Structured Chaos in a Messy System | John Yip
28 January 2026 · 56 min · as at 2026-01-28
Daniel Atlin (host) · John Yip (guest)
Listen to the episode on iono.fm · MP3
About the guest
John Yip
President & CEO · SE Health · Ontario
Studied marine biology at Dalhousie; worked at Digital Foresight in the early digital economy; previously led Kensington Health, which operated a 350-bed long-term care home; has worked in healthcare for 30 plus years.
In John's own words:
“Well, my parents wanted me to do pre-med, but I did marine biology. Wow. Yeah, at Dalhousie, so, East Coast Canada and Halifax, Nova Scotia.”
“But having worked in healthcare for 30 plus years and working in some amazing organizations, there is something very unique.”
“And so my previous role in another not-for-profit, it was called Kensington Health, located in downtown Toronto in the heart of Kensington Market. we did operate one of the city's larger, long-term care homes, so 350 beds.”
Guest details come from the published episode notes or the guest's own words in the episode.
Episode analysis
Analysis by AI, drawn only from this episode; every point links to the moment it rests on.
Daniel Atlin talks with John Yip, President & CEO of SE Health, a not-for-profit home and community care provider. John traces his path from marine biology and early digital-economy work at Digital Foresight to healthcare, argues that home and community care is misunderstood compared with hospitals, and describes how he builds alignment across a distributed national organisation. He recounts leading a long-term care home through early COVID, sets out SE Health's approach to digital transformation and health data, and uses his project of running every street of Toronto to explain his idea of 'structured chaos'. He closes with advice on treating leadership as a grind, like chopping wood.
Key ideas
- John argues people wrongly treat the hospital as the healthcare system, while home care builds long-term, trust-based relationships inside patients' homes. [10:27]▸ [11:48]▸ [12:16]▸ [12:50]▸
- John describes building alignment across a fragmented provincial system through Gemba (going where the work is done), flexible work and a nationally distributed leadership team. [14:56]▸ [15:33]▸ [19:55]▸ [20:34]▸
- John's COVID story shows crisis leadership as improvisation: working the floor himself and hiring family members within 24 hours; the host calls improvisation a key element of sensemaking. [27:20]▸ [28:09]▸ [29:20]▸ [30:19]▸ [30:46]▸
- John says digital transformation should keep the playbook's core but add safe experimentation, and sees healthcare data as the greatest data opportunity. [34:49]▸ [35:18]▸ [36:12]▸ [37:18]▸ [38:34]▸
- John holds that mission and margin work together: 'no margin, no mission', and consistent quality of care produces financial benefit. [41:15]▸ [41:15]▸ [42:17]▸
- John calls his leadership style 'structured chaos', linked to running every street and rewiring his perspective. [48:28]▸ [48:28]▸ [49:58]▸ [50:06]▸
- John advises accepting leadership as a grind, like chopping wood, to stay even-keeled through highs and lows. [54:14]▸ [54:19]▸ [55:07]▸
John's strategies for building alignment across SE Health
- Gemba: go to where the work is being done, visiting frontline teams across the country, not just leadership teams.
- Allow flexible work through the SE Flex policy while scheduling planned team meetings to keep human connection.
- Recruit leadership nationally so the leadership team is not centred around Markham, Ontario.
- Rely on the embedded 118-year DNA of serving, the unwritten code that 'you're here to serve'.
As described in the episode: [15:33]▸ [19:55]▸ [20:34]▸ [22:02]▸
Lessons
- John suggests leaders go to where the work is done to understand frontline realities before making system-wide decisions. [15:33]▸
- In John's COVID account, unconventional ideas his rational brain doubted, like hiring family members, worked because the organisation was willing to try them. [27:20]▸ [29:20]▸ [30:19]▸
- John recommends experimenting safely with technology, using known clinical scenarios instead of real personal health information. [35:18]▸ [36:12]▸
- John tells his younger self to stay groovy: step back, watch things unfold and make small moves rather than going full bore. [52:05]▸ [52:31]▸
- John says acknowledging that leadership is messy and a grind makes the lows less severe. [54:19]▸ [55:07]▸
Who it's for
Leaders of mission-driven, distributed or healthcare organisations, especially in home and community care, and anyone interested in crisis leadership, digital transformation in health, or balancing social mission with financial sustainability.
Facts stated in the episode
- John says 2.5 million Ontarians do not have access to a primary care practitioner. [10:01]▸
- SE Health was founded 118 years ago out of St. Michael's Hospital in Toronto to provide free postpartum care. [16:47]▸
- SE Health operates in four provinces and serves 25,000 patients a day. [17:18]▸
- Graduates of SE Health's college have worked in over 500 Indigenous communities. [17:57]▸
- Of SE Health's leadership team of nine, only three live in the GTA. [20:34]▸
- Kensington Health's long-term care home had 350 beds. [23:49]▸
- During COVID, John's organisation hired 20 family members within 24 hours after a four-hour crash course. [29:20]▸
- Runner Ricky Gates ran all the streets of San Francisco in 50 days, inspiring John's project. [45:40]▸
Questions this episode answers
- Why is home care different from hospital care?John Yip says home care involves longitudinal relationships lasting months or years inside the patient's home, requiring trust, whereas hospital care is bedside and short. [11:48]▸ [12:16]▸ [12:50]▸
- How do you align a large organisation spread across Canada?John describes Gemba visits to frontline teams, the SE Flex policy with planned team meetings, recruiting leaders nationally, and SE Health's service-focused DNA. [15:33]▸ [19:55]▸ [20:34]▸ [22:02]▸
- What did leading a long-term care home during early COVID look like?John recalls two weeks of masks left, two thirds of staff missing, a call for volunteers, working six months as a residential aide, and hiring 20 family members within 24 hours. [25:15]▸ [27:20]▸ [28:09]▸ [29:20]▸
- What is the biggest mistake in healthcare digital transformation?John says the standard playbook is still useful at its core, but SE Health deliberately goes beyond it with a skunkworks lab for safe experimentation, adding 'a little bit of Picasso'. [34:49]▸ [35:18]▸ [36:12]▸ [39:10]▸
- Can a not-for-profit be run like a business?John cites the founders' phrase 'no margin, no mission': surpluses are reinvested in the social mission, and consistently good care drives financial benefit. [41:15]▸ [42:17]▸
- What does 'structured chaos' mean as a leadership style?John says driving change and reinvention requires chaos, but it should be structured, much like pre-planning a run but going off route to explore. [48:28]▸ [49:58]▸ [50:06]▸
- How can a marine biology degree lead to healthcare leadership?John says marine biology is about systems, ecology and supply and demand, and that thinking maps onto healthcare's stakeholders, power dynamics and economics. [07:03]▸ [07:07]▸ [07:50]▸
- How should leaders cope with the grind of leadership?John compares leadership to chopping wood about a third of the time; accepting the grind makes breakthroughs feel bigger and keeps you even-keeled. [54:14]▸ [55:07]▸
In their own words
Longer stretches of the conversation, word for word from the transcript, turn by turn.
From marine biology to leading in healthcare
Note (AI): John explains how systems thinking from ecology carries over to healthcare economics and stakeholder webs, framing his career in hindsight.
John Yip, guest · [07:03]Whoa. I'll take that as a compliment. Well, my parents wanted me to do pre-med, but I did marine biology. Wow. Yeah, at Dalhousie, so, East Coast Canada and Halifax, Nova Scotia. One of, I think, at the time, I think three programs in the country. And you're kind of wondering now, fast forward, you know, 30 odd years, 30 plus years, you know, how the heck did you start …
Read the full passage (237 words, 07:03–08:47)
John Yip, guest · [07:03]Whoa. I'll take that as a compliment. Well, my parents wanted me to do pre-med, but I did marine biology. Wow. Yeah, at Dalhousie, so, East Coast Canada and Halifax, Nova Scotia. One of, I think, at the time, I think three programs in the country. And you're kind of wondering now, fast forward, you know, 30 odd years, 30 plus years, you know, how the heck did you start in marine biology and end up in healthcare? And, you know, the quote is exactly that, is, you know, I've lived the life, but I'm, I've lived it now, and when I look back, it, it makes perfect sense. And not to, take up much more time, but, marine biology is based on systems. It's based on ecology, it's based on food supply and supply and demand, and that the natural world does have some order to it. If you take some of that thinking and apply it to other industries or sectors like healthcare, You can start to see the connections, you know, the web of stakeholders, the power dynamics, the demand and supply. The environmental economics does bridge over to healthcare economics. And so at first blush, an undergraduate in marine biology and, you know, isn't a straight line to leading one of Canada's largest not-for-profit entities in healthcare is not obvious. But when I think about it, you can draw a straight line almost.
Why home and community care is different
Note (AI): Sets out John's case that long-term, in-home relationships distinguish home care from hospital care, and why he sees the system as broken.
John Yip, guest · [11:48]And I'm guilty as well, Daniel. I was very, pro-hospital early in my career, especially when I was working consulting. hospitals could afford the consulting fees, home and community organizations could not. But what I learned through a decade in working in a home and community before Joining, the sector itself was that it is an incredible sector. the difference being that there is longitudinal long-term relationships that are formed …
Read the full passage (295 words, 11:48–13:59)
John Yip, guest · [11:48]And I'm guilty as well, Daniel. I was very, pro-hospital early in my career, especially when I was working consulting. hospitals could afford the consulting fees, home and community organizations could not. But what I learned through a decade in working in a home and community before Joining, the sector itself was that it is an incredible sector. the difference being that there is longitudinal long-term relationships that are formed between the provider of health services and the recipient, versus when you go to the hospital, it's bedside, hopefully you're out in less than ten days, hopefully, or hours, and, and not months. but our relationship with our patients is months and of- often years, and not in a sterile hospital unit or ward, but in your home. and there's no more intimate place than your own home, and so in order to provide the care, the great care that home and community providers provide, is to establish that trust and relationship because we are in your home. And often when I do ride-alongs with our staff, I see the difference. It's not a transactional, you got a health problem, we'll fix it. It's much more about getting to know who you are, your environment, and customizing that care plan with your local context. And that to me has, in my opinion, far greater impact than, other parts of the system. That's not to say that hospitals and, and, and family physicians aren't important. They're absolutely important. They're also underfunded. But we do not work like in marine life. We do not work in a ecosystem that works the way that it should. And that's where I feel where my passion is. How do you make this into a system that's better for all Canadians?
Staffing a long-term care home in early COVID
Note (AI): A concrete crisis story: volunteers, the CEO on night shifts, and hiring family members within 24 hours as unconventional improvisation.
John Yip, guest · [27:20]but I think the most vivid memory in the early days is showing up and two thirds of our staff are not, aren't there. And we have 350, people to take care of, largely with, cognitive impairments, dementia, Alzheimer's, who need support. So I did call an all hands on deck and, and made a call for volunteers. It's like, I, you know, you're not trained to take care, but …
Read the full passage (445 words, 27:20–30:40)
John Yip, guest · [27:20]but I think the most vivid memory in the early days is showing up and two thirds of our staff are not, aren't there. And we have 350, people to take care of, largely with, cognitive impairments, dementia, Alzheimer's, who need support. So I did call an all hands on deck and, and made a call for volunteers. It's like, I, you know, you're not trained to take care, but we just sit and, and help feed. Sit and play cards, sit and help, conversation, and just to give a semblance of normalcy for our residents and to shore up the, lack of staff. And that's when I decided to say, hey, if I do it, then I'll have no qualms about asking our staff to put themselves at risk. And remember, early days, we didn't really know what this was. amazingly enough, thirty people signed up. I worked on the floor as a residential aide for a good six months. That was my job. we, mostly overnight shifts where there was, it was, not well-staffed weekends. One of our team members came to me and said, well, why don't we ask the loved ones, the family members, To work for us because the families wanted to come in, but as you were calling them, your listeners will recall, no one was allowed in nursing homes. So I said, well, that's a crazy idea. Our lawyers will say no way. Our union will say no way. But when we called the union steward, he goes, absolutely. We called our labor lawyer and he said, well, this is unconventional, but this is how you could do it. So within 24 hours, we had hired 20 family members on a temporary full-time contract, did a four-hour crash course in training, and managed to shore up some of our COVID floors and non-COVID floors. Amazingly enough, almost all the 20 donated their wages back to the organization. And to my knowledge, one or two of them Five years on are still working there. So in a time of crisis, yeah, the unconventional, you got to look at that because my rational brain was saying, this is not going to work out. We're never going to be a higher family members to come on the floor, and we're going to lose more people. and so there's a sort of defeatist attitude in my head. but the willingness to try something, explore it, compelled the organization to take a chance. And as a result, in the end, we came out of the pandemic, less scarred than I think we would have been had we not tried some of these things.
Digital transformation beyond the standard playbook
Note (AI): Describes how SE Health combines playbook basics with a safe-experimentation skunkworks lab and LLMs trained on clinical scenarios.
John Yip, guest · [35:18]But I think there is a opportunity to take the core of the playbook around, you know, mapping current processes, future state processes, the target operating model, the enterprise architecture, and so on. But we're in the era of AI, and I don't talk about AI as the mass media talks about it, and certainly AI has existed since our day, 28 plus years ago with the dot-com, there, you …
Read the full passage (213 words, 35:18–36:58)
John Yip, guest · [35:18]But I think there is a opportunity to take the core of the playbook around, you know, mapping current processes, future state processes, the target operating model, the enterprise architecture, and so on. But we're in the era of AI, and I don't talk about AI as the mass media talks about it, and certainly AI has existed since our day, 28 plus years ago with the dot-com, there, you could almost see it. AI is just the fancy label to, decision-making, smart computing, data, and using data, in this case, for good. So our, part of our non-traditional way is, at least in healthcare and, and particularly in Canada, so this is maybe a little, a bit more common in the US, but, is to have a skunkworks lab, so-called in the basement, puts a bunch of smart people, to experiment in a safe way. So don't use real personal health information, use scenarios that we know well, clinical scenarios like falls, which happened to a lot of frail older Canadians. we know the data, teach these large language models, the clinical context, and train it so it provides options around clinical, best practices so that we can leapfrog where our sector is, which is far behind the hospitals in digital transformation.
Running every street and structured chaos
Note (AI): John links his running project to rewiring perspective and to his 'structured chaos' leadership style at SE Health.
John Yip, guest · [48:28]By having set patterns, my three or four routes I used to do, and then getting that changed completely, where I actually haven't run the same route since then, is I actually found my neurons, my brain getting completely rewired. Things that I didn't pay attention to, I started paying attention to, because if you're running every street, you got to pay attention to signs, road signs. And I used …
Read the full passage (435 words, 48:28–51:06)
John Yip, guest · [48:28]By having set patterns, my three or four routes I used to do, and then getting that changed completely, where I actually haven't run the same route since then, is I actually found my neurons, my brain getting completely rewired. Things that I didn't pay attention to, I started paying attention to, because if you're running every street, you got to pay attention to signs, road signs. And I used to blog about it and take, I've taken thousands of pictures, by the way, thousands. Someone said, I showed a couple of them, particularly the street art in the city, which is phenomenal. Someone said, you should write a coffee book, like do a coffee book. So hey, Daniel, maybe I will get to write a book after all. But I do feel myself being completely rewired, having a conversation of art, like street art, pictures, how to tell a story visually. And all of a sudden in my work life, When I talked with the playbook, when we talked about digital transformation, it's, yeah, absolutely following the basics and foundational what a playbook is around leadership and other initiatives, but then starting to really widen the aperture of what's possible and how to get to the same outcome by doing different things, by running a different street, plotting a different route, and the thinking and the process around doing that. And to a certain degree at SE Health, that's kind of how I've led. To the chagrin of our leadership team that think it's chaos, and I have coined this, and I tell our team, it's structured chaos. Like it's, yes, it's chaotic, but to drive change and reinvention, it does require chaos. But let's try to be structured about it. And it's kind of like running every street. Some days I would, I got one hour, I have to do this route. But I guarantee you, 99% of the time, even though I pre-planned the route, I would kind of ad-lib because I go, hey, what's this cool little laneway here, which is not on my route? And I just go adventure and it could hit a dead end. And then, or I run into a person I start talking to, and then it's so worth going off the planned route. So there are a lot of parallels around adventuring, exploring, exploring your own backyard, and doing that within your own organization, your personal life. And so I found myself, I've grown tremendously despite the challenges of COVID and managed to bridge active lifestyle into weaving it into my professional and personal life.
Leadership as chopping wood
Note (AI): John's parting advice on accepting the grind to stay even-keeled through highs and lows.
John Yip, guest · [54:14]Well, the name of your podcast is messy. Leadership is messy. It's not always clean. If it's always clean, then maybe you're not leading. So when it's messy, it's actually okay. And this is something I tell myself that leadership is sometimes, not all the time, but sometimes, probably about a third of the time, chopping wood. It's like chopping wood, right? You got these cords of wood, and I …
Read the full passage (235 words, 54:14–55:48)
John Yip, guest · [54:14]Well, the name of your podcast is messy. Leadership is messy. It's not always clean. If it's always clean, then maybe you're not leading. So when it's messy, it's actually okay. And this is something I tell myself that leadership is sometimes, not all the time, but sometimes, probably about a third of the time, chopping wood. It's like chopping wood, right? You got these cords of wood, and I don't know, Danny, if you ever chopped wood, but it is hard. That axe, and I'm not strong, that axe is heavy, and it just Chopping, and you think you're done, you got that accords there, and you're trying to, you know, get through it, your back hurts, you're sweating, or it's cold out, or whatever, and it's a grind. But if you acknowledge that, that that's part of leadership, that it's messy, that it's a grind, and it's chopping wood, then when you hit those breakthroughs, those breakthroughs give you that, the amplitude is massive. But if you think that that's what leadership is all the time, then the lows are super low. So instead of these wild swings where it's messy, is try to calibrate it within a narrow band that there's going to be highs, there's going to be lows, but if you stay even keeled and like chopping wood, then you're going to come through the messiness a little less messier.
Quotes
“hindsight is 20/20. You know, while we just talked about digital foresight, you know, hindsight is also part of foresight.”
“people think that the hospital is the healthcare system, and that's not true.”
“there's no more intimate place than your own home,”
“The staff are crying, and I want to just run away and hide. But you have to show leadership and the ability to provide calm, in, in the face of adversity.”
“One day left, a box of 10,000 masks showed up at our doors. It was life-saving.”
“But unfortunately, I think society has moved on. I haven't.”
“we'll do some of that and we'll do some little bit of Picasso, little bit of art.”
“But the, the sisters of St. Joseph's that founded our organization have this phrase of no margin, no mission.”
“You know, people call us the organi- the organization with a halo. sometimes I have a pitchfork with smoke coming out of my ears,”
“I had this mantra that you can find adventure or travel in your own backyard.”
“it's structured chaos. Like it's, yes, it's chaotic, but to drive change and reinvention, it does require chaos. But let's try to be structured about it.”
“Leadership is messy. It's not always clean. If it's always clean, then maybe you're not leading.”
“more recently, I am much more into data sovereignty as well as a country, given the geopolitical context of our time.”
“people call us the organi- the organization with a halo. sometimes I have a pitchfork with smoke coming out of my ears, but I think, most people know us as the, organization with a halo.”
“we also use the college to, bring refugees, into the country and give them meaningful work to be able to support the Canadian healthcare system.”
“the divisiveness That showed itself during the vaccines where the, the haves and the have-nots, people who had not gotten their first vaccine, were being pushed aside by those that wanted to travel and, try to get their second and third vaccines. So, at the expense of the vulnerable who still hadn't had their first vaccines.”
“I think the day or two days after, the streets of Toronto were empty, like just empty. And I have three or four set running routes from my house. But that day, for whatever reason, I was completely disoriented because there was no cars and I could just Jaywalk across the traffic lights, you know, busy corners, like very busy corners in normal times. But when there were no cars, I just felt disoriented. So I actually found myself three or four kilometers in the opposite direction from where I normally go, and I've never been there. And I went, wow, this is a really cool place.”
What was said, by topic
Sensemaking across long arcs
“But I think the biggest difference is some of the things that we worked on, Daniel, you may recall terminology that we used, like value as the custom, customer manager. So customers actually taking control of markets.”
“I'm also nervous as a father now with two teenage children and to see what they're going to go through and knowing that's going to be slightly different than what we went through for the last 25 years, that being the speed of change.”
“And we are living really in that Twitch economy where people have no sense of focus, their attention is being distracted, and that's the commodity too.”
Career journey
“Well, my parents wanted me to do pre-med, but I did marine biology. Wow. Yeah, at Dalhousie, so, East Coast Canada and Halifax, Nova Scotia.”
“marine biology is based on systems. It's based on ecology, it's based on food supply and supply and demand, and that the natural world does have some order to it. If you take some of that thinking and apply it to other industries or sectors like healthcare, You can start to see the connections, you know, the web of stakeholders, the power dynamics, the demand and supply.”
“don't think what you're studying in university is going to be a direct line to your future, because odds are you're going to take a very convoluted and twisted path,”
“But having worked in healthcare for 30 plus years and working in some amazing organizations, there is something very unique.”
“But I think what I would say is, don't be so uptight, like, to my 2000 self. I was really uptight, really intense, and probably to my own detriment. So what I would say is, to my 2000 self, stay groovy,”
“And I think it's more taking a step back, watching things unfold, and then making small moves to be able to get to where your objective is instead of going full hard, all, a full bore, all out every single time.”
Home and community care
“Often, if you don't have a family physician here in Ontario, where we live, 2.5 million Ontarians do not have access to a primary care practitioner. So the default then is to go to the emergency room, for the most basic, non-life-threatening health issues.”
“I was very, pro-hospital early in my career, especially when I was working consulting. hospitals could afford the consulting fees, home and community organizations could not.”
“the difference being that there is longitudinal long-term relationships that are formed between the provider of health services and the recipient, versus when you go to the hospital, it's bedside, hopefully you're out in less than ten days, hopefully, or hours, and, and not months.”
“and there's no more intimate place than your own home, and so in order to provide the care, the great care that home and community providers provide, is to establish that trust and relationship because we are in your home.”
“So every day, we are, we operate in four provinces. we serve 25,000 patients a day, which accounts to millions of interactions over the course of the year.”
“We also have a accredited college, Daniel that, provides training to, personal support workers and healthcare aides, mostly to indigenous communities. And so, our graduates have, gone on to work in over 500 indigenous communities across the country.”
Leading distributed organisations
“So in Canada, we don't have a national health system. We have ten provinces and territories that operate healthcare in a very, as you said, distributed and fragmented way.”
“And, Gemba is go to where the work is being done. So I have spent two years, and I continue to do this, and it's quite a bit of effort, to visit all of our teams across the country.”
“we created a policy called SE Flex, which varies by business unit, but we have shed a lot of office space and allowed our teams to work where they feel they're most productive, but also encouraging frequent and scheduled planned team meetings so that we don't lose that human Connection.”
“Post COVID, I'm recruiting nationally. And so we have leaders from, right across the country. In fact, there's of our leadership team of nine, only three live in the GTA. So the point being to ensure some national cohesion, our leadership needs to be national.”
“There's a special sauce within SE Health that binds a, a service coordinator in Victoria, BC to a nurse practitioner in St. John's, Newfoundland. And, there's an unwritten code of, hey, you're here to serve.”
Mission and margin
“We were founded 118 years ago, out of St. Michael's Hospital in downtown Toronto, which was to provide free postpartum care to new mothers and their children who could not afford to pay.”
“we do have an impact venture fund we're about to launch, and so we're quite excited about that, where SE Health is the anchor investor to support, Canadian entrepreneurs, around living well, caring well, and aging well.”
“But the, the sisters of St. Joseph's that founded our organization have this phrase of no margin, no mission. So in order to fulfill our social mission, which is to serve older Canadians and vulnerable Canadians, we need to generate a margin.”
“if we are consistently good for twenty-five thousand interactions, then I think the financial benefits will come out of it. I think good quality of care, you focus on that, good things will happen, financial and non-financial.”
“in our domain, what we do is all about social responsibility. It's not a token checkbox thing for the board or shareholders. We don't have any shareholders. Our board's volunteer board, we don't pay our board.”
COVID crisis leadership
“And so my previous role in another not-for-profit, it was called Kensington Health, located in downtown Toronto in the heart of Kensington Market. we did operate one of the city's larger, long-term care homes, so 350 beds.”
“And I remember going up to the floor We're all masked up. We have two weeks of masks left. The staff are crying, and I want to just run away and hide. But you have to show leadership and the ability to provide calm, in, in the face of adversity.”
“And that's when I decided to say, hey, if I do it, then I'll have no qualms about asking our staff to put themselves at risk. And remember, early days, we didn't really know what this was. amazingly enough, thirty people signed up. I worked on the floor as a residential aide for a good six months.”
“So within 24 hours, we had hired 20 family members on a temporary full-time contract, did a four-hour crash course in training, and managed to shore up some of our COVID floors and non-COVID floors. Amazingly enough, almost all the 20 donated their wages back to the organization.”
“but the willingness to try something, explore it, compelled the organization to take a chance. And as a result, in the end, we came out of the pandemic, less scarred than I think we would have been had we not tried some of these things.”
“Improvisation is, is so important. We forget about how, how important it is, and, and it's a key element of Sensemaking too.”
“Well, sadly, I think society has forgotten about our, older Canadians. So out of the pandemic, there were significant policy changes that has made the long-term care home sector a lot better, at least in Canada.”
Digital transformation and data
“But the playbook on how to implement the change management, the, adoption, the clinical adoption of these digital tools remains pretty standard. and what we're doing at Estee Health is, surprise, surprise, not according to the playbook.”
“AI is just the fancy label to, decision-making, smart computing, data, and using data, in this case, for good.”
“is to have a skunkworks lab, so-called in the basement, puts a bunch of smart people, to experiment in a safe way. So don't use real personal health information, use scenarios that we know well, clinical scenarios like falls, which happened to a lot of frail older Canadians.”
“but I do feel the greatest opportunity around data isn't the banking industry or manufacturing, it's healthcare.”
“So for us at SE Health, part of our strategy is to be a health intelligent company, is we are sitting on a mountain of data that we don't do anything about it. So what can we do to accelerate health and wellbeing for older adults?”
Running every street
“And so inspired by this professional runner named Ricky Gates, and he made a YouTube video. He ran all the streets of San Francisco in 50 days. Now, I'm not that fit and don't have that time. San Francisco is really hilly, but I decided to run every street of Toronto.”
“So for five plus years, I have Not run the same route. And so, to date, I've run all the streets in the town of Collingwood, town of Blue Mountain, but new streets keep being added when there's development.”
“I'm pleased to say that three of those, WhatsApp chat group members, who I'll call my friends, have actually run the entire city. It took them three years, but they have run the entire city.”
“By having set patterns, my three or four routes I used to do, and then getting that changed completely, where I actually haven't run the same route since then, is I actually found my neurons, my brain getting completely rewired.”
Structured chaos
“To the chagrin of our leadership team that think it's chaos, and I have coined this, and I tell our team, it's structured chaos. Like it's, yes, it's chaotic, but to drive change and reinvention, it does require chaos. But let's try to be structured about it.”
Leadership is messy
“But if you acknowledge that, that that's part of leadership, that it's messy, that it's a grind, and it's chopping wood, then when you hit those breakthroughs, those breakthroughs give you that, the amplitude is massive. But if you think that that's what leadership is all the time, then the lows are super low.”
Episode notes (as published)
From the episode notes published with the podcast.
A little playbook, a little Picasso. Healthcare is often treated as a hospital story, until you need care at home. In this episode of Messy, I am joined by John Yip, President & CEO of SE Health, to talk about leading at the intersection of health systems, digital transformation, workforce innovation, and social purpose. John shares how his early work in the digital economy still echoes today, why home and community care is both essential and misunderstood, and what it takes to build alignment across a complex, distributed organisation operating in Canada’s fragmented provincial landscape. The conversation goes deep on COVID-era leadership: uncertainty, moral pressure, scarcity, and the real-world improvisation required when there is no playbook. We also explore what “digital transformation” should mean now and how to ensure technology serves care (not the other way around), why safe experimentation matters, and the potential of healthcare data to improve aging and wellbeing. John offers a powerful metaphor from his personal endurance project: “running every street” as a practice of curiosity, resilience, and rewiring your perspective. Key themes: • Sensemaking across long arcs of change • Healthcare as a complex, fragmented ecosystem • Leadership in distributed, mission-driven systems • Frontline intimacy and relational care • Crisis leadership requires improvisation • Resilience through exploration and “structured chaos” If leadership sometimes feels like chopping wood, this episode is a reminder: the grind is part of the work and purpose is what helps you stay even-keeled through the mess. If you like this episode, write a review and share. Leading through the mess is easier with friends and colleagues. SE Health Website · Running magazine Canada article about John running every street · Website · Connect with Daniel on LinkedIn
Every quotation and passage on this page is copied word for word from the episode audio transcript and linked to the moment it was said. Quotations are never written or altered by AI; topic labels, passage notes and the episode analysis are AI-generated. Guest details come from the published episode notes or the guest's own words.
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