Transformation isn’t a switch—it’s a long, messy, and deeply human journey. In this insightful session from Prodacity 2025, Siobhán Mc Feeney, VP of Digital at Kohl’s and former Pivotal executive, shares hard-earned lessons on how to lead lasting change in large organizations.

With a focus on operating models, people development, and stakeholder engagement, McFeeney breaks down the three critical areas every leader must focus on to drive sustainable transformation:
1️⃣ Operating Models: Why org charts don’t change organizations—operating models do
2️⃣ People & Culture: How to invest in and inspect your teams for long-term success
3️⃣ Stakeholder Engagement: Why tension is necessary, and how to turn skeptics into allies

🔹 Key Topics Covered:

• Why transformation takes time (and why patience is essential)
• The biggest mistake companies make—focusing on org charts instead of operating models
• How to build inspection systems to ensure people are growing (or moving on)
• Why radical communication is key to keeping teams aligned and engaged
• How to balance control vs. empowerment when scaling a transformation
• The importance of stepping aside as a leader to enable others to rise

🕒 Key Highlights & Timestamps:
[00:03] - Introduction: Why transformation is harder than you think
[04:08] - The 3 critical focus areas for successful transformation
[06:45] - Why org charts don’t drive change—operating models do
[09:35] - How to design inspection systems that ensure real progress
[12:54] - The biggest leadership challenge: Do people truly understand the change?
[16:35] - Letting go: When to empower teams and step back
[19:59] - How to turn tension into productive stakeholder engagement
[21:15] - Why frontline employees embrace change faster than corporate teams
[23:12] - Where leaders should spend their time for maximum impact
[25:25] - Final advice: Be kind to yourself—this is a long road

🔗 Stay Connected:
Learn more about Prodacity: https://www.rise8.us/prodacity
Follow us on X: https://x.com/Rise8_Inc
Connect with us on LinkedIn: https://www.linkedin.com/company/rise8/

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#Prodacity2025 #SiobhanMcFeeney #DigitalTransformation #OperatingModels #Leadership #EnterpriseChange #BusinessStrategy

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Siobhán Mc Feeney (00:03):

In the spirit of everything changes on the fly. I have horrible vertigo, so instead of falling over and people would have to come get me, I invited this cat on the stage with me who we work together and have been driving a lot of change together. So I'll probably just luck here if I left, left and right, I might fall over. So appreciate the patience of it all. So I think some of you might've met Josh yesterday. Josh runs all of our digital assets at Kohl's work together at Pivotal and lots of other companies. So all the mess, his fault,

Josh Kruk (00:39):

Yeah, it's me,

Siobhán Mc Feeney (00:40):

It's all him,

Josh Kruk (00:41):

But I can move my head side to side. So...

Siobhán Mc Feeney (00:43):

He's got skills I don't have today. It's awesome. That's great. All right. So we really, it's such a, I've been listening to all the things from yesterday and today and this theme of transformation and see some really close friends in the audience. This idea that you have to nurture this journey of change and there isn't a shortcut to it and there isn't a shortcut to it. That is part of sort of this lesson over the last few years of you actually have to do the work and if anyone has read anything on stoicism, the obstacle is the way sucks, but the obstacle is the way and you actually do have to go through it if you want to get to the other side and see this kind of change. So of all the work we've done in various companies and right now at Kohl's, a huge part of this is sort of accepting your reality, editing the things that you have to and will edit. And then recognizing that you will get asked a lot of questions about when is it done and can we get there? And the tangible, show me the evidence and resetting that we're five years into this journey at Kohl's and we have made phenomenal progress five years. And I know for certain the day I started, I absolutely would not have had the patience to imagine that this was a five year journey. I dunno how you feel.

Josh Kruk (02:13):

Yeah, I had the luxury of starting three weeks later when you asked me to come over. I think one of the gifts of this transformation thing is you don't realize how big it is when you get into it. If you did, it would be insurmountable and you would have no idea. But this idea of consistently figuring out what is the next problem, how do we make progress on the next problem? How do we use that as a proof point to get other people to come along with us? And as we start to think about a journey that's not just one or two people coming into a company or three I think as it was at Kohl's, and it's starting to build this groundswell by folks really digging in to say like, wait, wait, what did you do? Why did you solve that problem differently? Why am I so uncomfortable with the words that you're saying is pretty valuable and a big piece of that and it gets easier over time. But what I think it's a little bit like Dory, right? You have to do that with each new person that you encounter every day. And none of us get it right the first time. You have to go back and do it again and again and again.

Siobhán Mc Feeney (03:16):

And Dory will be a feature later on in this. You think you've said it 500 times and it truly does feel like you're bringing up a new topic every time and you're like, all right, we're patience is going to be one of those things. So as we've learned from the various companies we've either consulted with or worked for, a lot of things need to change. You will join or you sit in an organization and you've inherited a lot of stuff and the chess that you've inherited might not be the one you want and it might not have all the things you want in it, but it is yours. It's yours, and you get to sort of enhance it, change it, do different things with it. But sort of accepting that and understanding what that landscape is at the beginning is pretty tricky. And it isn't just the talent, it's all the culture.

(04:08):

It's all the underlying processes. It's the whole machine that actually makes up this thing. And so what we wanted to share today is lots of you're going to hear and you can hire every consultant on the planet who will tell you how to get through transformation. This is really, there's many, many things that need to change, but if you really focus, I believe on these three areas and these three things, your chances of success go up doesn't mean it's easy and it definitely doesn't mean it's perfect, but your ability to see tangible change go up and they're these three simple things. I say that really hard things, your operating model, and we'll talk about why that does not mean an organizational chart, which is what everybody does out of the gate, the people, which obviously but becomes much more complex as you get into it.

(04:57):

And our favorite business partners and stakeholders who are actually foundational to this, and you may fight with them and you may have a hard time, but without stakeholders involved and a part of it, this does not sustain over time. I think that's actually the most important thing. You can make change without them, but it will not stick for, it will not be the long game. So those are the three we're going to focus on today. There are a million other things absolutely that you'll hear about that you should do. These are the things that we've found if we invest here, this is the longest shot we've had and we've seen sustainable, really sticky change in a very large organization.

(05:39):

I'm just going to start and Josh will sort of continue on this one, but when you talk about changing how you work, and years ago when I was at a previous company, we had a consulting firm come in, very, very successful consulting firm. And the first thing we did was the org chart because it's tangible, right? It's an easy thing to show. We're going to make a big change and product goes here and design goes here and you can present it to someone and people feel like you've made a change and they're like, excellent. Got it. And it's honestly names in a box and it doesn't do anything. And we all know that the operating model deeply understanding how the work is done and how work gets transferred and who has power and who loses power. Hopefully it shifts to the customer, but people feel like they're losing it when things change. That actually is the single most important piece of work to do that work. Eventually you get an org chart, but our experience has been people start on the org chart and not the operating model. It is just easy. You build a thing and you have a slide deck and people like it.

Josh Kruk (06:45):

Yeah, well you're a product manager now it's on the title, right?

Siobhán Mc Feeney (06:48):

You're a product manager designer. Go be

Josh Kruk (06:51):

The hard part about that too. And I think where I've certainly done this to somebody who paid a lot of money in the audience I'm sure is when you start there, you set everybody up to fail the sudden empowerment of I have a new boss and I have a new title and I'm responsible for the journey of the customer and all the rest of you are ***** and it's all me. We encourage that behavior when we do this thing with the org chart and then you've just created a whole new problem fundamentally where I think the biggest thing is number one, define what an operating model is. Most people don't know what it is. We had a recent experience with a super senior person in a moment of vulnerability who we've worked with for five years, said, I don't know what that means, Josh. I don't know what I was just asked to do. Which is a huge, when we talk about people and transparency

(07:43):

Asset, but really defining it and really working through the practical implications of, hey, we're going to change the way decision making is made around digital at Kohl's. And that means we're going to measure these things and we're going to make every decision with this lens. And having a set of principles that then get talked about and well understood and documented very, very clearly because I'm saying that out loud that we haven't been as successful at that as I want. But those types of changes way before anybody gets into their new gig or their new title so they understand where are the rules and where the guardrails is super, super important. I would say spend way more time upfront there than you think you need to. And then spend 10 times as much time repeating it over and over and over again. So everybody knows they still won't like it, but you don't get to say, I didn't know.

Siobhán Mc Feeney (08:33):

And on that we talk about radical communication or you will have to pick 10 to 15 different vehicles that I told you in a meeting or I wrote it down. So one of the things that we have instituted, it's probably exhausting to others in the organization and we used to blog daily but blogging and then we do drum beats and meetings and standups and stand downs and stand sideways and there's no avoiding all of it. And I do see people eye roll going, here we go again and there's this document and long form writing and growth boards. I mean, I'm exhausted even telling you all the stuff we do and it's still not enough. And this is where the, we like to call it DOIs comes in. People are like, what happened? There's product management. I don't get to decide. But having all of that for two things, other people will come in and having the documentation for posterity, they can catch up, they you can asynchronously stay engaged, you don't have to be in the room.

(09:35):

We're a fully virtual organization in a company that does have a headquarters where a lot of decisions are made. So how do you set a technology organization up to stay current? And information is power, how do they say? So having all these communication vehicles unbelievably important. This operating model will change. It morphs a little bit. I would say the core tenants of the one we have built at Kohl's has stayed intact. But knowing that it might have to flex a little bit as the organization changes is never super comfortable because people, I actually wanted to share this story.

(10:16):

When I first got to Kohl's, this wonderful person came up and said, we've started the operating model. We've done the first thing. We built a product charter. We're magic, we have it. We know the products we're on our way. And then they gave me a PDF and I was like, yay. First of all, stop the PDFing. I don't know what that is. That means you don't want feedback. They gave me a PDF and they were so excited that it was done and it was my first day. So I'm not great with poker. So I was trying to keep my face straight going, first of all, stop, this is a living document. The product will change. But just that mindset, if they were like, I did a thing, it's finished next thing. And I'm like living document, it'll change, move on. And so just knowing even enthusiastic people who want to be on this journey, they're themselves having to change as you go on.

(11:10):

Okay, not new, you have to invest in people, right? This is some new thing. But this goes back to when we got to Kohl's. There were a lot of really smart people working there with a lot of tenure and understanding a lot on the retail business. And I didn't know anything about retail. You might've known slightly less. We were not retailers. So understanding that balance you have and the talent you have and you're going to have to bring folks along, you're going to have to hire new folks. And probably the most important thing that I know you will have some input on here is you got to build inspection systems inside every layer of the organization to know whether or not the pool of talent, the, that you've invested in are progressing. Maybe they've stagnated, maybe they don't want to be here, maybe they just agreed because you're the boss and of course this is a fabulous idea.

(12:03):

And when you leave, the next idea is the most fabulous idea they've heard. So do you have genuine commitment, those inspection systems? I'd say we didn't do enough at the beginning. They are singularly, they will bite you in the ***. Absolutely. You have to have them. Are my leaders really committed? Do people really know? Are they really changing? Are they really coming along on the journey? And we'll talk about that with the stakeholders too. But this piece here, we got people involved, we got people jazzed, and I don't know that we put the inspection systems in as quickly as possible. We can talk a little bit about what are some of those inspection systems and what are some of the signals that I think work really well and give you indicators of the health of your workforce and the health of your workforce is really a direct reflection on how successful you will be in driving outcomes and changing the culture. What would you add to that?

Josh Kruk (12:54):

Yeah, I think there's inspection and the way that we think about that word is the thing happening is somebody doing or taking the action? The one that I think Coles has taught me the most is does the person understand what they're doing even when they're doing the thing? And that becomes really important. And to be candid, much harder to detect unfortunately because all of the outward signs are there and you got to do a lot more work or my piece of advice would be bring in somebody to help you do the inspection because everybody will behave different around the authority figure. And that's certainly us in this transformation at Kohl's. And we were fortunate enough to have a couple of folks in our organization who rose up and a couple of folks who came in in the role of coach who really helped us figure out not just as somebody saying the word to you and are they saying the word to those people, but do they understand why that word is important and are they enacting those systems and not in a punitive way.

(13:51):

That's important. You're never doing this with a stick and don't ask your coaches to divulge private things to you. That's a terrible thing. So please nobody interpret it that way. But it does. It helps you get a feel for the organization, how it's progressing, because you can't be everywhere. And at least for me, and I would say my experience with you, the desire to be a player coach is really, really strong. In an organization of a thousand people, you will never stop playing or coaching and you will never make a difference if that's your approach 100% of the time.

Siobhán Mc Feeney (14:23):

I think it's important to say, so the internal folks who can help and that external balance of people who understand the mission you're on and are able to help really focus on, and there are key people in your organization who will make that difference. And so how do you make sure they're coming along? We've been talking recently about how do you also know when people have reached the maximum capacity they can, like this is it. They are afoot, they're authentic, fabulous humans, but this is it. They're not going to take it to the next level. And how do you help them in the right role? How do you make sure that they are focused on the right work because not every single person is going to be this breakthrough artist who's going to take it to the next level. That's really hard, especially when you've worked with people a long time and just my experiences just as employees and organizations, we don't love to give bad information or we don't like to disappoint or it's hard to be direct in feedback.

(15:19):

So how do you do that in a very empathetic way? But also if you are not the right person for the next phase of this journey, you're just not the right person. The one thing I would maybe just wrap up the people piece in, when we came into Kohl's, we really gave everyone an opportunity. Everyone had, we were very transparent about the operating model and we introduced new roles in design and data science and product management, and we gave everyone an opportunity, said, it's available to you, we will train you, we will coach, we will give you access to building your craft and you will have this much time. This isn't, you've got to have it tomorrow. You get time and you don't have to be expert, but you have to show progress. 18 months, two years. We may have left it too long to be honest, but we give people time and that took a lot of stress out of the system. So we didn't do an org chart and say, you are now a senior product manager. Go forth and be brilliant. We did the operating model and we said, you will be moving into product management. We expect that your mastery is very low, and all we ask is that you start to show progress in that craft over the next 18 months and then we'll continue together to invest. And I think that took a lot of anxiety out of the organization.

Josh Kruk (16:35):

Yeah, I think there's one other thing we did there that was subtle. You have to make progress as an individual, but also you have to share that progress with the individuals around you of heated leadership meetings, aggravation over that, not working as well as we wanted it to is probably thing number one, the first three years. But in year four and five, it is the thing I am the most grateful for because now all of those product managers in the organization, genuinely no more than the people who started it, about product management. And many of them are finding new ways, whether that's tools and techniques or ways to innovate in the craft. And I think that's a direct result of us forcing both of the things you have to get better and you have to share.

Siobhán Mc Feeney (17:17):

Yeah, no, that's absolutely right. Okay, so for the most fun part of any of these transformations you are, I always think about stakeholders and business partners, especially in the role we sit in here or you may be sitting in your organization, you are pushing this change. There is a higher burden on you, kind of sucks, but you are literally carrying a higher burden to a point. So we think about wouldn't it be great if everybody came on board day one? And I disagree, I want some tension. I think tension with business folks who will push back, who question things not just for the sake of it, but questioning why has been the healthiest relationships we've had by a long shot. You will eventually find allies in the business partners who now speak. We have a person in the supply chain who very candidly I could close my eyes and he could have come from any organization, whether it be Pivotal or any of these organizations that we sort of learned some of these practices and he has been a tenured retail supply chain employee 25 years.

(18:32):

And he's talking about the next riskiest assumption. I'm like, who is that? This person just gets it and has come on this journey. They've seen the value. You can't really measure it. You see it in real life and real practice. And those allies come about. The other piece of this that I believe is a really important thing is this, as a leader, as a person who's enacting the change, at some point my voice is no longer impactful. I mean this personally me, shavonne, I can no longer be heard by the stakeholder. They need a different voice in front of them.

(19:09):

That's kind of right. I feel I'm great at this. How could anyone be better at this than me? There's better people out there for the next phase of the journey. And you got to know when to step aside and let those people, I've been doing this for five years, is it seven years? But there's always a time where somebody else with a different voice or a different style who may not be you can take the mantle, whether it's in an icy role or a leadership role. And I'm not sure that we're as self-aware of that. And it really does enable people to move to the next stage. So on that one, tension is good. You do need to bring people along and it is, you'll get a lot of arguments, but you will find allies along the way and they are so much more successful at being the microphone than you are. Anything you'd add

Josh Kruk (19:59):

Consciously enlist those people in the journey. Maybe that's the other piece. We had a really early on in our transformation, the woman who ran our stores organization, I would say early ally, very vocal proponent of what we were doing internally. But if that doesn't happen outside of the meeting room that you're in, you make way less progress. Way less fast. So getting folks to start to amplify that back in their own organization, you have to be deliberate about. And it's a little bit weird sort of asking somebody like, did you help me sell this thing? Please. But you have to be deliberate.

Siobhán Mc Feeney (20:34):

And maybe the last thing on this is my personal experience both at Kohl's and other places, the most progress and the fastest progress we've ever made with business partners, with our business partners is those partners who work more closely with customers. So folks who are very close to the customer tend to be easier to work with and understand this folks who maybe exist more in a corporate setting and maybe not as close to the customer, there is a far steeper hill to climb to convince folks there that changes needed. And so start with those who work closely with the customer or associates who serve the customer definitely has a lot of win.

(21:15):

So as a leader of a team or leader of an entire effort, this is a big, big deal, you will need a lot of skills. You all have a lot of skills, but the things that we have found to be most impactful are really these three things. And sometimes you forget, right? So the number one thing we've talked about endlessly is be really intentional about where you spend your time. And I just ask everyone to think through it. Do you spend your time in the field? Whatever your version of in the field is. Do you spend your time with your customers or do you spend your time in a maybe corporate setting or do you spend most of your time with your team? And where you spend your time is a very strong, that has a really strong correlation with how impactful this change ends up being. And that has been true for every transformation I have ever worked on. And so maybe to be more direct, do not spend your time in the office, spend your time outside the office and your chance of success goes way up. Spend your time with people who aren't your direct reports.

(22:20):

Your chance of success goes away though. I was trying to avoid words like empowerment and all of that, but there will be a point when the organization is skilled enough to go and do and you, you have to resist the urge to medal or do it for them. And it's like watching your teenager drive for the first time is terrifying, right? Or the first time they take off when you're not in the car with them and you just close the door and go, oh sweet baby Jesus, I hope that works, but this is that. It's not going to be done the way you want it. It'll just be fine. It'll be good enough. And that unless you do that, you will never scale this ever. And that is at all levels, whether it be engineering or product management or whatever decisions in front of the big boss who gets to present being okay letting go.

Josh Kruk (23:12):

A hundred percent. And I think the thing that I, it is always easier for you to do this is the actual learning piece. If you don't do this, they don't learn. And then you go back to slide one, start over. You're probably doing it at a different company given the timescales of these things and then it didn't work. So I think this is, when I think about leadership, this is the number one thing. You have to let people go and you have to let teams go. And then you have to do the really critical piece of how was that thing that you just did? How did you live out these principles? We talked about, yes, there's a pile of poo on the floor that we just made. How are we going to clean it up using the same principles? But this is at least for me, and the reason I jump in on that is that this is the most important thing. And certainly for me, who's a bit of a control freak and a bit of a worrier, the single hardest one, it seems like that control freak and worry thing is pretty common with everybody I've talked to in leadership. So you really, really have to focus on this. And the other thing I would say is every time I've thought a team was ready, I was probably three months too late. They had been ready long before.

Siobhán Mc Feeney (24:23):

Yeah, it is totally true. I am cognizant of time, so I just want to share the last one. Self-awareness. Just at some point, somebody else will probably have a bigger impact. This is hard, is a grind. I will say it's extraordinarily fulfilling when you see the results, but it is a grind. You need allies, you need a bunch of folks who you can talk to about the hard day you've had. It's probably no surprise why certain of us move in certain circles and end up working together over and over. We really understand when things get hard, you need people there with you. You need a hug sometimes it's really important. You've got to have a place to go. And I don't even mean just vent, but just you get stuck. Sometimes things aren't moving and it's a reality of this thing is hard. I don't even want to say it's a journey, but if I were to leave anything, when you do these pieces in a reasonable sequence, you will see.

(25:25):

We see the actual tangible results. The Kohl's technology transformation, which started five years ago, has foundationally changed Kohl's as a company. But it didn't happen overnight. It literally happened. And one day I looked around and went, oh, finance talks differently. HR organizes differently. People are talking about outcomes. It does happen and it will not be perfect. So if anything, I would share with you, be really cognizant of where you spend your time. Get out and talk to your customers, whomever they are. Be kind to yourself and make sure you have allies. This is a long old road. Appreciate it. Thank you so much.

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