Speaking of Allyship: A Podcast of The Boston Club

Speaking of Allyship with JD Chesloff of the Massachusetts Business Roundtable

• Season 1 • Episode 2

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In our second episode, Lisa Prior, President of The Boston Club, is joined by JD Chesloff, Executive Director of the Massachusetts Business Roundtable.

Together they discuss:

  • How our upbringing can shape our allyship
  • Developing empathy in our leadership journey
  • Natural allyship vs intentional allyship
  • Practices for promoting & providing access in our organizations

Tune in then subscribe to the show and follow JD Chesloff, Massachusetts Business Roundtable and The Boston Club on LinkedIn.

Welcome to Speaking of Allyship, a podcast of the Boston Club, New England's premier women's leadership organization. I'm your host, Lisa Pryor, president. Here we bring you personal stories and proven leadership practices for allyship, including what it means, how to be an ally, and how to receive or ask for allyship too. Leadership is expansive in the workplace, across gender, race, orientation, identity, or how about just thinking differently? This podcast brings you together with amazing business and thought leaders of greater Boston, Massachusetts, and New England to hear their personal stories and journeys and how their experiences and lessons learned shaped their leadership approach. You'll take away insights and tips, learn how allyship and mentorship can play a role in your career and how you can pay it forward, and leadership practices on everything from, how to create inclusive work environments to how to be brave and prepared for challenging conversations. Let's get started. Welcome back to Speaking of Allyship, a podcast of the Boston Club. I'm Lisa Pryor, president, and so excited to be here today with our key partner and stakeholder JD Chesloff, president and CEO of the Massachusetts Business Roundtable. JD, welcome. It's so great to have you here. Thank you, Lisa. Thrilled to be here and to have this conversation with you. It's exciting. And we're trying to have this sort of natural conversation about allyship and what it means. And our conversation with you today is a lens on allyship that's really about allyship across gender. Men working with women in advancing diverse women into leadership roles. And so JD, where I'd love to start is just to hear a little bit about your perspective along your leadership journey. And especially as you have moved through organizations and roles, what have you noticed about differences between the journeys of men and women when it comes to leadership? Yeah, thank you, Lisa. So just a little bit about my journey. I run the Massachusetts Business Roundtable. I am essentially a business lobbyist. My dirty little secret about that is I was raised by hippies. I was actually raised by communists. Oh my goodness. Somehow I ended up being a business lobbyist, right? Love it. Which is really interesting. I think it's important to kind of highlight that as part of the beginning of my journey because there's a perspective that comes along with that, right? And I think embedded in that upbringing is a feeling of empathy, a call to help people. It's part of why I got into public service. That was really the first part of my career, was in public service working for a congressman and then up in state government for a state. Representative. I worked for the state treasurer and then the Ways and Means Committee. I have a variety of positions in state government. I think there was a calling, there's a public service calling that I think came from my upbringing. Embedded is that, is this sort of natural tendency to be supportive, nurturing, right? Sort of these elements of allyship. That was part of my upbringing that I think I then brought to my professional career. With regard to what I've noticed about women leaders, the first woman leader who I was really exposed to and worked very closely with was Shannon O'Brien, when she was state treasurer. She then ran for governor. This was 20 years ago now in 2002. That was when I really saw the different standard to which women are held. I mean, I kind of knew it, but I saw it up close. There were times where I would go to our campaign office early, somebody would call and be talking about the color of her dress at an event the night before, on TV the night before. How she pronounced certain words. It was just a different set of questions that I was getting as opposed to. Previously having only worked for men. How would you characterize those kinds of questions? It's funny. It struck me as unfair. But when I was receiving them, to me, it was more, reflection on the person asking them, a level of ignorance on their part as opposed to a reflection of her, which I thought was, it was just kind of an interesting lens to have on what she experiences, that I just never would have experienced. I then came over, I mean, after a few stops, I ended up here at the roundtable and we've had three women chairs of our board. The first one was in 2010, a woman named Donna Capello, who was the region president of Verizon. It was the first time we had a woman chairing the board of the round table. And the round table has been around for over 40 years. Wow. Marcy Reed followed her from National Grid. Jane Steinmetz is our current chair from EY. And what I guess what I how I would describe their leadership wouldn't necessarily compare it to. The male leaders of our board. But what I noticed about women leaders is there's an empathy to their leadership. They're very engaged, very strategic, and there's a kindness about them that I think is. Part of their leadership style. And those are all pieces that I, you know, over the course of time, try to incorporate into my own leadership style because I've just found them to be very effective. I love that. And you know, I appreciate where you started, which is sort of the space of where you grew up and who you are naturally. And I just need to say we are just so appreciative always of your support of our mission at the Boston Club. You are a natural ally in that way. I can see, as you were describing your journey, what you brought to that. And the reality of you even, and observing that experience for Shannon O'Brien. That is bringing empathy, but you're paying attention. It caught your attention and we have to be kind of dialed into empathy to even have that observation. So thank you for sharing that. And you described a little bit about how that began to shape your own leadership journey and perspective. And I'm curious as you reflect on even more broadly broadly women leaders. How have you seen the journey? How is it different for women, particularly who are diverse, who might be in our BIPOC community, our LGBTQ plus community? What do you observe about the journey for our diverse communities of women leaders? I guess for their journey, what I've noticed is the journey for them isn't about talent, right? They have the talent. It's about access. And how do you make sure the right people are seeing the talent? I'm always struck by this passage in White Fragility. It talks in there about how many of the major institutions in our society, the decision makers are all white men, right? Whether it be media, the church, the military, business, sports, right? They have all these examples. And they talk about how do you provide access to decision making, right? And I don't think that the people who are in the decision-making positions of those institutions are more talented. Than people who are not. It's just the people who are not don't have the access, right? And so how do we as allies think about providing that access? And so that's what I think about the the platform that I have at the round table, right. Is how do we use that platform as an ally to have that talent exposed to places that otherwise might not be exposed? And it's such an important question. And let's come back to that in a second, because it's sort of at the heart, isn't it, of allyship? There's empathy, there's understanding, there's self-development. But at the end of the day, what are we to advance women and our diverse women communities. You and I had a conversation previous to this one about an experience you had along your own leadership journey, this sort of concept of natural allyship versus intentional allyship. You described a situation where one of your female colleagues gave you a book. I wonder if you'd be willing to share that story with us. Sure. Yeah. years ago. You know, I think what happens is people like me with an upbringing like me, right, like this very progressive upbringing by hippies and communists. I think we have this view of ourselves, particularly as a white male, that we get it, right? We understand allyship, we know we're good people, we think we're good people. And yeah, I had this friend who gave me a book on misogyny. And at the time, I didn't know what misogyny meant. I didn't know. I. I couldn't define the word. It was a new word to me. I was in my, well into my 20s. And somehow I had missed that. Now that's on me. But I missed it. And here's a person who by all rights should have known that and been empathetic toward it. And I got this book and I'm like, what is this about? And she's a misogyny. I'm like, what is that? And it just went downhill from there to that conversation. But it was just. It showed to me that I don't have it all figured out. I think a lot of us in my position don't and probably need to admit that. And you never stop learning about this stuff. You never stop learning about how you can be a better ally. And I thank you for sharing that story. It's that moment in the leadership journey, right, where this is what leadership is all about. It's this self-awareness. And there's a lot about leadership that's wonderful and fun, sharing a vision, being out there, bringing people together. But where the real leadership happens is kind of looking at ourselves and those uncomfortable things about ourselves. And you've just role modeled a way for us to just kind of talk about the journey and make it safe for each other to say, you know, I didn't realize I was thinking this way. And now that I have, you know, one of the comments that we had kind of talked about before was how that experience of seeing yourself as a natural empathetic ally being raised by hippies and communists, but sort of transformed your way of thinking about is natural ally enough and what does it mean to be more intentional? And so, curious to hear and it picks up on that thread, how do we as allies provide access? So can you help translate this idea now from natural allyship and our good intention to what does it look like day to day when you're providing access or you're acting as a male ally for all women. Yeah. So natural allyship to me is you're just fundamentally a decent human, right, who is concerned about other people, supporting them, nurturing them, understanding that. Their journey is not your journey, right? I don't want to dismiss that because I think there's a fundamental undercurrent of kindness in that, right? And so if you're going to be be just a decent human, you will naturally be an ally to people. I think what I've learned over time though is that's not nearly enough in terms of what underrepresented, marginalized, discriminated groups need. And so that's when I think it sort of kind of skips to this concept of intentional allyship. And that is where you take action, right? You use the platform to be an ally. And I'll give you an example. A couple of years ago, I was having lunch with a very good friend of mine, Pratt Wiley, who runs the partnership, dear friend. And his organization is an organization of extremely talented mid-career, early career, and C-level people of color. And he was talking about the kind of experiences that the program exposes them to as a professional development opportunity for them as they're thinking about advancing their careers. And it was things like engaging in public policy, sitting on boards, building out their personal networks, right? These kinds of strategies. And I said to him, well, geez, that's what we do at the roundtable. Let's think about a way to provide access to our board, to some of your folks. And I think there's mutual benefit there. There's a lot of layers to that relationship. But it's sort of a proactive thought about using the platform to be an ally. And what we found is. We had a few folks join the roundtable, sit on a board. They are now in leadership positions in the group. As I said before, it had nothing to do with talent. These are extremely talented people. In fact, in this case, two women who are now in our executive committee helping to lead the organization. And so I think about, yeah, I could be nice to people and be an ally to people. And I know that I have done that, but for folks like me, I don't think that's enough. And if you be more intentional about it, you can have some impact. I really appreciate in that. For us at the Boston club, you've heard us talk about our mission and vision, but what do is engage people in conversations that matter to build relationships that matter, that advance women to tables that matter. What you just described was that process that, and you use the word relationship because at the end of the day, it's getting to know each other. It's that intention and appreciate how that transformed your own thinking about your own practices because it really is at the end of the day for business leaders, especially for any organizational leader, what are the practices we're putting in place to create, that access? Well, Lisa, just to get back to something you said earlier about feeling uncomfortable, I think what gets in the way sometimes is folks feeling discomfort in taking that leap, feeling threatened by taking that leap. But once you're there, it's not uncomfortable, it's not threatening at all. In fact, it's soul nurturing, soul enriching, you know? And it's also, you can see the benefit of your action, right? I mean, folks benefit from it. And that feels good. That's part of being an ally, I think. Yeah, and that discomfort, JD, it's an issue in leadership, right? Because it's a barrier to actually living the things we say we believe in, but leadership is really leaning into that discomfort. Curious as you think about the landscape now, just kind of elevating the conversation to, as you look across Massachusetts, when you think about what's happening here with respect to allyship and that access, what's happening in Massachusetts that might be different or interesting compared to other regions? So let me answer that two ways. One is my day-to-day experiences with leaders in large companies, corporate leaders in large companies. Here is definitely an intentional focus on allyship amongst business leadership here that I've seen. And you can cite a variety of examples of companies who are elevating DEI within their companies to not just an HR function, but as a direct line to a CEO, for example. You can see companies who are very intentional about their board composition and being very public about it. And then there are ERGs. There's all sorts of stuff happening internally to make sure people are heard and to have the employer be an ally in the development of people's careers. I think that's going on and I see that. I think politically what's interesting here is we don't really have a far right here. As I talked to colleagues of mine around the country. Where there is more of a far right politically active group in those states, it does seem to drive a discourse in a way that's just not driven here. And I think that gives folks a little more freedom to be allies. Interesting. So the political context enables our business leaders to be more open in their own allyship and advancement of... Yes. I think that is absolutely true. And I also, you know, I hear more and more business leaders talking about it as a competitive advantage here. And if you think about it from their view, it's we have an ecosystem here that would attract people. But from the employee or from the people who are coming here because of that ecosystem, they view it as an atmosphere that is more supportive. And I think fundamentally in that, the ability then to come and either be an ally or have somebody be a mentor to you. It's really encouraging. That's really encouraging. I know you have many amazing businesses, business leaders as part of your community. Who comes to top of mind standing out with these practices and bold new ways of providing access and advancing all women? You're asking me which one of my children I like the most. There you go. It wouldn't be an interview without a tough question, JD. Come on. I know you had Jane Steinmetz on recently in the podcast who's done some incredible stuff around neurodiverse populations and hiring, really kind of groundbreaking work at EY. Bob Rivers over at Eastern Bank is doing incredible stuff around board diversity, and elevating women leaders on and on PNC Bank, State Street. I can go on and on. I don't want to because I'll leave somebody out. But I do think that I do feel lucky here, to be in an environment where you have. Employers and business leaders who really do focus on this and are intentional allies, right? It's not just oh We're good people but it's there's real intentionality behind what they're doing, Yeah, and what I appreciate about that so much I'll go back to that word you used about the ecosystem when the ecosystem, you know allows. For discourse it allows for sharing of best practices because it's a bit of what you just I really you know You had the practices right there for business leaders to learn from one another. At the Boston Club, we believe our vision is how do you be a force for change? How do you harness your collective agency to be a force for change, not just for healthy organizations, but for a healthy and just society? And what I appreciate in this conversation, the connective tissue really between business and society and the very specific ways that you're creating that bridge at the Massachusetts Business Roundtable. So JD, can you as we we begin to wrap up here, what's one idea or wish that you would want to leave us with for the future of a practice or something that might seem out of reach today? You know, I think you're never you're never too old to be mentored. Right. And I think you can have a role model while being a role model. As I think about being an ally, that's not that's not a one way relationship. Mentoring is not a one-way relationship. I mean I'm a mentor at a program called Conexion, which is for mid-career Latino and Latino professionals. I learned just as much from them as they learned from me. And I think if you are committed to emulating good behavior, you're never really too old to be mentored. It's a constant learning journey. Fantastic. JD, how can people continue the conversation with you on your Twitter, LinkedIn? Yeah, so the roundtable is on both Twitter and LinkedIn, as am I. And if folks want to connect, I'd be more than happy to do that. Well, JD, with gratitude, you role model the way to be an ally. And you do that, what you shared with us today, just your willingness to share a vulnerable story, to share your own learning and insight at that interpersonal level, kind of being okay with being in that discomfort and realizing you can come out of it and be even better, especially as a leader and how important that is, but also that macro view that you're bringing and the tone you're setting at the Massachusetts Business Roundtable for this kind of collaboration, this kind of vibrant ecosystem that at the end of the day really is about healthy businesses and a just society. And we're just so thrilled and appreciative to be in your partnership sphere. JD Chesloff, president and CEO of the Massachusetts Business Roundtable, thank you so much for being with us today. Great. Thank you, Lisa. And thank you for all the work you and the Boston Club are doing. It's great to be partnering with you on this. Thanks for listening to Speaking of Allyship, A podcast of the Boston Club, New England's premier women's leadership organization. You can find resources and links from this episode in the show notes at www.thebostonclub.com. Follow us on LinkedIn and Twitter. This is your host, Lisa Pryor, president. Be well and ask yourself, what's one thing I could do today to be an ally?