About Sinead Condon
Sinéad Condon, Chief People Officer at Guidewire Software, has spoken in recent appearances about the human side of organizational change and the importance of storytelling in leadership. In an April 2025 podcast, she said that when leaders feel they are "banging your head against a brick wall" during transformation, it often reflects "a fear of the unknown and a lack of education" because they have not clarified what they are trying to drive. She emphasized that empowerment requires providing people with accountability, resources, information, and authority, and that modern leaders must be skilled storytellers to articulate purpose and direction. Condon also urged listeners to ask themselves "what are we in service to" as a way to stay focused.
In earlier appearances, Condon discussed operationalizing empathy and vulnerability in the workplace, arguing that organizations should prioritize authentic conversations over formal programs. She described self-advocacy as knowing one's value system and feeling empowered to make decisions, and said that diversity of thought should be intentionally designed into teams. Condon also noted that Guidewire is intentional about both equality and equity, and that the company's shift to hybrid work has created an opportunity to recruit globally and become more inclusive. She has described her own career journey, including starting her first company at age 18, and has encouraged others to seek out mentors, coaches, and sponsors.
Source: AI-verified profile updated from Sinead Condon's recent appearances.
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Transcript (41 segments)
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Stacy Louie0:09
Welcome everyone to today's episode of Goals and Game Changers. We're here to explore key insights on business transformation, leadership, and product innovation. My name is Stacy Louie and I'm your host and the CEO of Hyperdrive. So Sinead Condon is the chief people officer at Guidewire Software where she leads global people strategy. Here she's responsible for making sure this company has the best talent on the planet working for their organization. She's got a background in organizational transformation and agile methodologies, but mostly she's passionate about building high performing teams and ecosystems where employees work with purpose and can make a profound impact. Sinead is here with us today to talk about leadership and the human side of change. Emphasizing the importance of storytelling, ownership, decision-making, and listening to learn in driving successful business cultural evolution. So, let's get started. We're so delighted to have Sinead here. Sinead, great to have you.
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Sinead Condon1:12
Great to be here. Yes, this is going to be a fun conversation. You and I have navigated lots of different things together. So, I'm looking forward to chatting with you.
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Stacy Louie1:22
Likewise. Now, I don't want to take the surprise or anything, but you've had a great Silicon Valley history. You've done some amazing things out here. Could you just take a minute to introduce yourself and a little bit of your background?
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Sinead Condon1:37
Sure. I'm sure the Irish brogue gives it away. I'm originally from Ireland, born and bred. Came to the States back in 1998. I was hired by an Irish guy into an SAP consulting firm. I had been doing really well in Ireland. I was managing some SAP projects over there and really got the bug to come to the US and continue my SAP career over here. So came over, had a number of projects under my belt, integrated into Siebel projects, and then stepped into the agile world which may come up in our chat today. Then kind of fast forward to my career now. Who would have thought that I would wind up as the chief people officer, historically known as the head of HR, but I think one of the reasons that I leaned into it is because it too has gone through transformation and evolution. I'm very much part of the senior executive team that runs the company and my lens on people and great talent is something I'm very privileged to do every day. I live in Silicon Valley. I have a dog. I have two kids that are gone off to college. So, I'm an empty nester. Life's good.
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Stacy Louie2:54
That's terrific. And on top of that, you spend your time being a startup adviser.
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Sinead Condon2:57
I do. When you've got this many scars. No, I'm just kidding. It's been an interesting ride. I've learned a lot. I continue to learn a lot. I believe very much in sharing the love. We've got to support each other and build communities where we can. If we can give back in that way, I think that's great.
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Stacy Louie3:17
That's great. Now, Sinead, you've had this history of transformation and transforming organizations. I've seen you help transform executives. You kind of talking through what the world of business is happening today. There's this growth of business transformation across the globe, how we're actually changing everything from our operating models to the ways we work to the mindsets. In your past and the things that you've worked on, what sort of transformations have you been involved with and specifically which one would you call the biggest challenge for you?
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Sinead Condon4:01
I think it's an interesting question and it's definitely worth reflection. I don't know if I would necessarily say one was the biggest challenge. I think they all have their challenges in different ways. I used to go in and sometimes still do say you've seen everything until you haven't. Whether it's, I used to think that the greatest challenges for me as a tech leader or as a people leader was the technology piece. You're doing these complex integrations, you're pulling stuff out, you're re-engineering both the technology and process, and that's complicated and complex, and there can be chaos involved. But in the reality of it, I think what I've learned along the way is that the most complexity happens when you really dial into what's happening on the people side. That really and truly is where the most complexity comes from. When we think back, any of us, including your listeners, think about the challenges that you have in work. Sure, we can check off a whole bunch of boxes on the things that come up on the tech side, but really when you do reflect, many of those challenges are blockers on decision-making. Why? Because you have lots of different characters, right? The team's not quite gelled, or any number of people related things. Often times we don't put it down to the people, we put it down to everything else. Sometimes because we're so embedded in everything that's going on, we can't see the leaves from the trees. For me, it has always been really on the people's side. I recognized that with a thud, probably about 15 years ago when I was on a project. It's probably more than that, maybe 20 years ago. I'm showing my age. I was managing an SAP project and we were coming towards the end and I was walking past a lady who was sitting in her cube that was crying. I was walking with the CEO. I'll never forget it. I did a double take. I could hear her crying. I walked in and she looked at me and I with compassion said, 'Are you okay?' and she looked me in the eye and she said, 'You're taking my job away today. I just got let go.' I swear to God, Stacy, it hit me like a ton of bricks. Sure, did I have it as a line item for change management? Yeah. But did I really consider the impact? Not to say in reality, hand on heart, that it might have changed the outcome of her maybe being displaced, which is awful. But the way in which it was done could have been so much better had I had the wherewithal to really put the people's side with the weightiness that it needed in that moment.
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Stacy Louie7:19
That's right. It's funny in managing these transformations, we often think about what's in the checklist and we often think about the mechanics and not necessarily the people and lives that we touch.
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Sinead Condon7:33
Yeah. There will be different times to put different weight on things but you do have to look at these things holistically because it's not one thing that's going to get you over the finish line. There's not one silver bullet. As much as we can all look in the mirror and say what's the silver bullet, that's where intuition comes into play and you have to look at your environment and do a lot of sense making.
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Stacy Louie8:02
Yeah, for sure. Now, looking back comparing where you were back then and what you were doing, clearly you had focus. You're working with CEO, you're making this big change happen with SAP which is an incredible amount of work and the pressure that I'm sure that you're under. How do you reconcile that? Knowing what you know now, how would you coach yourself back then? What would you tell yourself as you went into that transformation knowing what you've developed skills that you've developed over these most recent years?
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Sinead Condon8:38
When I say it, it's going to sound really obvious, but it just shows you how clueless I probably was back then. When we go into technology projects, I think we're all so busy thinking about the outcomes that the technology will bring. Even today when we talk about AI and automation, we're all in hustle mode to just optimize all the right things to be doing. Back then we were so focused on the endgame of getting SAP in and getting it up and running and really shifting the entire backdrop of how that company operated. I didn't think to ask some obvious questions. Sure, do we talk about process and re-engineering? Yeah. But I didn't lean in hard enough to asking the people related questions. As we optimize in one area, what do we compromise on the other side? If we get success with this particular outcome, what's the human impact of us doing that? What are the gives and takes on that? What will hinder us and what will help us? Sometimes we're so busy in optimization mode and becoming strong operators that we forget the most fundamental thing is what is the foundational environment with the people around us in order for us to drive and execute on what we're doing. Maybe it's because I'm so attuned to that and I have to be careful because you don't want to overindex on it. That's the balance when I think back. What would I do differently? It was balance that I missed. I overindexed on the tech, but I also have to be careful as the chief people officer that I don't overindex on the people's side. It has to be this tension that I'm intuitive enough to recognize where the pressure points are for both.
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Stacy Louie10:55
Yeah, the tension is such a good word, Sinead. Even looking at where the world's at today, I'm seeing the tension growing. There's this sense of hey, this is where we're at with the economy. Economy is doing some strange things over the last couple years. It's been hard for a lot of companies, a lot of folks. Then we see this new injection of technology of AI and how that's shifting things and the projection of where executive staff and executives are starting to see where the future's going to go, how they manage their capacity, where they invest. Between rounds of investment on AI and rounds of reductions in force on the other side trying to calibrate that, I'm sure every technology company's going through something similar. Not only that, I'm sure that other companies are going through the same thing whether they're in tech or not. Are you seeing things like that kind of float around challenging managers and executives to make some of the tougher decisions in business?
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Sinead Condon12:01
Of course. I think every company is going through transition and if they're not, they become irrelevant very quickly. Somebody asked me the other day, how do I see leadership shaping up in the next 5 to 10 years? It's less about what does leadership look like? It's more about what will our environment look like? What are we literally shaping our work to be that we back into leadership on? When we think about AI, it's a good one. If we think about AI and what AI is helping us to optimize on, what it's shaping our future to be, I think we have to get really good very tactically on storytelling as leaders. It is so deprioritized in terms of a skill, but that storytelling part of being able to stand up there and articulate with the gravitas and education that's needed to say what is the future of our company? What does that growth look like? How do we see us jumping onto AI? How do we see it optimizing what it is that we do today? What is the impact that's going to have on us? That is a thread that has to be pulled in such a way that it helps people to ground themselves, to get purposeful and intentional about what the future looks like because there is an individual and collective piece to that. The individual might be the employee, it might be the leader, it might be the entity that is the company. Then there is the collective piece which is the community. How do we band together and what does that all look like? That storytelling piece, which is really about the framing and the way in which we talk about it, is so important right now. It is so important because people are looking for clarity. Am I going to lose my job? People hear AI, it's becoming a bit of a trigger. You don't want to stifle the innovation of that, but you want to ground people so that they can go on the journey with you.
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Stacy Louie14:29
That would be a great skill to have as a manager or being a leader in your company, being able to articulate the story and offer direction. It sounds a lot like Simon Sinek when he talks about the why.
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Sinead Condon14:45
100%. It's core. In fact, we're getting ready to do a summit here at the end of March. We were talking amongst the management team what would be one of the core skills that we want to make sure that everybody has and storytelling was one of the top core skills that we want people to understand. Not because, in Ireland, we talk about the Seanchaí, the storytellers of Ireland, and everybody has the gift of the gab. We're not talking about that. We're talking about clarity around purpose and outcome, making sure people understand how to articulate the why. If you can't do that as a leader, your days are numbered. It's fundamental to being able to be a leader in the 21st century.
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Stacy Louie15:34
That's fantastic. It seems like a key skill with any kind of transformation or any kind of growth going into leadership to be able to explain the why. If senior level executives are great at explaining the why, then it cascades down and everybody takes ownership of that and then they can integrate it into their day-to-day work. Why am I actually doing this work? It's because I'm here for the greater good. It might be something where I'm working for this particular consumer or this customer base. It's very product minded instead of a project minded approach, isn't it?
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Sinead Condon16:14
It is. It's so funny when you talk about ownership because ultimately, any one of us coming into work every day, which we hope has purpose, you feel a sense of ownership. A couple of weeks ago, we were doing a talk on the use of language in leadership and how ownership and owning something can have just a different meaning to different people. It's highly subjective. We were talking about the difference between what it means to own something in work versus if you own something outside of work like your house or your car or your bike. The feeling of that ownership and how it manifests in what you do and how you own it at home can often feel very different. How do you get that true sense of ownership in a work environment? Of course you need to have the autonomy and you need to have the skills and you need to have all of these things that create that for you. It was a very interesting exercise to talk about the difference of what that looks and feels like when you are outside of work versus inside of work and how that relationship feels.
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Stacy Louie17:27
That's right. Back in the day when I was in packaged goods, I used to be a product manager. My first product I ever managed was raisins. Of all things, raisins. It sounds so minute and silly, those little raisins, but there's nothing more special than seeing your package of raisins sitting there on the grocery store shelf. It's like, I did that.
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Sinead Condon17:51
That's right.
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Stacy Louie17:53
You have that ownership and you feel like...
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Sinead Condon17:55
That's right. You'll do anything for those raisins.
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Stacy Louie17:57
Yes. That feeling, that sense of pride. How do we as leaders recreate that sense of pride? Because that's so associated with ownership. Yet so many people own things in the workplace that don't have that. Why is that? You mentioned decision-making. Do you think decision-making has a lot to do with that? I see some of the things that teams get involved with and sometimes teams look frustrated because they're not in a position to make a decision on one thing or another and it feels like it takes things away and that management scheme.
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Sinead Condon18:43
It does. There's a great book, I hope your listeners can write this down or Google it on Amazon. It's a book by a guy called Kimball Fisher. I want to say it's Self-Directed Work Teams, Stacy. I don't know if you know that book, but there's a chapter in the book where Kimball Fisher talks about empowerment. He uses this acronym ARIA. In that he breaks down that for someone to feel a sense of ownership, they need to have accountability, resources, information, and authority. So much if we think about every single person that's listening to this podcast about what they feel they're empowered. Bit of a dirty word, right? Empowered. What does it even mean? Often we're anointed with 'you are accountable for this project' but yet you feel you have no authority to make the decisions or you're the last to hear about some very key information in the decision-making because you didn't have a seat at the table over there that was talking about a certain thing. There's a recipe to that to get that sense of ownership. Kimball Fisher, highly recommend it.
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Stacy Louie20:03
Kimball Fisher, okay, definitely look that up. Well, here you mentioned empowerment. Is this might be a little controversial? Maybe not. Is empowerment a management thing or is it a personal thing? Is empowerment something that management has to do or something a person has to take on?
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Sinead Condon20:23
I think that's a great question and quite honestly maybe it's a little bit of both. I heard somebody in work say the other day we were talking about leadership and they said, 'Do you wait for influence or do you lead with influence?' I freaking loved that. So much of what we do is waiting to have the influence to make the decision versus kind of leaning into it and saying, 'Here's my intent is to do this. Here is what I believe we should do.' That's leading with influence. You come out the other end of that, people are going, 'Yeah, you go girl.' I do think so much of it is on our own desire and curiosity to know how to create that for ourselves. But in reality, you have to be surrounded by people in your orbit that create the space for you to do that. I do think both need to be at the table in order for that to happen.
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Stacy Louie21:32
Yeah. It really captures the essence of your intention as a worker whether you're a worker at the executive level or a management level or maybe you're an individual contributor. What is your stated intention? Why do you want to be at work? It goes back to looking at the organization thinking, 'Gosh, organization, you're going to transform,' but maybe there's a lot of it in ourselves. What are we doing to help create that transformation?
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Sinead Condon22:01
Absolutely. Some of the questions that we have to ask, if I am a manager and I'm talking to somebody that I have this assumption or expectation that they own something, some of the questions without leading the witness has to be, 'Hey Stacy, what do you feel you have control over? Stacy, what's it going to look like for you when this has reached the outcome and we're successful? What does that look like?' Those types of open-ended questions I think very much put some color around how much authority and empowerment that person actually has.
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Stacy Louie22:39
Excellent. Well, we're coming to the end of our podcast today, but I'd like to take just a moment to do a postgame review on some of the transformations you've seen and some of the work you've done. As far as the key takeaways of things that really materially made a difference in the years that you've been doing this, you mentioned some great things, storytelling, we talked about intention, we talked about having that ownership, decision-making, all these great things. Is there one thing that kind of sticks out at you that says, 'Hey, if there's one thing I could share with the audience, what would that be?'
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Sinead Condon23:18
I think one of the things that I've learned, Stacy, is that, and maybe this is controversial, oftentimes when you are leading transformation, when I've been leading transformation and you feel like you come out of a meeting and you're banging your head against a brick wall and you're like, 'Why do they not know that this is a good idea? Why are they not interested in the outcomes that I'm talking about?' I've realized a lot of the time what's showing up is a fear of the unknown and a lack of education because I have not done a good job clarifying what it is that we're actually trying to drive and the impact and value realization of what's to come. I have a lot more empathy and compassion now for people not necessarily jumping on the boat right off the bat. Gaining some empathy around where people are coming from, we say it's almost cliche 'meet people where they are' but really do. The other thing is build relationships. My whole career has been based on having true relationships with people because it is at the end of the day all about trust.
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Stacy Louie24:38
Yes, absolutely. You got to be able to trust your peers, your bosses, the people around you. Decision making that's been made, right?
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Sinead Condon24:46
That's right. I love assuming that people are making their decisions based off of the best intent possible. It really creates a very wholesome relationship.
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Stacy Louie24:58
Yeah. And is one thing? Are you listening to learn? Are you listening to understand? Or are you listening to win?
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Sinead Condon25:09
I think many of us can be around a table and know who the people are that are both listening to win and listening to learn and understand. Be a listener who's looking to learn and understand first and foremost.
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Stacy Louie25:25
That's fantastic, Sinead. That's a great way to wrap things up today. Before I let you go, we have this player of the week part of our program. Think about what organization or person that you've seen in the world that's kind of aligning towards sorts of things that you would say this is an ideal person on change or ideal situation. Can you think of a player of the week, something that you see changing the world or someone you see changing the world that's just been stellar really exhibiting some great characteristics?
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Sinead Condon26:01
It's a person from my past who was a mentor for me. Can I use that?
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Stacy Louie26:06
Absolutely.
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Sinead Condon26:07
His ears would be burning. I had a leader in a company that I worked for very early on in my career. His name was Sean Corkery. He's still a leader today, Sean. He taught me what leadership is and what leadership is not. He's one of the most profound characters that I've met who treats everybody with respect regardless of hierarchy. He's a guy that knows how to listen to learn.
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Stacy Louie26:51
I think that's today's lesson is listen to learn. I think that's a great highlight, Sinead. Well, thank you. That went by fast. It was so fun to talk to you. It's great. Thank you for coming out and talking with us on Goals and Game Changers.
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Sinead Condon27:05
Thank you.
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Stacy Louie27:08
As we wrap up today's conversation, let's reflect on some of the key takeaways from Sinead's insights. First, people are truly the complexity in a transformation. While technology and process change are challenging, the deepest complexities arise from the human side, the emotions, decision-making dynamics, team cohesion, and empathy. The second point she makes is modern leadership requires storytelling and balance. Leaders must come as skilled storytellers to help articulate the purpose, direction, and impact that their work is having to the organization. The third thing is empowerment stems from both systems and the self. Meaning Sinead emphasizes the importance of leading with influence and listening to learn not to win. Cultivating trust and clarity are the foundation for organizational change. We hope that today's conversation has inspired you to rethink how your organization approaches transformation and leadership. If you're interested in taking the next step in business transformation, please feel free to reach out to us. We'd love to hear from you and help you apply these key insights to your own teams. Keep following us on social media at hyperdriveaggel.com. Thank you for joining us today on Goals and Game Changers. Stay curious, stay customer focused, and we'll see you next time.