One of the most talked-about breakout sessions at the inaugural LeadHER Women’s Summit was “Speaking Up When the Stakes Are High.” Facilitated by Lisa Fleischer and Nancy Robles, the session encouraged honest conversations about confidence, authenticity, allyship, and creating workplaces where every voice is heard.
Following the Summit, Monitor Editor-in-Chief Rita Garwood sat down with Lisa and Nancy to continue the conversation, discussing the inspiration behind their session, the challenges women often face in speaking up, and the lessons they hope attendees took home.
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Rita Garwood: Hi everybody, welcome to the podcast. I’m Rita Garwood, editor in chief of Monitor. Joining me today are Nancy Robles and Lisa Fleischer. They both facilitated a breakout session at LeadHER, which we’re going to talk about today. Before we get into that, I wanted each of you to say something about yourself and something that inspired you from LeadHER or a big takeaway from the event. Nancy, could you go first?
Nancy Robles: Sure. I think what inspired me was seeing that there were so many women in an earlier phase of their careers who were so eager and open to real conversation. They were eager to connect with other women, and that was really refreshing. Obviously, it motivated me to continue doing the work.
Lisa Fleischer: I agree. I was going to say the same thing. The connections were pretty amazing, and the openness that I observed and was a part of among the women who attended—from the most senior levels to the most junior levels—was really astounding. It was a beautiful connection between the equipment leasing industry, women, and the issues and experiences that we all face.
Garwood: It was such an awesome event. The energy in the room and all the connections everybody was making — it was unlike any event I’ve been to. I know it was ours, but it’s honest. Both of you facilitated a session called “Speaking Up When the Stakes Are High.” I wanted to know what sparked that topic. What made you think it was important for this event and for women in the industry?
Fleischer: Well, Lisa Rafter gave us a bunch of topics, and this one spoke to me because I know that very early in my career, I would sit and be quiet when I was the only woman in the room among a lot of men. It took me a number of years before I realized I might be younger and I might be female, but I have a perspective and I have something to say. Over the many decades I’ve been in this industry and in business, I recognize that sometimes our younger women experience the same thing. I encourage them to speak up, and I call on them in meetings. We had a very robust discussion. Nancy, what do you think?
Robles: Well, when Lisa Rafter and I spoke about my potential engagement with the Summit, we talked about many of the things that are part of who I am and how I present myself. One of those things is being very disruptive. For many years, I have found myself in rooms pushing for conversations that are uncomfortable—for example, mental health, diversity, unconscious bias—conversations that are typically uncomfortable. I push for authenticity and honesty in those conversations. When Lisa and I talked about the potential of the Summit, very early in the discovery period, I told her I wanted to push for authenticity. I didn’t want to be part of something that would be cliché, where people just show up and everything is superficial. I wanted us to talk about the real things that are difficult and critical in our lives and that impact us at a deeper level. She knew that was my mindset going in. Then, when we discussed different topics, this one obviously spoke to me.
Garwood: Nancy, it sounds like you really push the envelope and you’re used to having those tough conversations. Lisa, it sounds like when you were younger, you stayed quiet. Coming from that place, as someone who did stay quiet, what’s going on behind the scenes? If someone feels like they have something to say but chooses to stay quiet, what are the common things happening in their mind during that moment?
Fleischer: I’m an older person at this point in my career—more senior and more mature. Back when I was young, first of all, there were very often no other women in the room. Second, I’m a petite woman. I’m physically small. I used to wear really, really tall heels—something I don’t do anymore—just to feel bigger in the room. Part of it was simply thinking they all knew more than I did during those first handful of years in my career. I assumed the other people knew more, so I stayed quieter. I look back now and think, “My gosh.” Some of the things that were said and done back then—I wouldn’t allow that for five minutes today. Now I’m very outspoken at my company, and I’m very cognizant of women’s issues. If I see something, I’m usually the first one to, in a politically correct and respectful way, call it out. Or, if it’s someone I know well, I’ll go behind closed doors because I never want to embarrass anyone. I’ll say, “Do you realize that when you praised this gentleman over here, this woman said the same thing five minutes ago and you glossed over it?” Generally, no one intends to do that. Sometimes it’s simply how people were brought up. I’m very attuned to it now and pretty outspoken about making sure everyone can be heard in the room.
Garwood: And what helped you get to that point over time?
Fleischer: Experience. Recognizing that I do have a voice. I have a lot to say. I know what I’m doing. Making sure our younger people don’t feel like they need to go eight years in an industry feeling like they know less, so they’re not as important or their voice is not as important. Every voice in the room is important. What I tell my team all the time is, “I do not need 20 people who look like me, who sound like me. You have me. I want to hear different opinions. I want to hear constructive pushback on what I think, even though I’m their manager.” We all get better because of it.
Garwood: So true. The session was about speaking up when the stakes are high. What would you consider high stakes? Is this only business that you were talking about in the session, or could there be personal situations that are high stakes? Nancy, what’s your take on that?
Robles: First, I want to add that I wasn’t always outspoken. Early in my career, just like Lisa, I had been socialized to accept a lot of poor behavior. It was normalized. Not only was I socialized and set up to accept it, but within the workforce it was normalized. I often felt like I didn’t even belong there. So who am I to correct these people or say something that goes against the grain? What I’ve tried to do now that I’m much more senior, older, and experienced—and I feel like my voice has more influence—is create a safer environment for other people. I’m not the only one speaking out, but other people feel safe enough to speak out or at least safe enough to say, “Hey, this happened when you weren’t there.” That comes with time, confidence, and awareness. When something’s socialized and normalized, you’re not even aware of it. You just accept it as everyday life.
In terms of what “high stakes” means to me, I think it’s both personal and professional. On a personal level, as women—and for me as a woman of color—I have been impacted by poor behavior, sexist behavior, and discriminatory behavior. Speaking out in those instances is very difficult, especially when there are so few women. Oftentimes we feel like we’re making things up, we’re being oversensitive, or people minimize it because it’s normalized for them. We feel like we’re being disruptive. We feel like we’re the problem. Helping women understand, “No, you’re not making it up. No, it’s not okay. You’re not the only one. This has happened to most of us,” is so helpful when you’re feeling isolated.
From a business standpoint, how do you build the confidence to speak up when, like Lisa said, we often feel like, “These people must be smarter than me. These people must know more. Do I even belong here?” The more women find themselves in situations where they’re the only one, the more isolated they become and the more they think it’s just their problem, their shortcoming, their weakness. Being in a group together as women and acknowledging together that we’re all experiencing the same thing builds confidence because you realize you’re not alone. Then we talked strategically about how to deal with these situations and overcome fear. Most of the time, it’s fear. How do I survive this moment and not get fired or lose my job? To me, high stakes are any time someone feels unsafe or passes on an opportunity because they don’t feel able to use their voice.
Fleischer: I completely agree with Nancy. Our industry has gotten a whole lot better. We have a lot more women than we did before. We’re not where we need to be yet, particularly with people of color and other minorities. When I started, I used to read the sports page or watch sports on Sunday—even if I wasn’t interested—so I could contribute to the conversation on Monday morning when the guys were talking about football. I don’t do that anymore. If I watched the game, great. If I didn’t, I didn’t.
What was interesting during the session was seeing so many women’s faces light up. They’d say, “Yeah, I was having that same issue.” “How do you deal with that?” People opened up because they realized it wasn’t just their own singular issue. Many other people felt exactly the same way. The closeness the women developed during these sessions and throughout LeadHER—I could almost see a transformation on the faces of many of the women who attended from day one to day three.
Garwood: For sure. It was visually palpable. At LeadHER, attendees were able to select the sessions they wanted to attend. What did you hear from attendees about why they selected your session?
Fleischer: A number of women said it was a confidence thing. How do I get the confidence to speak up? They’re confident in other situations, but not always in certain work situations. There was a lot of discussion about how you get the confidence—how you get the nerve. One of us asked, “What’s the worst that’s going to happen?” Do you think you’re going to lose your job by speaking up? What’s the upside? You could see the women’s faces light up because there’s so much upside to speaking up and having other women’s backs in the room. I try very hard, both at work and elsewhere, to make sure women who are speaking up are heard. If they’re not, I’m pretty good at scanning the room and calling on people. Sometimes it’s my most introverted colleagues who have great things to say but just aren’t comfortable speaking. “Hey, what do you think about this issue?” The more they talk about it and the more they speak in public, the more comfortable they become.
Garwood: Nancy, anything you would add to that?
Robles: Generally, confidence was probably the most common word that we heard. I don’t know that confidence necessarily described exactly what everyone meant because, when we went deeper into the conversations, it wasn’t always confidence in their skill set. It wasn’t necessarily confidence in the subject matter. It wasn’t necessarily confidence in themselves. Sometimes it was the environment. The environment was not inviting. The environment didn’t lend itself to people speaking up. They didn’t feel that other people were receptive to them. So it was a variety of things. I think confidence was just the word the women used most commonly, but it described a lot of different scenarios. Some of them were personal. Some of them were, “I feel like an imposter.” “I feel like people don’t take me seriously.” “I feel like people are not listening.” It was a number of complicated, layered issues. The one thing that was very common was that everyone was looking for tools to overcome that hurdle.
Garwood: Both of you have talked about being heard when you speak. Can you break that down a little bit? What does it take for someone to truly feel like they’ve been heard? If you’re on the receiving end of someone coming to you with information they feel is really important, how can you ensure they feel heard by you?
Robles: For me, anyone who wants to come in and have a conversation—whether it’s personal, work-related, or anything else—first of all, I need to be present. That means I’m not doing other things while we’re talking. I’m not checking my phone. I’m not looking at emails. If I’m doing that, I’m not fully present. One of my weaknesses is that I want to jump in with solutions. A lot of times I catch myself and say, “Nope. I want to wait until you’re done.” I often take notes while people are talking, and I’ll tell them, “I’m writing things down because I want to come back to them. I don’t want to interrupt you.”
When people come to me with something, I always ask, “What are you looking for?” Sometimes people just want to vent. Sometimes they want someone to brainstorm with. Sometimes they’re looking for solutions. Sometimes they’re looking for actual advice. Part of listening is understanding what the person is looking for when they’re coming to you. I try to create an environment where they know I’m present and actually listening. I try really hard not to interrupt. Then I ask what they want from the conversation so I can respond in a way that gives them what they’re looking for.
Garwood: Lisa, anything you would add?
Fleischer: That’s really good advice. How I handle it, in addition, is I’ll usually shut my laptop so there are no distractions. I do tell people that if they’re going to tell me something that violates our code of conduct or involves a legal issue, I want them to know up front that I may have to act on it. I’m here for you, but if it’s something I have a responsibility to address—as chief legal officer—I will have to do that.
More often than not, though, it’s exactly as Nancy described. Someone tells me something, and I may make a suggestion. “Here’s what I’d like to do with this.” “Are you okay if I go talk to A, B, and C?” Or I’ll simply say, “Thank you so much for bringing this to my attention. I’ll handle it from here.” It depends on what it is. But you have to have a safe environment for people to come to you.
When I’m in the office, I hear more because people stop me more often than they did during COVID when we were all working from home. Maybe there were fewer issues because people weren’t together, but they were less inclined to call me on Teams than they were to stop me in the hallway or down in the gym. I get great intel at the gym. Wherever it is, people should feel comfortable coming to senior leaders so we can help fix problems if they want us to. Sometimes people just need to vent, and that’s really valid as well.
Garwood: What if you’re going to a leader with something really important to say and they’re not being present? They’re not giving you their full attention. What can you do to change that? Can you say, “Can you please give me your full attention?” What are your recommendations for someone who’s trying to have these conversations with someone who’s just not doing what you suggested?
Fleischer: If you recognize that person is very distracted at that point in time, my suggestion would be to say, “I see you’re super busy. Might you have some time for me later today or tomorrow?” I wouldn’t say, “When you’re not distracted,” but simply ask whether they have some time. Read the room. There are definitely times that are not optimal to bring issues to your manager. I pride myself on doing the same thing. When I wanted to ask for more money for some of my team, if I could see my manager was having a bad day, I’d think, “Nope. Not today.” I didn’t want to get a “no,” so I waited for another day. Make sure it’s a good time, unless it’s an emergency.
Robles: I will add that not feeling heard isn’t necessarily always about going to leadership with issues. Sometimes not being heard means I made suggestions in a meeting and no one took them seriously. Or I’ve made recommendations to my manager, my team leader, or my colleagues, and they’re not implementing them or even considering them. It’s not always about leadership. A lot of times it’s just in the day-to-day of their work that people feel like they’re not being taken seriously or heard. Lisa mentioned earlier those situations where a woman says something, nobody pays attention, then a man says the same thing five minutes later and suddenly it’s a great idea. That is a perfect example of not feeling heard.
Fleischer: Sometimes it’s not even a women’s issue. It can simply be a communication issue. If I have someone who isn’t the clearest communicator, I’ll suggest a coach. We have internal coaches at DLL, and we’ve also used external coaches. I’ll ask, “Would a coach be helpful to you?” I don’t think anyone has ever come back after working with a coach and said it was a waste of time. Not once.
Garwood: I know often with women there is a pattern where a man could say something and it’s labeled as being assertive, but when a woman says something, it can be labeled as abrasive. How do women navigate that double standard at work or just in life?
Fleischer: To me, I think you need others. If you’re the only woman in the room, that can be difficult. People may make up their minds about who you are or what you are. Having allies in the room who say, “Yep, that makes a lot of sense to me,” if it does, of course, or, “Yeah, that’s a great idea,” helps. I think it takes the abrasiveness out of it and makes the rest of the room realize she’s coming with a good idea and she’s being clear.
Robles: For myself, I’ve definitely been labeled abrasive. I think that’s because I’m outspoken, proactive, willing to take risks, and willing to push conversations. For me, I’ve had to get comfortable with understanding how these things work. Just because someone labels me that doesn’t mean that’s the way I need to see myself.
At the same time, I also reflect. Should I change some of my language? Am I frustrated because I’m not being heard or I don’t feel heard? When I finally have the opportunity to speak, am I coming across as frustrated and angry? I think it’s both. One, who cares if you’re labeled whatever? Granted, it’s wrong, but who cares? Two, self-reflect a little bit because oftentimes I’ve been frustrated because I’ve been overlooked, or someone’s mansplaining me, or someone behaved poorly and nobody else said anything about it. What’s coming out of me is all that anger and frustration that has nothing to do with the topic, but I sound angry. I had to learn to pause. I had to learn to compartmentalize a little better. Just because I’m frustrated about one thing doesn’t mean it has to come into another conversation.
And you know what? Not every environment is for me, and that’s okay. Sometimes this just isn’t the place for me. Sometimes I need to be somewhere I’m actually appreciated, where someone is going to see past my big hoops and my red lipstick, hear what I have to say, and appreciate the skill set that I bring. It’s complicated. It can be a number of different things.
Fleischer: That’s really true, Nancy. There’s a big world out there. There are a lot of jobs and a lot of companies. If it’s not a good culture fit, I say this to my own children: give it a chance, but if you know in your gut this is not a culture fit, go find one. There are great companies out there. I’ve worked in both places. As a grown adult, I really know the difference. I stayed in a place that paid me super, super well, but the culture was really toxic. When I look back, I think, “Wow, I stayed too long.” I’ll never do that again.
Garwood: How do you know when you’ve reached that point? Is it just that you’re not being heard? What are some signs?
Fleischer: Honestly, it’s not being heard. Frankly, it’s your blood pressure. It’s what my daughter calls the “Sunday night scaries.” It’s saying, “I just don’t want to go to work tomorrow.” For me, trust your gut. Maybe not on day one, but shortly after, you know whether the company is a fit for you. It’s okay. You’re not a quitter if you leave after two years because it’s just not working. I’m someone who’s stayed a long time at many of the companies I’ve worked for, but it needs to work for you. No one can make that decision but you.
Garwood: It sounds like all of this requires a level of confidence from the person who’s speaking up, but it also requires an organization, managers, or teammates who create space for that to happen. I’d like to talk about allies—managers, colleagues, or sponsors who can help people on their teams speak up. What does good allyship look like on a day-to-day basis in the office or in any role?
Fleischer: Frankly, I love to—I’ll call it pre-gaming. If there’s going to be what I think is a difficult conversation in a meeting, I’ll talk to a friend or colleague beforehand. I’ll say, “This is where I’m heading on this subject. What do you think?” If you can pre-align and have an ally in the room, two voices are better than one.
I also like to use that allyship after the fact. To Nancy’s point, if I have a day where I think I may have been a bit abrasive, I’ll go to a trusted friend afterward and ask, “What did you hear?” “Tell me honestly. Was I too loud? Was I too strong?” Almost always, I’m thinking I was too much, and my ally will say, “You were the only one in the room who called it out. Somebody had to.” I also want constructive feedback. Was I too loud? Did I cut somebody off when I didn’t mean to? Sometimes that mirror is really helpful.
Garwood: Nancy, how about you?
Robles: For me, allyship is more than anything someone who’s willing to stand up on my behalf—or on behalf of someone else—when they’re not in the room. That’s when it really counts. Are you going to let other people throw me under the bus or say dishonest or unfair things about me? Are you going to hear or see something that’s inappropriate, offensive, or hurtful and stay quiet? Whether I’m in the room or not, an ally is someone who, although they’re not impacted the same way, is willing to stand up as if they were. That’s critical, especially in spaces where there isn’t fair representation.
Lisa’s example from earlier is perfect. A woman says something, it’s ignored, then a man says the same thing and suddenly it’s a great idea. An ally is the person who says, “That wasn’t okay. She already made that point.” That’s allyship. That’s what I hope to bring to others—not just women, but anyone from an underrepresented group. I try to create an environment where people are allies to each other and really have each other’s backs.
Garwood: If you are coaching women—or anyone—on how to speak up, would you change your approach depending on where they are in their career, or would you give the same advice to everybody?
Robles: I would never give the same advice because there are so many things to consider. First of all, it’s the organizational culture, but then there’s also a subculture within their own group. You have to understand all of that. Sometimes things are political, and you have to be very tactful in the way you approach them. Sometimes things are clearly unfair, and they need to be called out right then and there. It’s not one size fits all. It depends on the organization, the issue at hand, her experience, and her role within the organization.
I remember one time my therapist told me that I was really quick to fight for others but not for myself. That was about me. You have to understand where people are coming from and how they see the world. Sometimes you just have to put things into perspective. Is that really what you want to hang your hat on? Or maybe it is. Maybe you’re absolutely right. Let me validate you because what you’re dealing with is extraordinarily difficult. Then let me give you advice on how to navigate that. Or, you know what? Send me your résumé because you need a new job. It can be anything.
Fleischer: Spot on. Rita, you mentioned coaching. Coaching is different than mentoring. In a coaching situation, I wouldn’t be telling someone what to do. I’d be trying to pull it out of them. “What would you do?” “What would be the worst thing that would happen if you did say that?” Let them come to that realization themselves.
Garwood: We’re just about out of time. I wanted to hear if either of you had any final thoughts or takeaways from the session you led—anything you wanted to leave the audience with.
Fleischer: I think, as in many areas, we’re much more alike than different. We’re all working women. We have different backgrounds. We come from different places. But at our core, everyone wants to be a good significant other, a good employee. Most people are interested in climbing the ladder, but some aren’t, and they’re very happy where they are. At our core, we’re the same. The friendships that were formed during those two or three days together were pretty amazing.
Robles: Along with what Lisa said, I think showing up in an authentic way is hard because that means putting your guard down and taking off your armor. But that’s what creates true connection. It’s also what validates our experiences as women. So many of us feel like it’s just us, when in reality, in one form or another, we’re all experiencing some sort of social construct or social issue that’s impacting our lives. While those experiences can be unique, they all fall under pretty much the same umbrellas.
Being in a space like this, where we were able to put down the armor, take our masks off, and show up authentically, gave a lot of us validation. In that validation, there’s strength. Now you know, first of all, you’re not the only one. Second, you’re not making it up. There’s a lot of motivation that comes from that. I would say everyone needs a really good friend they can be authentic with. If you can find someone to mentor you—and not everyone’s equipped to be a mentor, but some people are really good at it—and sometimes you have mentors you don’t even realize are mentoring you. All those things are valuable. More than anything, we hope to see more and more women join us next year.
Garwood: Definitely. Thank you both for joining the podcast today and talking about your session. I hope if you do another one, I get to attend next time because it sounds like it was awesome. Thank you for everything you’ve done for the LeadHER event and for everything you’re doing for women in the industry. We really appreciate it.
Robles: Absolutely. Thank you. It was fantastic. Take care.
Fleischer: Thanks, Rita.
