Luke Entrup is an executive coach and consultant who works with high growth startups to strengthen their organizational culture and leadership in an ever-changing environment. We know Entrup because he spent many years as director of innovation at West County Health Centers and Petaluma Health Center, and he is also an alumnus of CCI's design thinking training program. In this discussion, Entrup shares his foolproof meeting structure that supports a culture of innovation, as well as the role of leadership in its success.
Luke Entrup is an executive coach and consultant who works with high growth startups to strengthen their organizational culture and leadership in an ever-changing environment. We know Entrup because he spent many years as director of innovation at West County Health Centers and Petaluma Health Center, and he is also an alumnus of CCI's design thinking training program. In this discussion, Entrup shares his foolproof meeting structure that supports a culture of innovation, as well as the role of leadership in its success.
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This is an automated transcript. Please excuse any errors or hilarious mistakes.
We have Luke entropy, who's joining us as a, yet another catalyst alumni. Who's gone through catalyst program. He's coached in the program and, uh, the whole career in public health and healthcare, and was at west county and helping them, uh, deliver new innovations and work through lots of, uh, new ways of serving their patients. And now he's with evolution, right? Is it evolution? And he's a executive coach and team, a team builder where works to build cultures of innovation and help leaders become more conscious about their leadership, uh, and improve the performance, uh, while creating a great culture in the organization. So we're really happy to have Luke here with us today, and he agreed that we talked about a number of topics and he felt that there's a particular works type of work session.
He does with many organizations, whether they're in community-based healthcare or some of the fastest growing startups in the valley, um, and around the country, it's a, it's a work session he does with them to identify their pain points, really try to figure out what's going on with the teams and the culture, and then start to work with those things and get them on the roadmap for possible solutions. And he's starting to incorporate much more design thinking and human centered design in the techniques of leadership development and organizations. So we're really happy to have Luke Luke, I'm going to welcome you and ask you to kind of tell us a little bit first about your journey and how you kinda came into the world of, uh, human centered design and using design thinking in both healthcare and now leadership development. And then we'll go on to, to your topic. So welcome.
Wonderful. Yeah. Thank you so much, Chris. Uh, it's really exciting for me to be here. Um, and I'll just answer that last question straight away, which is I came in, uh, to design thinking through this group right here. Um, so it's, it's nice to be back. Um, I've not been working in healthcare for the last several years directly. And so it's nice to be back with, uh, back back with my, my roots and to share a little bit about how I've taken the tools that I've learned specifically from, from this group, uh, CCI and, and Chris, and then now applying it into my work. So yeah, a little bit about my background. Um, I spent about a decade in my early twenties, uh, working with coaching emerging talent and, uh, coaching young leaders and training training, young leaders. And, um, then got the itch to do a little bit more mission work in the world and, um, decided to go into public health.
And that landed me initially working in global health, but Miami squarely in a community health clinics. Um, and as you mentioned, I worked for west county health centers. So I know as part of the CCI network, I also worked for the Petaluma health center. And so kind of spent some time in the north bay, uh, and in various roles. But really my primary role was always the innovation director within these, these organizations to really help bring a lot of what CCI is doing into, into those organizations. So, um, and then, uh, about five years ago, I started to get the edge to kind of head back into my roots and have been, uh, squarely for the last three years, working with organizations, mostly high growth or organizations and companies to help them scale their leadership and their culture and create more strategic alignment within the organization.
So I work currently in my coaching firm, we work mostly with, um, high-growth companies working with, uh, firms are organizations like slack, Dropbox, Twitter. So a lot of tech companies, not exclusively tech companies, but we're, we're, um, that's mostly what I'm doing. And I've been able to really, um, take a lot of the skills that I learned through the training at CCI and begin to apply that into leadership development and culture building within organizations. I think that's a little bit about what we want to talk about today. Cause I certainly think that, you know, the things I'm doing in the tech companies are, can be done within the healthcare space, especially with the skills that exist in this, in this community. So nice
And just real quick on that whole notion of you got introduced to human centered design design thinking, uh, with CCI, do you remember what it was like to first encounter some of the, um, mindsets behaviors, principles? What was your initial reaction and why did you take to it?
Yeah, I mean, and that's, that's actually well said. I think I, the skills were nice, but I think the thing that impacted me most initially were the mindsets it's really like when I get, um, when I really reflect back on that time, it actually is a shift in how we do work and how we actually relate to our role. So things like deep empathy and, um, really being curious first, rather than defensive and the amount of energy that can happen through the collaborative process, like energy, we feel in our bodies that by the end of a good session or just energy about, uh, an idea that we're, that we're working on together collectively that really impacted me pretty deeply and knew that this was something that I wanted to make a major part of my work. So,
Yeah, yeah, yeah. Uh, we could have a whole session on talking about how is that in contrast to how, you know, companies and organizations normally develop talent and problem solving and, you know, the top down or being right all the time or being the smartest person in the room, uh, and how this is really a shift and it's much more human centered, collaborative. Um, we had a more effective and more effective. Yes. Why do you think it's more effective?
Well, I think that, you know, what we're doing with a lot of these tools is we're harnessing the collective creativity of an organization as opposed to being stuck in an expert driven culture, which is, you know, I think we find this particularly in health care, a little more so than other industries where we have experts and we rely on them a lot to jump, not just generate the ideas, but drive the projects. And, you know, these tools really flatten out temporarily flatten out an organization. So it really captures the brain power and the creativity from across all quarters of an organization. So both with the mindsets, but also with the tools. So I think that's way more effective at coming up with better ideas, more novel ideas, ideas that are gonna hit our help us hit our targets. So nice.
So, you know, one of the things not just on innovation projects, but one of the things you're doing now is really helping organizations develop, uh, getting in alignment, understand why they're not clicking as a team, um, uh, helping them pursue their goals in a more effective way. And you talked about when we were preparing for the meeting and you talked a lot about this notion of a work session that you do with them that you find highly effective. So if you could, can you take us through that and why you do it or who you do it with and just, uh, the background and what you go through to make
That happen? Sure. Yeah, absolutely. And I, you know, I think about this partly from my own experience working in the safety net. Right. But also just, this is something that I think is broadly applicable. I've, I've run, I'll describe the process in a moment, but just a little background on it. I brought it up. So, you know, two, three dozen times now, um, in a lot of different types of organizations, mostly at this point, I work with these like, you know, startups, essentially tech startups at various stages, you know, or very early to some that have already gone public and have thousands of employees. Um, and the, really this, I use this process when in two situations, when there is, uh, maybe some sort of strategic misalignment with the key decision makers in the organization and the teams that they're leading. So the organization is not totally, uh, synced up with where they want to be, where they want to go together.
Or there are a lot of cultural issues that are undermining the strategy. So the, they maybe have a clear roadmap that they agree upon, but they're not quite able to execute in the way that they want to execute. So, um, so that's really where we'll pull out this, this tool, which I think those that have done the catalyst program, a lot of this maybe will sound familiar because we're essentially using a lot of the catalyst tools, but we're applying it less around workflow design or product design. We're applying it to organizational design and culture buildings. Um, so that's, that's a little bit of background on it and maybe it, would it be helpful if I kind of walk through a few of the phases around how this goes or perfect can be a good next step. Okay, great. Yeah. So I'll, I'll, I'll use basically I'll use like one case study around this, knowing that there's been a lot of permutations and kind of revisions on this, but I think I'll just pick one and then we can talk about how this has been modified, how we use it differently.
So I'm thinking about in this case, I'm thinking about a, um, a financial technology company that's grown pretty rapidly. One that most people would recognize and they, uh, decided they wanted to gather their 50 most senior leaders in the organization. They've got about 2000 employees at this point, so big, pretty big. Um, and they have had a lot of challenge around getting everybody on the same page and they've had some challenges around some culture, uh, culture, not quite being aligned with, with strategy. So what we did initially was we got everybody in an offsite for two days, uh, outside of the office, which is really important to do this type of work, uh, especially when we're talking about strategy. And we, um, first had the founders come up and do a timeline of the founding of the company until now and in high-growth companies. And I think this is true in healthcare.
There's, there's always kind of a bit of churn, especially in the management ranks that we're constantly kind of like in resource strapped environments in particular, we've got a bit of churn. So it's always nice to do like the story of like the organization up until this point through the lens of leadership. And, uh, so we get, um, we do this kind of as a journey map up on the wall where we get, um, you know, some butcher paper and like, um, people bring artifacts, historical artifacts related to the culture or certain moments in the company's history. And, uh, we get it to present day. And then a little bit of conversation, usually from the key leaders around the vision of where we want to, we want to be going and the conditions, the environment in which we're operating right now at which point. So we've got, uh, we've essentially got some strategic directions that the organization wants to take.
We, then this is where we really get into some of the skills. So we will, um, take each kind of strategic priority and we'll start by just using sticky notes and mapping out all of the pain points, whether they're strategic pain points, cultural pain points. And we just get a mass of pain points, um, under each of these priorities. And, uh, usually this takes up a lot of space. In this case, we broke them up into groups because there were 50 people. Each of 10 people took one of five or six of these priorities and we just mapped everything out around all of the pain points. And then we do a little bit of sorting. We use some two by two matrix of people. Remember that we're, we'll kind of try to find the ones that are like the biggest impact, the most painful pain, the biggest pain points we'll do somwe voting and we'll really surface the key pain points. Then we'll use some,
What level are these pain points, uh, flying at? Like w when you're talking about kind of priorities for an organization or a group, what kind of pain points do they surface and how does it keep from getting too negative?
Yeah, I mean, we actually, so there's a lot of different, a lot of different altitudes. Uh, some of the more important altitudes are like, you know, a need and these environments, something like, I don't know, marketing and sales aren't talking, right? So like we're not getting good leads from marketing into sales, for example. Um, and those, those two teams aren't talking, or, um, we are, we're, we've had a series of failures around design in our user experience, um, because we haven't included enough users in the design or something, you know, there's been some, some something around the product design cycle, um,
Issues that are happening in the organization that they see as they want to art, they want to identify as a potential problem. Yeah,
Exactly. And this is the beauty of this process. It really flattens it out. And so, um, people can essentially have their, their point of view heard in a way that isn't as hierarchical, that needs to go up the chain of command. We set the conditions around these conversations to make them as safe as possible. So we can flatten it out and surface some of the underlying issues from across the organization. And I think this is the beauty of design thinking in a lot of ways is that it allows these conversations to unfold in a way that's a little safer and a little more, um, effective at taking action around.
So, um, so once we kind of surface the key ones, we'll, we'll, we'll do some heat, like a ranking and voting. So we surface a few key, uh, challenges. And then we'll go into an ideation phase around doing ways of statements for solving these, you know, we may surface, like, I dunno, five key pain points that we want to spend the rest of our session designing around, and we will do kind of the classic then ideation session of brainstorming and, um, and create work groups. And usually at this point, we have created enough alignment and endorsement that it's pretty clear that the organization needs to address these three or four, um, these three or four initiatives. And then there will be a process that will help guide them through after these offsites, where they'll set up a project groups and go back and collect data from the people that these ideas are really going to impact. And then it becomes much more of a, you know, three to six to one year process around how to really solve these big pain points. Um, so that's it, in a nutshell, there's a lot of nuances to it, a lot about adaptations, but it's, it's essentially a lot of the, you know, the sticky notes and we'll use storyboarding a lot in mapping out either the solutions or the pain points. Um, so I'll pause there.
Yeah. What you're describing as the Genesis of organizational change in a more human centered way where you're involving the folks that are, um, that are, that are experiencing the pain points, um, that feel the dysfunction, or feel the, uh, lack of performance or lack of achieving their goals. And it starts with them, but it really kicks off essentially projects. And so these aren't innovation projects, but it's really to help develop the organization to achieve their goals.
Yeah, yeah, that's right. And I think, you know, I've seen these surface problems that I definitely would not be surfaced otherwise in kind of the classic, uh, you know, one-on-one meetings and team meetings. The way business usually happens because we temporary temporarily flatten out the organization. So some really amazing things have come out of this, you know, in organizations that have been really locked otherwise. I mean,
I love that you're describing a process that we all find very familiar, but using it in a context that we all need and maybe a little bit harder to work on is cultural things or organizational things. Uh, I'm sure that, you know, as we get into Q and a sure people are going to be curious about how I, how I apply this to a small, non high growth startup, right. Uh, in my own organization. And how does it, you know, how does that translate? But you're, you're using, uh, the skills that we've all learned in a context that has a big impact on an organization. So I think that's, it's not like it's some mysterious process, but it's a way of applying the method with people working on the organization. That's
Right. Yeah. Yeah. And I just, just to add on that a little bit, sometimes I will actually get way more specific around the question. So I gave you this example around strategic initiatives that the organization wants to embark on and what are the pain points it's related that sometimes we'll go in and we'll run the same process that I described, but we'll just ask about the culture of the organization and say, tell us about the pain points that people are experiencing related to, um, working at this company or at this, at this health center. And we'll run this exactly what I just described, but be much more strategic about culture or employee experience, or what's it like to lead within this organization. So we look at how we're developing leaders using all of these same tools, but very much around culture and leadership. Right.
Nice. Okay. We got some questions coming in, uh, and I think that's the best way to move forward. So somebody chatted in, how big are these groups? What kind of permission do you need to get from a leadership to set expectations and level set beforehand? How many, how much prep work is there in developing this approach and permission to work?
Um, so my point of view on this, and I know this, this is sometimes a little complicated, especially in the healthcare space, but my point of view on this is I usually will not really work with organizations unless the leadership has really bought in to this. Um, and so there's usually some work that we need to do first with, with the C-suite top leaders. And so for me, that often looks like at least having a series of conversations over the phone, but often we'll actually do a one day offsite with them first around this and have them kind of run through their own process and talk about how they're functioning as a team. So that's that aside. I mean, that's basically how we work, but I think there is a way in which, um, we can make the case for, um, these types of conversations, um, to help people really see the benefit around solving some really persistently sticky problems. That's usually a good way to make the case, but, um, I do think you need, you need to have organizational buy-in to, especially when we start talking about surfacing pain points in a non-traditional way that isn't necessarily hierarchical. Right. Um, so
Can I, can I ask a up question on that? Um, if, uh, the, like you said that you might narrow it down to five pain points, or like, do they help framing your, your, your, your learning question or like the Eric, the design constraint, like, how are the leadership involved in like, so that you don't go through all this and they're like, this actually isn't the direction, or do you get some people who are like, you can do what you have cramp launch? Like what normally
Such an important question. So what I do is I prep the leadership team ahead of time and say, there may be some really, there may be some ideas that get surfaced in this that, you know, you're just not going to pursue and it's not aligned. And, um, and there may be some ideas that are a little hard for you to hear, but like, and that need to be addressed, but, you know, you don't like, we don't really need to invest in that. We treat this as kind of like an information gathering session and I let them actually lead the discussion. I set them up and kind of teach them like, you're going to lead the discussion about narrowing these down. So when we get into like using the two by two matrix and highlighting which initiatives we're actually going to, uh, we're going to Greenlight and move forward and then ideate on, they actually, this usually the CEO or the co-founder team, I have them actually lead that so that they can make the case against an idea that maybe had a lot of popular support. Um, and they, they drive that. So that's, uh, this is where I think leadership buy-in is really important around some of the stuff. So that helped that answered the question. Okay, cool.
I mean, in some ways though, want, I mean, you want things to surface from the organization that the leaders will address that maybe they weren't aware of. Um, and they're not really, you're not saying that they go in with their own agenda of what problems they want to solve, because that would defeat the whole purpose in some ways.
Yeah, exactly. So there's a lot of prep that goes in that I do with them around, like, you know, as I described, like, there's going to be some things that you hear that might be uncomfortable, are you really okay with this? And, um, and, uh, the good ones do most of them that I work with, they want, they want this, this is why they're doing this process is to surface things, especially around dynamics that are, we call the PTP persistently painful patterns, right. That just moving through an organization. Um, that's what this, I think that's what this process really helps solve is like getting at root cause. So yeah, we just don't want to box if we don't
Persistent fleet, painful problems, patterns,
Speaker 2 (21:51):
Patterns. Yeah. Yeah. We just, I also just don't ever want to box anybody in to have to make a decision in the moment around that. So we build in a lot of mechanisms for them to be able to kind of shape that conversation as we're going.
I mean, I think that's one of the hardest things to remember as we're talking about any of these things, as this is all iterative, I was going to make that point earlier and it starts a process. It doesn't end it and you, aren't making all the decisions and you could come back after a little, you know, information gathering on one of those pain points and you've you take it in a whole new direction because of what you learned from actually going and looking at what's happened. Right. So it's iterative, it's not this finite, um, thing that just happens and it's done. Okay. I want to, um, Wendy, are you, do you have, uh, do you want to turn your microphone on and ask the question? Do you want us to read the chat? I'm just looking over at the chat
When you seem to send these to bump into each other. Great. Thanks. Um, yeah. So this whole issue of, you mentioned flattening it out, so folks are more not, or non-hierarchical in this retreat and establishing psychological safety. So can you say more about both of those so important?
Yeah, sure. I think some of it is what we've talked about. So making sure that the leadership has really bought into the process so that they're not actively undermining the ideation phase or surfacing of the pain points. Um, we also do a lot around, um, so we'll do some kind of warmup exercises around, um, uh, kind of the creative thinking and, and, you know, I think one of the tools that, that CCI used to teach, I don't know if you still teach, but like the idea of sacred cows or, or kind of these like untouchable ideas that, um, so we'll introduce that concept in a slightly different way we'll use, um, uh, we'll do some kind of like, um, interactive exercises that get people kind of thinking outside the box. And so we, we prime them so that it's, um, uh, we're suspending kind of public judgment around ideas so that you get the most ideas out at first.
And, and then there was a process of like, you know, the narrowing phasing of like, all right, what are the most important ones, but we want, we want to set the conditions so that people can just speak what's on their mind, knowing that some things are a little riskier to mention, especially when we start getting into like office politics and, and kind of like cross-functional collaboration that things can get a little hairy there. Um, so we, yeah, we just, we, we also, like, we were, we're very tight in our facilitation around like, not cross-talking we do. Um, what else do we do around, uh, we have a cone of silence around all of these events. So we ask people not to share outside of who's there at the end of the session, we'll come up with a communication plan that we communicate out to people that weren't at the session, otherwise, everything that happens there stays there. I'm trying to think if there's anything else notable about that for me, I mean, the key really comes down to what we talked about a moment ago, just around like making sure we have clear, uh, we have the leadership team set up in a way that they're ready for this conversation. Is that helpful, Andy?
Yes. All very helpful. And for the leadership, are they the top leadership or in the room the whole time? And if so, how do you work with that leader who just can't help themselves when they want to say something that's going to kind of shut down the others
I pull. I definitely pull. So I'm in the, I have the luxury of being an external consultant for this. So I think that's a little bit different than a lot of the people that are on this call where you're actually maybe reporting up to this person. So what I do is I pull them aside and tell them we're not going to do it this way for this meeting. Remember what we talked about? Um, and I do a lot of prep with them say, so what my, my pitch to them always is when there's an opportunity to share something, you're learning about yourself as a leader and share about how you're growing as a leader in this process, it's best if you're the first person to do that and model that when it comes time to us surfacing new ideas and surfacing pain points and surfacing, uh, fresh, fresh observations about the organization that you're leading it's best if you're the last person to speak. So we want them out front on kind of like vulnerability, and we want them bringing up the rear on generating ideas.
That's a really great insight or coaching point. I, I love that, but the whole notion of having people be, uh, showing their vulnerability and sharing, reflective thinking in the moment, and then not jumping into say what, everything that they think is wrong with the organization first in one last and the other beautiful, a beautiful articulation of that point. Love
It. Yeah. So, um, if they're, if they're not bought in and, uh, you know, this is where it gets a little, uh, complicated, and, um, I have done this in some work groups as well, where then we, you know, we'll do this in like a smaller organization within an organization, and then I'll work with that leadership team to develop a communication and kind of an influencing, managing up plan about how to get a buy-in from the top. But that's definitely not ideal. You can run it in smaller groups though. Love it. Thanks. Oh, just one last thing on the, on the flattening things out that I'll just mention, Wendy is I make very clear that it's a temporary process, right. We're just going to flatten this out for a couple of hours and then, you know, and then we'll go back to kind of like the leadership team will need to decide what we're going to do with this. So everybody knows, like, just because you put an idea out, it doesn't mean that we're going to pursue it.
Yeah. That's so important that whole decision-making structure, um, being clear. I think that's a big one. Yes.
Nice other, uh, observations or questions for Luke from the
Folks in the gallery. Chris, we talked a little bit about the difference between, um, healthcare and what I see in startups in tech. Would that be a useful thing? Just,
I was going to ask that, but go ahead. Yeah. How does, how to, I mean, you have experience with the healthcare organizations and now, um, you know, with a lot of leaders in large organizations, fast growing startups technology, but how, how do you think about that now, if you put yourself back in the, um, healthcare field or even community development, uh, working with, uh, social service organizations, how do you see these things translating or different kind of strategies given that you might be working from within rather than bringing in a consultant?
Um, well I think, you know, partly Wendy's question illuminates part of that, which is, you know, there's, there is typically a little bit more kind of internal buy-in that needs to happen in, in this, in our world here. Um, but I, I, the thing that has struck me is that there are, like, when we look at just like using design thinking to impact and create change within an organization, I've seen just as much, if not more within the group here on the CCI call, as I have seen within some of these tech startups that a lot of these tools kind of were created adjacent to. Right. Um, and so the scrappiness of people that work in resource, um, constrained environments, I think really lends itself well, to be very connected to your end user, AKA your patients or your, you know, your frontline staff, there's a way in which you have your finger on the pulse of your users in a way that a lot of other sectors don't, um, where I think there's a difference.
So I think that's just, you know, the, the, the concept of patient centered care has been around for awhile. So there's this, there's this kind of, um, there's these circuits open within a lot of health systems, health centers that know how to be close to their patients, where there is a difference, I think is, um, a lot of the startups have people that are designers. And so they're using these tools for product design and, um, workflow design, service delivery, you know, uh, where they're not using it is in what we're talking about. Org design and leadership design and, and getting teams aligned. And so what, one of the things I've been trying to do is actually grab a lot of these designers that are doing product design and have them start facilitating a lot of these meetings internally. Um, so that's a little bit of a difference here. They have the capacity within the organization they're just solely using it, usually I'm product designer engineering.
So what do they bring that you see? Why do you pull them? What do they bring in terms of mindset, behavior, talents that helps in that situation?
Yeah. I mean, a lot of it is the like, um, greeting every statement with curiosity, slowing the conversation down to make sure that we're really understanding a problem, very clearly framing. I mean, just the simple techniques of using where, um, um, how might we statements or, um, you know, they, they come with that already. They come with knowing how to storyboard or knowing how to cluster, uh, sticky notes, you know, that maybe other people in the organization don't, so they come with the toolkit and they come with the ability to take a team through a process. Even though we may, I may send a designer in with an HR, uh, team to work on redesigning their hiring and onboarding process. Right. It's like a problem. That's not about tech design or user interface, but they have the skillset to go in and be able to do that with just a little bit of help.
Yeah. I think that's really important. Some of the skills that you mentioned the orientation towards, as you said in the beginning, working this way, which is a little bit different than treating every question with curiosity. This is the designers Bain, as they're curious about the world, they're curious of why, why can't we do it a different way? And they're always looking for that opening to do something a little bit different, better, more interesting way. Um, so if you don't have, if you don't avail yourself of hiring designers, those are the skills you want to start cultivating in your team. Those, those are the skills you want to keep practicing and realize it's not just a, you know, a human centered design method, just a individual tool or a technique that CCI has, you know, advocating for. It's really a way of working in a, in a behavioral profile that you're developing to have in your culture to have in your organization. So you can solve many different kinds of problems, um, with these tools.