Credit: Margaux

We just announced that we have two co-chairs for the Charter Workplace Summit taking place on Nov. 9 and 10: Edith Cooper and Jordan Taylor, the co-founders of Medley. We reached out to this mother-daughter team because their organization, which recently announced an investment round led by Andreessen Horowitz, contributes to transforming workplaces by helping people at all levels grow through discussions and coaching within diverse small groups.

Cooper, a board member at Amazon and Pepsico, is formerly a partner and the head of Human Capital Management at Goldman Sachs, and one of the most senior Black executives on Wall Street. Taylor is a former BCG consultant who also worked in media. We spoke to them about the theme of our upcoming summit: “What kind of leader do I need to be now?” Here is a transcript, edited for clarity:

What leadership skills and competencies do you think are most important right now?

Cooper: If you really think about what a leader's baseline responsibility has always been, it's been to create an environment where everyone can really perform to their potential. And then, in doing that, create a culture and an ecosystem where everyone's moving towards common goals and objectives of a group, the business, the firm, etc.

One of the biggest changes I've seen in my career—it's been exaggerating the last two years, but I saw it start five years ago—is that the criteria for moving people in the same direction has to include how the work and the objectives are going to impact not just the group or the firm's bottom line or the individuals' bottom line in terms of how they're recognized, but how it fits into the broader system of communities and environments where people live and work, etc.

That is not just limited to economic impact narrowly defined. It includes everything from equality, broadly defined, climate, broadly defined. The list just goes on and on. What that means for leaders is that you actually have to really invest and be very intentional about the skills that are required to connect with each member of your team as an individual, and really understand what it's going to take to create that collective, that team. The requirement for that ability to understand the human dynamic is greater than it's ever been before. It's always been important, for sure. But now it's non-negotiable, and that's why people are really seeking out Charter to try to get some, some sense of what they need to be doing. Because I do think it's a different skillset for many leaders. In my generation, which is increasingly irrelevant, what got people to leadership positions was your ability to produce or to connect in the narrowest of senses. Now, you've got to really meet your people where they are as humans. You have to understand that they are not willing to leave who they are outside and become this different person. They really must figure out how to think about the personal and professional priorities and then interactions that create that sense of confidence that fuels people forward. That's what's really exciting about Medley, and that's why I was very eager to work with Jordan in building this business, because I really believe we believe that everyone needs Medleys in their life. I have Medleys. I have people who I have gotten to know from Goldman.

People will give you perspective across different pieces of your life. That's what Medley is. I'm excited about a lot of things, working with Jordan as a co-founder, as a parent working and learning every single day, but hearing from our members that the interactions that they have in their groups at Medley have actually helped them think about how they're interacting with their colleagues at work or with their family, because it's real, it's authentic, it's trusting. Modeling that in their groups gives them more confidence to do that in their day-to-day lives.

You linked two things that people generally talk about separately, the leader's broader responsibilities in the ESG bucket and the need to connect with team members where they are. Can you explain that connection more?

Cooper: I connect them because I think that the first set of things going on in society that I mentioned are actually very important to so many people who are living on the planet. People want to work in organizations that appreciate that, and that have spaces where people can explore the different perspectives in each one of these topics. I personally highlight it because I recall, probably five or six years ago unfortunately it was an instance of a Black man being killed—I think it was Eric Garner. At the time at Goldman the leadership was wringing their hands around whether it was their role to talk about race in the workplace and to get involved in that conversation.

I ended up writing something and, more importantly, we started having open forums where people got together to just talk about how they felt about it. For the most part of my career, that was just not something that would happen. As a result, what does it do for people, both who are very close to it personally and those that don't know anything about it, it gives them a sense of creating a vocabulary around things that are relevant to each other. Therefore, when you come into work the next day and sit at your desk, if you've been in one of these conversations with one of your colleagues, you have a different sense of self. You have a different level of confidence. You feel like this person that you're sitting next to and working with so closely actually is seeing you as a human being, not just as this person who puts on a different set of clothes etc. and shows up at work. Therefore I think those things are very, very linked. Human beings have increasingly a sense of responsibility outside of their comfort zone and their lane. That matters. Leaders have to understand that and be able to create spaces where that can happen.

Taylor: Another piece of that is the fact that this sort of blending of life that we've seen over the past year and a half, from our point of view, isn't going to change. Not only are leaders going to need to be able to accommodate what's happening in the environment, employees and people just have expectations to be able to integrate different parts of their life. They are one person. They show up as one person. Right now the boundary is certainly challenging. You might even hear my dog barking in the background—I apologize. He sometimes shows up, we can't get them to stop. But there really is something around this that is going to impact the landscape going forward, where people want to be able to show up as they are in their work environment. Leaders have to be able to accommodate that too.

Cooper: There's one point that is so important: I 100% believe that this is all centered around creating environments where people can perform to—or beyond—their potential, which leads to greater productivity, which leads to greater performance in companies. I try not to get discouraged because I just want the conversations to keep going and people are like, 'Look, this is a job. This is not a group-think session. There's time you just have got to put your head down, you just have got to work.' That's really missing the point. There are things that are probably out of the comfort zone of many, the list is long. But then there are other things which are, 'Hey, how are you? How was your weekend? You've been in these meetings with us for the last five weeks and you haven't actually said anything. Why don't you come by my office and let me know what you're thinking about these things? Because I'm sure you've got some really interesting perspectives. Just know I'd like for you to participate.' Paying attention! When you pay attention to people and to your teams and to your culture the same way that you pay attention to your product design or software, whatever the case may be, you'll get stronger, you'll get smarter. The teams will get stronger, smarter, and inspired to work and produce exciting things.

As I understand, Medley is focused on making coaching more accessible to people outside of the senior leadership of companies. What does such early coaching unlock for younger employees? And how can managers better coach their employees?

Taylor: It's this combination of not just coaching, but also the group experience that we think is really, really valuable for people. Because firstly coaching can be a very powerful tool. It can help people better understand themselves. It can help them better relate to others and even just be more confident in what they're doing, where they want to go. But when you pair the power of coaching with a group experience it gets really even more interesting. Because you're not only able to work through challenges that you're facing, but also see other people work through challenges that they're encountering that you may not have even realized you may experience or you are currently experiencing. What we see in the feedback from our community is that people are truly learning just as much from each other as they are from the coach.

They value the fact that other people in their group are in different industries, different states, different countries. Sometimes, depending on how the group is matched, they might even be at different stages in their career. They actually really appreciate that because it helps them get out of their current way of thinking. Right now executive coaching has really been limited to executives. Additionally, even the concept of a really high commitment peer group has traditionally been limited to executives. You see organizations like YPO, even Chief, that are really targeting the most senior leaders. We've been amazed and inspired by the fact that we've had people at various stages of their careers, even ones who are running businesses and who could join a YPO or could join a Chief. They actually say, 'I know I could learn just as much from someone who is 20 years younger than me but also wants to join a group to help manage work-life balance.' That's really cool for us. Ultimately we believe that everybody deserves this chance and this space to build their confidence, to work on what were previously known as soft skills. We believe they're absolutely tangible and not to be dismissed. And they learn with one another.

Cooper: I've seen the benefits of executive coaching applied to senior people. Often it's to fix something that they need to develop. It's an investment that produces returns. But as I've looked at this in the past, I've realized that if you apply those coaching resources earlier in one's career, particularly as they start to manage other people, the returns are really multiple of other alternatives. Because you're going from being an individual person, doing great at your job to actually having to do that plus influence others. I just have a tremendous amount of respect for the fact that you have to learn how to do that.

There are some people who are better instinctively at managing people. But even those people have to work at it and have to learn how to communicate. Coaching applied to sort of that middle belly, which is often high impact, is really very valuable. The other thing that we know is that there's benefits to group coaching. I always had an open-door policy because I just felt like I've learned so much from others. People would want to come as individuals and I'd say, 'Listen, I'd love to meet with you as an individual. But if you bring six or seven people, ideally people that you don't know, I'll meet with you guys once every month'. What happened was that they were very focused on me for like a half an hour, and then they were really focused on each other.

So this model of coaching applied more broadly is really exciting. And I think it's driving why we've gotten so much inbound interest from companies to pay for this, for their employees, particularly their high-performing employees. Because (1) it's an investment purely in them. (2) It gives them the skills to actually navigate different kinds of personalities, and different points in their career. And (3) they get to benefit from the fact that people come to work inspired and engaged in a way that that actually will in the long-term help with not only just how they're doing their jobs, but how they're thinking about their organizations.

There's that McKinsey research saying that only 10% of people are naturally equipped to be managers or leaders...

Cooper: There was a guy that I worked with who I respect and is still a dear friend who used to say, 'You're really good at this nice-nice stuff.' The more I got upset about it, the more he yanked my chain. The argument that I made, which has come true, is that ultimately technology is going to help us get smarter at so many things. In finance, we used to apply human beings to do analysis where now you just would never do that. But having an instinct and investing in how you're actually interacting with another human, when it goes well, and learning from when it's not, is a hard thing to replicate. Now, those 'nice-nice skills' are our definition of leadership. So maybe I should give him a call and remind him of that.

What's your top advice for managers based on what you're seeing with people who come through Medley?

Taylor: The biggest area that most people can likely improve is listening. Truly listening to people on your team, clients, or people across other parts of the organization. Because you'd be surprised what you can really learn when you try to hear what someone's trying to say. In my own managerial journey, that's been one of the biggest things that I've been working on and that I consider now to be one of my strengths. But it has taken me time to really gather a hold of that. The other big thing is especially now the importance of just recognizing the people's full experiences and what they might have in their life right now.

We are encountering a moment of real burnout. I'm seeing it among various communities and people at various levels in their career. This is just sort of a holdup of something we've been seeing really over the past 20 years where productivity is increasing and increasing and increasing—but at what cost? People need to be in a strong place in order to perform, and in order to show up every day. So the role of the manager now is also making sure that employees are taking care of themselves and advocating for the resources that they need.

Cooper: You have to really respect it, and the responsibility and the learning that we all have to put into being a manager. Because you're thinking about them as a leader, it's not static. You can do all the work right now and think about all the things that are impacting people, and you're locked and ready to go. Like two years ago, you do all this work, you engage, etc. And wow, multiple pandemics, Covid, racial inequality, it goes on and on. So you've got to really think about how is that going to impact my people and how should I think about adapting my style. And, oh, by the way, it's not going to be in person anymore. It's going to be virtual and, oh, by the way, it wasn't perfect when it was in person anyway. We fantasize that it was wonderful before.

It wasn't. It wasn't perfect for everyone. So you really have to be facile and interested in the pursuit of learning and expanding your perspectives, particularly as a manager. Because it's not just about you, it's about all these other people that you're influencing. You have to be able to take all that in, listen, connect with those that are not the loudest, who are not in your sweet spot of the way that you work. But also, you have to as a leader and as a manager, know when it's important to focus on the jobs and the innovations in the work at hand. We've got to make sure that we give space for everything. And part of everything is having the job satisfaction of being great at your job and learning and growing and getting more responsibility. To do that, it's important to have a way of communicating good and challenging feedback so that people continue to learn and grow. All of those things have always been important. They're critically important now.

One of the macro things that's changing workplaces is the presence of multiple generations. How do you think about navigating that, especially given your own partnership?

Cooper: It's part of the reason we're working together. Because I know that I don't know as much as Jordan does, as our team does, about what the future will look like. I have a lot of reps, I'm older, I've been through different environments etc. But I've got to really keep learning. And who better to learn it from than another generation? I had the best job in the world and I have a better job now because we just get to be in touch with all sorts of different perspectives and minds across generations. It's inspiring. In most leadership constructs at companies— like the management teams, leadership team, committees etc.—you look around the room and we're really just all setting the table for the talent that was coming through.

Providing enough of our experiences, but ideally giving people enough room to really put into place the different ways of thinking and doing things that is the future. I have done a lot of really interesting things and I've learned to ton. I love being uncomfortable. But I tell you, I'm, I'm uncomfortable every single day working with Jordan. Because she looks at things often in a very different way. I love that. We don't just always go there, but there's always a moment every day where I walk away thinking, ' It's only had I not thought about it—there was nowhere in my brain I could have thought about it.' That's exciting for me for working outside of your generation. It also cuts down the arrogance. It keeps you grounded.

Taylor: Much of Medley's traction so far is a result of our ability to draw in different types of people and really build community. That includes for Edith and I, being of different generations. Our age difference actually is a gift that helps push each of us in various directions.

Register for the Charter Workplace Summit. (It's virtual and free.)