Why Trying to Please Everyone Will Destroy Your Leadership
30 May 2025 · 27 min
This is a May 2025 episode of the "Negotiate Anything" podcast (host: Kwame Christian) featuring Nancy Medoff, a speaker, coach, author, and podcaster, who recently ran for and won a seat on her Cape Cod town's select board. The conversation covers her campaign experience in a ~2,000-resident town (running in January with the election in May), the intensity of local political communication (memes, door-to-door outreach, lawn signs), and major leadership lessons: resisting people-pleasing, speaking authentically, accepting that not everyone will agree, and using persuasion to get stakeholders to consider alternative views. Practical negotiation/communication takeaways include using a rule-of-three messaging strategy, answering the question asked (not pivoting), validating opposing views, and aiming for mutual understanding rather than total agreement.
Questions this episode answers
About 2,000 year-round residents.
She ran back in January and the election was in May.
A seat on the town's select board (five-person board).
She moved there right before the COVID-19 pandemic.
She initially ordered about 25 lawn signs but ended up needing over 100.
Hey, I'm Kwame Christian, and you are about to step into the world of Negotiate Anything, the number one negotiation podcast in the world, where we teach you how to make difficult conversations easier while getting more of what you want in the process. Each episode is packed with practical tips and strategies from the experts. We delve into negotiation, conflict resolution, and leadership skills that are crucial in both business and and in life. Whether you're closing a deal, managing a team, or navigating personal relationships, Negotiate Anything provides you with the tools you need to succeed. Our conversations are real, relatable, and most importantly, rooted in practicality. So if you're ready to transform your conversations and elevate your negotiation skills, join me on Negotiate Anything. Subscribe and listen on Apple Podcasts, Spotify, or wherever you love to listen. Let's make every conversation a winning negotiation. Nancy, thanks for joining us today.
Thanks for having me, Kwame. I love talking to you. Love it.
Yes, likewise. This is what, number three or four? You're a fan favorite?
Three. Third time's a charm. Yes. Well, you're a fan favorite. I love, love, love listening. I love watching. Love your YouTube. Love your YouTube.
Thank you. I appreciate that. Thank you. Well, listen, how about we start off by telling the listeners about yourself and what you do and then we will flow into this new chapter in the life of Nancy Medoff.
Yes. Thank you. Well, I am a public speaker, I am a coach, I'm an author, I'm a podcaster. Basically, I work with women and I train them how to advocate for themselves at work. So it could be the job, it could be the promotion, it could be speaking up in meetings, whatever the case may be. I, I teach women how to advocate and step into their strengths so that they can thrive at work.
Amazing. And speaking about thriving, I think you have some news to share from earlier this year.
Yes, I do. I don't know what I was thinking. I ran for public office in my small town. So I live in a very small town on Cape Cod and it's about 2,000 year round residence and I ran for public office which the position is select board. So instead of a mayor, we have five people and they are the board that sets the policy and really kind of manages the policies for the town. So I ran back in January and the election was in May and I am pleased to report kind of that I did get elected and it was quite an experience. It was definitely a life changing experience in many, many, many ways. So I'm excited to talk to you.
A little bit about it. Absolutely. And this is great because don't worry, listeners, we're not talking national politics. I know you're tired of that. We are too. Okay. We are just fortunate right now to have somebody who is a top level communication expert who also ran for office successfully. And so what I want to do in this episode is talk about how your view and approach and strategies around communications have changed or evolved because of this experience. So how about you set the stage, tell us the story about the election, because I know it got a little bit. It got a little bit harrowing at times. So just let's start off with the story and then we'll go into the journey.
Great. I love it. So, as I mentioned, I live in this small town on Cape Cod and I moved here right before the pandemic and I joined a few town boards and committees because I wanted to get involved and help lead the town forward. I was thinking about running a few years ago. I chose not to at the time because my business was really taking off and I didn't feel that I could allocate the time needed. Fast forward a few years. My business is in a great spot in terms of running itself and the systems and the support. Had a talk with my husband and said, hey, I'm thinking about doing this. What do you think? And we decided, if you're going to do it, now's the time to do it. So I ran for office. I had no idea how much effort, time, energy, head space, everything that it would take. And it's interesting because we're a town of 2,000 and I figured one of my colleagues who's on the board, this is a great example, she had one lawn sign made one, and it said, you know, I'm so and so first select board. And she was elected. She was elected twice. One sign. It's a small, small town. Everybody kind of knows each other. In this race, there were two spots open and four people running. So there was all kinds of competition, if you will, who's taking a position on what. I ordered about 25 lawn signs and I said, oh, you know, whatever's left over, I'll just keep them, it's fine. And I ran out and I ended up needing like over a hundred. And this is how much people were paying attention to this election, which was really interesting and somewhat of a parallel to what's happening or what happened in America recently. And they were paying attention. They asked really good questions. A lot of people really wanted to meet one on one. I mean, I went door to door and met with many People that I never would have met with or never would have met in my ordinary course of being. And it was fantastic and it was exhausting and it was a game changer in terms of. It was probably the hardest thing I've ever done. I would say it was the hardest thing I've ever done. Yeah, it was. Yeah.
What elements were the hardest?
Right. So it was so long ago that I forgot. Well, the. One of the things that was hardest was when some people that were running decided to be really catty. And it's like there was memes about me floating around on social media and I just. I kind of laughed. I was like, wow, like somebody's making a meme about me. Well, first of all, that's ridiculous. Second of all, it's distracting. Third of all, it wasn't true what was being said. And there was nothing I could do about it. So I ran because I felt I could make a difference. I have no hidden agenda. People still don't believe me. I have no agenda other than I would like to move the town forward. It does not benefit me at all, other than moving the town forward. So the memes and the people assuming that they knew who I was or what I stood for without ever having a conversation with me, that was really interesting and really just the sheer magnitude of. Think. Here's how I would describe it. Think about interviewing for a job. You're interviewing for a job and everybody in the company gets to decide if you get that job. That is what running for public office is. You are running for a job and the people get to vote you in. So think that through. So you have executives at the company that understand what you're trying to do. Maybe on the same page, maybe not. You have middle manager people at the company who care about something very different than what the executives care about. And then you have people just starting with the company who really don't have a lot of experience and don't really know necessarily if you'll be good for the company. And they get a vote. So all these people get a vote and your job is to persuade them to vote for you. It's fascinating.
Tough. It sounds nerve wracking. And I want to start in an interesting spot because we will get to the conversational strategies. If you've listened to Nancy's other episodes, it's very strategy heavy. So you always know what to do. And then also just a little shout out. We did have a. That role play where. What was my name? Steve the Steamroller.
Steve the Steamroller. It's One of my favorites.
Yes. So if you want to see Nancy and I go toe to toe in a sparring session, we should probably link to that episode here too. But I want to talk about mindset here because one of the first things that you said when we were just chit chatting beforehand is that now you've gotten to a place where you don't care about what people think about you. And I think especially for people who are leaders, it's not just about making sure that you're making the best decision you possibly can for the company or organization. It's also recognizing that there will be a lot of forces working against you, working to distract you. And some of those forces come in the form of the opinions of other people. Whether well founded or well researched or well informed. We can let the opinions of others sway us negatively. But now you have evolved, Nancy, to this point where you're unfazed by this. So can you tell us about this evolution and how you think about communication as a result after versus before?
Yes. Great questions. So I think it sounds a little harsh to say I truly don't care what people think of me. We all want people to like us and that's just inherent that that's how we're, that's who we are as human beings. Once you realize that, it doesn't matter what you do or what you say, not everyone is going to like you and not everyone is going to support you, even if you think they should, for good reasons. Once you realize that, you can start acting in true integrity, true authenticity. Here is who I am. Of course I'm going to listen to your opinion and here's mine. And if that's going to lose me a vote, I'm okay with that. So that has been really a game changer. And it's interesting because even after getting elected, even now I have conversations with people and I have to preface it by saying, I want you to know I heard you. I don't agree with you. That doesn't mean that I didn't hear you. I heard you. Here's my viewpoint. You're probably not going to like it. I say that probably five times a week. And it's rather than beat my head up against the wall trying to get these people to, to understand the people that I'm differing views of, trying to get them to understand and agree with me, it is easier for me to say, I'm going to try to state my opinion, I'm going to state it and I'm going to articulate it. Hopefully persuasively. If they do that point and they decide not to support me for whatever reason, I'm okay with that. I wrote down a couple days ago I went on a vacation to clear my mind and I said, I'm not here to make friends. I'm here to make a difference. That thought popped into my head and again it sounds like, wow, didn't. Isn't she. Doesn't she think she's all that in a bag of chips? And I don't. I'm not here to make friends. I'm here to make a difference. And that's going to alienate some people or that's some people are going to be upset with my policies and, and that's okay. That just is. So I don't lose sleep over that anymore. Whereas I did. I did six months ago, and I don't anymore. And it's incredibly liberating. And it's liberating as a leader too.
Hello, my friends. Before we get back to today's episode, I want to ask you a question. Have you ever wondered how to elevate your team's negotiation game and how you can help the folks on your team have better, difficult conversations? At the American Negotiation Institute, we offer transformative keynotes and workshops tailored to empower professionals with top tier negotiation and conflict resolution skills. Whether it's a keynote for your next event or hands on training for your team, we've got you covered. Don't just negotiate. Master the art with the American Negotiation Institute. Click the link in the description to find out more. Elevate, negotiate and succeed. Yes, and I want to go into that feeling of liberation too because a lot of us can be imprisoned within a. A trap of other people's opinions and emotions and we don't even recognize how it's limiting us and holding us back from doing what we want to do and saying what we want to say. And there's a fear that holds us back. We can see a cage of others, creation that can hold us back. And we're saying, I don't even want to touch it. I don't even. Yeah, hypothetically it would be cool if I was free from. But I'm not even going to try to break free because it will hurt. And what you're saying is that I've been on the other side. I'm at this point where I've. There's so many arrows that have been slung in my direction that I realized that this is the price of progress. So if I'm going to try to do Big things. And I'm trying to make a difference in my own way. This is one of the consequences of that. And now I'm free. And so can you just speak to just how that feels now that you're not allowing other people's opinions to hold you back inappropriately?
It has brought me much needed, more peace than before. It has taken kind of the shackles off in that before, I might have said, well, before I opine on this, I got to think about what these people are going to say and what are these people going to say. And I don't want to upset these people, not for votes, but because I care about them. You know, they're people that are in my community. I care. And I'm never going to make everybody happy. And I will run myself into the ground and so will you as a leader. You will run yourself into the ground if you try to make everybody happy. Because you can't. You can't. And that doesn't mean that you're authoritarian. It doesn't mean you're a dictator. It means that if you can get it right, 80% of the time, that is all you can ask of yourself. And once I realized that, the stress kind of dissipated and I was able to actually enjoy what I was doing.
Powerful. It is powerful. And I'll tell you, for me, that's something that I've been working on for my whole life. And I just recognize that you get to different levels and then you have to relearn that in different ways with different people under different circumstances, you know, And I think a lot of people who are listening can identify with being a people pleaser or needing to overcome that. And then you've had to deal with the, the fear of most people pleasers. Like, people don't like me. They don't agree with me. I'm not getting that approval or validation. And a lot of times that stems from the fear of abandonment and a bit of a scarcity mentality where we say that this person, this relationship, this is what I need. I cannot survive without this. And so it's really encouraging not only first of all to recognize that we can overcome this, but also recognizing that you as a communication expert, you're relearning this and putting it into practice. And as a result, you feel more free and more effective.
I learned that I'm a closet people pleaser. I never in a million years thought I was ever. You know, I grew up the youngest of four. I grew up pretty scrappy. I'm not afraid to advocate for Myself. And I learned that I am a closet people pleaser. So when I can recognize that and just kind of check myself and say, okay, why are you acting in this way? This could be in, you know, when I'm speaking, when I'm coaching, when I'm, you know, in the government job, you know, you're not going to keep, Everybody's not going to be happy. So what is the best decision to make at the time? And just follow my instincts and just own it and step into it. It's all we can do. It's all we can do.
Agreed, Agreed. And I think this is so powerful too, because there's no real step by step process that you can take in order to do that. It's kind of like jumping into a cold pool. You don't do that incrementally. You just kind of have to do, deal with it, jump in and your body will acclimate. You have to trust in your own resilience and know that you will acclimate. And for you now transitioning into the communication aspect of it, the strategic communication. And what has shifted? Because again, I just, I always want to hammer this home. You are still a communication expert before this, right? And now your approach has shifted because of this experience. So what are some of the biggest learnings.
Okay. That people want you to take a stand. And I remember the first, we didn't really have any debates. We had a panel where we were asked questions and I had my talking points, I had my rule of three, you know, remember things in threes. And what are your main points that you want to continue to get across. And I had that whole, I had a whole strategy and I was able to stick to it. You know, one of the things that I teach is if there's three things that, let's say it's a job interview. If there's three things you want the interviewer to remember, what are those three things? And you weave them throughout your entire discussion. You know, same thing with a client presentation. It's what are your three things? So I had all of those and I was able to do that. At the same time, people will call you out if you do not answer their question. And I tried to do what we saw in some of the debates, right? You don't ask the question that you don't answer the question you're asked. They answer the question that they want to answer. And I tried that and it didn't work. So it just didn't work because then you have. So let's say somebody asked Me, you know, what do you think about, should we have milk chocolate or dark chocolate in the town, right? And I say, well, you know, I think all chocolate is good. And in my experience, I've had milk chocolate and dark chocolate, and, you know, there's benefits to both. And, you know, rather than talk about the chocolate, really what we should be talking about is xyz, whatever that is, does not work. No, no, no. A, you'll lose votes. And B, people will say, well, you didn't, you didn't answer my question, so I'm gonna ask it again. Or, you know, you didn't answer my question. I'm gonna pull you aside. Or in the, you know, the newspaper will say, you know, she, she talked a good game, but she never answered the question. So it's a spotlight. I mean, there's the spotlight of leadership, which many of us who are in leadership have experienced. The spotlight in public office is 10 times as bright, a million times as bright. It's. Everything you say is recorded and everything you say can and might be used against you in the future. It's wild. Wild.
You know what's funny? And tell me what you think about this. I think let's use comic books as an example. In comic books, growing up for, for decades, for years, we always have a hero and we have a villain. And now we have the era of the anti hero, right? Like Deadpool, he's. He's not a traditional hero, but we still love him because of all his flaws and everything. And I feel like we're in an politics where we have the politician and the anti politician, where the rules of politics that used to exist no longer exist anymore. And we're looking for people who are bold, who will say things even if we disagree. We will say, at least I know where they stand. At least I'm clear. I know who they are. I might not like who they are, but at least know who they are. And so are you. Tell me what you think about that perspective as it relates to the way that you answer questions.
I think I agree with you 100%. The challenge with that, and one of the first things that I have said and will continue to say, one of the things I said when I was running, I can't say it anymore, is I'm not a politician. I have no interest in politics. I didn't and I don't. I was running because I think I can help move the town forward. It is that simple. I don't, you know, people ask me, oh, are you going to run for a Senate next, or what about, you know, blah, blah, blah. No, I'm not, I don't. I'm going to do this job and then I'm going to go back to my life and like, no, I'm not interested in politics as much as I say that you can't be in a government role and not succumb to some politics. You will not be effective or some political positioning or capital or however you want to phrase it. So the long answer is, I am the anti politician. And at the same time, if I want to be able to do what I want to do, I have to play the game. I have to. I won't be able to get it done. And it's the same thing in business. You can be true to who you are, you can be authentic, you can stand in your integrity, but. Or at some point you're gonna have to play the game to some extent or you're going to have to acquiesce or compromise or however you want to phrase it, or you won't, you won't achieve what you want to achieve. So it's a little bit of a cognitive dissonance, I think, actually.
Yeah. And I think I feel like a lot of times when we say, when we think about what a politician is, there is a. We might not know specifically what that entails, but we all know exactly what it means. Right. It's never a compliment. And so nobody wants to be seen as a politician. But then we have to recognize, recognize that in everything that we do of substance, there will be a political element of it. There are political elements within our family units that we need to pay attention. With current family and extended family, there are going to be political types of vibes within our organizations. The nonprofits, the churches, the. Everything that we, we are in involved will have political nature to it. Right. So there's a difference between somebody who is a politician and somebody who accepts that politics are part of what is required to ex at a high level within any type of group of humans. And so I want us to paint a clearer picture too, because when you say I'm not a politician, that speaks more to your integrity and clarity of communication. You're not pulling the wool over the eyes of the voters. You're like, here I am. But then when you're playing the game of politics, we recognize that in order to get things done, you have to make some deals. They won't always feel good, but that's how you make things happen. Right.
That's it to a T. And I want to Go back to one thing because I this was the perfect opportunity to talk about it. What I learned is for some people, the reason why I didn't want to answer a specific question, one specific question, was because I knew that half the room wasn't going to like my answer. And I believe that we are more than that one answer. So this is, this goes to one issue, voters and I experienced it before the US election. So you know, you could agree with me on 90 of the things going on in our town. And this one issue that's important to you, if you don't agree with me, so you're going to go with someone else because 5% of the time I didn't agree with you. It, to me it's dangerous and it's polarizing and it's very short sighted. And that's why I hesitated to answer the questions. Not because I wanted to be sneaky or slippery, but because I knew the minute I answered that question, that person was going to tune out, turn off and vote for someone who was less qualified, maybe or maybe not a good candidate. So I didn't want to see them make that mistake. And it wasn't about ego, it was about, I can disagree with you on this one issue and we can still have a very positive, collaborative, forward moving relationship. I have the emotional maturity to be able to do that. I can disagree with you on this one thing. We can move together, we can still move forward together. A lot of people feel so strongly about that one issue, they can't. So it was kind of in my head I was trying to save, save the conversation, like move it away from this one thing because it's about so much more than this one thing. And at the same time, for some people it's not. And that was a big learning for me that one thing is everything.
It's tough. And it's especially tough because it feels a little bit helpless because you're saying I want to be authentic, but I recognize that in my authenticity I might lose people. And that's a tough situation. And it's the reality for so many people who are operating at a high level. We are constantly bombarded with that. And that can create a lot of noise in our heads as it relates to making good decisions and taking actions and being authentic. And I think for the folks who are listening, who are in leadership positions, they're going to run into similar situations where they're trying to make a call, they're trying to get everybody rowing in the same direction when it comes to a strategic approach. That we're going to use. So as leaders, as we're communicating this vision to people who are on our team and we recognize that similar to politics, they're going to be some people who agree, they're going to be some people who disagree. How can you still be that bold, visionary leader and communicate authentically while making sure that you can at least get people on board enough to row in the same direction?
It's by having the conversations. You know, I just had a conversation with someone yesterday and he is very, very strong willed and very strident in his beliefs. And at the end of the conversation he's. And we don't agree on something. And at the end of the conversation he said, well, you know, I can always count on you to give it to me straight. I can always count on you to have a productive conversation. And even though we don't agree, I learned something every time I talk to you. And that's all like, that's enough for me. That, that for me is enough. We're not going to agree on this. Could you consider this point of view? Consider this. I'm not trying to shove it down your throat. I'm saying consider it. And I know you're probably still going to have your same viewpoint on this. I'm going to have mine. I'm asking you to consider this alternate view. And if I can do that with as many people as possible, that to me that's success. It's not necessarily winning my point. It's getting people to understand the other perspective, which is all about persuasion, which is. That's it.
Yes, I agree. And sometimes the most persuasive thing you can do is validate and respect the other person's perspective and say we don't see eye to eye on this. And that's okay. I want to learn from you. And here's some information that can help you to see where I'm coming from too. And if we leave this conversation understanding each other a little bit deeper, then that is still a mutual win. And if you can have that straight talk at the beginning and set that expectation, then it makes things a lot smoother because now we're not going into this conversation with the hidden agenda of me trying to convince you, you trying to convince me. Neither of us achieve our goals, so we both feel bad unnecessarily after the conversation. And when we think about persuasion, it doesn't mean that we convince them to agree with us holistically on every single thing that we are saying. And I think what is surprising to A lot of people is that sometimes the best persuaders are people who can get somebody on board with an agenda or a strategy, even though they don't fully agree, but they trust the process enough to move forward. And I think having a more realistic perspective on what is achievable in these conversations would make these conversations much more palatable and likely to succeed for everybody involved.
I agree. I agree. You should run for office, by the way, because that would be very. You should.
I get.
I might actually use that tonight. I have a meeting tonight. I might. I might replay this and say exactly what you just said. Not going to try to change your mind. You're not going to try to change mine. Let's have a conversation about the different viewpoints. That's all. That's all.
I love it. I love it. Well, listen, Nancy, you have my vote. We're not in the same jurisdiction. You have my, you know, my vote of confidence from a distance. But again, before you go, I want to make sure that you get an opportunity to shout out and remind people about the core business that you have and how they can get in touch and how they can work with you.
Thank you. First of all, if you are listening and you have not watched Kwame's breakdown of the first presidential debate, the one you did from the hotel room.
Yes.
On YouTube.
Yes.
That was epic. So that's the first thing.
Thank you.
I loved it. I didn't get a chance to say that. So I'm a speaker and a coach and you can find me@nancymeadoff.com I also have a podcast. I have a bestselling book called Unmute Yourself and Speak up to stand out. I do one on one coaching and public speaking, so you can find me basically just about anywhere. And I just, I want to help women especially, but anyone really thrive in their life and step into who they know they can be. And that's. That's what I'm here to do.
Amazing. Nancy, thank you so much for joining us. Really appreciate it.
Thank you.
Kwame, if you've made it to the end of this episode, you're now part of our negotiation community. Every conversation, every deal, every tough negotiation shapes the world that we live in. And the more we grow together, the stronger our community becomes. If this episode gave you something valuable, don't let it stop with you. Share it with someone who needs it. A friend, a coworker, or anyone looking to take more control of their conversations, their careers, and their lives. Every time we bring somebody new into this space, we make negotiation a tool for real change. And if someone shared this with you, take a second to acknowledge that they see you as part of this journey and as someone who belongs in this community. Let them know you appreciate it. This is how we build something meaningful. We do it by looking out for each other. So if you haven't already, join us, subscribe, stay connected, and help us to grow this movement. Because when we become better negotiators, we create better outcomes for ourselves and for others. Hit, subscribe and share this with someone, and let's keep building together. I'll catch you in the next one.