The Power of Generalists Part II with Siobhán O'Riordan

In this episode, Erin Cox and Scott Knox welcome back leadership coach and author Siobhán O’Riordan to continue their deep dive into the power of generalists. Building on their previous discussion, Siobhán introduces key ideas from her new book Reframe, exploring what defines a generalist, why their careers often look nonlinear, and how their curiosity, adaptability, and pattern-connecting strengths are uniquely suited to today’s fast-changing world. Together, they reflect on their own zigzag career paths, the environments where generalists thrive, and why this often unseen group is critical for navigating complexity, leading change, and driving impact across organizations.

Hosted by Erin Cox and M. Scott Knox
Edited and Produced by Stephanie Cohen

Transcript

Welcome to the Lead and Live Well podcast. My name is Erin Cox, and I'm thrilled to be here with my co host Scott Knox on the Lead and Live Well podcast. We sit down with leaders in the social impact world to learn about their leadership journeys. 

We talk about their strengths and passions, the transitions they have made in their career, and And how they have crafted their own paths to leadership.

Our goal is to highlight a diverse array of leaders and journeys, so that our listeners learn from relatable and compelling examples of what it means to lead and live well.

Erin: Hello everybody, and welcome to another episode of the Lead and Live Well podcast. I'm Erin Cox. Joined here once again by my amazing co-host, Scott Knox. Hey Scott.

Scott: Hey Erin.

Erin: Excited to be here today and this is a first for the podcast. We are having a return guest, for a new and exciting episode that will continue our previous conversation around generalists.

We got a lot of feedback on that episode. A lot of interest, a lot of people feeling called forward by this definition of generalists and this idea of who they are and how they work. And we're excited to have the person who is the genius behind all of those thoughts and ideas here back with us today.

She is a strength certified coach and a consultant, and now is an author, which is super exciting. So we're gonna be talking about her new book Reframe which is specifically tailored to the needs and the professional development of generalists.

So with no further ado, let's welcome back Siobhán O'Riordan back to the podcast.

Hey Siobhán!.

Siobhán: Hello. Such a treat to be back with both of you.

Erin: Exciting. 

Scott: It's great to see you Siobhán.

Siobhán: Great to see you, and thanks for that very kind introduction.

Scott: So Siobhán, I, there's so much for us to talk about and just to highlight one of Erin's intro comments about. Folks being seen, being called forward. I definitely put myself in that camp and a great place for us to start is, why did you decide to write a book?

Siobhán: I think, there's two reasons. I I wrote a book, and a third I would add to that actually I really value writing as a better way to understand my own thoughts. So I, I have a regular writing practice and a regular writing group. And I find it's a, a very powerful tool in and of itself.

But writing for myself is not necessarily helping others, right? And so why write a book that's really for others? And it was because I was having so many of the same conversations with clients that I was seeing patterns and insights that I was having that I think I could, I could share more easily in a book.

So I was doing it both to quantify and un understand my own knowledge about generalists and how to help generalists but also writing it in a way that I think was and is useful to others. And then of course, our, our, our shared connection Andrea encouraged me to, and I think sometimes when, when, when you have a sense that people really believe in you and encourage you to do something you do it.

Scott: That's

great. Thank you. 

Erin: Well, we've already heard that this book has has really just impacted so many people and it's only been out and about for what, a couple months now Siobhán. So truly congratulations. I know it was a labor of love and really done in service to the significant population of people out there who, whether they know it or not, are generalists.

And I think so many of them are, are self-identifying in ways that are empowering and helpful to their professional development by reading your words.

So let's, let's jump to the beginning. Because, The concept of generalists might be new to some folks, and you provide a functional definition, which we haven't had before. And I quote "widely curious, creatively connecting information to ideate and test solutions."

But at the same time as we have that definition of who generalists are, you also say that every generalist is unique. And we know that because we are both generalists, but our, our strengths profiles could not be more opposite, which I just find so intriguing.

So help us understand if if generalists are all so different in terms of the strengths they have, what actually are the ties that binds that make us generalists?

Siobhán: Yes. Yes. And I think you know, the one thing, that's not included in that definition. That definitely contributes to this question of how you can be a generalist and still unique is also context, is your operating environment, where do you work best?

So, the truth is everyone is unique in terms of their the talents that they bring to their role. And as you said, Erin, you and I are generalists. I think we've had some similarities in our career, but we approach them very differently which also helps us be great partners in the work that we do together.

So specialists really benefit from a structured career path. And generalists have to find their own way. And yet there are things that generalists share. Right. So it's not that generalists are just defined as not being specialists, but it's that they have a curiosity that is ranging. And David Epstein really talks about this in his book Range. That's the title. And, and that book is he does a really great job of looking at all these different people who have succeeded coming from having been exposed to a bunch of different points of view and, and different areas of expertise, et cetera.

The other thing is that, discerning solutions or addressing problems is not done in a linear manner. So generalists will borrow, knowledge from the all their different kinds of lateral learning and apply that to how they problem solve and that sort of creative outta the box.

Dot connecting thinking, and you hear generalists use that term a lot outta the box or, connecting the dots or seeing patterns. And those are all things that generalists share. So we, so we know from behaviors that are different from specialists and that, that generalists share that there is a, what I call a functional definition. I don't wanna be bold enough and say this is what a generalist is, but this is enough of a definition based on the shared attributes.

Generalists are inherently adaptive. While a. Specialist will be an expert and necessarily, and importantly, so, a generalist will always be open to experimentation and, and this idea of practice. A specialist will be very skill-based. And that is also really important where a generalist is necessarily strengths-based, right? They can't compete with specialists on that deep expert knowledge and the skills that go with that.

I think the, challenge for generalists is if you just say that you're one, it's also saying like you're anything and it opens you to being defined by others. And I think this has been a long-term problem for. Generalists and you say yes to everything because it's interesting. And yet we'll have up and down experiences whether you succeed or fail. And I think generalists as we move forward, need to both elevate what, what a generalist is, but also differentiate in terms of what we individually bring to what the outcomes or impact might be. Does that help answer that question?

Erin: Yeah, and I'm guessing there's some listeners who are starting to feel like, okay, hey, hang on a second. That might be me. So I, I'd love, maybe each of us can add something to this answer, but like, you may be a generalist if, and I'm hearing themes of, you're widely curious, you're able to creatively connect information or connect dots, you fill gaps with I'll say what I've noticed in myself and others, with certain amount of fearlessness, regardless of content knowledge, but just a real desire and a, an ability to solve problems and move things forward. What else would you put at the end of that sentence? You may know you're a generalist if 

Siobhán: I think, there, there's I jokingly always say, if you've had more than one major, that might be a hint,

Erin: Hmm.

Siobhán: double, triple, major. Or, it, it, or or you're really great at trivia. That's another uh, hint. No, it's, it's I think those are really good examples. I think generalists also like to think about solving a problem in service of, or with specialists. Um, So there isn't always necessarily this desire to go deep and, and become focused in one area. So sometimes a generalist might find they're interested in one thing for a while, and then they, they, they get frustrated or bored and wanna transition into something else, and that can work both for and against you.

I think you are, when you talk about fearlessness I think that's really a drive for curiosity and so we can really we have our sense of risk is is I think in direct proportion to our curiosity. So I have a very, I'm high, I'm very risk tolerant and I think a lot of generalists are because they're thinking much more about how to solve the problem and meet the immediate need or connect the dots that need connecting. I think a lot of generalists are also incredibly good at at people management or managing processes or even projects and they're willing to get into what collaboration can look like and, and, and be adaptive in that as well. And I bet Scott has some ideas too of what might make it good generalized.

Scott: Oh my gosh, Siobhan and Erin, I'm, I'm just loving this conversation because Siobhán, whenever I read something you've written or hear you talk, just to say what Erin and I feel like, I just feel incredibly seen and it helps me, you know, kind of define my career path. in, um. in a more defining way.

 One of the things I feel like you're a generalist if you've been with an organization, for five plus years and you've had really distinct and different roles. And I think, I had the great fortune of being with Edward Brook Charter schools for eight years and you know, started as their founding chief operating officer for three years, moved into their founding Chief Development officer for four years. And then, as I was thinking about departing had a conversation with the co-founders, John Clark and, and Kimberly Steadman.

And they convinced me, I convinced me one more act Chief People officer, the founding, you know, um. individual in that role. And I think, you know, as I think about that experience, everything you've said really resonates. And I'm also thinking about what was really unique about being at Brook and being able to make those shifts in professional roles was being inside an institution that had a really strong theory of change, and that allowed me to anchor the work I was doing, even though it was continuously new and different to how am I in best service to the impact that we're doing and the theory of change. And, and, and for Edward Brook, for those who know, it's, it's about supporting great teachers. So everything was tethered back to a decision of how does this support great teaching and learning for kids.

And I think, so that's one when there's a strong theory of change. And then I think, generalists thrive when you're fortunate to work with great supervision and management and colleagues who all embrace growth mindset. Because, that just allows you to dial up your generalist superpowers when there's just an atmosphere of, okay, we're going to figure out how to collectively get in that direction and what are the skills that individually or team that we need to, to add and, and pursue.

Siobhán: And you speak so beautifully to that need of context and the ideal operating environment. And so you were in one where your strengths, whether you knew them or not, were seen by the people who are leading the organization and and this is another sign of generalists, is you often get hired by the same people over and over again for different roles because they really understand your ability to often create a role or create systems where there's an emerging need and to do it in a way that is aligned with both the theory of change, but also the values.

And I think, this is another important part of, for anyone actually, whether a generalist or not, but that kind of values alignment, particularly when you're going through change. Vital, absolutely vital.

Scott: co-sign, absolutely.

Erin: The other thing I heard, Scott, in your story in your time with Brooke, which resonates with me, is you said founding in front of every title. Um, And there's something about that, I, it was, it was the founding chief specialist role, right. Operating, development, people. But you as the founder, you were figuring out what it is.

And getting it going. And my guess is when you left, you handed it off to somebody who had maybe more of a depth of subject matter expertise. I'm seeing you nod your head. 

Scott: That's exactly right. 

Erin: Yeah, that resonates with me. That was my journey at uAspire in particular. I kept kind of like, okay, we were, we were growing really quickly and it was like, oh, now we need a people function. Okay, I'll get it going.

And then to Siobhan's point earlier, oh wait, we're getting too deep, or I'm getting too bored, or there's another thing I need to jump to, spin it off to a specialist.

Next. Research and evaluation. Getting it going, figuring out what it is. Getting too deep, getting boards, the other problems to solve. Spin it off to a specialist.

And I think that type of trajectory, like, and, and also it's a, it's an organizational building function that I think is, is really powerful and not necessarily available. And specialists who come in, perhaps sometimes with expectations of a certain amount of infrastructure that's been built, or a certain amount of practices that are embedded.

Like there's something about a generalist coming in and figuring out what it is, whether you're doing it for a few years or you, you get it going and then. Find the right person, this right specialist to run it, that I think can be really powerful for organizations that are on a growth trajectory.

Siobhán: Yeah, and you're pointing out the generalists thrive in startup environments, and usually a startup team is all generalists, doing what's needed. And then of course, as you become more specialized and grow as an organization, you need the skills and expertise that specialists bring.

There's still room though for generalists within larger organizations and large corporations, particularly in between teams and particularly around managing any change. Or helping to support and adapt to change. 

we like to feed on the new, we like this idea of trying to figure something out. but it always is in relationship and connection with specialists. When we do it on our own by ourselves, we're just, we're just spinning really. We, we really have to be with within a purpose and ultimately with others to do the work that we do well.

Scott: It's a, it's a, a healthy codependent relationship, and specialists.

Siobhán: Yes. Yes. And it's, it's, it's healthy in that it's codependent because, it's ultimately collaborative. And I think the most important thing that a specialist and a generalist who are working together can do is really understand what each other brings and stay connected to, again, that shared purpose.

Because when you collaborate, there will always be compromise. We hear this all the time. But just because you're compromising in how to get there doesn't mean you're compromising the excellence or the outcome.

Scott: That's right. That's right. So, so Siobhan, you, you described generalists as unseen and unsung, yet there's, there's data that you cite showing that half of Americans identify as generalists and that 90% of CEOs studied had general management experience. How can something so prevalent be so hyper invisible?

What's really going on here?

Siobhán: Yeah. Yeah. I think, there, there's so there was, those are two different studies. One and actually in one study, the other is quoted, but the other study is also quoted many times elsewhere. So, OC Tanner in 2023 did a a study of 36,000 employees. And they they were a, a, a firm that consults on on talent. And of those 36,000, 52% identified as generalists. And they also quoted what is a, a Harvard Business Review article that had a study that talked about 10,000 leaders and CEOs of organizations and 90% identified as generalists. So, it's fair to say that people who get to the C-suite have often either found their way, they've often had mentors who have seen their their capacity and potential in their earlier on in their career and have helped develop and grow them. And there's a really good example I shared in my book about how GE used to do that when GE was a big believer in generalists and how they cultivated that within their their company.

So it's such a good question around, if generalists are everywhere but unseen why is that? So it also turns out that of those generalists, 50% feel overlooked and they feel and they feel about 43% 43 feel unsupported overlooked and not getting promotions or having a clear path.

And this is in large part because people have hired for specialists and then they fill in with generalists. Now what's changing is that organizations are increasingly hiring more generalists because they're more adaptive. And that's to meet a lot of the external drivers.

Erin: I would agree with that. I, I think one of the things that this question makes me think about is, this experience I had when I was I had to interview people to get a better sense of like what my skills were, what my strengths were, as I was figuring out what I was gonna do with phase two of my career.

Don't know how many phases there will be, but I'm currently in phase two. And they, one of the answers that we got a lot was. I can't really say what she did, but we couldn't have done it without her. And I was like, well that's really, I'm, I'm both, I both feel complimented by that, but also very lost about what to do with it.

But as I reflected more on it, and I've seen this with other generalists as well, and those who I've managed, it's because it's not a function of our skill sets, what we bring, it's not necessarily a function of what we do, it's how we go about it. And like you said, Siobhan though what we do is how we title, how we promote, how we develop, et cetera, careers.

And so having folks who are so nimble and varied in terms of the, what, it's harder to, it just doesn't come as naturally to describe who they are and what they bring because it's, it's more behavioral it's more contextual.

Siobhán: And it's always adaptive.

Erin: Mm-hmm.

Siobhán: And, which is, which is why generalists matter so much now because we are living in a time where particularly the social sector, but you could, you could argue any sector is really no longer trying to drive change. We are now, we've been working so hard to drive change that we've generated this, a velocity now that we are now responding to change and really trying to navigate that.

And that's where generalists really have an ability to help teams and organizations be more discerning in their direction especially when plans have to remain super dynamic. But bringing that adaptive let's try this, let's iterate on that. This is still aligned with our goals. This isn't. How can we mitigate, modify, et cetera.

So I think it's, it's, it's it's a role that is becoming more important because of exactly as you said, Erin, it's the how, and we're very much living in a how time. So in the nonprofit world, it's about that theory of change, right? That there are going to have to be people. It, it just can't be the people who are experts in delivering the program or the experts in looking at the data, right? Or the experts in terms of raising the funds, right? It's, it's how does that all come together in a way that's really operationalized in a way that's really moving whatever needle, right?

To where it needs to be. And which actually brings us to the point that a lot of generalists do come out of operational roles. And like you, you were leading operations first. And that gave you such insight into an organization that made you a really trusted leader to be then external facing and then. You're seeing both, that you could really go then and look at the talent piece. Which is the Yeah, yeah.

Scott: Well, and, and I, and I think that, Erin and I have some shared experience around operations, either in title or in function, and that exposure to systems building and thinking about like procedures and policies as, as you've shared earlier, Siobhan, like that is an incredible skill in the connecting of dots in, thinking outside the box in new settings, new roles, new teams. So one of the things I love about your book is you start with examples of people who experienced what you call a generalist, zigzag, or a rollercoaster career. I know this started from your own personal insights, but like, what made you realize that that type of a zigzag or a rollercoaster wasn't just unique to you, but something much bigger for generalists?

Siobhán: I was always a little bit confused of if I was the same person, why was I really flourishing and you know, and then completely failing? Like I was not in the middle of any job I ever did, it was either lots of accolades or like, see you later. Right? And I thought, well, I am the same. I'm showing up.

And people who knew me when I was younger would say, you know, I was, you know, could be a forceful personality for sure. I, I'm sure that's, I've slightly matured on that front, but, and I really I really didn't understand it. And and I didn't really have the tools or structure to really self-reflect on that because I was just getting like, oh, maybe, maybe this is it.

And, and, and what I kept thinking of was, oh, it's change. I love change. You know, I'm, I'm running towards change. And what I never really understood was, is that what they're really talking about? And so when I was in organizations that really needed change or was leading change, that worked.

But when I was in organizations that was trying to mitigate risk that did not work right. But this I found out a lot later and what. What really happened was when I moved back from DC back to the Boston area, I was having all these conversations and I really brought a beginner mindset to my work and I was like, I don't know what I'm gonna do.

So I think Erin, a little bit like you, that second career and I was just talking to people and I started, doing a lot of reading, a lot of learning. And when I read range, I saw myself in there. When I read the Squiggly career, which is a book out of England I saw myself in there and I, finally said, had some aha moments and I was having conversations as I started coaching that so reflected my early experiences.

And I realized I am not alone in this, but lacking a framework to understand it. I, I just, I just could not find my way in. So once that door was opened for me around that framework, I could, that's when I started to sort of explore what it really meant to be a generalist and what we could do to elevate all generalists and also understand who I was and help others understand who they are individually as generalists.

Erin: That's really helpful to hear that, that part of your journey. And so it, and I just, I guess I wanna just dip into this real quickly. So if there's, if there're generalists who are listening right now, who now have realized that they're generalists and they're like, wait a second, I'm in one of those low no thriving places.

What could they look at? What could they point to that might help them understand why they're in that place?

Siobhán: I think, the, the I think the first thing that is really important for a generalist is to start thinking about what a generalist is as a subject, as objective. Right? Externalize it from you. And my book can be helpful. I would read Range also by David Epstein. There's, I have, there's a substack and all sorts of things to read on, on, on my website.

But I would, the, the first thing I would really start to do is start looking back at your own career and where did you shine? And start focusing there. What was it that you were bringing that allowed you to shine? And what was it about the environment or the leadership that also allowed you to shine?

and then really hold onto the good as you start navigating all the learning out there, and, and, and Erin, you and I have a program that we do. There's a book, there's a workbook that comes with the book. There's a, a handy QR code in there. I think, I think those are good places to start. 

Scott: speaking of things that you know, individuals can do, I wanna piggyback on your last comment. Your course helps generalists, distill and define their narrative. What does it actually mean and look like in practice? And what shifts when someone finally understands and can articulate their generalist value?

Siobhán: Yeah. You know, That's a really good question and something I've been thinking a lot about. I Think the thing that really shifts and, and we don't really use this word, is confidence in owning what they do well and what they need from others to really succeed. And I think there is a confidence in engaging in conversations that are not just, three words long. But are really focused on the difference someone can make, the impact that they have, and owning their ability to be curious and learn and how they really think about the kinds of problems they're interested in.

So I think there's clarity around problems, and I think there's clarity with the kinds of solutions that they bring. Are they a systems thinker? Are they into people management? Are they you know what, when, when you're in this, this, this cohort of people, and I, I, I'm curious what Erin thinks about this as well. Having people come from different experiences but yet are all in a moment of trepidation.

Um, There is a sharing that builds each other's confidence, but also they start to recognize what's in common. And I think that that really fuels a view forward and an approach going forward that is more powerful. They're not going to the default of what other people have told them to be.

Erin: That, that's a really important point. I, I think one of our course participants from last time she, she summed it up beautifully. She, she said, and this is about halfway through the group coaching experience, she said, she had thought about her career as reactive to opportunity.

She just kind of like signed up for whatever came her way or kept working with the same people like she was seeing all these things that we now know are true for generalists and are part of what allows them to express their impact. She was seeing it as from a scarcity mindset or like that she was reactive, wasn't planful, wasn't in charge of her career, et cetera.

So she was really in that kind of like negative scarcity place. And as she was going through the course, she started to, reframe it to a strengths-based approach. She was like, now I understand why I made these choices, because working with that person, again, I knew I could catapult impact forward in a more powerful way.

Or that the context that was available in that organization enabled me to fill in gaps, connect dots, and made things happen that were, that were truly impactful and unique to my skillset. And so she, she saw it as a transition from, I've been doing this all wrong to. My instincts were right now I can proactively explain that so I can continue on this path that really has been working for me. And I thought that transition was just beautiful.

Siobhán: Very beautiful and I'm thinking of that person and I'm thinking that person in conversation and the confidence that she would give to others. When she shows up with that clarity of her own instincts and being able to then, particularly as change accelerates, it gives a lot of people comfort, frankly, to have someone like that on board.

Erin: A hundred percent. So, Scott, you mentioned AI and all the different winds have changed that are currently blowing like Gale four. Hail infused winds that are blowing. So I, I just, I wanna poke at that a little bit more. In the book Shaman, you write that quote, the thinking that created the problem will not be the thinking that solves the problem, unquote.

So when you think about AI, global challenges, unprecedented change is this moment that we're in. Help us understand why generalists are so uniquely positioned for this moment. And, maybe as a warning to folks, like what's at stake if we don't support them properly in this moment?

Siobhán: I think the answer and importance of generalist is what's unsaid in that, in that statement. We cannot specialize our way out of the time that we're in. It's going to take new thinking going to take new structures. There will be a lot more new roles. Some roles will go away like, making barrels and shoeing horses did.

 And that generalists, because they are adaptive and bring a practice mindset, they can create safer containers and safer approaches. Or maybe were trusted might be a better word to adapting to that change. And, and they're not gonna throw in the all or nothing.

Scott: Hmm. So Siobhan, this has been an incredible conversation and as we wind down, you've mentioned a number of resources during our conversation. Where can folks find out more about your book, Substack and group coaching program?

Siobhán: Sure. you can find me on LinkedIn if you can spell my name. S-I-O-B-H-A-N-O, Rearden, O-R-I-O-R-D-A-N. The website is Big C Strategies. My book is for sale anywhere books are sold and i'm on Substack as the generalist specialist, but that link is also available on my website and if anybody is interested in the generalist Essentials program, they can reach out to me or Erin, or any number of the people who've taken the course before.

They're always happy to share.

Erin: Their testimonials are all over LinkedIn. Check 'em out. Thank you so much Siobhan, for, for coming back on and, and sharing this next level conversation in support of generalists, we know 'em, we are them, we love them, and we're so grateful that you are around spreading, spreading your genius. in support of them.

Siobhán: Well, thank you both for having me. Um, I wish I could have this conversation or another version of it every Friday.

Scott: Same Siobhan, same.