Why You Need To Have More Women In Your Sales Team With Fred Diamond, Creator Of The IES Women In Sales Program [Episode 69]

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What is the best sales skill you learned from a woman?

It is often said that women are better than men when it comes to selling, so why don’t we have more women in our sales teams? And even if they’re there, why do men dominate meetings and conversations? These questions were on Fred Diamond’s mind when he started to create the Women in Sales program. Fred is the Cofounder of the IES Women in Sales program, whose mission is to help employers attract, retain, motivate, and elevate top tier sales talent. In this conversation, Fred shares his thoughts on how women can be empowered to take more roles in sales and how having a community like the IES Women in Sales program can help. They also discuss the qualities that both women and men in sales need to have in order to navigate a more customer-centric sales environment. They also tackle how sales employers can attract, retain, and grow female sales talent in the rapidly changing world of sales. Tune in for some great insights!


In this episode you will learn:


Episode’s guest – Fred Diamond

CSS 69 | Women In Sales

Fred Diamond is the host and producer of the award-winning Sales Game Changers Podcast and the co-founder of the Institute for Excellence in Sales (IES). He is also an advocate for Lyme disease treatment and is a frequent article contributor to LymeDisease.org. His books, “Love, Hope, Lyme: What Family Members, Partners, and Friends Who Love a Chronic Lyme Survivor Need to Know” and “Insights for Sales Game Changers: Lessons from the Most Important Sales Leaders on the Planet” are now available on Amazon. 

Visit his website: www.i4esbd.org

Fred is giving away a a copy of his e-book Insights for Sales Game Changers. Click this link for more: One-Page-Insights-for-Sales-Game-Changers.pdf


Why You Need To Have More Women In Your Sales Team With Fred Diamond, Creator Of The IES Women In Sales Program

I’m bringing another amazing guest. His name is Mr. Fred Diamond. He owns a company called the Institute for Excellence in Sales. We’re going to be talking a lot in this episode about women in sales. Men, before you go and say, “This isn’t for me,” believe me, it’s for you. It’s about how women are entering and starting to dominate the field in many capacities, why they’re doing so, and what we can learn from this process.

For example, empathy. Not a lot of men are as empathetic as women. It’s pretty much across the board, but the reality is that men have strengths. Women have strengths. We’re going to talk about the strengths of women. We’re also going to talk about why you, as an employer, may want women on your staff to balance out what you’re trying to do. Sales have shifted over the last few years. It has been shifting a little slower. With the pandemic that happened, it’s starting to shift in a very big way. Fred has been working with women and focusing on women in sales for a long period.

He has a lot of great things to say. We have a bunch of cool information we were talking about that we could bring to you so that you can also adjust your sales process if you’re male to sell to more women. If you’re dealing with more women in general, you can also understand where they’re coming from. Women, you can also understand where men are coming from because Fred and I also discussed that. Without further ado, let’s go to Mr. Fred Diamond. Here we go.

Fred, welcome to the show. Thanks for being here.

I am excited, Doug. I’m very excited to hear your questions. Let’s get to it.

We’re going to talk about women in sales. I find that this is a topic of fascination for me because I have three women in my household. They sell, but when it comes to employers and the corporate environment, it’s a little different than the men’s selling world in some regards. I disagree that it should be, but I found it to be. Why don’t I turn it over to you? Why do women, in general, even make better salespeople than men?

It’s a funny story. I run what’s called the Institute for Excellence in Sales. We’re a member-based organization. I’m based in Northern Virginia, right outside of Washington, DC. Typically, we call our customers partners. They are companies with at least 100 sales professionals. Our mission is to help those employers attract, retain, motivate, and elevate top pure talent. I’ll tell you how this whole thing started. It’s great that the two men in sales are talking about women in sales because we’re proud to be an ally to help women in sales.

Years ago, there was a guy in the DC area. He runs, at the time, a $1 billion company. It’s an $8 billion company. When we created the Institute for Excellence in Sales, he said, “If you could think about this, I would be interested in helping support what you’re trying to do.” At the time, he said, “Half of my sales professionals are men and half of my sales professionals are women. The women perform 8% to 9% better than the men.”

He was very meticulous in his metrics. He said, “I can’t understand, though, why they shut down in meetings. It drives me nuts. I know that they perform 8% to 9% better than the men, but whenever we’re in a group, it’s like eighth-grade science class. Men will take over. These women who I know are better at sales because I know their numbers shut down. If you could do something, I would love to support you and things like that.”

That led us on a journey to creating the Women in Sales program. We have had a couple of iterations of it to get it right. We finally have gotten it right. I have a partner. Her name is Gina Stracuzzi. She was announced as one of the Top 50 Most Powerful Women in Sales by Demandbase. Here’s the answer to that question, which I have discovered over the years of having worked with hundreds of amazing men and women in sales.

If you were to ask a guy, “How would you solve this problem?” All of a sudden, you and I would come up with three answers. We would say, “There are three things we need to do. Number one. Number two.” We wouldn’t even know what the number three is, but we would be thinking about it as we’re giving our answers. The women would sit down and say, “That’s an interesting question. Let me think about what the answers might be.” The next thing you know, the meeting is over. The men have superseded the women.

The other thing I’ve learned over the years with our Women in Sales program is that if a guy is applying for a job and meets 1 of the 10 criteria, he’s going to apply, go after it, and sell himself. Women might say, “I only meet 8 of the 10 specifications. I’m not going to apply.” We have heard that from hiring managers, women in sales leaders, and also women in sales professionals as well.

There are some things that come up time and time again that are inherent in how there’s a difference, but the one thing that has been impressive running the Institute for Excellence in Sales is that there are so many talented women that we have come across at companies like Oracle, Microsoft, Cvent Software, and Salesforce that are amazing. They’re customer advocates. They’re committed to doing great work for their companies.

There are inherent biases that discourage some women from pursuing careers in sales. Women need to support each other to be successful. Share on X

I can hear all the men on this line here reading this and going, “Doug, I’m going to get you for saying women are better than men in sales.” It has been my experience that women do outsell men in most cases. I do believe based on what you were talking about that part of the reason that men are showcased in that fact is if somebody answers a question, we’re going to have an answer. That’s it. Women, in general, think through things differently than men, but I also believe that they’re far more astute in finding problems and asking questions more than men. Men will tend to direct more. Women will tend to ask more circular questions. That has been my experience. How about yours?

There are great men in sales. There are tremendous women in sales too. To be honest with you, we don’t even have the stats. We have tried to gather some stats to show if the statistic that the CEO mentioned to me years ago is still valid. I can’t say that but what I can say is one of the reasons why we created our Women in Sales program is the mission of the IES is to help employers.

We’re here to help employers get their people better at sales so that they could be more proficient with their customers. We have noticed a number of things over the years that make it difficult for employers to attract the best employees. We’re doing this show in the late summer of 2022. The competition for talent is ridiculous. It’s so fierce even with the best companies in the world.

We have all heard of the lingering effects of the Great Resignation. On my podcast, one of the VPs I interviewed called it the Great Reshuffle as companies are rethinking how their sales organization is going to be put together as people are still resistant to going back to an office. Customers, in some regard, are still resistant to fully going back. How do we put our organization together and be successful?

I want to tell one quick story that changed my whole impression of the women in sales story. I was very excited when the CEO said, “You should do this,” because it gave us another reason to bring something to the market. The customers that we serve at the Institute for Excellence in Sales are typically B2B companies, tech services, and hospitality, usually with at least 100 salespeople.

We created our Women in Sales program. We had two types of people. We had those who said they’re salespeople. It doesn’t matter whether male, female, whatever it might be, short, or tall. You’re a sales professional. You need to be doing sales professional work. There was another group of people on the other side, which said, “This makes a lot of sense because women need to support each other.” There are inherent biases that discourage some women from pursuing careers in sales.

We launched our Women in Sales Leadership Forum. One of the partners that we brought in was in the first camp, “You’re in sales. It doesn’t matter if you’re male or female. You have to do the stuff that’s necessary.” After three sessions of our program, she came to me and said, “I was wrong. I’ve never thought about the support that we need to give each other to be successful.” You see it in different organizations, women in tech, women in hospitality, or whoever it might be about women being champions of each other.

That has been a big part of our program too. It’s to build that build those networks across companies and within companies too of support. Maybe it’s a more senior sales professional with a junior sales professional or people at similar levels. It’s something that you and I take for granted. We probably know that we have our supportive networks. I have ten people I could call right away, but it’s different when you’re in a separate demographic or separate group that needs a certain type of sport to succeed because the odds are against them to start.

In some regards, that’s what makes them superior. Men, don’t send me hate mail because it has been my experience too in running teams of probably 1,000 salespeople over my life. Women usually outsell the men because they’re more patient in a lot of ways. Men are so linear, “Let’s get to the point and the problem. Done.” When we are dealing with men who are high driver types, that works well, but there is a whole separate issue of people who are methodical and humanistic.

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Women In Sales: One thing that has been so impressive running the Institute for Excellence in Sales is that there are so many talented women that we’ve come across. They’re customer advocates, and they’re really committed to doing great work for their companies.


Women, for some reason, can tap into a power that men have a hard time tapping into. The feminine energy is what I have found. When they’re in those situations, they will tend to outsell the men in most cases. I keep thinking about the movie, My Big Fat Greek Wedding. There was a scene where Toula, the daughter, was talking to the mother. Toula was saying, “I want to marry this guy, but dad will never let me.” The mother said, “The man is always the head of the household, but the woman is the neck. She can turn the head any way that she wants.”

Right before the pandemic, I did an interview with a sales leader. Her name is Alyssa Merwin. She’s on LinkedIn. She’s one of the top sales leaders at LinkedIn Corporate. This was maybe a month or two before the pandemic. We talked about vulnerability. She talked about how she was a vulnerable sales leader. She was an open book/ she was honest with her people.

She should be honest, but she was to the vulnerable level, getting a little bit deeper than, “I’m concerned that we’re going to make our number this quarter.” It was a well-received podcast that we did. I launched it in early 2020. The reason I referenced that one is that it was one of the first that we had done of my over 550 Sales Game Changers Podcast where that was the angle.

The pandemic kicks in. One of the big words that we talk about all the time is empathy. Empathy is table stakes to be successful. If you can’t be empathetic towards your customer, then it’s not sympathetic and those kinds of things. Empathetic means being able to put yourself in a position where you understand where your customer is coming from.

A lot of men I found, in the beginning, were struggling with that. It was probably the most commonly uttered word maybe besides value over the entire course of over 300 shows that we have done during the pandemic. We even had one episode. It was maybe four months after the pandemic kicked in when someone asked a question to one of our speakers. We were doing our podcast live at the time.

The question was, “When can we start taking a break from being empathetic?” My guest, who is a senior VP in many different industries, his name is Dan Cole, said, “If you have to take a break from being empathetic, you better go to the beach, take a day, and process it because sales are all about being empathetic. It’s truly about understanding what your customer is going through.”

Sales have changed. We all agree on this. It has now shifted from more of an interruption-based to a permission-based type of process. When I look over the numbers that I’ve had over the years with women versus men, women will tend to out-edge the men. Blair Singer wrote a book called Sales Dogs. It described salespeople as different types of dogs. With the shift that has happened, there are more empathetic sales dogs now than there ever were in the past. You can’t be that pit bull-type person to come in and still be as successful as one was in the past. The golden retriever or something of that nature is much better received.

I’m looking for your feedback on this one. Part of it is before, sales corporate-wise and business-wise used to be made at the sales meetings more. Now, the majority of the decision is being made up prior to even meeting with the salesperson. It’s more of fulfillment and who’s the right fit for us versus, “Do we need this any longer?” The need is already established front. What’s your thought on that?

One of my good friends, you may know him, Tom Snyder, used to run Huthwaite. He has been a frequent speaker at the Institute for Excellence in Sales and a frequent guest on my podcast. I was in a meeting with him once. He said, “Sales professionals used to be walking brochures.” I remember being in meetings. I worked at Apple and Compaq.

If you have to take a break from being empathetic, you better go to the beach, take a day and really process it, because sales is all about being empathetic. It's truly about understanding what your customer is going through. Share on X

We would have full-day meetings where the sales professional would present our roadmap because the customers wanted to know, “Where are you going, Apple and Compaq, in the next 5 to 10 years?” so that they can prepare. You don’t need that anymore from the sales professional. You can get that probably on the internet by googling the Apple product roadmap or something but at the time, that was the main function.

We all know now that the customer can get not just from the internet but from social media all the information that they need. The role of the sales professional has radically changed. The sales professional has a lot more pressure now to be able to show that they truly understand what the customer needs. It’s not from a product perspective. It’s usually from a solution perspective to meet the demands and the needs of their customers. The profession has changed.

As we’re talking about this, the one thing that we need to still keep in mind is that the sales professionals still need to lead the way at their companies. It’s still about revenue. It’s still about how we get our customers to make transactions with us for the products, solutions, services, or whatever it might be. It’s usually the sales professionals, the great ones, and the good ones, who are doing that, but the value and the role have radically changed over the years.

We’re speaking with Mr. Fred Diamond for the Institute for Excellence in Sales. We’re talking about women in sales. I find this a fascinating subject personally. I have three of them in my household, all selling now or grooming to be knock-down top 1% salespeople in their respective lives. Let’s talk about getting out in the public’s public view because in the past, men have done a much better job than women, but there are far more women now in the power of leadership roles that are coming along.

When I look at them, I’m seeing women getting more into the PR side, getting into that public square, getting the message out, and positioning themselves better than even sometimes their male colleagues are within the company. They’re embracing that a lot better than men are. I was curious. Do you have any thoughts on why that might be happening? You’re dealing with women all the time. This may be an unfair question because I didn’t even think we were going to ask this. Do you have any thoughts on that?

There has been a lot of movement in society. There have always been powerful women. There are a lot of women who’ve been very successful in sales. It’s interesting. In our Women in Sales Leadership Forum, we have two types of facilitators. We have women who are 30-year sales professionals and then we also have a lot of facilitators or people who train for a living. For the women who have been 30-year professionals, almost all their stories are the same.

Years ago, they were the only woman in the room. There are a lot of cliche types of things. They were asked to get coffee and all those kinds of things, but the ones who succeeded all talk about how they have had someone who supported them, a mentor, or someone who took them under the wing and gave them some guidance on how they need to be more effective with the customer and how they need to become more powerful as a sales professional.

There has been so much happening over the last few years. You go back to a lot of people in politics like the Michelle Obamas of the world. They could see a powerful woman not having the traditional type of roles. That led to women in more industries. As we think about women in sales, one of the things we have noticed is that there have been inherent biases that discouraged women from moving into sales.

There are industries. In pharmaceuticals, there are a lot of women. We have some of the top pharmaceutical companies involved with the institute to attract more women into professional sales. In hospitality, there are a lot of women in sales. In tech, not as much, but they’re starting as more women move into college degrees in technology or engineering. They could take those skills and then apply them to the sales profession.

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Women In Sales: The role of the sales professional has radically changed. The sales professional has a lot more pressure now to be able to show that they truly understand what the customer needs.


I’ll tell a quick interesting story about this bias that we talk about. We launched our Premier Women in Sales Employer. This never even occurred to me. We were asking senior VPs of sales and women typically, “What would make a great employer for women in sales?” Here’s what makes a great employer for sales, but what would make a great one for women in sales? The needs are different in a lot of ways. One thing that was discussed was the concept of networking activities. We talked about team building and bringing the team together.

In a lot of cases, even with the best intentions, they are inherently biased toward men and golf outings. You heard a lot over the last couple of years, “Women should learn how to play golf because it’s a networking event that we’re going to do. Deals are made on the golf course.” It’s probably not a bad thing for a woman to play golf but, to be honest with you, you and I are probably going to get more excited if the company says, “We’re going to go play golf for the day,” than most of the women will.

One of the women that we interviewed for our application process for Premier Women in Sales Employer said, “I argued that golf is fine, but at the same time, we should also have a day at the spa for the women who would prefer that type of network or team building thing.” It didn’t even occur to me. I thought, “Golf is going to be fun. I’ll learn how to play golf.” That’s starting from a man’s bias type of thing. There are a lot of those things that you and I don’t even think about that are out there and that women in sales who have been participating in our programs have let us know.

You bring up a cool point. I don’t know if everybody caught this, but as men, most of us are not that good at cueing in on what women are thinking about. Sometimes we say, “Women are not good at thinking about us as well and understanding us,” but the fact is that there are far more women coming into leadership roles and decision-making roles. If I’m a man which I am, and I want to learn to sell to women, which I do, and I do quite well, I’ve got to develop that empathy. I’ve got to be able to understand what’s important to them because it’s no longer that male-dominated space.

I remember when I was growing up. If you had asked me, “Name a few powerful women figures,” I would have a hard time thinking about it, but I know with having children, they were talking about Michelle Obama, Oprah Winfrey, and Meg Whitman, who ran Hewlett-Packard even though she got in some trouble or something like that. They were talking about people like that. They were looking at books that were written by women on leadership. Some of the guys were starting to read them as well.

The time has changed. Those of us who were in sales and want to continue to be in sales have got to adapt as well. We must understand how women think. What you are doing to me is something that men should embrace because this is going to continue to keep growing no matter what. I was watching a movie called 42 with Jackie Robinson and all the crazy things that he endured going through. I remember one of the themes. The coach came in and the players were pushing back because they didn’t want Jackie Robinson to be on the team because of the color of his skin.

The coach said, “Here’s the deal. We’ve got a lot of great players coming up. They’re all going to have all different colors of skin. You better get used to this because they’re hungry and they’re looking to take your job.” Women are now catching on. They can be successful in that type of world. The ones I’m talking to, especially, are like, “I can compete with men on any level,” but they still have that woman’s side or the feminine side to them.

If they don’t have all ten boxes checked, then they’re not going to pursue it forward. What do we say to women who are like, “I don’t have these two boxes checked,” because, to me, good is great? Once we get them to great, then we can bring them to the top 1%, but the reality is we can’t get them into the field because they’re thinking, “I don’t know if I have all the qualifications to get into that.” It’s hurting the whole movement of what you’re building out. What do you say to women who are thinking like that?

There are a couple of things. More women at college are getting into business, technology, or engineering. We do our Sales Game Changers Podcast. In one of every four shows, we will be interviewing a woman sales leader. One of the questions that we ask is, “What did you major in college?” Most of the ones who are successful in tech or professional services sales were in engineering. Some were in sciences like biology or something. They have that type of analytical thinking.

Mentors are great, and having a sponsor is critical to your success in sales. Share on X

A lot of success in sales is not, “What do I have to do to get you to buy this pencil type of thing?” It’s thinking through a problem and thinking about how the customer is challenged with solving their customers’ challenges. During the last few years, it has been, “How do I help my customer not just solve their challenges?” It’s not just their customers’ challenges because it’s a supply chain. There are customers’ customers challenges. The analytical mindset that a lot more women are being nurtured in college is a great feeding ground.

Here are two of the things I want to focus on. We give an award every year. It’s called our Lifetime Achievement Award. It’s like a Hall of Fame in sales. We started a conference earlier in 2022. It’s called the Women in Sales Leadership Elevation Conference. Our Lifetime Achievement recipient from a couple of years ago was a woman named Teresa Carlson. Teresa led Microsoft Public Sector. She led Amazon Web Services Global Public Sector. She was our keynote speaker.

She’s brilliant. She’s a hugely wonderful and successful person, but one thing that she kept harping on was the need to have data. She kept saying, “For you to be important in the room, ladies,” and we had about 120 women at this conference in May 2022, “You need to come to the table with pertinent data that’s going to help leadership understand where we need to go or help our customers understand how we can help them.” She kept pounding away on it.

I could see people feverishly writing notes. We keep talking about that too. It’s not that I feel that you should. That doesn’t mean anything. Customers want hardcore data. They want to understand that you’ve thought this through and that you’ve given some prep. The other thing that we recommend all the time is not just having mentors but having sponsors.

Some of the women that we have had in our network who have achieved the highest levels of sales success, reaching VP at companies like Splunk, Microsoft, Amazon Web Services, and Datasite, for example, have all said they have had mentors along the way but they have also more importantly had sponsors. The mentor is somebody who can give you some guidance, “Here’s how I would handle this.”

The sponsor is somebody who has power and is going to take you under their wings, make sure that you get invited to the right meetings, and make sure that if they know there’s an opportunity out there, they’re going to bring you in because you’ve proven to them that you should be out there. It’s one of the things we recommend all the time. Mentors are great. Have them. A sponsor is critical to your success. Thirdly is data. Come to the table with valid facts and things that show that you’ve thought this through and that you know what’s in the best interest of the customer.

I imagine people saying, “I want to get ahold of you. I want to figure out the next steps.” How do they access you or your company?

The best way to reach me is on LinkedIn. I’m on LinkedIn every day. I typically do one post every day. It usually gets about 5,000 to 6,000 impressions and 100 or so comments. I’m very careful with what I do. I don’t overpost. I do one post every morning at 7:30. Usually, it’s one of our podcasts, a poll, or maybe one of our events. Every once in a while, I’ll do something on the weekend as well. I’m also on Facebook. People can very happily reach out to me on Facebook as well. In Sales Game Changers Podcast, we do three shows a week. The organization that we run is called the Institute for Excellence in Sales.

Fred, I appreciate you being on here. Folks, we’re not talking just about women in sales. We’re talking about a movement that’s happening. It has been happening. I can tell you some of the greatest sales leaders I’ve worked with are women. They seem to be natural at coaching far more than men. They seem to be empathetic when things need to be empathetic far more than men.

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Women In Sales: Times have changed. If those of us who are in sales want to continue to be in sales, need to adapt as well. We must learn to understand how women think.


Men, I’m telling you this if you’re reading this because the world is changing. If you think twenty years from now it’s going to be the same, it won’t. That’s the way I see it, Fred. I’m so grateful that you came onto this show here and we had this discussion on this very important topic that’s moving forward and has been for a while now. The pandemic escalated it even more so. Thanks for being here. I appreciate it.

You’re welcome. This has been fun. You did a great job. I appreciate it. You were on my show years ago. It was a fantastic show. That’s the one thing I want to wrap up on as we’re talking here. The women in sales who are successful are also great sales professionals. They reach revenue, bring in revenue to their company, and make deals happen. That’s what we do. We’re about bringing in revenue and making transactions for our company. The way that we go about it may be different.

The way that we’re going to have to go about it has shifted and morphed over the last couple of years for reasons that we talked to, but they’re students of the game. They work on their game, “How do I get better? How do I provide more value to my customer? How do I team the right way?” All of those things are critical to the sales profession, “How do I be a more impactful sales professional?” I want to applaud you for the work that you’re doing on helping your readers, clients, and people who read your book get better at the art and science of selling.

Thanks, Fred. I appreciate it. Once again, Fred Diamond at the Institute for Excellence in Sales, thank you for being here, sir.

Thank you.

That was pretty cool. Here’s the thing. Empathy is going to take you a long way in selling. Most of the decisions are being made prior to them even talking to a salesperson. If you’re a person that’s out there even knocking on doors, you better get empathetic and understand what homeowners are going through if you’re knocking on homeowners’ doors in the B2C world. If you’re knocking on corporate doors, then you’re going to want to know what the corporate folks are thinking in the B2B world.

There are a lot of facets that make people successful in sales. One of them, I believe, is drive and hunger. One of the reasons I believe that women are making such great strides in this is it’s not just about selling for them. It’s about a movement. They’re looking not only to be successful and have more money, but they’re looking to be more empowered and make a statement in the world. When that happens, people pay attention more.

If you’re going to employ women, understand that they’re hungry, aggressive, and looking to get there, but they think differently than men. It’s that simple, not on every single aspect, but they do think differently. They can bring great strength and balance to an organization. When you as the employer, look at this and say, “I can titrate this in the right way.” If you’re selling to women, you can learn a lot from studying these types of processes that we’re talking about and delving into what psychology is and what’s important to them, and what’s important to the organization.

Without further ado, I’m going to be signing off here. If you like this episode and you think, “That’s great,” I also have a topic that I would love to talk about. If you think it would be good for the show, reach out to us at YouMatter@CEOSalesStrategies.com. We will be happy to entertain the idea and see if it works. We will put you on the show. If you love the show, please subscribe to it, tell other people, and give it a five-star review if you don’t mind.

If you want yourself or anybody in your company that’s looking to get the top 1% of income earners in selling worldwide or in your state if you’re in the United States, reach out to me at Doug@CEOSalesStrategies.com. Until next time, go out and sell things. Sell a lot of it, make it profitable, help a lot of people, and do a lot of good for the world and your success.


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