"Founding, Twice" with Irene Shih, CEO of Pave HER Way

"Either you hired the wrong CEO, or you need to take a step back as a board."

Irene Shih has sat on both sides of the governance table, as Board Member and CEO, and she's direct about what each one owes the other. She's the Founding CEO of Pave HER Way, a new nonprofit empowering women and girls facing systemic barriers. Before that, she built Minds Matter Bay Area from the founding up so she's just lived both halves of the founder story: the leaving and the starting again.

What we get into:

• The founder's real problem isn't scarcity, it's abundance — too many good ideas, too many willing hands, and the discipline to pick three
• Why culture, not documentation, is what a successor actually inherits
• Irene's mother: an immigrant who took odd jobs, went to teach at a local Chinese school, and became an award-winning educator rewriting curriculum across Northern California
• Christina's mother: told she couldn't get a PhD with a child, and what happened when she said "we'll try it"
• Meeting people where they are — Irene's approach to developing talent, and why coaching has to feel like an offering
• How Irene will know at the twelve-month mark whether Pave Her Way is working

Transcript

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SPEAKER_01 0:02

Welcome back to Higher Ground. I'm Christina Greenberg. Listeners to the show know that we talk with the leaders behind mission-driven organizations about how great people and great organizations actually find each other and what it takes to lead once they do. My guest today is someone I'm really excited to have on, both because she's an excellent example of leadership and mission-driven commitment. Also, we had a front row seat at Agility to her latest chapter because we supported her in the match with Pave Her Way, which she'll be talking about in a moment. Irene Shee is the founding CEO of Pave Her Way, which is a brand new nonprofit. It's dedicated to empowering women and girls, especially those facing systemic barriers, to reach their full potential. She also brings more than 20 years experience serving students and communities. She's been a classroom teacher, a strategic advisor to school districts, a state level policy advocate, and most recently the CEO of Minds Matter Bay Area, which she built as from the founding up. Welcome, Irene. Great to see you.

SPEAKER_00 0:59

Thank you so much, Christina. What a kind introduction. Really appreciate it.

SPEAKER_01 1:04

Of course. So one of the reasons I was most excited to talk to you, Irene, is we've been thinking a lot about founders, both in terms of founder starting and founder transitions. And you've just done both, right? You were a founder at an organization that you left, then found a new organization. So starting with the founding part, when there's no playbook and no predecessor, what does the job require of you? And how do you set up those systems for success?

SPEAKER_00 1:30

I think you, if you have a really great mission, one of the embarrassment of riches you you get is that you have a lot of people who are excited to contribute and get involved in some way. And one of the tougher jobs of being on in the founding stage of something is really figuring out what good ideas you're going to start with, what's the sequence of priorities, and then how to kind of get everybody excited, you know, while we might not be able to do 25 or 30 things all at once, getting people really excited, even those who had some different ideas of like the potential of them to contribute to these like top three things that we're going to do this year. And then being able to paint like that roadmap forward. Maybe this year we're focused on three things, but in three years from now, you know, if this builds, there's a potential to grow in these areas and helping people see that there's the today, there's the tomorrow, and then there's the longer term. So I would say one of the things that I think is a challenge, but it also comes from the fact that there are so many opportunities and embarrassment of riches when you have a great mission is that you attract people who have a lot of good ideas and want to contribute in some way. And helping people to really put a container around all of those great ideas and think about the sequence and priorities, you know, that you're going to do things in and getting them excited about that.

SPEAKER_01 2:45

And having just experienced a founder transition as well, I'm sure it's on your mind, but how do you set up the structures for a new organization such that someday when you're no longer leading it, it still can thrive without the founder?

SPEAKER_00 2:58

Yeah, that's another really great question. I, you know, I've always really believed in systems, infrastructure, making sure that you are documenting things that you are doing so that it lives somewhere where people can see it, read it, all of that. But the other part of it that I think is even more important in a in a transition of any leader, whether they are a founder or not, is that the culture they built survives you. And I think because, you know, there will always be things that are the spirit of your organization that don't live in documents. You know, you you just you need people to know what it is. And I think if you've built a culture that understands your core values, it's not even just about saying them every day. It's that, you know, everyone knows what it looks like to live into these core values because you've lived it so much as an organization over and over again. You've celebrated it, you've showed people what it looks like, people show you what it looks like. You have a culture that is going to continue to run on those values and on those ways of doing long after you leave. And if that's the case, you can have a new leader step in and yes, they'll have the documentation and you know, some of the infrastructural pieces that are still there. But even more importantly, they have a culture. And that's the engine that's really driving them forward. And if they can come in and absorb that and really live it and walk with the community that's been living this culture for many years, that's really the thing that's going to continue to carry forward. So I think of both of those things. I think of the, you know, the what's being documented, but I also, maybe because I have a bias toward thinking about culture a lot, I really think it's about the resilience of the culture you've built.

SPEAKER_01 4:34

Transitioning to a little bit, we've been personal, but a little bit more of the personal and your connection to your new org, Pave Her Way. You've talked openly about your personal connection to Pave Her Way and its work. But can you talk a little bit about your personal story and how that connection to what Pave Her Way is doing changes how you lead and makes you more effective as a leader?

SPEAKER_00 4:54

You know, my my origin story, it goes back to my family, my my parents, and I think a lot about my mother, especially. So I I grew up in a low-income family. But that being said, you know, I would say emotionally there was an embarrassment of riches and communally there was an embarrassment of riches. And a lot of it had to do with the fact that my mother, even though she struggled, so my mother came, my parents immigrated from Taiwan. I actually did too when I was very young. My parents were in their 30s. My dad was able to find work as a software engineer. My mother struggled to find work. And she kind of took on odd jobs, including at one point being an in-home care provider to often the younger siblings of some of the kids I went to school with. And, but she really found her calling when I was in sort of middle of elementary school, so early like third grade, my third grade, she decided to go teach at a local Chinese school. My mother has always had this orientation that, you know, she's always had an orientation as an educator. And she thought of herself as an educator even before she became one. That was the way that she parented us. One of the reasons I'm I'm recalling that she actually decided to teach at the local Chinese school is because she wanted to be a part of a community that she felt would bring invaluable resources also to her family. You know, we didn't have access to all of the things that, you know, as an example, I didn't go to preschool because I was difficult to, you know, you know, we we couldn't afford that. Um, there were other things along the way, you know, in terms of, you know, getting ready for for high school, getting ready for college. There were a lot of preparation resources and guidance that we didn't, you know, necessarily have the resources to ourselves get access to, but it, but we were plugged into these communities that helped us get that access. And my mother thought a lot about that when she decided to go teach at this local Chinese school. But the unintended benefit of her choosing to teach at this local Chinese school was that she discovered her talent as a teacher. She became this award-winning teacher just two years into her tenure. And then she got invited into doing leadership work that was actually completely volunteer-based. Um, and she did so well that she ended up becoming essentially like the chief program officer. And that wasn't her title, but essentially that's what it was. She oversaw the curriculum not only to her school, but helped rewrite the curriculum to all of the Northern California Association of Chinese Schools. And in those years, when I saw my mother do that work, not only did me, my sister and I like get the direct benefit of the community resources that came into our living room, but we also got to see my mother, you know, work with other volunteers, especially many of them women, building an organization, building a new curriculum, having this incredible influence on other children and on other families. And so I got to live that, you know, with you, you learn a lot by osmosis, I would say. And I was kind of swimming in the waters of that for so many years. And it inevitably made me realize, I would say, two big takeaway points. One is that when women are empowered to lead, and that's something I saw them do all of those years, they make the world better. They think, you know, women think in these ways that are about community, collaboration, service. And that was something that I saw very deeply. The second thing I took away was, my gosh, my mother is so talented. I didn't even, I mean, I knew she was talented, but I didn't know she was so talented. And what, you know, a shame it would have been if she never got to see her talents through the way that she did. And what a shame it would have been for me as her daughter to not have that formative experience of seeing my mother thrive and do so many great things for others. And so I think that instilled in me this deep passion for yes, nonprofit work, service work, community work. And I think now at Paver Way, getting to do that in such a way where we're empowering women to chase their talent because that's what I got to see my mother do. And I have such deep belief that when women are allowed and empowered to chase their talent, they open the world up for others in beautiful ways.

SPEAKER_01 8:57

It's a really beautiful story. Thank you for sharing, Irene. I think it's neat for those of us who've seen our moms, you know, develop in their careers while we were growing and developing. I had similar experiences with my mom. It's really neat to see that that parallel connection. I've heard your story, Christina. Would you share? Oh, sure. Yeah. My mom, when I was little, my mom was a secretary. That was the work she could get. She had a BA in psychology, but it was the 70s. And so that was what she was able to do as a working woman. She actually showed up to a job interview when I was little, and the person said, Well, you have a baby. You can't work. And she's like, Well, I need to work, pay for my family. She put my my dad through law school and then um through a series of circumstances, ended being a single mom soon after. And she applied to PhD programs in psychology, University of Kentucky. My grandfather had actually been a professor there for a year. She'd gone to undergrad there. She did straight A's in undergrad. They told her, Yeah, you're very qualified, but you have a child. We don't think women can be in PhD programs with children. And she said, We'll try it. And they did. And she did really well. I think it was neat for me to see my mom develop her career and work so hard, right? And try so hard. And ended up becoming PhD psychologist. She's actually managed a number of different counseling centers and had a private practice and mentored, you know, dozens, if not hundreds, of therapists throughout the Bay Area. So it's been it was a neat story in the end. But yeah, it was definitely interesting to see that and definitely inspired my sister and I in our careers. And how do you make sure that of course you're making time for family and caring for your family, which she did, but also looking forward to your own career and your own work and giving contributing what you can. So thank you for asking. I appreciate that.

SPEAKER_00 10:35

It's an incredible story. How inspiring. And just hearing each step along the way, your mother advocating for herself. That must have been an incredible model to see too.

SPEAKER_01 10:45

She was in a place you would not have imagined, right? You know, when she was firstborn in rural Kansas. Speaking of people and talent development, that's kind of what Pave Her Way's mission is, right? Is developing people. So tell me about your philosophy around developing people and how that's showing up in Pave Her Way and your model.

SPEAKER_00 11:01

I think in terms of working with people, I love to hire people that I think are have a lot of intrinsic motivation. And that is their motivation because they feel connected to the mission of the work. Um, that they feel connected to the kind of culture that we're hoping to build. But I really do also believe in getting out of people's way. I've gotten better and better, I should say, over time at knowing what my strengths are, but also knowing where my blind spots may be. And I love to hire people who I think can help complement me and the team in a really great way. In terms of developing people, I tend to think people learn a lot by doing. And there's a little bit of mentoring and coaching on the side that that, you know, I'm happy to offer, but I also think it has to feel like an offering. I've worked with different kinds of people. Some people will say they want that, like, they really love the tactical on the ground. Watch me in an interaction, in a meeting, and then give me feedback directly after. I've also worked with people that are really good at self-development. And it doesn't actually help them that much to feel like they're being overly watched. And so rather what they prefer is to live the process themselves and just be prompted to self-reflect. That's really the thing. And so I've worked with different kinds of people and I like to meet folks where they are. I hire people with the sense that this is absolutely someone who will grow to be this incredible leader. And then I ask myself the question: can I meet them where they are? Because I need to make sure that I'm meeting them where they are so they can unlock their greatest gift and offer that to the organization. So that's probably the general approach.

SPEAKER_01 12:30

I think you're exactly right that part of our job as leaders is to do that individualization with our people, right? And kind of thinking about, you know, what do they need and how can we support them? And it's going to look different for each person. And I love that you're thinking that way. This is, you know, I think to sort of transition to a broader scale of boards and CEOs, you I know you're on a board. What is a healthy board CEO relationship look like? I think this is one of the biggest questions in nonprofits. A lot of people don't even know what it should like like, what the board's role is, what the CEO's role is. And how do you think about that given you've been on both sides of the coin?

SPEAKER_00 13:05

Yeah, I can speak to my experience and how that's led into my thinking around this. And first of all, John is a wonderful human being. I'm glad we both know and love him. Um, I actually am quite lucky, you know, my journey was that I didn't start serving on a board until after I actually had the experience of being a CEO. And so I walked into the board experience with that kind of lens on. And what I realized was that I wanted to do something different as a board member than I would have been doing as a CEO. So there was a recognition because I had walked in with that experience of what I needed from my board as a CEO. So I really was like, I would like to offer that. And at the same time, recognizing like I'm not the driver and I should not be. As a board member, it is not my job to be in the weeds of an organization. It is not my job, nor is it appropriate for me to be overly driving decisions. And I think of the board's role, and I think of this both in terms of how I work with boards, but how I am a board member as well. I think I really do think boards are there to hire great CEOs and then empower them and partner with them where the CEO most needs the board to be. I think that if a board is getting to the point where they feel like they should be doing things that the CEO has not, you know, explicitly asked them to do, either you hired the wrong CEO, this isn't the right person, or you need to take a step back as a board and really examine like, am I showing up the way that my CEO needs me to? That really is the orientation that I take and continue to take. I think. And oftentimes the way that that works out is of course, we need boards to support, you know, to bring the fiduciary responsibility side of the work. The fundraising side is often very important. I think where I often see boards and CEOs really needing to align is actually around like what role does a board play in strategy making? And that's actually a conversation we're really deep in now at Faces, which is the organization that I'm on the board of. And I feel really good about where the board has landed. You know, we're going into this strategic planning process. And the board has landed on at the end of the day, that one, the staff has to feel very invested in, that leadership team has to feel very invested in, involved deeply in the strategy making. The board is here to help be advisory in many ways. And we're also here to take point on things where the staff feels like, gosh, we just don't have the capacity to do that and be really great if the board could step in. But at the end of the day, where we all landed as a board is the staff has to really feel like whatever we decide on as the vision for the organization, that's actually their vision. They think it that's where we should go as an organization. We're gonna pursue a process where we're all a part of it and we all have a role to play, but the leadership team has to feel like it really is a vision they can own. And so that's something that I think feels like the right orientation. Boards will not be executing on strategy. And I think we have to give a lot of credence and respect to those who will actually be doing the execution and know the community very well.

SPEAKER_01 16:14

My friend Leah Eisenberg and I had a conversation on the mic a few months ago about this that strategic planning is often broken. And kind of our thesis was because a lot of times it's done in a vacuum where people hire consultants and they pay a lot of money and they go off and do this whole process mostly with the board, maybe somewhat with CEO, and they come back with this beautiful plan and it kind of sits on the shelf, right? And it's not really actualized or operationalized within the org. So I like that idea of that close partnership with CEO and staff so you can make sure it's not even just a good idea, but it's something that they're bought into and they feel comfortable executing on.

SPEAKER_00 16:50

Totally. A hundred percent. You can often feel, I think, while you're in the strategic planning process, whether this thing is going to work or not. And I think that has to do with how collaborative it feels, how much ownership those who will have to execute actually feel over it. You can sense that in the process.

SPEAKER_01 17:08

Definitely. So you've talked about year one being about proving Pave Her Way. I mean, this is a brand new thing, right? So just starting to say, like, we have this model. Is this going to work? Let's do some pilots, let's figure out initially where we might go. And then you mentioned in your opening that a lot of being a founder is setting culture and habits and vision for the organization. So a year from now, how are you gonna know and how's the board gonna know that you're on the right track with Pave Her Way?

SPEAKER_00 17:33

Such a good question. And a year is a really good timeline to be thinking about because the bigger aspirations of the organization take a little longer, right? We obviously want to fund, sponsor, you know, mentor women to go on and build amazing things that will help other women and girls. Those longer-term impacts will take a few more years to realize and to see. But a year from now, what we will know is whether the first cohort of women recipients in our program, whether they feel they've gotten value out of the Pave Her Way experience. And I think we would look at that, whether we've delivered that value as one, just what they're what they're telling us about their experience. But the other is the extent to which they would be proud and excited to share this opportunity with others that they know. That would tell us, that would be a really great leading indicator of like, wow, this was such a positive experience for them, life-changing enough up until this point for them that they'd go out and recommend it to other people. So that's on the recipient side, which is the North Star. We're here to make sure that we're serving and empowering women. And that's that's the purpose of the organization. I think there will be other parts of that as well, this being such a volunteer-driven movement and mission. I think another thing that we would be looking at as a leading indicator is just the health of this overall community. You know, not only do we hope that recipients will say, gosh, you know, this was great. I want to talk to other people about being a recipient in this organization, we hope volunteers are saying the same thing. We hope our mentors, our connectors, our builders are saying, gosh, I really believe that this organization is making a difference. And I love being a part of it. You know, there's one thing to have a really good mission that everybody can agree with, but it's another to have a culture and a community where people who are on the inside of it can say, yes, we are in fact doing the things that we say we're doing. And in fact, it's really fun to do it together. And so if our volunteers are also saying the same, and again, like that word of mouth, that excitement to get, you know, more people that they know involved, we will know that that's you know, we've built something here that that can last.

SPEAKER_01 19:42

That's really wonderful, Irene. Thank you. What else should people know about Pave Her Way before we close up?

SPEAKER_00 19:48

Yeah, great, uh, great question, Christina. You know, I think ultimately what we really want people to know about Pave Her Way is that we, you know, you you told the story about your mom. I told the story about my mom. I think you and I both fundamentally have a deep belief that women, when they are empowered and that is sponsored, invested in, and having people remove barriers, get get out of their way, get things out of their way. They can go on to do these amazing things for the world that truly makes the world better for others. And that being what we believe in, I hope people know that that's like that's the real mission of Pay for Way. It isn't just to say, let's go fund, you know, individual women. It's to do the whole enchilada of making sure we're sponsoring women and mentoring them and supporting them so that they can go on to do these great things. So that's the thing is like our longer-term vision and impact for the organization is all the women and girls that the women that we support will go on to change lives for. That's what Pave Her Way is here to do.

SPEAKER_01 20:55

Well, thanks so much, Irene. Where can people find you or find Pave Her Way if they want to get involved? Great question.

SPEAKER_00 21:01

Paveherway.org is our website. Uh, you can find us there. And from there, you can find our social media channels on LinkedIn, Instagram, YouTube, but start with our website and I'll take you to wherever you need to go.

SPEAKER_01 21:13

Well, Irene, thank you so much for your time. It's always really exciting to see folks that we've matched be, you know, in that role and thriving. And so we're looking forward to continuing to see your success over the years to come. Thank you. Thank you, Christina. Thank you so much. Thank you.