’s happening for leaders is really about misalignment. There are three key areas I focus on. First is understanding how you’re naturally wired to thrive. If you’re not working in alignment with that, you’re two to three times less productive, experience more stress, and feel less fulfilled. Most people don’t know what that is.

Second is beliefs and conditioning. These shape behavior and keep people stuck. People think they can override them, but they can actually be changed if you understand them.

Third is environment. People think they need a new environment, but often it’s about understanding what you need and how you communicate and interact within it.

Kathryn Valentine (13:45.731)
The framework is—I love frameworks—the frameworks are always helpful.

Blake Schofield (13:48.965)
Okay, so then I started to see this, and I began to see that the leaders I was working with became exponentially better leaders as they developed these tools for themselves. So Corey, for example, specifically talked about how much less stress she has, how much better she understands how to operate within the organization—with communication gaps, struggles, growth pains, and all the problems they’re having—no longer taking it personally, being able to step back, see what’s going on, and show up as the leader she wants to be regardless of what’s happening.

That has enabled her to do the same amount of work she was doing before in less time, and now she’s able to spend more time developing her team and helping them grow so they can be promoted. They’re taking on more work as a result, and she’s been able to reduce stress and anxiety, show up authentically, and have more space, time, and energy. She’s getting positive feedback at work about her leadership and her team, and her family is happier because she has more energy.

So where does that connect to what’s happening in companies? I think it’s really important. This learning—from my personal journey, from helping hundreds of leaders, and now taking this inside companies—has shown me that we are at a critical cross point where the ways we’ve done business no longer work. With AI and the speed of global change, we cannot continue to operate the way we have before.

Kathryn Valentine (15:25.326)
Mm-hmm.

Blake Schofield (15:39.284)
It needs a top-down and bottom-up approach. So when you talk about the people caught in the middle, the younger generation is coming in saying, “I want more feedback, I’m going to have boundaries, I want work-life balance, I care about efficiency—it’s not about hours, it’s about output.” And then you have older systems and structures and people who built their careers based on face time, hours worked, hierarchy, and history.

So much of that is breaking. If you look at what’s happening today, I’ve been sharing that the Edelman Trust Barometer shows that 70% of people are hesitant or unwilling to listen to people with different perspectives or problem-solving approaches.

Kathryn Valentine (16:41.036)
I’ve been tracking this too. This weekend I happened upon an episode of The West Wing, and even the opening made me emotional because it was about doing your best even when it’s hard. The Edelman data is concerning, but not surprising.

Blake Schofield (17:07.281)
Yeah, 100%. So to your point, leaders today are under more pressure than we’ve seen in generations. And from my perspective, I’m actually encouraged by that. I’ve spent the last nine years understanding patterns and what it takes to create transformation. I was known as the transformation leader in corporate because I would take stagnant or underperforming businesses, analyze them, identify what was misaligned, and restructure them for growth.

I never thought it was unique—it felt obvious to me—but others pointed out that it wasn’t common. So I’ve spent years understanding behavior change and what keeps people stuck. And what I know to be true is that you often need a breakdown before a breakthrough. Everything operates in cycles—creation, destruction, rebirth.

We tend to repeat patterns because that’s how we’re wired. So when I look at what’s happening now, I see opportunity. The leaders and organizations that recognize the gap and don’t want to operate this way anymore are in a position to learn new skills—how to operate in uncertainty, how to adapt, how to leverage technology and leadership differently.

So yes, that middle layer is struggling, but this is a macro shift. This is the future of work changing. The old ways are no longer sustainable. And the people who learn how to navigate that change with more ease are the ones who will succeed. What do you think?

Kathryn Valentine (20:22.562)
Yeah.

Blake Schofield (20:24.891)
What do you think about my perspective? That was long-winded, but it’s not an easy question to answer.

Kathryn Valentine (20:34.734)
I was a political economics major, but the thing I still don’t understand is why we’re not talking more about the research showing that if women stayed in the workforce at the same rate as men, it would add $28 trillion to global GDP. We talk about the economy and competitiveness, but the solution is right there. I don’t know why we’re not focusing more on that.

Blake Schofield (21:15.441)
What’s your perspective on the challenges women are facing today? I’ve heard conversations around the Lean In study and debates about ambition, but I’m curious about both the research and what you’re seeing in real-world experience.

Kathryn Valentine (21:47.180)
When you mentioned the Lean In study, my brain immediately went down a rabbit hole. As a McKinsey alum, what stood out to me most was the fine print about who they surveyed. They surveyed significantly fewer companies and fewer women than before. That was the most interesting part to me. This study has been running for years, and suddenly there wasn’t enough participation—likely because companies were being advised not to participate. That’s the part people weren’t really talking about.

Blake Schofield (22:45.863)
Yeah, it’s interesting because part of this is challenging the belief systems we have about what it looks like to be a woman in leadership. I know for me, I always knew I didn’t want to be a stay-at-home mom. That was very evident. I wanted to work. I wanted to feel like my career and my life gave back and had impact, and I wanted to be a mom too. I didn’t want to sacrifice those things.

I was on a networking call yesterday, and one of the women said to me, “Some of the worst leaders I’ve had in my career are women, and I wish women supported each other more.” Interestingly enough, some of my worst leaders were also women, and I have a perspective from my experience on why that is.

We talked about conditioning and belief systems around what it takes to be a successful woman in business. Often that meant operating against how we would naturally operate—less empathy, more fact-based, making sacrifices or compromises to move up the ladder. I think a lot of women have said, “I’m not willing to do that,” or they’ve watched women lead in ways that don’t feel authentic and said, “I don’t want that.”

The reality is, if you override your emotions and values every day, you’re going to become someone who is disconnected, under stress, and unable to show up as an inspired leader. That’s what I’ve seen. I had a leader earlier in my career where my entire team had been working 70 to 75 hours a week for over two years.

She emailed me on a Saturday saying that a report needed to be in Arial font size 10 and updated. That was the first time in my career I said no. She pushed back and said leadership needed it, and I said I’d take the heat—I wasn’t going to ask my team to do that. The ironic part was that when I checked on Monday, it already was in Arial font size 10.

Kathryn Valentine (25:49.782)
So I think you identified something important, which is that the sacrifices it took to reach leadership, even 10 to 15 years ago, were significant. In some cases, authenticity had to be sacrificed. I was fortunate to work for a couple of incredible women leaders, but I also saw examples that weren’t great.

When you look at networking research on how women advance, one key point is that women are often over-mentored but under-sponsored. When women look for sponsors, they tend to look toward other women. But the research shows that while having a female sponsor is great, your second sponsor should ideally not be a woman. That’s because different networks provide access to different opportunities and perspectives.

So while it may feel counterintuitive, having a mix of sponsors can be more beneficial for advancement.

Blake Schofield (27:28.296)
Yes, that’s interesting. I’ve had phenomenal leaders—both female and male—and also some challenging ones. It took me about a decade to really understand the power of having a board of directors and sponsors to help develop me.

My time at Target was impactful because mentorship was built into the culture. Before that, I had been at three companies where I didn’t even know that kind of support existed. It completely changed how I understood growth.

I’ve consistently seen that women often don’t realize the importance of mentorship or haven’t been guided on it. There was also research showing that women are less likely to be given leadership development opportunities inside organizations, which creates a gap.

Kathryn Valentine (28:58.102)
I agree. There was also a study by Robert Walters showing that men were receiving 24% more in retirement benefits, 42% more performance bonuses, 12% more equity, and were significantly more likely to receive leadership coaching.

Blake Schofield (29:25.010)
I’m interested—what’s your perspective on why that is?

Kathryn Valentine (29:38.072)
I don’t know that I have a perspective on why it is, but I do have a perspective on how we solve it.

Blake Schofield (29:44.518)
I’d love to hear that.

Kathryn Valentine (29:46.562)
I think the solution is negotiation. There’s a systematic solution that I wish was happening faster, but for an individual woman who can’t solve the systemic issue overnight, negotiation is the most immediate tool available.

Blake Schofield (30:11.684)
I’m so excited to dive into this with you. That idea—that you can’t solve systemic issues immediately—applies to so many areas. We’re in a time of massive change, uncertainty, and division, and a lot of people feel powerless.

One of the biggest things I’ve learned is that advocacy matters—we’re far more powerful than we think. It’s easy to look at big systemic problems and feel like we can’t change them, but I’ve seen that change often starts with small actions.

We get overwhelmed by the scale of problems, but real transformation happens through consistent, small shifts that create a ripple effect. So yes, systemic issues exist, but we still have agency.

I’m excited for you to share how negotiation can help people take control of their careers and create change for themselves, because that’s something we can influence.

Blake Schofield (33:13.278)
So I’m going to turn the floor to you. I’d love for you to share your expertise, your passion, and your knowledge with my audience so they can feel more empowered to negotiate, stand up for themselves, and create the careers and lives that they want.

Kathryn Valentine (33:40.406)
I’m happy to do that. I’ve been researching this for 12 years, so I could talk about it for a long time. But to make sure I’m as helpful as possible to you and your audience, is there anything specific you’d like me to focus on?

Blake Schofield (33:55.774)
You mentioned that women are not getting the development they want, they’re being underpaid, and opportunities aren’t coming. They’re feeling stress and pressure inside organizations.

From my perspective, negotiation is about understanding what I want, what the other person wants, and how to build a case that creates a win-win outcome—where I get more of what I want and the other person also feels they benefit.

What I’ve seen is that many women haven’t been taught these skills. They don’t understand their value, how to build the argument, or what’s expected in a negotiation. And generally, I think this is something men are more often taught than women.

Kathryn Valentine (35:20.670)
I would take it a step further. If a well-intentioned woman goes to Google or AI and asks how to negotiate, she’s often given the wrong advice. The advice available is typically built for and works for men.

There’s a clear body of research on gendered negotiation, and that advice is very different from what’s commonly available. That’s a huge disservice to women, because even when they take the time to learn, they’re often learning from the wrong framework.

Blake Schofield (35:53.716)
That’s so powerful. I think AI can be both a great tool and a huge detriment.

Kathryn Valentine (36:02.824)
Exactly. It takes what already exists and returns it faster. So to answer your broader question, the first step is knowing what you want.

What we see is that women are not only influenced by societal expectations, but they internalize them. When I ask, “What do you want?” many women struggle to answer. I often have to guide them through sub-questions to help them separate their own desires from conditioning.

So if you already know what you want, you’re ahead of the game.

The second step is understanding how to achieve it. I teach a three-step framework. First is thinking holistically—we’ve identified 76 different things women have successfully negotiated. If you’re only negotiating salary, you’re leaving value on the table.

Second is the relational ask, which is what my TEDx talk focuses on. This is a structured way of asking that works particularly well for women and significantly reduces the risk of backlash.

Third is shifting into a collaborative mindset—it’s not me versus you, it’s us versus the problem. The problem is anything that prevents you from delivering your best work. That’s a shared issue, and you work together to solve it.

Blake Schofield (38:02.419)
I love that. And I think it’s important to highlight that negotiation isn’t just about salary or job offers—we’re negotiating every single day.

Kathryn Valentine (38:23.584)
Exactly. Those micro-negotiations shape your career—who gets credit for an idea, what your deadlines are, what resources you’re given, what gets taken off your plate when something new is added. All of that impacts your experience at work.

Blake Schofield (38:41.171)
Yes, and often there’s a lack of clarity about what we want, how to communicate it, and fear about what might happen if we do.

That’s why I talk about starting small—building the skill through small experiments. Learning to advocate, to push back, to find alternative solutions. These are critical skills, especially given how women have historically been conditioned.

If we keep saying yes to things that don’t align with our lives and values, eventually we reach a breaking point. And many people then leave the organization thinking it’s the company, when really it’s a pattern or lack of skill in how they’re operating and making decisions.

Kathryn Valentine (40:28.482)
And a yes to anything is a no to something. So the question becomes, what are you saying no to, and is that a trade-off you’re willing to make?

For women specifically, when saying no, I recommend the “yes-no-yes” framework. It allows you to decline something without losing political capital or risking backlash.

Blake Schofield (40:51.955)
So if AI is giving gender-biased advice, what are the biggest shifts women need to understand about negotiation compared to what’s traditionally taught?

Kathryn Valentine (41:14.382)
First, we need to acknowledge that fear around negotiation is real and justified. Women are at higher risk of backlash when negotiating for themselves compared to men.

The good news is there’s a solution. The key is to stop using tools designed for men. Instead, structure the conversation differently—highlight past performance, outline future goals, then make the ask, and follow it with a collaborative question like, “What do you think?” or “How could we make this work?”

This approach aligns with how women naturally communicate and significantly reduces backlash.

Blake Schofield (42:06.918)
That’s so powerful, and I think it’s really important for people to understand that. It’s not about doing less—it’s about doing things differently and more effectively.

I’ve seen so many people hold themselves back because they assume the worst will happen if they speak up or ask for what they need. But what I’ve learned is that often the stories we tell ourselves are much worse than reality. And when we start to challenge those stories and take small steps, we begin to build confidence.

Confidence doesn’t come from thinking—it comes from doing. And the more we practice advocating for ourselves in small ways, the easier it becomes in bigger situations.

Kathryn Valentine (42:54.273)
Exactly. And one thing I always remind people is that negotiation is a skill, not a personality trait. It’s something you can learn and improve over time.

And the stakes are high. The research that is making me really nervous right now came out about six months ago showing that if women use AI to guide their negotiation, AI will recommend that they ask for 21% less than if you tell AI you are a man.

So if we don’t address this and start equipping women with the right tools, we’re going to perpetuate the cycle that already exists.

Blake Schofield (43:31.662)
That’s incredible—and honestly concerning. It just reinforces how important it is to be intentional about where we’re getting information and how we’re applying it.

I think about this in the context of leadership as well. If we’re not aware of the biases that exist in the systems we’re using, we can unintentionally reinforce them. That’s why conversations like this are so important—because they bring awareness to things people may not even realize are happening.

Kathryn Valentine (44:04.715)
Exactly. Awareness is the first step. Once you know better, you can do better.

And the more we talk about these things openly, the more we can start to shift the narrative and create change—not just individually, but collectively.

Blake Schofield (44:24.508)
I love that. And I think that’s such a powerful place to land this conversation.

If people want to learn more about you, your work, or how to work with you, where can they find you?

Kathryn Valentine (44:36.812)
The best place is my website, and I’m also active on LinkedIn. Those are the easiest ways to connect with me and learn more about my work.

Blake Schofield (44:48.193)
Amazing. Thank you so much for being here and for sharing your expertise. This was such a valuable conversation.

Kathryn Valentine (44:55.204)
Thank you so much for having me. I really enjoyed it.

Blake Schofield (45:00.118)
As always, thank you for joining us. If this conversation resonated with you, share it with someone who could benefit from it.

And remember, you have more power than you think. Advocate for yourself, take small steps, and create the career and life you truly want.

Until next time, lead with intention and create your impact with ease.