The 2026 job market has been brutal.
If you’ve been looking for a job, you know how tough it is. If you already have a job, I’m sure you’ve been told that you should just be grateful. Keep your head down, don’t make waves, ask for a raise when things “settle.” My guest today thinks that instinct is completely backwards, and after this conversation, so do I. Kathryn Valentine –– executive coach, one of the country’s leading experts on women’s negotiation, and repeat guest –– coaches women inside communities like J.P. Morgan, Bain, and KPMG. And her work starts with an uncomfortable finding: women now negotiate as often as men, but succeed about half as often. Today we’re talking about what to do when your company says there’s no budget, why the timing of your ask matters so much, what AI gets wrong about your salary, and how to survive the messy middle of a negotiation without folding. If you’ve been telling yourself you’ll just wait a year to ask, listen to this first.
Key takeaways:
The problem stopped being “women don’t ask”
Women caught up on asking. The book Women Don’t Ask named the gap years ago, and the data now shows we’re negotiating at the same rate as men. The problem is the toolkit. Most mainstream negotiation advice was built for men, and it doesn’t come with a warning label that says “higher chance of backlash if you’re a woman.” Kathryn’s whole approach starts from there: stop using tools that weren’t designed for you, and use the ones research shows actually work.
Layoffs don’t take negotiation off the table
Kathryn worked with a woman whose boss was cut in a layoff. That boss made 50% more than she did. So when the company asked her to absorb the role, even a 25% raise was a deal for both sides. The framing that makes this work is simple: nobody can do their best work without the support they need, and fair pay is part of that support. You’re asking so you can deliver, which puts you on your manager’s side.
Ask six months before your review
This one blew my mind. At a typical company, annual reviews happen in December, but manager budgets are due in October. So when you ask in December and your boss says “my hands are tied,” they may be telling the truth. Kathryn’s fix: make your ask in June or July. And if the answer is “I’m not sure you’re ready,” follow up with “What do I need to demonstrate to be ready next time?” Getting that checklist in writing makes the next conversation way more objective.
Use the relational ask, then stop talking
Walking in and saying “I deserve this” (yes, a Wall Street Journal “expert” actually recommended this) is one of the fastest ways to get backlash. Instead, Kathryn teaches a three-part structure: your past performance, a future vision everyone can get behind, and the specific ask. Then close your mouth and finish with a collaborative question like “What do you think?” or “How can we make that happen?” It frames the whole thing as you and your manager versus the problem. Bonus: research shows even walking side by side while you negotiate improves results.
Base salary is one of 76 things you can negotiate
Kathryn has a list of 76 things she’s seen women negotiate, and only one of them is base salary. Performance bonuses, 401(k) contributions, sign-on bonuses, a learning stipend, a better title, team headcount, even a $2 million inventory system that saved a team 30% of their time. And the gender gaps in those other areas are way bigger than the roughly 20% gap in base pay. If cash is frozen, ask for things you can monetize later, like a promotion or a training you can point to at your next review. Also: always have a back-pocket ask, because people are much more likely to say yes after they’ve already said no once.
AI will lowball you. Use real humans
Research shows AI tools advise a woman with the exact same background as a man to ask for about 40% less. Biased in, biased out. If you’re short on time and using AI anyway, add “Please remove all gender bias in your response.” But the gold standard is still talking to real people: former employees, mentors, and yes, as Kathryn says, ask a white guy. Try “I’m thinking of asking for X, what do you think?” Most people will give you directional feedback, and sometimes the person you benchmark with ends up hiring you.
The average negotiation lasts 25 days
If you walk out of the first conversation without an answer, you didn’t fail. Big conversations take time, and “let me go check with some people” is the most realistic outcome. Your response: “That sounds great. Is there anything I can send you to make that conversation easier?” Taking a 24-hour break when things get tense is completely normal too. Kathryn’s calculator showed that a 30-year-old making $75,000 who negotiates a 12% raise could gain around $569,000 over her career from that one conversation. That’s worth 25 uncomfortable days.
Pick your support system carefully
During those 25 days, the people you talk to matter. Loved ones who’ve never negotiated (or who grew up with pensions and “just bring your resume to the office” advice) will often sow doubt because they want to protect you. Save the conversation for the people who’ll back you up. Plan a reward after that first conversation just for being brave. And build an alternative, whether that’s another company, a plan B, or even a plan C that involves building something of your own.
Notable quotes
“It’s a biased in, biased out system.”
“Don’t get advice from the messiest person you know about how to organize your closet.”
“The good news is women are actually negotiating as often as men are. The bad news is we’re only successful half as often because we continue to do it with the wrong tools.”
Episode at-a-glance
00:00 Intro
02:13 Why negotiation matters: career, stress, and $1M
05:24 Women ask now, but with the wrong tools
06:30 Negotiating during layoffs
08:28 The relational ask (and the WSJ advice that backfires)
11:36 Common negotiation mistakes women are told to make
13:12 What to ask for when raises are frozen
15:33 The 76 things you can negotiate
19:42 The gender gap goes way past base salary
26:42 In the room: what to say when it goes off-script
31:08 The three biggest mistakes that sink negotiations
34:15 How to find your market rate
37:32 “Ask a white guy”
40:34 Should you use AI to prep?
44:29 The average negotiation lasts 25 days
45:57 Live calculator: what one raise is worth
50:25 Who to talk to (and who to avoid) during a negotiation
56:54 Changing jobs when the economy is bad
59:25 When to leave corporate and build your own thing
66:27 Why mid-sized companies are best for flexibility
71:07 What to do this week
Thanks to Rocket Money for sponsoring this episode!
Thanks to BetterHelp for sponsoring this episode!
Kathryn’s Links:
76 Things You Can Negotiate at Work
Learn more about Kathryn Valentine
Additional Resources Mentioned:
Negotiate Like a Woman with Kathryn Valentine
Women Don’t Ask, Negotiation and the Gender Divide
Learn the exact strategies to save money, pay off debt, improve your money mindset, and increase your net worth. Get your personalized plan: https://herfirst100k.com/ffpod.
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Meet Kathryn
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 Forbes. Her TEDx talk on negotiation was the #1 most trending talk on TED.com and she’s spoken at companies like JP Morgan, Bain, and KPMG. Kathryn lives in Atlanta with her husband and two sons – who keep her leadership skills sharp and her coffee consumption high.
Transcript:
Tori Dunlap:
Right now, a lot of women are watching the headlines, AI layoffs, hiring freezes, low hire, low fire, and quietly deciding, “This is not the year to ask for a raise. Just keep your head down, be grateful you have a job, and wait for things to settle,” but my guest today is here to tell you that that instinct is actually backwards. So what we’re getting into today is how to respond when they tell you there’s no budget for raises and how to make an ask in a way that puts you on your manager’s side, not on their firing pile.
Kathryn Valentine is back on the show. She’s an executive coach and one of the country’s leading experts on women’s negotiation whose TEDx Talk became the number one most trending talk on ted.com. She coaches women inside communities like J.P.Morgan, Bain, and KPMG, and her whole body of work is built on one uncomfortable finding, that women negotiate as often as men now, but succeed about half as often. If you’ve been telling yourself, “I was just going to wait a year before I ask,” or don’t even know how to go about preparing for a negotiation, I want you to hear this episode. Let’s get into it.
But first, a word from our sponsors.
So Kathryn, welcome back to the show. I need you to walk us through what you’re actually seeing right now. Are women negotiating more or less in this market, and what is that actually doing for them long-term?
Kathryn Valentine:
So I have good news and bad news. The good news is women are actually negotiating as often as men are. So yay, we’re doing it. The bad news is we’re only successful half as often because we continue to do it with the wrong tools, which I know is something we’re going to solve today.
Tori Dunlap:
So for the woman who’s never really thought about negotiation as a skill she needs, you mentioned maybe having the wrong tools to do this, why does learning this matter so much, especially right now?
Kathryn Valentine:
I’d say there’s three reasons. One is because it will advance your career and it will give you more control over the way things happen. Are you getting credit for that work or is somebody else? Do you have an additional resource to do it with? When is the deadline? These are all things that help you continue to move upwards, and we know that promotions are really where you get a lot of that financial gain, one. Two, it reduces stress. I bought a car on Monday, and they didn’t have the hitch on it that I needed. Instead of me driving another four hours, he drove to me and put it, my car, in my driveway. And so those are the kinds of things. I just got half of my date back because I was able to negotiate that. So you can negotiate to lower your stress at a time when we see unprecedented levels of burnout in women.
And then the last one, which I know you talk about a lot, is just the financial ramifications of this. The kind of stat that people toss out a lot is Linda Babcock’s choosing not to negotiate is like leaving $1 million on the table over your career. Margaret Neale at Stanford did a different version of it that shows that it’s equivalent to working an additional eight years to do the same wealth. But then what I was thinking about actually in listening to one of your episodes is that a lot of it depends on how old you are and how much you make. We created this new custom negotiation calculator, and I’m happy to do it live with you if you want right now, where you put in your age, what you make, and what you can think you can negotiate, and it’ll show you the lifetime value of that one conversation. Because much like compound interest, our brains don’t necessarily understand that that $5,000 raise is a raise that you get for the next 40 years.
Tori Dunlap:
Well, and the thing that you just talked about, I think, was the belief that also the data was backing for a really long time, which is that women were not negotiating at the same rates men are, we’re now at parity there, but what you said is that we’re not seeing success in the same way. And of course we know that, partially, this is because of society not liking when women ask for more money, that being really uncomfortable, and believing that men might deserve money over women. Those are the systemic reasons, which of course we talk about on the show, but I want to talk about what can we do at the individual level. You said it’s not landing the way that it should. Women are negotiating now, but we’re not doing the right things to make that negotiation work in our favor. So what changed, and what does that really tell us about the problem and where that real problem is?
Kathryn Valentine:
So what changed… And what you’re referring to is Women Don’t Ask, which was this amazing book that came out in the ’90s, and that was the problem. Now, women are very aware of this. Good job for us. Let’s celebrate that win. The problem now is that we continue to walk to the negotiation table with tools that were not built for us, but they don’t come with that warning like, “Warning, higher chance of backlash if you do this.” We’re not talking about that. And so instead of giving you the sort of set, quote, unquote, “ways to do things” that we know aren’t working, today we’re going to talk about a completely different set of tools specifically for women that we know allow you to get a higher chance of success and virtually eliminate the risk of backlash, which means that all of a sudden you can ask for anything you want because there’s no downside. If they say no, it’s the same way they say it’s raining. It’s okay.
Tori Dunlap:
You were quoted in CNBC as framing negotiation as a us versus the problem. Does that framing get easier or harder to make when the company is cutting costs?
Kathryn Valentine:
I’m going to argue it’s just about the same. I just did a negotiation with a woman whose boss was fired for massive layoff, but her boss made 50% more than she did. And so when they asked her to take on those responsibilities, even if her raise is call it 25%, that’s still a deal for both parties. If they ask her to take on that role and there’s no raise at all, there’s no way that anybody could deliver to their full impact when they don’t have the support that they need, and that raise is part of that support. And so what we see with even negotiations and layoffs is that it’s still a very individual situation, and a lot of times, it’s still very much true.
Tori Dunlap:
I want to highlight what you just did because you’re so good at this, it just happened naturally. But for the average listener, what you just said was, “This person will not feel fully supported in the work that they have to do if they’re undercompensated.” That is the framing I think that is so important. Because what I hear, especially when the economy is bad and layoffs are happening, is women go, “I can’t possibly negotiate more money. They’re going to laugh me out of the room.” But that framing, even what you just said, that was so subtle, you almost miss it because she did such a good job at framing it. But that’s what we’re talking about here of saying, “Basically. If you want me to do more work, I have to feel incentivized and supported to do that.” So talk to me about that framing in particular.
Kathryn Valentine:
That framing is a little bit of what we’re going to call a relational ask, and we can kind of break that down if you want to. But what I like the most about this is you aren’t going in there and saying, as the Wall Street Journal advised you to do was walk in and say, “I deserve to be promoted.” Well, we know from the research that is the quickest way to end your career. What you want to do is you want to go in and say, “Hey, as you know, I was able to add,” whatever it is, “three great clients last quarter. I think I can do that again this quarter. In order to achieve that, I wanted to talk to you about X, Y, and Z.”
I mean, let’s be realistic about the world right now. Things are expensive. If you make more money, what? You get to move 30 minutes closer to the office, and now you have an extra hour a day, at least half of which will probably go to being better at your job. You’re able to get better childcare so you can go to the client meetings Tuesdays at 7:00 PM. There’s all kinds of things that that enables that allows you to advance faster. Better for them, better for you because you’re delivering the impact that you’re capable of.
Tori Dunlap:
Yeah. I mean, let’s talk about that Wall Street Journal article because… I want to say you and I talked about it. I remember seeing it and just being like, “Oh, of course. Of course, this is the answer from the Wall Street Journal.”
Kathryn Valentine:
Yes, and this is from a negotiation, quote, unquote, “expert.” I think when we talked about this, I said the same thing, which is like, “I didn’t sleep for days because I can’t imagine the careers that were derailed because somebody took that advice.” And by the way, Tori, it’s not just in… Since you and I chatted last, the research lens has grown. It’s not just in negotiation, it’s also in time management. How many productivity bros are like, “Well, you just want to get to inbox zero, blah, blah, blah”? “Well, listen, dude, I do 750 to 950 more hours of unpaid labor every year than you do, so your tool’s not going to fit my life, and that’s okay. That’s totally fine, but stop acting like you know what this is, because you don’t.”
Tori Dunlap:
So talk to me about the advice that is commonly given to women that does not work. And we mentioned this in your first episode, but I think it’s worth talking about again, especially since this advice in national publications is still being talked about. So one is, yeah, you can’t just waltz in there and be like, “I deserve more money.” Talk to me about the other common mistakes that women are making that maybe even they’re encouraged to make.
Kathryn Valentine:
I think one of them is to make an easy ask like, “Oh, you should make it easy for them to say yes.” That’s actually not how negotiation works. We want to anchor high, and then we want to be able to agree to something. This is how we appear to be a very good team player. That’s number one. Number two, and I hear this all the time, is people who are like, “Well, I thought this negotiation is scary, but somebody said it’s just in my head.” Let’s go ahead and wipe the slate clean on that one. It’s not just in your head. This is your spidey sense trying to protect you. And Tori, I’m happy to go into the building blocks of what’s happening here and what leads to backlash. But essentially, as early as the age of eight, women know that there’s something about negotiations that means we need to tread lightly.
I have an eight-year-old. He doesn’t know that the tooth fairy isn’t real, but his female counterparts know that there is something about negotiation that is set up for them to lose. That’s right. The way that we’ve played the game, we’ve been set up to fail, and so what we want to do is we want to talk about changing the game so that it’s fair again.
Tori Dunlap:
So when we look at negotiations in this moment, because I want to talk about backlash in a second, but at this particular moment where everything seems awful, if cash is frozen, what are other things women should think about asking for instead if you do hear, “You know what, raises are not on the table right now”?
Kathryn Valentine:
So two things. One, I want you to ask for whatever it is that you wanted six months before your annual review. Companies have gotten really smart. They’re freezing budgets now, or budgets are due a couple months before your annual review, so let’s front-run that and ask for them as soon as possible, and then you can revisit.
Tori Dunlap:
Okay. So what you just said, I did not know that. So we have companies that are purposefully not budgeting in, “Oh yeah, we’re probably going to give this person this kind of raise.” They’re purposefully having those conversations six months before annual reviews are happening. Is that what I’m hearing?
Kathryn Valentine:
Let’s do kind of the average company calendar.
Tori Dunlap:
Yeah.
Kathryn Valentine:
Annual reviews are in December. Budgets for managers are due in October, which means that if you ask for something in December, your manager, when they say, “My hands are tied,” they might be telling you the truth.
So what you want to do is you want to make your ask in June, July, so that you can say, “Hey, I’ve passed performance, future vision that we’re all excited about. In order to accomplish that, I want to talk to you about this ask. What do you think? I want to talk to you about being promoted. I want to talk to you about a 10% raise. I want to talk to you about adding people to my team. What do you think?” And what you want is for them to either say, “Yeah, that sounds like a good idea,” or, “Ooh, I’m not sure.” At which point in time, you say, “I understand you’re not sure right now, or I understand you don’t think I’m ready for this opportunity. Can you tell me what I need to demonstrate to prove that I’m ready the next time it comes around?” Because objectivity reduces bias. So if you can get that checklist from them, then you can run that thread through. So that was to your first question.
So we have a list of 76 things that we’ve seen women negotiate. Plenty of them are compensation-focused. Only one of them is base salary. And so if salary increases are frozen, “Okay. What about a performance bonus? What about more in my 401(k)? What about X, Y, and Z?” That’s definitely a path you can go down.
Or if money itself is not negotiable, then let’s talk about all the other things you can negotiate that you can monetize later. Can you get a promotion which later on will come with a raise either at that company or a different company? I worked with somebody the other day who got a training at Harvard. It was a couple thousand dollars, but that, she’s going to be able to monetize in her next review. What else is it that you can ask for that you can either monetize later, which is my favorite, or that just allows you to have less stress and more joy in your day?
Tori Dunlap:
You’re going to be so proud of me. I helped counsel my partner through his first salary negotiation. And yes, he is a man, but I was very excited for him to get more money. They played such hardball with him, and not even in a way that was like, “Oh, we know what we’re doing.” It was just like, “We’re trying to get this role landed quickly, and we’re just trying to move things.” And I kept being like, “You control the pace of this because, at this point, you know that they want you.” I don’t think they were doing it intentionally. Some companies do. They try to purposefully get you to say yes quickly with the sense of urgency. I think they just weren’t aware of that. But the thing I kept telling him is I’m like, “You control the pace of this.” And they couldn’t pay him more money, but they gave him a sign-on bonus and they got him to where he needed to be with a creative version of that.
And so I think that this is what Kathryn’s saying is, yes, if we can negotiate base salary, absolutely. But when you’re looking at your total compensation, it is everything in that. It is their health insurance premiums that they’re covering, the ability to work from home, some, if not all of the time, sign-on bonuses, a better title, a learning stipend. There’s so many things that you can negotiate, especially when a company is saying, “You know what? Actually, our hands really are tied, and that’s not just a fun little thing we’re trying to get you to do so you don’t negotiate. We don’t have budget.” There are other things you can negotiate for.
Kathryn Valentine:
Well, and I think that time pressure is especially pulled in severances where we need you to sign this right now. Mm-hmm, don’t sign that right now. There’s so many things that you can negotiate. You’re a human being. You deserve a second. I also really love that he negotiated after he got the offer. One of the mistakes I see people make is they negotiate in the job interview process. We don’t want to do that because your leverage is highest after you’ve gotten the offer and everyone has said, “This is my person. My name is now next to their name,” and they don’t want to lose face by you saying no, and so that’s when you’re most likely to get what you’re asking for.
Tori Dunlap:
Yeah. They’ve also put in all of this work to find this person, and if they’re offering you a job, that means you are the candidate. So you have a lot more power in that moment than you do when you’re fighting 20, 40, 100,000 other people for this job. Yeah, exactly.
Kathryn Valentine:
I think the other thing I would want women going into job offer negotiations to know is that the gender gap in base salary is about 20%. That’s still dwarfed by the gender gap in other compensation thing.
Tori Dunlap:
Stock options is the big one. Yeah.
Kathryn Valentine:
Stock options, 80%. Performance bonus, 72%. Equity, anywhere from 10 to 40%. Number of people on your team, anywhere from 25 to 40%. When we do a negotiation, I would love for you to think really creatively and very holistically about what it is that you want to negotiate. I mean, I’ve worked with people who have negotiated parking spots because they were an expecting mother to a dedicated conference room because they wasted half their day trying to find a conference room to meet with their team and to a $2 million inventory system that saved their team 30% of their time. You are only limited by your own creativity when it comes to this stuff.
Tori Dunlap:
Okay. So we talked about bias and we have to keep talking about that when we’re worried about pushback or we’re worried about the optics of negotiating. So talk to me, you said you have a solution, and please, dear God, if there is a solution out there, tell me what it is.
Kathryn Valentine:
Let me tell you a little bit about where backlash comes from so that the solution makes sense. Is that okay?
Tori Dunlap:
Yeah, it’s great.
Kathryn Valentine:
So backlash is sort of two parts. Part one is societal concepts of gender. If somebody’s listening to your show, they’re very familiar with this, right? But I am expected to be others-focused. My husband is not expected to be the same. Let’s add that to negotiation, which is generally perceived of as this aggressive competitive battle. Even folks who have taken a semester’s worth of collaborative negotiation, when you say, “Okay, now picture negotiating with your employer,” they still default into this winner or loser thing. So backlash is when we take somebody who is expected to be others-focused and put them in an environment that expects a winner versus a loser. That’s inherently set up for us to fail, so what we want to do and the solution is we want to change that. So we’re going to wipe that off the table. We didn’t create that. That wasn’t created for us.
The three things we’re going to do to maximize our negotiation and eliminate, the researchers say virtually eliminate, so I’m going to use that language, the risk of backlash is, one, we’re going to think holistically. Again, what we talked about, it’s not just base pay, but what other things would allow you to deliver more impact, have a better time, reduce your burnout, any of those. Two, we’re going to use that relational ask that we talked about. So past performance plus your future vision that everyone can get behind plus your ask and then stop talking. Because women are so great, we’ll end up negotiating against ourselves. End up with a collaborative question, “What do you think? How can we make that happen?” that sort of thing. And Tori, if it’s helpful, I’m happy to run through some examples.
And then the third step we want to do here is we want to negotiate collaboratively, and that is a you and me versus the problem mindset. Interestingly enough, some new research came out last year showing that if you walk with the person while you’re negotiating, you get better results. And it’s because anything that we can do to avoid this being a face-off, we want to do, because we want to remind people, whether it’s how we’re standing, how we’re interacting, whatever it is, that we’re on the same team. We want the same thing, which is for the company to be successful. And part of that is for you as an individual to be able to be successful within the company.
Tori Dunlap:
Kathryn, this is so validating because I’ve been teaching this exact method of negotiation to thousands of women since 2019. So I feel very validated in that the research is now not only talking about this, but supporting it. I literally have talked about negotiation being a collaboration, not a conflict, and using collaborating statements so, “I want to work together with you on this. I want to find a number we can collaboratively agree on. I want to make sure that I can stay and do my best work. Help me do that.” That’s the kind of collaboration we’re talking about here, right?
Kathryn Valentine:
Well, yes. And Tori, there’s a reason why, when I read your book in 2022, I was like, “Oh, I have to email this woman.”
Tori Dunlap:
Well, and it was because I was seen in my own life and experience with talking with other women. It was like all of the research, especially in this time. My corporate career was 2016 to 2020, and it was very much the, “Yeah, you just negotiate like a man,” and I’m like, “If I try to do this, it will not work.” Again, it this, “I deserve this.” It’s like, “It does not work.”
Kathryn Valentine:
It doesn’t work, and it doesn’t feel good. So people just walk in uncomfortable. You don’t want to walk in uncomfortable. You want to know that what you’re doing is good for everybody, right?
Tori Dunlap:
Yeah.
Kathryn Valentine:
Who wouldn’t want that?
Tori Dunlap:
Yeah. So talk to me about what this actually looks like in practice, but especially not just the prepared speech you have. Because this is what my partner realized is it’s like I gave him the script of that first reach-out after the offer, but then as things started going back and forth and back and forth, this is where you start feeling out of your depths because it’s suddenly… It’s kind of like me when I try to speak French is it’s like I’ve planned the first sentence, and then they’re off and they’re having a real conversation with me, and I’m like-
Kathryn Valentine:
And they’re just like yes-
Tori Dunlap:
… “Fuck, I don’t…” Yes, and you did not stick to the script that I had in my head of how this was going to go. So talk to me about when we actually are in the midst of the negotiation. We may have already done the, “Here’s what I’m looking for in terms of my range, and here’s how we can do this collaboratively.” When we actually start talking back and forth, what am I saying, what am I doing, especially while my palms are sweating?
Kathryn Valentine:
Yeah, so a couple of thoughts. One, we know that the closer you can get to in person, the better your results. So people, right now, really want to negotiate on text or over email because it’s, quote, unquote, “easier.” That might feel better in the moment, but it’s actually not going to get you better results.
Tori Dunlap:
Interesting.
Kathryn Valentine:
So if you can do it live or as close to live as we can get, that’s what we want to do, one.
Two, a couple of general rules of thumb. One, don’t say yes too quickly. If you say yes too quickly, they’re going to assume that there’s more there that they can go get, and they’re going to go after it. Two, never give something without getting something in return. Because if you give something without getting something in return, again, it’s like children, they’re going to think there’s more cookies in the cookie jar because you didn’t tell them there was nothing else there.
“Hey, we’d really like for you to start immediately.” I’m going to try and riff off a little bit of the situation. “We really want you to start immediately.” “I understand you want me to start immediately. That’s going to be really tough because of X, Y, and Z. I think I might be able to pull it off, but in order to help me do that, can you throw me a couple thousand dollars in signing bonus because I’m going to have to move faster than I thought I was going to?” or, “I’m going to need additional childcare that I wasn’t expecting,” or, “I’m going to…” Whatever it is, help them make it easy for you to do the thing they want you to do.
Tori Dunlap:
The thing I always keep in mind too is it’s like if you can understand why they’re asking you, you can acknowledge why that’s important to them. So if you didn’t want to start early, for whatever reason, you were like, “No, I want to take a vacation,” or whatever, you can be like, “I am so excited about this job, and I really value that you’re excited to get me started. That means a lot to me. That tells me that you’re so excited for the work that I’m going to do, and that makes me even more excited to take this job. I’m wrapping up a three-year job at this other place. I would love to take some well-deserved rest so I can hit the ground running when I get back.” That is my way of saying, “Oh, you want me to start immediately because you want me to get going, and that’s great and I appreciate that and I see that. I’m going to go take some rest.” And then you brand it as, “Of course, I’m taking rest so that, when I start, I am ready to go.”
Kathryn Valentine:
And brand, to your point, it doesn’t mean it’s a lie.
Tori Dunlap:
No.
Kathryn Valentine:
It’s an absolute truth. Yeah. In the before times, I was working at a global firm that, quote, unquote, “didn’t negotiate.” I was just getting married to somebody that I’ve lived across the country from and wanted to have this really amazing month-long honeymoon was in my brain. But the firm was like, “Oh, everyone has to start on X date.” And so to your point of asking questions, I got on the phone with the HR rep and I was like, “Can you tell me why this date is important?” And she was like, “I am required by our legal team to have all of the new employee information uploaded by that date,” and it was like, “Oh, okay. Well, what if I start on that date, and then two days later I go on an unpaid leave? Does that work?” And she was like, “Yeah, that works.” So I started, and I just went on a six-week unpaid leave. Fine, win-win. But it only happens when you ask those questions that you were talking about of like, “Can you help me understand why this matters?”
Tori Dunlap:
What other places are we sinking the entire negotiation? Where else are we shooting ourselves in the foot?
Kathryn Valentine:
So I would say there’s sort of three, I don’t know, biggest mistakes that I see. One is undervaluing ourselves. So we know that women tend to undervalue ourselves by about 40%, starts when we’re eight. One of the course corrections you can make on that is benchmarking is great. But if you need to figure out how to course correct quickly, it’s what would you advise a friend of yours in the exact same position or same place to ask for, and that, we know, course-corrects. You’re usually spot on after that. So number one, don’t undervalue yourself.
Number two, don’t wait until your back’s against the wall and there are no other options. This is when we’re so tied into this one big conversation that we end up shooting ourselves in the foot because we don’t feel like we have other options. I would much rather you negotiate proactively than defensively.
And then the last one, I think, is negotiating just one thing. If you can negotiate a package of things, that’s great. Or if there’s one thing you really want, like that base pay, I would love for you to have a back pocket ask because they’re seven times more likely to say yes to you once they’ve said no to you. So if they say no to that… And actually, I think your partner’s example’s a great one. If they say no to that raise, “I understand you can’t do the raise right now. What about a signing bonus?” And like, “Oh, okay, I can make you whole on a signing bonus.” “Okay, great.”
Tori Dunlap:
Well, and the funny thing, he didn’t even have to ask for it. They gave it to him because he kept asking for increased compensation, and they were like, “We can’t do that, but we can do this,” and that was their concession prize. And he was like, “Yeah, sure. Great.”
Kathryn Valentine:
I also think the negotiation is a really good litmus test of whether or not that’s actually somewhere you want to work. If they were working with you-
Tori Dunlap:
Oh, I’ve been saying this for years.
Kathryn Valentine:
Yeah.
Tori Dunlap:
And it was actually halfway through the process. Again, I don’t think that this was vindictive, but they were trying to move so quickly. I kept telling him, I was like, “This might be a red flag. I don’t know if it is yet. But because they’re pushing you so hard, it might be something where you realize, ‘Actually, there’s this sense of urgency about everything at the company where… We’re not curing cancer. This is not an emergency room. This not a triage center.’ It might be a red flag.” And I completely agree watching how they move throughout the negotiation, because if they’re not willing to see your value now, they’re not going to be willing to see your value through your entire tenure of employment there.
Kathryn Valentine:
Agreed.
Tori Dunlap:
So the thing I hear from women all the time, and you said it like, “Figure out how to value yourself correctly.” How does someone actually do that? How do they figure out what their market rate is generally, but how do they figure that out, especially right now in this moment where there’s AI and there’s layoffs and all of that shit that they have to deal with?
Kathryn Valentine:
This is a great question. Okay. Foundationally, the way to do it is benchmarking. And we have, on our website, the Ultimate Guide to Benchmarking. It has a ton of resources on how to do this. Okay, fine. So we talk to people who have left the company because they don’t care anymore. We talk to people who are in the same role somewhere else. We talk to people who are in a different role, but in the same industry, yada, yada, yada. You kind of get yourself there. In the age of AI, what’s really interesting is that AI has the possibility of shortcutting that. And what I love about that is that we know that women have less time, and so I want a shortcut when I can get it. The problem we’re seeing right now is the research shows that AI is advising a woman with exactly the same background for exactly the same role to ask for 40% less, 40% again, that magic number. I don’t love that.
Tori Dunlap:
I’m not shocked by it.
Kathryn Valentine:
It’s a biased in, biased out system.
Tori Dunlap:
Yeah. Do we tell AI I’m a man?
Kathryn Valentine:
Here’s what I would do is I would use AI as one data point. And if you don’t have a lot of time, don’t let this stop you from negotiating, just stop there. But type in the phrase, “Please remove all gender bias in your response.” It’s not going to make it perfect, but it’s going to make it a lot better. In my ideal world, you’re also going to talk to a former employee and you’re going to talk to one of your mentors who knows what everybody’s making and all of that stuff. But if you don’t have time, just type in that phrase, and we’re going to do the best we can.
The other thing about market value is so much of it is perception. Are you a high performer? Are you a low performer? We’re so busy right now, people don’t actually know. They just know how you present. Research by Northcroft and Pinkley shows that people end up taking what you make and using that to deduce how valuable you are, not the other way around. And so accepting less implies that you’re bringing less value to the company. And so I would actually prefer you to ask a little high and then negotiate down because that’s how we’re going to put forth and then reemphasize the perception, which I’m going to argue is probably true, that you’re a high performer.
Tori Dunlap:
Well, and you’ve given some really blunt advice before, asking the real benchmark, which is just, “Ask a white guy,” that’s where we should be going. Do we need to be adding that into who we’re asking beyond our mentors and our colleagues?
Kathryn Valentine:
I’m really glad that you brought that back up. So we know with networks that people tend to flock with those that are like them. The problem with women benchmarking then is we benchmark a group of people who are all being paid 20% less. Ask a white guy’s a pretty good one. I also, in asking, like to say, “Hey, I’m getting ready to negotiate. I’m thinking of asking for X. What do you think?” And what I found is, most of the time, that person is like, “Oh yeah, I make Y, so X makes sense,” or, “Hey, I make Z, you might want to ask for a little bit more.” And so if I get a little bit, the majority of the time, they’ll give a little bit back, or at the very least, they’ll say, “Oh, that seems a little high,” or, “Oh, that seems a little low.” And directionally, that’s helpful.
Tori Dunlap:
And everybody listening, I really want you to take that advice to because it’s so easy with the negotiation to avoid talking about money and being like, “Okay, I’m going to go on Glassdoor,” or I guess the 2026 equivalent is, “Yeah, I’m going to just talk to AI.” And it’s like you have to talk to real people, even if it’s uncomfortable to talk about money. One, because you need real data. You need real data from other people, especially if you are telling your boss or your potential boss, “I have done research to know what my market rate is.” It can’t just be, “I type my job title into Glassdoor.” That cannot be the research. But also in addition, if you want this negotiation to go really well where you’re about to talk about money with somebody that seems a little intimidating and you’re not comfortable talking about money with somebody that you know or somebody who’s mentored you, then we got to start there because you’re going to get more comfortable being uncomfortable the more reps you put in.
Kathryn Valentine:
Agreed. The other thing that I’m always surprised by is how many people I work with who are doing a negotiation and they benchmark with somebody and then end up getting hired by the person they benchmark with.
Tori Dunlap:
Interesting.
Kathryn Valentine:
Because while they were talking about it, they were like, “Hey, I’ve done X, I’m getting ready to do Y. I think I’m going to ask for Z,” and that person says something like, “Oh, shoot, you’re great. We need you,” and then three or six months later ends up swooping in and hiring you. Great. I love that for you. Let’s plant some more of those trees.
Tori Dunlap:
So we mentioned AI. I don’t want to spend too much time talking about it, but a lot of people are leaning on AI right now to prep their resumes and their interview questions and also to negotiate. Is this a good idea?
Kathryn Valentine:
So with benchmarking, I think we’ve done kind of a course-correct. It’s not great, but sometimes we walk before we crawl, crawl before we run. When we’re talking about negotiating, role-playing, actually going through it, is one of the most underutilized tools. It does help you have better outcomes, and people hate doing it. Please do it. I don’t love when people only do it with AI because AI again has consumed what’s out there, and 98% of what’s out there is negotiation strategies for men, and it doesn’t say that. AI is going to give you back something that probably isn’t research-backed, at least not for women.
And so what I would love is if you listen to… Go watch my TEDx, it has 400,000 views, listen to this podcast again. But work through your relational ask, then work through it with somebody else who’s a real human being. I think AI though is really good at predicting what things the person you’re negotiating with… what concerns they might bring. So that allows you to prep your response, like, “Hey, I’m going to ask for a raise. I’m going to say the following thing. What concerns might the person I’m negotiating with have?” And it’s a really good way to tease some of those out in your prep.
Tori Dunlap:
Yeah. And this is also where the voice-to-text can be really helpful if you’re literally just like, “This is what I’m planning on saying and the way I’m planning on saying it,” if you don’t have a negotiation buddy to do this with.
Kathryn Valentine:
Yeah. Great point.
Tori Dunlap:
Again, I’m living this because my partner just did it, and this is the first time I’ve been knees deep in a negotiation in a very long time, at least on the asking side. But the thing that I had him do is I gave him his script and he was doing it over the phone, and so I had him literally write down what he was going to say on the paper. But then I also purposefully tested him of like, “Okay, he’s not going to follow this script. The person you’re negotiating with, he’s not going to do exactly what we expect him to do all the time.” So we ran through like, “If this negotiation goes totally sideways and he gets really defensive or weird, here’s how we’re going to respond. If he gives you exactly what you ask for, here’s how we’re going to respond.” Likely he’s going to do something in the middle, which is go like, “Oh, I’m not sure if we can do that. I have to go back to some people and have a conversation.” That’s the most realistic version of this.
So I want to talk about that because that’s the murky middle of, “Oh, I got to go talk to somebody.” I see women go either, “Oh, don’t worry about it. It’s okay, blah, blah, blah,” and they just accept whatever’s going on, or they don’t know what to say next. So when somebody gives them the like, “I don’t know if this is possible. I’m going to go have to talk to somebody,” what do you say to that?
Kathryn Valentine:
“That sounds great. Is there anything that I can send you that would make that conversation easier? How can I help you?” A couple of things came into my mind when you were giving this really helpful example. One, the average negotiation lasts 25 days. People come to me and they’re like, “Oh, I failed. I just got out of the office and we don’t have an answer.” It’s like, “No, no, these are big important conversations. They deserve time. Don’t sweat it. It’s a series.”
Tori Dunlap:
Kathryn, I have to stop you. I’m so sorry. Everybody, 25 days, so over three weeks, nearly a month long. It’s like all of February basically. So if you’re going in and thinking, “I will have one conversation, and if I didn’t get what I want after that one conversation, it’s over,” it is not over, not even close. So 25 days. And if that seems like a long time, think about that $1 million stat. You are making over $1 million more in your lifetime for having 25 days of discomfort. We can tolerate 25 days of discomfort for 35 years, 40 years of making what we’re actually worth. I just wanted to pause you there really quick. 25 days is a long ass time. It’s a long time to experience discomfort.
Kathryn Valentine:
Tori, I love this point so much because I love that you’re doubling down on the motivation to get you through the messy middle. And so what I would love people to do is go to our website, look at that negotiation calculator, and figure out what your number is. So I’m filling it out now. If you’re 30 and your current compensation is $75,000, Tori, why don’t you pick an increase? The average increase is 2.7. People who take our course get about 10%. The people I work with in coaching get about 28%. Why don’t you choose a raise?
Tori Dunlap:
Let’s do 12%. That seems like a good amount.
Kathryn Valentine:
Great. So let’s say you’re 30 years old, you’re making $75,000, and you negotiate a 12% raise. That is $569,000 over the course of your career just because of that one negotiation. Let’s assume you never negotiate again, you just sail off into the sunset, right? That’s half a million dollars. To your point of getting your motivation in line, fill out that calculator, write on a post-it note what your number is.
And then the other thing about it being 25 days that I actually love is it makes breaks normal. So if things start to go off the rails, as you said earlier, if somebody that you’re negotiating with gets upset, or sometimes I like to start negotiations with, it’s now a good time because I’ve been in situations where somebody’s uncle passed away the day before and they’re at work because they’re in shock. This is not a good time for this. So it takes a little bit of the time pressure off. It also means that if you feel like it’s going off the rails, you can say, “Hey, this is a really important conversation and you’ve given me a lot to think about. Why don’t I take 24 hours and think if there’s some more creative wins here, and can I come back to you tomorrow? Can we talk about it next Tuesday in our meeting? Can we, whatever, grab dinner?” Feel free to take a break.
Tori Dunlap:
Yeah. And the other thing is it’s just a lot of… As somebody who now is on the opposite side of it, who’s hiring people, it is often, “Oh, I have to get my contracts together,” or, “I have to go and chat with legal,” or, “Oh, the person I need to talk to, they’re out sick or they’re out on vacation,” and it’s just like… I think it’s so easy to believe that if this is taking a long time, it’s because you fucked up, and I think that’s such rarely the case. And if it truly is, it’s taking a long time because either this company is turned off by you asking for more money or because they don’t have their shit together, that tells you everything you need to know about this organization.
Kathryn Valentine:
Do you want to know the number one reason why in my client’s negotiations it takes a long time?
Tori Dunlap:
Oh, because the companies don’t have their shit together.
Kathryn Valentine:
Because the companies come back and say, “We actually think you’re overqualified for this role. What do you think about that role?” It’s amazing what you can do in a negotiation.
Tori Dunlap:
Yep. And it’s realizing, when I say don’t have their shit together, it’s either disorganization or it is going, “Oh, we actually need something different out of this role than what we thought.” And I will say candidly, that even happens with us sometimes. And it is, we find a great candidate, and we’re like, “Oh, actually we could do this with them as opposed to the role we had envisioned,” and so then we have to do some reorganization. We have to figure out if this person is really great and we want to make sure that they have a place here. I want to make them a place as opposed to trying to square peg round hole.
Kathryn Valentine:
Well, and with companies that do that, that take their time to do that, the employee’s going to be happier. They’re going to stay longer. The employer is going to be happier. I mean, I love it when companies think about, “This is the right talent. Now what box do I need to create for them?”
Tori Dunlap:
Totally. So you mentioned the 25-day discomfort of a negotiation process. What other things happen in the murky middle that cause us to panic?
Kathryn Valentine:
You spend time with someone who doesn’t believe in you. And I don’t know if this is friends, if this is your uncle, if this is… Actually, a lot of what I see right now is the parents’ generation saying, “Well, you can’t get a job if you don’t have a job. You need to get a job right now when you have a job. Don’t risk a layoff or anything else.” And that’s just not true anymore. I think that there’s a lot of fear from an older generation that sometimes gets put on when you have 25 days to wait. I will say one thing that we see that helps combat a lot of it is planning a reward right after the first conversation simply for being brave enough to have it. And having that dinner with good friends or the bottle of wine you were looking forward to or whatever it is gives you a whole new energy in that room.
So in the murky middle, one, it’s starting to question yourself. Don’t do that. You set up this negotiation for a reason. I believe in you. Let’s surround yourself with people that also believe in you. Sometimes people try and push it to a more async version to get through it. Sometimes that has to happen. It’s not ideal. So if you can wait for the meeting and have it all together, that helps.
Tori, is there anything that you’ve seen that I’m missing?
Tori Dunlap:
I think a lot of that is just the impatience. You cry uncle too soon because you are just uncomfortable with the uncomfortable because I think, again, all of the expectations for us as women is we just accept whatever’s given to us and we’re happy with whatever that it feels like we’re being difficult just because it’s like, “Oh, it’s taking 25 days,” and it might take more than that. That’s the average. “This is taking 30 days, 40 days. I don’t want to piss anybody off, so I’ll just accept whatever.” And I think that’s all mindset work, and that’s all reminding yourself that this is normal and that the very reason you’re having a conversation about your compensation is because you want to be compensated fairly so you can do your best work. And that’s it. It’s not greedy. It’s not selfish. You’re stalemating. You are having a collaborative conversation about how you can get compensated fairly so you can do your best work.
Kathryn Valentine:
I think the other thing that I would build in there is develop an alternative, right?
Tori Dunlap:
Yeah.
Kathryn Valentine:
Well, most people don’t date one person their whole life. If it’s not this, what else would it be? I just bought a minivan on Monday. I’m in that phase of life. It’s not just the Honda Odyssey, it’s also the Toyota Sienna. What other things are that could be a good path forward for you? Because when you have options, you’re in a better place to maximize that negotiation. And so I think what we’ve said in terms of the messy middle is motivate yourself, remember that number, look at our calculator, remember that it’s normal, it’s just so normal, 25 days, and that’s an average, don’t sweat it, surround yourself with the right people, especially during that point in time.
Tori Dunlap:
One, too, with the surround yourself with the right people that I think about is there are certain people I go to for certain things. And if you go to the person in your life who unfortunately maybe plays small or can’t believe you would ask for more money, they’re going to sow doubt in your brain. And they might be great friends or… Your mom might be great for other things in your life, but I know there are certain things I go to my dad for that my mom will freak out about and vice versa. There are certain things I can tell my best friend that I might not be able to tell this other friend that I have. I think that you have to understand in that specific season who are the people that are going to rally behind you and go, “Yeah, I’ve negotiated. I know how to do this.” “100%, you should be doing this.”
Don’t talk to the people who have never negotiated. Don’t share this with them because it’s going to end up freaking you out when they go, “Wow, you’re asking for that much, but the economy’s really bad right now. Are you sure that’s going to work out for you?” They care about you. They’re trying to look out for you, and that’s how they think they’re going to take care of you is preventing you from having any sort of discomfort or pain. But those are not the people in a salary negotiation that are actually going to help push you and challenge you and confirm, “Yeah, you’re right for negotiating this amount of money.” So I think it’s having people that support you, but understanding that, for that 25 days, I’m not calling my mom. I’m not calling my mom and talking to her about that particular thing because she will freak out.
Kathryn Valentine:
Right. It’s don’t get advice from the messiest person you know about how to organize your closet.
Tori Dunlap:
Ooh. Yeah. Yeah-
Kathryn Valentine:
Right?
Tori Dunlap:
… it’s true. And specifically about that thing, because money and career and negotiation, it’s of course very gendered, but it’s also very generational. The amount of times that my mom early in my career were like, “Just go and show up at the office and bring your resume and they’ll give you a job.” And it’s like maybe, maybe that’s not really how it works. Sometimes it is, but it’s very different advice in how her career was approached versus mine.
Kathryn Valentine:
Or also don’t take on any risk whatsoever because we don’t want to put your 30-year career and your pension there at risk. Well, guess what?
Tori Dunlap:
Yep. The pension’s already at risk. Yeah, totally.
Kathryn Valentine:
It’s gone.
Tori Dunlap:
It’s gone.
Okay. So before we get into a rapid fire, the question I have for you about all of this, about making sure we negotiate, making sure that we are helping mitigate any bias is what happens then when we’re in a career for a while and we’re starting to wonder, “Oh, is there something else out there?” Maybe that’s a different job, maybe that’s even a different career path, but then all of the… Gas is $6 and the economy’s bad and layoffs and AI start creeping in. How do we reconcile that the economy might be bad with also understanding, “Yeah, we can find something else”?
Kathryn Valentine:
I mean, part of it is remembering how big this world is, right? Six billion people, you’re going to tell me this is the only one job that will hire you? That’s not true. I think the other part of it is, and actually back to something that I learned in your book about what are the three things that you care the most about, it’s okay if you’re in a season where one of those isn’t X, Y, or Z. So early in my career, I was in a season where I wanted to learn as much as I could. I didn’t care as much about the title. Fine. Right now, I have these little kids that think I’m cool, so I want to spend all my time with them, and so right now negotiating for the schedule is the most important thing. I’m not necessarily totally maximizing on the money the way that I would have before.
And so I think part of it is being really honest with yourself about what the next couple years should look like. Don’t ask a forever question we can’t answer. But on the next couple years, what do you care about? And then what are other options that could give you that thing? And frankly, I would love for you to always be able to answer the question, if you weren’t doing this, what would you do tomorrow? I’d love for you to know that. I mean, this is why we network. Because if we lose our job, we want to know what are the three phone calls we’re going to make that night. And so keeping those options generating is always going to be, I think, the most helpful thing you can do.
Tori Dunlap:
I lied. I have one more question. When I look-
Kathryn Valentine:
Tori, you know I’ll talk to you for ages. Let’s do it.
Tori Dunlap:
I know, I know, I know. The thing that I experienced very acutely is I realized obviously very early on in my career, mid-20s, that I did not want to work for somebody forever. And in fact, every year that went by, I was like, “Oh, I had one foot out the door. I am ready to be my own boss,” because of many reasons. But one, my salary was pretty capped. Two, I was working for a lot of men I didn’t respect and who didn’t respect me, quite frankly. And three, I just realized it was going to be very hard to do what I emotionally, financially wanted to do in a structure that I did not build. Obviously, we know that the corporate environment, that work, that life, that the world in general is not built for women. So at what point do you counsel somebody to say, “Yep, go build your own thing”? At what point should a woman think, “Actually, I am not going to get what I need to get out of this corporate environment, and I’m ready to bet on myself”?
Kathryn Valentine:
Tori, I have to be honest with you. I wish I had an insightful answer to that question, but I think it comes from within the person, right?
Tori Dunlap:
Yeah.
Kathryn Valentine:
I Mean, obviously, I did the same thing a few years ago, and it came because I no longer could deal with the fact that I wasn’t in charge of my time. Before it didn’t matter to me, and then all of a sudden I couldn’t handle it. There’s pros and cons to that. I do think one of the things that I’ve seen in our negotiation coaching is that, sneakily, 20% of our clients now are entrepreneurs who are female, who are figuring out how to negotiate with clients. And so I think it’s really interesting, and I haven’t seen the stats on it yet, although you may have, of the movement of women saying, “Screw it, I’m out-“
Tori Dunlap:
It’s a lot.
Kathryn Valentine:
“… because I want to create an environment where I am able to be financially rewarded for the output that I create, not the input that I demonstrate.”
Tori Dunlap:
Yeah. I mean, I don’t have the exact stats on it, but post-COVID, we’ve seen so many more women navigate towards part or full-time entrepreneurship, and it’s largely because of children and time. A lot of moms realized in COVID, “This is not working for me and the expectations are too high for managing both at the same time.” And so I think a lot of women have been forced to build their own thing in a way that, again, comes with challenges, but is very, very fruitful. And I do encourage women that if your corporate career is not working for you, one, there’s a company out there that will treat you with respect. They do exist. And if you, A, don’t want to find it, or B, for whatever reason, are not finding it, then it’s time to build your own. And that’s what I kind of realized is it’s like any job I had was not running their business the way I wanted to run a company. And so I decided to run my own.
Kathryn Valentine:
Tori, I had this one interview, and when I had it, I had an MBA. I was one of the youngest advisors ever at McKinsey, I had already been involved in the sale of two companies, and I asked this major company what their part-time options for me would be. And the man that I was interviewing laughed and it was like, “Oh, that’s where we are. Okay. Okay, cool. You’re a children’s brand. But if you’re laughing about giving me flexibility as a mom, I think this is what I’m going to call it.” And I think we all, well, any of us who have making this decision that you and I have, have had that moment.
Honestly, you’re 10 years younger than me, I’ve been fascinated by folks like you and our friend Mallory who, and Mallory and I have had this conversation, made the decision because one day she wants to have the flexibility for X, and she knows that it’s going to be a boulder she has to push up a hill early, so she wants to do it before she needs it. And that to me, was like, “Oh, that’s impressive foresight. I just got hit by the boulder first.”
Tori Dunlap:
Yeah. And I think that maybe that is my question is it’s like, how can we start thinking about creating time flexibility in our lives before we might be at our wit’s end about it? And I think that that is a friction point where we’re both trying to just see the path in front of us the next couple years while also trying to solve a 10-year-from-now problem, and that leads to its own issues.
Really your advice about creating plan B and plan C, I think, is what this looks like. I encourage anybody listening to have one of those plans B, maybe I do my own thing, at least if it’s part-time. So that if plan A is this dream company, plan B is a good enough company, maybe plan C is entrepreneurship, maybe plan C is I am going to invest in myself. I just don’t ever want to take that off the table for women. Because in my own life, I have seen it radically change every single aspect, including my financial life. I would not be where as financially stable as I am at such a young age, if I would’ve kept corporate. It just wouldn’t have happened at the same rate. And I’ve seen it for other women in my life who run their own businesses, but make a quarter of what I do or even an eighth of what I do. And they have such freedom and stability in that when it’s often been labeled such an unstable choice.
Kathryn Valentine:
Well, and look at the richest people in the world, the richest people in America, I’ll do that, they’re entrepreneurs. The fastest path is entrepreneurship. It carries risk. That’s part of the deal. I will say, if you want to stay as a W-2, which what we know from the research perspective is if flexibility is going to be really important to you, you want to be at a middle tier company. So 30,000 employees is kind of the key that you see in the research. Too big and you’re very substitutable, too small, and you’re too important, so 30,000 employees or so. And find two really strong sponsors that will stand by you when you want that.
I mean, Tori, you and I are a certain brand of people. We also see people who… I did a negotiation recently with an incredibly well-compensated woman in tech. She’s W-2. And part of it for her is she loves her job. She doesn’t… flexibility isn’t as important to her. It’s agency and trying to grow that. It’s cool. Then maximize for that. You don’t need to maximize for what I’m maximizing for. We should be having different negotiations because we’re different people.
Tori Dunlap:
Yeah. And understanding what your motivation really is. What do you actually want? And I think that’s a really, really great piece of homework for people is it’s like, what do you want your career to look like? Do you want to make a bunch of money and have a big sexy title? That’s going to require potentially 60, 70, 80 hours of work a week. Do you not want that? Okay, great. Then you have to figure out, what do you want? Not what does somebody else want for you or what does society expect you to have, but what do you actually want your career and your life to look like? And you can make decisions that get you closer to that. You’re not at society’s beck and call about what the expectations are. You can find companies and organizations that support whatever dream you have. And again, your dream might be different right now than it is in five years.
Kathryn Valentine:
And I actually think the hardest part of negotiations I see is people who don’t know what they want to negotiate because they don’t know what their dream is. And I think in watching you, Tori, you are uniquely capable of this. But really separating out your voice from your parents’ voice or your sister’s voice or your partner’s voice or your kid’s voice or whatever it may be, what is your voice saying? It can be tricky to put your finger on that, but once you do, let’s build a whole world for you there. And I think negotiation is a really good tool to help you do it.
Tori Dunlap:
Kathryn, quick rapid fire. Are you ready?
Kathryn Valentine:
Let’s do it.
Tori Dunlap:
Okay. One thing everyone should stop negotiating for.
Kathryn Valentine:
Only base pay. Make it bigger than that.
Tori Dunlap:
Most underrated thing on your 76 things you can negotiate list.
Kathryn Valentine:
My favorite is new systems, new business systems, because it allows you to get your job done so much faster.
Tori Dunlap:
Worst negotiation advice you hear repeated constantly.
Kathryn Valentine:
Tell them you deserve it, or tell them that your own personal costs have gone up, rent’s gone up, da, da, da.
Tori Dunlap:
Oh, that’s my least favorite one.
Kathryn Valentine:
I hate that for you. That’s terrible, but we need to make a business thing.
Tori, I have another one. Tell them that it’s about asking for what you’re worth. I hate this. You’re infinitely worth things because you’re a human being. I think when we tell people make sure you’re getting what you’re worth, they get all wrapped up in this one thing. This is just market value. This is just dollars and cents. This is not who you are. This is not what you’re worth.
Tori Dunlap:
A no that turned out to be the best thing that happened to a client.
Kathryn Valentine:
A job she really wanted. They couldn’t come to terms on the negotiation, and three months later she found out it was because the firm was going belly up. She was like, “It’s so weird. It shouldn’t be this hard. I really wanted it.” It was her dream title. For 20 years, she’d wanted this title. But I think sometimes when things don’t go well, we end up finding out later what the story was. And actually, another thing I’ve been seeing a lot right now is people whose sponsors are backing away from them, and six months later we find out it’s because the sponsor was let go and knew you have two weeks to wrap things up kind of thing.
Tori Dunlap:
So for the woman listening who’s scared, she’s looking at layoffs and the headlines and thinking, “I should just keep my head down this year,” what do you want her to do this week instead?
Kathryn Valentine:
Grab a journal, grab your favorite drink, listen to your favorite music, and write out what your dream life would look like. And from there, figure out what’s one thing you can negotiate that would get you a step closer. Is it that you leave early on Fridays because you love hiking and that’s how you can get out to the place you like to hike? Is it negotiating that you’ll sit in as a silent observer in a certain meeting because you’re really curious how, I don’t know, X, Y, and Z is working? But think about what that one thing is and just start there.
Tori Dunlap:
I love that. Plug away, my friend. You have some of the best resources on negotiation I’ve ever seen. I’m so excited after your TED Talk. Everybody needs to go watch that, but tell people where they can find out more about your work.
Kathryn Valentine:
Tori, that means a lot coming from you. Thank you.
I think the first one is, if you want that list… Don’t reinvent the wheel here. Get that list of 76 Things. It’s at 76things, T-H-I-N-G-S, .com. And then we have a negotiation course. It’s 45 minutes because you’re busy. It’s supposed to be priced to be reasonable. We have negotiation coaching. It’s more expensive, but if it’s a big negotiation, I’m here for you. Let me know how I can help.
Tori Dunlap:
Amazing. Thank you so much for being here.
Kathryn Valentine:
Thanks, Tori. Always good to see you.
Tori Dunlap:
Thank you for listening to Financial Feminists, produced by Her First $100K. If you love the show and want to keep supporting feminist media, please subscribe or follow us on your preferred podcasting platform or on YouTube. Your support helps us continue to bring this content to you for free. If you’re looking for resources, tools, and education, including all of the resources mentioned in this episode, head to herfirst100k.com/ffpod.
Tori Dunlap:
Thank you for listening to Financial Feminists, produced by Her First $100K. If you love the show and want to keep supporting feminist media, please subscribe or follow us on your preferred podcasting platform or on YouTube. Your support helps us continue to bring this content to you for free. If you’re looking for resources, tools, and education, including all of the resources mentioned in this episode, head to http://herfirst100k.com/ffpod.
Financial Feminist is hosted by me, Tori Dunlap. Produced by Ellice Ellis and Tamisha Grant. Audio and video engineering by Jonathan Kirk. Marketing and Operations by Karina Patel and Amanda Leffew. Special thanks to our team at Her First $100K, Masha Bakhmetyeva, Rae Wong, Daryl Ann Ingman, Meghan Walker, Marciella Baietto, Demi Ganim, Taylor Toll, Zoe Rezek and Stormy McBride. Promotional graphics by Mary Stratton, photography by Sarah Wolfe, and theme music by Jonah Cohen Sound. A huge thanks to the entire Her First 100K community for supporting our show.
Tori Dunlap
Tori Dunlap is an internationally-recognized money and career expert. After saving $100,000 at age 25, Tori quit her corporate job in marketing and founded Her First $100K to fight financial inequality by giving women actionable resources to better their money. She has helped over five million women negotiate salaries, pay off debt, build savings, and invest.
Tori’s work has been featured on Good Morning America, the New York Times, BBC, TIME, PEOPLE, CNN, New York Magazine, Forbes, CNBC, BuzzFeed, and more.
With a dedicated following of over 2.1 million on Instagram and 2.4 million on TikTok —and multiple instances of her story going viral—Tori’s unique take on financial advice has made her the go-to voice for ambitious millennial women. CNBC called Tori “the voice of financial confidence for women.”
An honors graduate of the University of Portland, Tori currently lives in Seattle, where she enjoys eating fried chicken, going to barre classes, and attempting to naturally work John Mulaney bits into conversation.