Leadership today requires more than skill, strategy, or resilience alone — it requires courage that is grounded, aligned, and sustainable.

Eveline Shen, who prefers to be called Ev, is an award-winning leader and social change strategist with more than two decades of experience building movements and developing courageous leaders. As the former executive director of one of the largest women-of-color-led, multi-issue organizations in the country, she helped expand the national Reproductive Justice movement. Today, as the founder of Leading Courageously, Ev teaches leaders how to stay true to their values, transform adversity into strength, and sustain their impact through her Courageous Operating System.

In this episode, we explore how leaders can move beyond reactive leadership and instead operate from a deeply integrated system that aligns values, strengths, purpose, and courage.

What you will learn from this episode:

  • Why leadership tools alone are insufficient without an integrated system.
  • What the Courageous Operating System is and how it aligns nine core leadership components.
  • Why women and marginalized leaders often need permission and support to fully claim their leadership power.

“Leadership tools are helpful, but without a system, they can’t carry you through complexity.”

– Eveline Shen

Topics Covered:

02:45 – Ev’s journey from intern to executive director and movement builder.

05:10 – Building leaderful organizations within the Reproductive Justice movement.

07:20 – Why Ev founded Leading Courageously and shifted to leadership development full-time.

09:15 – Coaching, team work, and leadership programs as a sustainable business model.

11:10 – Why Ev wrote Choosing to Lead Against the Current.

13:30 – The leadership gap: why new leaders are promoted without support or training.

15:40 – Tools vs. systems: what makes the Courageous Operating System different.

19:05 – Courage as staying true to values, not people-pleasing or firefighting.

20:40 – Everyday acts of courage and why women leaders underestimate them.

Key Takeaways:

“The Courageous Operating System interlocks leadership components so they move in the same direction.” — Eveline Shen

“Courage is not just about bold moments — it’s about everyday decisions.” — Eveline Shen

“When leaders slow down, they create space to lead from purpose instead of reaction.” — Eveline Shen

“Staying true to your values often requires more courage than taking action.” — Eveline Shen

Ways to Connect with Eveline Shen:

Ways to Connect with Sarah E. Brown:

 

Full Episode Transcript:

(AI helped us put this together, so if you see any weird grammar or missed words—just know we nailed it during the actual chat.)

Eveline Shen

The courageous operating system I developed interlocks the nine critical components of leadership so that they are working in alignment, they are working in synergy, and they are moving in the same direction so that you can actually leverage all of what you have to bring to whatever goal that you’re reaching.

Sarah E. Brown 

Hello everyone. Welcome to the KTS Success Factor Podcast for Women, where we talk about challenges senior female leaders face in being happy and successful at work. I’m your host, Dr. Sarah E. Brown. 

My guest today is Evelyn Shen. She goes by Ev. She’s an award-winning leader and social change strategist who has spent over two decades empowering others to lead with courage and authenticity. 

As the executive director of one of the larger women-of-color-led multi-issue organizations in the country, she helped to build and expand the national reproductive justice movement. Now, as the founder of Leading Courageously, she teaches the Courageous Operating System. This framework helps leaders stay true to their values, transform adversity into strength, and sustain their impact. Her new book, Choosing to Lead Against the Current, offers a bold blueprint for changemakers committed to building a just and liberated future. 

Welcome, Ev.

Eveline Shen

It’s great to be here. Thank you for having me, Sarah.

Sarah E. Brown 

Oh, it’s my pleasure. So first of all, tell me about this larger women of color-led, multi-issue organization. What was that? And what is the reproductive justice movement?

Eveline Shen

Absolutely. So I was the executive director at an organization called Forward Together, and I came kind of close to the beginning of my career as an intern. 

And I was asked to lead a curriculum for young Southeast Asian women or girls in middle school. And I got to create this curriculum, which I wished I had when I was growing up in Colorado. So it was all about how to deal with gender, you know, looking at sexism and racism and how to be in your body. So I came in as an intern and I ended up loving it so much that I stayed for 22 years, became the executive director, helped to grow it from a three-person organization to, by the time I left, a 40 staff across the country. 

And so through that, I really was able to kind of grow the organization, but stay committed to building a leaderful organization and a leaderful movement. So the reproductive justice movement was also starting to grow at that time. 

And so, you know, I was able to bring my experience and also grow with the movement and help to build the movement to help people be able to protect and receive the rights and recognition they need over their bodily autonomy, their family formation, and their agency.

Sarah E. Brown 

Got it. Got it. And then you left to start this organization. Did you leave to start leading courageously?

Eveline Shen

I left because I wanted to focus full-time on courageous leadership because I saw that our challenges are so intense and complex and that we need to be able to welcome all different kinds of leadership styles. 

And I feel like for women especially, There are so many ways that we bring our leadership that often some of these ways don’t get welcomed, right, and are not supported. And so I want to help people be able to connect to their strengths, be able to connect to their core assets and be able to step fully into their power as leaders. 

And so that’s what I do full time is I bring folks together across strategy, across sector, across issues, across, you know, ways in which we’re normally siloed to build community, but also to have a space where they can focus on their leadership, because oftentimes we don’t get the opportunity to do that in our day to day lives.

Sarah E. Brown 

Mm-hmm. So one of the things that I do as a side product of these podcasts is I’m introducing people to new business models. So are you coaching in this? Is it primarily a coaching and training exercise or what is the business model?

Eveline Shen

Yeah, so I do kind of on three levels. I do individual coaching. I do team work. So I work with teams who are wanting to build a very robust organizational culture that supports leaders. And then I do leadership programs, which I just mentioned, which brings in leaders to be able to kind of work with the courageous operating system, which I developed.

Sarah E. Brown 

OK, we’re going to get to that in a minute. But what inspired you to write a book? And I’m asking that question because writing a book and getting it published is a non-trivial exercise. It is a huge commitment, and takes a lot of time. So why did you want to do it?

Eveline Shen

It’s a really good question. So about two-thirds way in my career as an executive director, there was one year where I started to get a lot of requests, requests from new leaders, requests from leaders who’d been there for five to seven years who were looking to move their organization to the next level. 

And I realized I wanted to help them, but there was only one of me and I was running an organization. So I decided to write this book as a resource to help new leaders be able to kind of anchor and have access to a system that can help them be able to navigate through the terrain as a new leader, but also for more seasoned leaders to be able to kind of hone their leadership, but also have access to ways to help mentor other leaders that they are connected with in their teams and who they work with that they want to build up. 

So I wrote this book because I believe that the work we do should not only be good for our mission, but be good for ourselves. And there’s so many ways in which I think that we as women leaders don’t take the time to really set conditions for our success. 

And so this book encourages all of us to, instead of adopting a sink or swim mentality, to be able to figure out internally and externally, what do we need to put in place so that we can succeed?

Sarah E. Brown 

Well, we’re going to get to the operating system in a minute, but I want to also highlight that it seems to me anyway, that companies have lost the capacity to train new leaders. New managers and supervisors are kind of thrust into their roles because they did a great job as individual contributors, but they don’t get a whole lot of mentoring and training on what is the difference between doing versus leading. 

And so, I think that any book that talks about that is filling a void that I see that’s pretty prevalent. Have you seen that?

Eveline Shen

Yeah, absolutely. And that’s another reason why I wrote the book, because there is just a lack of resources out there. And there’s not only just a lack of resources, but a lack of infrastructure in terms of a leadership pipeline, a way for people to plug in and to learn the skills. A lot of times people are, you know, stepping into new positions that were created for them and they’re kind of building the ship as they sail it and not have enough support. 

And so I think that if we can build within our culture, within the organizations that we work with, that we are building out some scaffolding to help leaders move to the next level. 

Like you said, people rise to the top because they are successful, because they have initiative, because they do things well. But then they’re put in a position where, oh, my gosh, they’re doing some new things. And there’s an assumption that they’re just going to be able to continue to do that on their own. And, you know, that’s not what I call setting people up for success. And so, thinking about how we do this in a systematic way is really important.

Sarah E. Brown 

Mm-hmm. So let’s talk about the courageous operating system. What is it? 

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Eveline Shen

So I like to start by saying that when we think about operating systems, many of us think about computers because that’s how the term was coined. But nature has operating systems, nature has leadership operating systems. If you look at orcas, for example, orcas are matriarchal in leadership. 

And it’s the grandmother orca that the pod kind of turns to when conditions are lean. When conditions are robust, the leadership is fluid in terms of the different female orcas taking leadership. 

But then when times are rough, they turn to the grandmother orca because she has been able to lead through the good times. I mean, she’s been able to live through the good times as well as the difficult times. So she knows where to find the salmon when they’re not abundant. She knows places to avoid in the ocean, there are threats. And so, she’s thinking about protecting her pod in a systematic way that bridges time and space. So I believe that we as leaders need to bring a systematic approach to our leadership. 

And oftentimes we use our leadership qualities and abilities in isolation of each other. And you can see this in the way when you go to any bookstore and you see on the bookshelves a separate set of books on courage, a separate set of books on purpose, a separate set of books on strengths. The courageous operating system I developed interlocks the nine critical components of leadership so that they are working in alignment, they are working in synergy, and they are moving in the same direction. So that you can actually leverage all of what you have to bring to whatever goal that you’re reaching. 

And because it’s a system, it can adapt to the different terrain that you are navigating through as a leader. And if you have a setback, it helps you be able to not only recover, but to be able to grow stronger in the process. And when I was younger and I wanted help, oftentimes I was given leadership tools. 

And tools are really helpful, but they’re very situationally specific. So a planning tool is not gonna help me if I’m trying to mitigate conflict within my team, for example. But a system, and the way I design the system, allows people to be able to access it no matter what challenge they’re facing, whether it’s trying on a new project, or managing your staff, or recovering from, you know, a crisis. So these are ways that I feel like a systematic approach to leadership can really amplify and bump your leadership game.

Sarah E. Brown 

So that I’m clear about the distinction you’re making between a system and a tool. I understand tools, by the way. That part’s clear. But can you give me an example of somebody who’s used the system and how the system’s approach is different from pulling a tool out of the toolbox, for example?

Eveline Shen

Sure. So many leaders that I work with, when they think about their purpose, and let’s say their purpose in the moment, They’re looking at needs around them and gaps, and they’re wanting to fill them. And I think that one of the things that is important is that, so for example, oh, the printer just broke. Now I’m gonna drop everything that I’m doing, which was really important, and spend two hours fixing the printer. Oh, someone on my team is sick. 

Now I’m gonna fill in, and the project that I’m working on is not gonna meet the deadline. This is kind of akin to sailing a ship as a captain and only paying attention to the wind gauge and ignoring kind of your compass, not looking at the water currents, and definitely not bringing to bear what you as the captain have to contribute in terms of your strengths, your lessons learned, your expertise. 

And so when I work with leaders using the system, when we think about purpose, we’re making sure that the purpose that they are working on right now is aligned with their mid-range purpose, with their longer leadership mission. We are making sure that their purpose is deeply informed by their values and that they’re able to leverage strengths. We spent a lot of time kind of looking at doing an audit of strengths. So which strengths can you use to be able to exponentially move much more quickly to achieve your impact? 

And where’s courage going to come up? If you’re trying something new, where are you maybe going to need some support? Where are you going to be able to kind of navigate and not be stopped by fear or imposter syndrome? 

So this is an example of just in terms of purpose, how kind of bringing in various aspects of our leadership in a systematic way can help us be able to like move directly to where we want to go if we’re just thinking about needs in terms of purpose, it could derail us from the direction that we actually are trying to achieve, trying to move towards.

Sarah E. Brown 

Okay, well, let’s go back to the printer example. Okay. Just went kapooey. So I’m using your system and the printer just went kapooey. How would I approach it differently?

Eveline Shen

Well, I think instead of oftentimes leaders and I did this too. Well, if I can fix it, then I’m going to do it. And so first of all, there’s a pause instead of a knee jerk reaction of like, okay, let me just fix that to pause and say, ground ourselves, what is the most effective use of our time? Yes, the printer is broken. Is there someone else that can step in and fix this? Right? 

So that’s just one way of just taking a pause and not reacting and staying grounded in what is important in terms of what’s the best use of our time. And even if I can fix that printer, there’s probably very few people that can do what I was doing. Am I spending my time doing right before the printer is broken? 

Hopefully, because that’s one of the things that I encourage leaders to do is to make sure that, you know, the majority of your time is something where you’re not toiling away doing meaningless tasks that you need to make sure that you are, you know, you are a leader for a reason. You bring all this expertise and you need to be able to use that in order to move your vision forward instead of fixing a printer.

Sarah E. Brown 

And remind us one more time where the courage comes in on this.

Eveline Shen

The courage comes in staying true to your mission and your values.

Sarah E. Brown 

It’s really about having the courage to stay grounded in who you are instead of people pleasing and meeting others’ expectations.

Eveline Shen

Yeah. And courage comes into every component of the system. That’s why it’s called the courageous operating system. Whether you’re thinking about purpose, whether you’re identifying your strengths, I can’t tell you how many, I have an activity that I do with leaders where I have them tell their story of when they were in their leadership flow. And we do this in small groups and other leaders are listening and they reflect back every strength that they heard in the story. 

So many leaders, especially if you come, if you’re a woman, if you come from other marginalized communities, it is the first time that they’ve been in a small group where that mirror gets reflected back. And it takes courage to receive it. It takes courage to claim their strengths. It takes courage to be able to bring that forward in everything that we do. 

And so if you start to slow things down in leadership, there are many ways that we can bring our courage to bear to be able to fully step into our leadership power that we don’t get taught, that we don’t get encouraged to do. And so that’s what I try to do with leaders.

Sarah E. Brown 

Well, that is well said. So, Ev, is there one thing that I could have asked you that I didn’t that would help my listeners understand what the courageous operating system is? In other words, should I have asked you something I didn’t?

Eveline Shen

I think that in this time, courage is the fuel that we need to kind of move forward. And so what I would say is that there are many times in our daily lives when we’re leading that we’re not even noticing when we’re using our courage because it’s just normalized for us. 

And so what I would say, encourage your listeners every time you come up against a moment in which you are doing something new, in which you’re scared, that feels daunting, that feels a little bit more vulnerable than what you would like to do, take a moment to just reflect and pause and see if this is a time for courage. 

Because if we kind of roll through those moments without being aware of our courage, we can start internalizing those moments as deficiencies, as, oh, I’m scared because I’m not good enough. I don’t want to do this because it’s something that is inherent in me that keeps me from stepping forward when actually there’s a lot of things happening in the external environment that can keep us from doing that. And so I would just encourage listeners and leaders to kind of make yourself more aware, and what I call them is everyday acts of courage. 

Oftentimes we think of courage with a big C, but I think about courage with a little c, these everyday acts of courage of setting a limit, taking care of ourselves, being able to have difficult conversations. These are the practices of everyday courage that make up and build up our ability to lead effectively and powerfully.

Sarah E. Brown 

Well said. And Ev, where can my listeners find you?

Eveline Shen

My website is leadingcourageously.com. 

Sarah E. Brown 

And that will be in the show notes. Ev, thanks so much for being with me today. 

Eveline Shen

Thank you so much, Sarah. It was a pleasure. 

Sarah E. Brown 

Thanks for listening to the KTS Success Factor Podcast for Women. If you like what you are hearing, please go to iTunes to subscribe, rate us, and leave a review. And if you would like more information on how we can help women in your organization to thrive, then go to www.sarahebrown.com. You can sign up for our newsletter, read show notes and learn more about our podcast guests, read my blog, browse through the books, or contact us for a chat. Goodbye for now.

Sarah E. Brown
Sarah E. Brown