Phronesis: Practical Wisdom for Leaders with Scott Allen

Dr. Tim O'Brien - Looking for the Devleopment in Leadership Development

• Scott J. Allen • Season 1 • Episode 248

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Dr. Tim O’Brien is a Lecturer in Public Policy at the Harvard Kennedy School where he teaches Exercising Leadership and Developing People in degree programs and chairs the Leadership for the 21st Century and Art & Practice of Leadership Development executive programs. Tim designs and delivers leadership development programs for government, business, and non-profit organizations across the globe. His research interests focus on the complex challenges people hope to address, the understanding they bring, and the meaning-making they need to address those challenges. This lens on leadership development emphasizes self, group, and organizational awareness over content and discrete skills. How to develop and cultivate that self-awareness is the primary concern of Tim’s research. His teaching methods are experiential, collaborative, and reflective in nature and help participants develop the insight, inquiry, and purpose they need to meet the demands of the challenges they face. 

Before his appointment at HKS, Tim was a leadership consultant for INSEAD Business School’s Management Acceleration Program and faculty for the Harvard Graduate School of Education’s Programs in Professional Education. Tim graduated from New York University and earned his Ed.D. in Human Development and Education at the Harvard Graduate School of Education. He earned his 100-ton captain's license directing sail-training programs aboard traditionally-rigged wooden schooners in the Atlantic and Caribbean.


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  • "To really make an organizational-level impact, you've gotta pull the work into the organization."


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About The International Leadership Association (ILA)

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About  Scott J. Allen


My Approach to Hosting

  • The views of my guests do not constitute "truth." Nor do they reflect my personal views in some instances. However, they are views to consider, and I hope they help you clarify your perspective. Nothing can replace your reflection, research, and exploration of the topic.

Note: Voice-to-text transcriptions are about 90% accurate, and conversations-to-text do not always translate perfectly. I include it to provide you with the spirit of the conversation.

Scott Allen  0:00 

Okay, everybody, thank you so much for checking in to ‘Phronesis: Practical Wisdom for Leaders.’ I have been looking forward to this conversation for a long, long time. Today, I have Dr. Tim O'Brien. He's a lecturer in public policy at the Harvard Kennedy School where he teaches Exercising Leadership and Developing People in degree programs and chairs the Leadership for the 21st Century and Art & Practice of Leadership Development executive programs. Tim designs and delivers leadership development programs for government, business, and non-profit organizations across the globe. His research interests focus on the complex challenges people hope to address, the understanding they bring, and the meaning-making they need to address those challenges. This lens on leadership development emphasizes self, group, and organizational awareness over content and discrete skills. How to develop and cultivate that self-awareness is the primary concern of Tim’s research. His teaching methods are experiential, collaborative, and reflective in nature and help participants develop the insight, inquiry, and purpose they need to meet the demands of the challenges they face. Before his appointment at HKS, Tim was a leadership consultant for INSEAD Business School’s Management Acceleration Program and faculty for the Harvard Graduate School of Education’s Programs in Professional Education. Tim graduated from NYU and earned his Ph.D. in Human Development and Education at the Harvard Graduate School of Education. He earned his 100-ton captain's license directing sail-training programs aboard traditionally-rigged wooden schooners in the Atlantic and Caribbean. Tim, that is a shift right there at the very, very end. (Laughs)

 

Tim O'Brien  1:39  

Yeah. It is a little too good to leave out; I had to sort of… 

 

Scott Allen  1:43 

That is awesome. So, talk a little bit about that. I always ask, “What more do listeners need to know about you?” But you have it right there, tucked in at the end of your bio. 

 

Tim O'Brien  1:51  

Yeah. In a previous life, I was looking for ways to teach and alternative education options, and I discovered outdoor education, which led to a wonderful little boat in Long Island Sound called Sound Waters. Largely day trips with fourth graders catching flounder and raising the sails. Then, I learned about the whole sail training industry. So, I spent four years sailing up and down the east coast between Nova Scotia and Venezuela with a crew of high school students, mostly 16.

 

Scott Allen  2:21 

I was just telling you before we started recording that one of the most powerful learning experiences I've ever had was attending the Art and Practice of Leadership Development, the executive program that you coordinate at Harvard Kennedy School. Just an incredible learning experience. One of my classmates in that program, Peter Mello, went to high school on a ship in Massachusetts. His high school was the ship, and so he talked and shared so many wonderful stories. He is now in charge of WaterFire in Providence, Rhode Island. I don't know if you're familiar with that. Just incredible, but what a wonderful, wonderful space for experiential learning. 

 

Tim O'Brien  3:03  

Yeah. Over the top. The story I like to tell sort of summarizes that whole era of my life, and what I learned was that we tended to get students who finished high school early and others who were struggling to finish. What they had in common was that they were bored in high school. And within two or three weeks on the ship, we couldn't tell those groups apart. We couldn't tell the honor roll students from the kids who were supposedly failing out of high school. With a little bit of… 16-year-olds -- our great-grandparents are probably running farms and having children at 16. 16-year-olds are ready for some responsibility, and I don't think the traditional high school setup really gives them much taste of responsibility. They don't really feel their own power. So, it was wonderful in that sense.

 

Scott Allen  3:55 

Well, Peter, his experience at Harvard, he was familiar with some of the ambiguity at times because he'd lived that, he'd experienced that. And we find ourselves in situations where, well, what's our best guess? What do we think?

 

Tim O'Brien  4:07  

So cool. 

 

Scott Allen  4:11 

Okay. So, I was so excited. You passed along this paper that you had written, and it was published in Journal Management Education, the title ‘Looking for Development in Leadership Development: Assessing Learning for Reflexivity among Graduate Students.’ I just love that title, ‘Looking for Development in Leadership Development.’ So, maybe take listeners through some of the learning that occurred at the Graduate School of Education and your experience with CDT, and then maybe we can pair that up with your work at the Kennedy School. And then, let's jump into some of your findings in some of this research because it's just fascinating. I love the phrase, ‘Looking for Development in Leadership Development.’ 

 

Tim O'Brien  4:54  

Okay, there's a lot there. I'll start where I want to start. 

 

Scott Allen  4:58

Please do, sir. 

 

Tim O'Brien  4:59

I think as I was getting ready for this, and as we've been talking, it put me in touch with my early years as an educator in K-12 education. There's a lot of emphasis on differentiating learning, differentiating based on what a kid's interest is, where they are, what they understand, what they're doing well, where they're struggling. It's a little bit harder to differentiate in a grad school, big classes. Here at the Kennedy School, I have students who are between 23 years old and 60 years old from a lot of different countries. So, there are lots of ways to differentiate, but I think that constructive developmental theory stages of development, which are really a sequence, liminal sub-stages, is a really important area of diversity we don't necessarily honor in our classrooms, and it has so much impact on what people are learning and how. So, this was one way to talk about this article is an effort to better understand how we could differentiate leadership education. 

 

Scott Allen  6:04 

Well, take us through the process as you think about differentiating because, especially for listeners, there's this beautiful segment towards the end of his paper where… And if we think about constructive developmental theory, this is the work of Robert Kegan, Lisa Lahey, and others; you can explore their work at ‘Minds at Work,’ and I'll put a link to that in the show notes. But you do a beautiful job of saying, Look, if you're teaching a group of students at the socialized mind, here are some considerations, here are some ways of thinking about that work. Or self-authored mind, here are some potential limitations of that learner and some considerations for you to focus on. But I would love for you to talk a little bit about the design of this study and some of the highlights that you found because there was a lot of work that went into this. As I said to you before we started, I don't know of an article that doesn't mean it's not out there, but I don't know of an article that really, in a beautiful way, shines a light as robustly as you have in this paper.

 

Tim O'Brien  7:13  

I interviewed many grad students. This paper focuses on, I believe, 35 who took the same course. During my research, I interviewed around 60 and all of those people twice before and after different leadership courses. Those are 90-minute interviews trying to understand how they make sense of things, how they understand themselves, and give that meaning, making a score. Some of the things that stuck out at me were the range of scores from Stage 2 to a little peak, a little glimmer of Stage 5 self-transforming. Without getting into all the details of the study and sort of jumping to the implications section, my own insights really revolved around what was possible. We teach a pretty intensive course. The course this is based on is a 14-week course that meets three times a week, and outside of those three meetings is about four hours of writing, reflective work, and maybe two or three more hours of reading. It's really hard to see more than one sub-stage of growth. I'd like to think that a foundation was laid that can accelerate growth, but I'm not sure. I don't know if the spring semester is another sub-stage of growth. I was also a little humbled. I was humbled, but maybe I also got in touch with how grandiose I might think I am as an educator, that the self-authoring students did not grow and didn't see that growth. And I think now it's obvious that the conditions aren't there in a 14-week course to challenge them enough that they have to reevaluate all their assumptions. But what was great about this data was that they did learn a lot. They just already had the capacity to pour that reflexivity; it just hadn't been sort of put into motion. 

 

Scott Allen  9:07 

You just used the keyword there, ‘reflexivity.’ Would you talk a little bit about reflexivity? Because I know that's an important piece of the paper and the course. 

 

Tim O'Brien  9:16  

Yeah. I love the literature on reflexivity, which is being able to think about your own thinking and what you might be missing. At least, being able to recognize there's a gap in your thinking, which, hopefully, would motivate you to ask a couple more questions and learn more in the midst of pressure to act. So, it's just a really helpful, superordinate, metacognitive ability. There are way too many tasks that people need to know. There's no way grad school could make sure people know all those tasks, but perhaps we can ensure people have the metacognitive tools to ask the right questions, slow themselves down, and think about what they're missing. So, as someone who's a creature of graduate school classrooms, I'm always thinking about what it is we're capable of, what we can actually do here, and what's the most important thing to do. 

 

Scott Allen  10:11 

And I love how you're thinking because, in that paper that I shared with you that Dave Rush and I worked on, I couldn't agree with you more. Are there some habits of mind or ways of being that we can potentially put into motion that, regardless of context, aren't necessarily negotiation skills or leading a meeting that type of work? Are there ways of being, habits of mind, some of the big pieces of -- I don't even have a word to describe it right now. It's not content, I'll just stick with habits of mind or ways of being that will ultimately serve the individual in any number of different contexts? It's almost like these meta-levels; they're not skills but meta-level attributes of a human that will promote that growth and promote that continual development over a period of time. Because I think you're right. In 14 weeks, it's probably going to be difficult to move an individual, and you're providing a pretty intense experience. That's a lot of work in those 14 or 15 weeks. And, to your point, hopefully it's not stopping after those 15 weeks, some of that is progressing forward. Do you have any sense in your practice and your work -- and these might just be hunches, I totally get that -- are there other things in addition to the reflexivity that come to mind for you as accelerators of growth or attributes that facilitate growth? This is just us spitballing here as a conversation. 

 

Tim O'Brien  11:51  

Attributes, as you mentioned, are habits of mind. Yeah, I don't know, but here's a reaction I'm having; one of the things I'm always chewing on in a classroom are the tasks that will do this. What are the things you have people do, talking about classrooms here, but also at work, that nudge and support development? You get at the curriculum, and it's so helpful because I just think we need… Maybe it's not necessarily the best way to get published, but we need more examples of curriculums that I really believe that it's the task that predict performance. We need to get concrete about our tasks. So, I have, gosh, a big hodgepodge of students. I guess most of us on campuses get this big hodgepodge of students from all sorts of different institutions, organizations, and sectors. So, the task that we anchor on is like a diagnostic task: understanding each other's leadership challenges. What is the challenge really? And looking at that as a task everyone's going to have to do. But I'd love to get more specific with if we had classrooms where people had more in common, or when you get an executive program where people work together; you can get even more granular with the task. Here is a task you face, and you can create classroom tasks, assignments, and simulations. Then, you can work backward from that task. If leadership development is preparing people for… That's maybe a whole other podcast of what do we mean by leadership, but there's work to be done or a role to be filled, what are the tasks that get people to practice that work or to take up that role? And then, they can debrief where they're overwhelmed by, and then that's where the sort of having a sense of developmental psych helps because then you can appreciate what's next for that person. However, leadership development has to flow backward from the tasks.

 

Scott Allen  13:50 

Say more about that. Would you give me an example? 

 

Tim O'Brien  13:54  

Sure. There are just so many. Where do I start? Like, if we're preparing people for management roles, then you'd want to work backward from, I guess, the big task. How do you manage the resources and responsibilities of a particular role? Then, try to figure out in what ways that task overwhelms someone. Then, you can figure out the support to help them meet the demands of the task, always trying to understand the gap between someone's complexity of mind and the demands of the job. And I guess there are two ways to look at the demands of the role someone's taking up or the demands of the challenges they face. So, on our campus, because we have so many people coming from so many different roles, we work backward from the challenges they face, where everyone has to write up a leadership challenge case. We try to understand what overwhelmed them about that case. How exactly did they misunderstand or underdiagnose that case? That helps me get a sense of where a student might be, at least you get a hypothesis developmentally, and to understand why they misunderstood or misdiagnosed that challenge.

 

Scott Allen  15:07 

Yeah. Because if I'm following correctly, please push back if I'm not, at least in the context of the program that I attended, and that was probably 2006, we had to bring a case of maybe it was a failure or a challenge, a failure, or I believe it was a failure or a challenge, and we had to write up that case. And we spent a lot of time talking about that with one another, providing different interpretations of what was happening. There was a very systematic process that we went through that was very helpful, especially in the parts, and I'm not sure if you still do it, but where I had to listen to them talk about my case, and I had to stay quiet and just observe and listen. And it was just fascinating to experience that and hear from them.

 

Tim O'Brien  15:55  

Yeah, and get some perspective on what you missed. What you weren't thinking about, how other people see it. We're always missing something, so it's not so much that you, Scott, missed it. 

 

Scott Allen  16:07 

I was the only one with a case, man, and everyone else… (Laughs)

 

Tim O'Brien  16:11  

But I guess there are two ways it can go. Sometimes, you listen to someone's case, and what seems to be the challenge is that they misunderstood the role they were in or the responsibilities of the role. They were overwhelmed by the pressure of that role, and they took it personally. And there's just sort of an organizational lesson there that anyone sitting in that particular desk is going to feel this current, feel these politics, whatever they may be. And then, other times, there's sort of like a challenge that people underestimate. They're trying to push through a project; they think it'll be helpful to people, and they just underestimate the politics. They can't imagine why it got so much resistance or why it was sabotaged by another group. And maybe you work backward from what it is you're trying to address. School reform is a pretty thorny issue that people have been trying to tackle for decades. Maybe it's something to learn about school reform or whatever the issue is. So, I don't know. I'm telling you -- gosh, I feel a little bit ranty -- I'm telling you a little bit about how I think about working backward from the challenge. I'm also warming up the article I want to write. I don't quite know how to write it or get it started, but I love all the questions people are asking now about leadership development, its ROI, and how to make it useful. What seems to be missing there is whether this is about preparing people for certain roles. Is that some of the mistakes leadership development programs are making like they're not clarifying the roles? I just keep reading ‘leader’ all over those programs versus something like individual analyst, team member, team director, manager, director, VP, or chief. That's one lane of leadership development, preparing people to take up the demands of that role. And then, another lane of leadership development would be there are challenges that descend on organizations figuring out how to address them.

 

Scott Allen  17:57 

Yes. One really kind of interesting offshoot, and you have, let's say, I don't know if you came across the Harvard Business Review article Snowden and Boone ‘Leader's Framework for Decision Making,’ but it's 2007, classic article, where, basically they define it as you have simple or clear problems, complicated problems, complex, and then chaotic. It would seem to me that an individual navigating a complex adaptive challenge, we could call them adaptive challenges, and this goes back to Kegan's title of his book, ‘In Over Our Heads,’ when we are confronted with some of these complex challenges, and if I'm trying to work through that through solely a socialized mind, my perspective and my paradigm is the paradigm and the correct answer, I'm going to really, really be very, very challenged in navigating that complex adaptive challenge and seeing all of the multiple parts and connections and blind spots that I have. I have cognitive biases, and I'm not necessarily going to be equipped to navigate them.

 

Tim O'Brien  19:06  

Then, the question is, what should we do about that? And I think where I'm at now with that answer is, just using you as an example, Scott…

 

Scott Allen  19:15 

Have you already diagnosed me? 

 

Tim O'Brien  19:18

No, no.

 

Scott Allen  19:20

Someone with an imperial mind like you. (Laughs)

 

Tim O'Brien  19:23  

That's awful -- is can we create a conversation or a space or a classroom where you can get honest about what was overwhelming for you? And then we don't need this language around stages, we just need a space where you can get honest about how it's overwhelming, and then we can work from there. We never have to talk about Imperial or socialized.

 

Scott Allen  19:45 

Yeah. And it's an interesting entree about what was overwhelming for you. That's a really, really interesting way of phrasing it. And how do you experience people answering that question? What are just a couple of snippets of what you hear when you say, “What was overwhelming for you?”

 

Tim O'Brien  20:03  

Oh boy, you hear everything. People may first describe the conditions that were overwhelming, “It was overwhelming because there were these four people with different perspectives, and they all wanted something different from me.” So, what was so overwhelming about that, or why for you? Or, I guess the nice follow-up question is, “Yeah, I could imagine that's annoying for anyone, but for you in this moment, what exactly made it so challenging?” You can get a little bit more of an honest answer, but it could take three or four rounds. Not because they're being evasive but because we don't slow down to think about these things, and it's hard to be honest like that. It's hard to eventually get to a place of, “I wanted all these people to like my decision.” “It was becoming increasingly clear that it would be impossible to make a decision for all four of these people that they would all like.” Yeah, it's a conversation, which I guess makes this work so much, so hard. You need to protect time for it. 

 

Scott Allen  20:57 

Yeah. As I interface with organizations, the perception, the feeling, or the narrative that I continue to hear are things like ‘time-starved.’ These individuals are time-starved. “Can you get that done in 30 minutes?” People can't attend for that long because their time is starved. And that quadrant too of, Covey, the stuff that it's important but not urgent, gets chopped most readily. And then how are we creating that space for people to even begin to reflect on some of those situations? They just plow forward to the next one.

 

Tim O'Brien  21:36  

Yeah. A quote I increasingly use, and in my work is I forget the precise words, but we seem to have plenty of time to keep making the same mistakes, but never enough time to change them. So, yeah, we're time starved, but imagine if we actually just protected some time to have a real honest conversation and did things differently, we might recoup that time.

 

Scott Allen  21:59 

(Laughs) Or the old John Wooden; if you don't have time to do it right the first time, when will you have time?

 

Tim O'Brien  22:06  

Yeah, that's great. 

 

Scott Allen  22:07 

So, as soon as we know it's not working, let's pause and create that time. Yeah. You had mentioned this kind of next paper that's on your mind that you're thinking about, take us a little deeper into that. What are you reflecting on right now as you do this work? 

 

Tim O'Brien  22:21  

Oh, I think I just want to break down the length of leadership development, large leadership development, and focus more on the roles and responsibilities of different authority positions as a lesson to everyone to sort of depersonalize all the personalities and bosses in your organization, and think of them more as someone's filling a role that's loaded with expectations. And just managing that role, managing the demands and expectations of that role, is a lot of work. Then, the other lane is that there are organizational challenges and adaptive challenges that require cross-boundary learning. It's often because the expectations and pressures of the people in more senior positions are so high; they're often the folks who everyone's looking to address, but they have the least time and the least bandwidth, too. So, the other lane of leadership development is, what do you do from whatever position you inhabit about a challenge that you see keep recurring? And maybe there's not much of a paper there, and it's just saying that and drawing two lines on the blackboard, but they just seem to be an overlooked part of the leadership development conversation: preparing people to meet the demands of the role and preparing people to learn how to address challenges that are not necessarily on anyone's job description.

 

Scott Allen  23:46 

Yeah. How we define ‘prepare’ can also be really interesting. A traditional MBA might prepare you with how to read a P&L and might prepare you with some other content, but it doesn't necessarily prepare you for the mental complexity of navigating some of those demands.

 

Tim O'Brien  24:07  

You might cognitively understand it, but then, in the moment, sitting on a team being the most junior person, or being a newer person, or feeling like you need to model something for junior people, like how to raise these things amongst colleagues takes a lot of practice and we don't exactly have… There's some spaces to practice that, but it's hard work to practice. 

 

Scott Allen  24:32 

Yeah. And I guess I can't even think of spaces to practice. Obviously, in some of the programs that you lead, but where else are people practicing that? Maybe Kansas Leadership Center in some ways. Maybe the University of San Diego, some of their wonderful programming. And, of course, there are some other spaces that are. I think of the case-in-point methodology as a nice container to help some of that work occur, but people are dropped into organizations and just put into the situation, and that's not a practice field. That's real work right there, that's real. That's your job, that's your livelihood, and it's hard to frame that as an opportunity, as a place for practice. So, where do people practice?

 

Tim O'Brien  25:15  

Yeah. That's the question. There are thoughtful people out there who are creating opportunities for their organization. 

 

Scott Allen  25:23

Yes. Yep, you're right. 

 

Tim O'Brien  25:24

But we're not necessarily connected, and they're probably figuring it out on their own.

 

Scott Allen  25:28 

That's interesting. I just love this framing that… There was a book that I came across in the early 2000s by Merriam and Caffarella. In the book, they very beautifully outline five basic orientations of learning. We could argue this a little bit, but, generally speaking, they highlight cognitivism, behaviorism, constructivism, humanism, and then social learning. And if I want to create a world-class pilot, do you have an individual who has the knowledge, the skills, the self-awareness, the mentors, and the experience? Or a surgeon, the same type of thing. And when it comes to leadership, we tend to do a couple of those pretty well. We got cognitivism locked down, your average MBA course, “We're going to make sure you know transformational leadership.” And well, by gosh, you did well in the exam, and on your way you go. Some of the faith-based organizations, some of the student affairs type leader development programming, oftentimes really hones in on some of that humanistic domain, but probably not putting into practice what you're talking about in the paper, like reflexivity is a habit of mind, and really that metacognition. We have a lot of people getting experience out there, but are they reflecting on that, making sense of that, and doing the after-action review? And really, truly, I think of Kegan and Lahey's last book, ‘An Everyone Culture,’ where you're really focusing on that feedback piece, those organizations that they highlighted. Bridgewater and Ray Dalio’s work is making sense of situations and getting feedback. But, to your point, in the paper that you just wrote, where's the development and leadership development? I think that word means a lot of things to a lot of people. Maybe one of those five different things, and I don't know that we're often hitting all five. I can't think of a program that really works in a nice way…Because go back to piloting, let's say you have a pilot, and they've practiced in the simulator a ton, they have some skills, they know how to fly a plane, they're self-aware, they've had great mentors, but they get on the PA, and they say, “This is my first flight ever.” Do you want to be on that plane? 

 

Tim O'Brien  27:50

No.

 

Scott Allen  27:52

Or the individual who's read the book but never actually cut someone open? You don't want that individual either, right? So, how do we more holistically design interventions that truly prepare people for these very challenging roles? As you use that phrasing. These roles are not easy. And I think, Tim, here's a paper that I'm thinking about. I think when you look at the engagement numbers, what is it? Two-thirds if you listen to Gallup, and there are other studies that suggest that the average American is not all that engaged. Or when you look at some kind of Gen Z's retention challenges that organizations have today, I think in one way to frame that is that we're being challenged to be better. The complexity of some of this work results in a lack of engagement, a lack of retention. Lawsuits if leadership is done poorly. In a lot of places, the law is really holding some bad actors accountable. And we're being called to be better, and I don't know that the education we're providing is preparing people for that. I don't know what it is. I think, again, some people are doing leader development, ‘quote-unquote,’ and just teaching people the history of leadership theory, and they think they've done leadership development. So, what do you think about what I just said? Say, “I disagree. This is terrible, Scott.” 

 

(Laughter)

 

Tim O'Brien  29:19  

Gosh, I have a lot of reactions. One reaction is that people are getting together on campuses, and students are getting together on campuses to do group work. Colleagues are getting together in meetings all around the world as we talk right now. And, in those meetings, the most senior person is doing all the talking while three to seven others sort of wait it out and go through the motions. They're either frustrated, or they're not even… The meeting will end in 20 minutes, and then they're just there doing their thing. Or, in some student group, someone is volunteering to do three-quarters of the work, and four other students are saying, “Oh, this works for me,” and no one even knows how to talk about… It's hard to even talk about that after the meeting with one or two people. Some people do that; they complain and grumble, but then they go back. How to sort of get people prepared to notice these things, interpret them, and then do something about them, I think, requires a lot of reps. So, the way we've been doing it on our campus is we ask questions every week: what roles are people falling into, and in what ways have people become predictable? How is that useful but also a little bit counterproductive? And then, what could be done about this? And, for a while, there's lots of one-on-one conversations between course coaches and the instructor and students, or a lot of feedback on papers, and that builds up to someone trying to do something about this. And now there might be a little bit of a stomach ache somewhere, but people have the experience of getting through a stomach ache, generating a stomach ache, dealing with it, usually getting to the other side without any heavy consequences, and learning how to speak to these things with a little bit more proficiency. But it requires practice, and there are all sorts of reasons not to want to make people do that or get into that. It gives us all a stomach ache. It doesn't have to give us a stomachache; we can create spaces, but it just requires so much time to be protected. And making that the task, not just the execution of the work the task. 

 

Scott Allen  31:31 

I like that phrasing. If we're not making that the task, then everything else will take over and that opportunity is missed.

 

Tim O'Brien  31:39  

So, a lot of people are easing into it. “These are the things we're going to examine. These are the things we're going to explore.” And everyone can name moments when they sit and listen to the most senior person sort of rattle on. Everyone has those experiences, but very few people know where to begin and who to talk to first. Maybe you avoid it, but you raise your issue in another way outside the meeting. But a lot of us don't want to be passengers, but we haven't found the opportunities to be more purposeful because there are consequences to speaking up, and it requires practice. 

 

Scott Allen  32:19 

Yeah. And that's why I love… I don't know if you're familiar with the work of Dr. Megan Reitz. She's at Oxford. She writes some with Amy Edmondson, but a question in my podcast episode with her that she brought up, "What happens around here when people speak up?”

 

Tim O'Brien  32:35  

That's great. 

 

Scott Allen  32:37 

Adventures ensue after that. But, yes, I remember that feeling from my experience in the Executive Education course: “I just don't even know how to intervene right now to make this better. I don't know what to do.” And I imagine orchestrating that experience, teaching that course and those courses, at times, there's a lot of learning there for you as well when you're getting some of those stomach aches and the temperatures rising. Could you just touch on that a little bit? Because I think that's a fascinating thing about using the case-in-point methodology or letting people experience those stomach aches. That can be challenging as well. 

 

Tim O'Brien  33:19  

Yeah. And it doesn't have to go on too long. I think, as I teach more and more, I'm getting better at trying to model and helping people figure out how to productively say, “I don't know what's going on, or I'm confused,” and everyone's sort of sitting on that, “I don't know how to intervene, I'm confused, what's going on?” And that could be the most important thing to say because, usually, the conversation's sort of really departing from the purpose of the session or the meeting or the project. And that isn't so much an admission that you don't understand things but more of a helpful redirect. There's lots of ways to say that, we all have to figure out how we say it in our own words. But the amount of energy people put into trying to figure out what's going on or look like they know when, really, not much is actually going on, everyone's distracted. In some cultures, everyone's just showing off. And you just need to reset the conversation. You're getting some practice doing that. It’s essential; it makes you an effective professional. It makes you a better human. But it's hard to practice.

 

Scott Allen  34:30 

Yeah. You mentioned kind of the future paper that's on your mind right now, or just kernels of that. Is there anything else that you're observing or thinking about as you do this work in the classroom, things that have caught your attention recently as just phenomena that are interesting?

 

Tim O'Brien  34:48  

I'm terrible at self-promoting, but the thing in my mind is designing some programs that are like nine months long; that's the classroom component. Follow-up, coaching, and people are in teams, running interventions, creating holding environments, and starting new conversations with constituency groups. It's expensive and time-consuming, but it's what works. If I could just be so bold, that's what works. There are ways organizations could steward that kind of work, but I don't know. Like we're both in the business of attracting people to our courses, but I think you gotta pull leadership development in.

 

Scott Allen  35:24 

Say more about that - pull it in.

 

Tim O'Brien  35:27  

I teach these courses. I love the courses I teach. I obviously think they're worthwhile, but to really make an organizational-level impact, you've gotta pull the work into the organization. It can't just be pushing people out into programs; that's not a novel idea to people, but sort of an obvious one. But there are lots of ways to design a long-term intervention, even just doing the work that a team normally does, and you just punctuate it with different two, three, or four-hour debriefs, where you give people an opportunity to debrief, give them some frameworks to think differently, some new vocabulary so they can find new ways to talk about their problems. Pair that with some coaching; I think that's where we'll really… That's where I see the field going with the proliferation of corporate universities where they're just building the courses they need.

 

Scott Allen  36:21 

I have great respect for how you're thinking about design and how you're thinking about other experiments that we could run to see if we can move the needle a little bit further. It would certainly be fascinating to observe what that looks like as just a way of being for the organization. And again, the only thing that I can come to hold on to is some of the cases that existed in ‘Everyone Culture’ by Kegan and Lahey and Associates. That's the only example I can come up with. But it's a really interesting puzzle. Another example that may come to mind for me would be the military, where, in some ways, there's at least an after-action review. We're talking through what happened. How did it go? What could we have done differently? And there's at least that strategic pause that's occurring and sense-making that, again, promotes growth and development and learning. But I don't know, to your point, but onto the next project, next, next, and we're continuing to make some of, and continuing to run the same workarounds and avoid the same conversations, and it's just how we exist. And, to your point, from a few moments ago, we spent a lot of energy pretending, not acknowledging, and avoiding.

 

Tim O'Brien  37:47  

Yeah. I know. There are excellent people in strategy roles, people development, and human resource roles that are changing direction. They're pulling leadership development in; they're doing cases. They're being intentional about cases with different people from different units, groups, and levels of their organization, so everyone's learning. New perspectives in their organization. There are great people doing exciting work, I think, because they've exhausted all the popular options and all the interesting stuff is already there. They just need a format for it. So it's happening. It's an exciting time to be in leadership development.

 

Scott Allen  38:26 

I could not agree more. I think we're being called to get better at not only the education component but we're being called to get better at the activity of leading others more effectively. The 80s and '90s, prior to that, had a little bit of a command and control, ‘do it because I said so.’ Sit around and put up with it. Is not anything that this generation is apparently interested in, so we need to be better, and we need to bring a lot more tools to the table into the game to be successful. I had a fascinating conversation with a gentleman the other day who was really designing, like, intentionally designing for the engagement of their younger workers and thinking critically about how we engage. How do we design our culture in a way that will feel energizing, will make a place where people want to build a career, and, again, I have so much respect for that way of thinking and that experimentation. I always close out these conversations by saying, “What have you been reading, listening or streaming recently?” What's caught your attention? It could have something to do with what we just discussed in leadership. It could just be like, “Hey, I've been watching ‘The Bear’ on Hulu, and it's caught my attention.” What's caught Tim's eyes in recent times?

 

Tim O'Brien  39:46  

Gosh, I've been making my way through a book called ‘Everyone Who Is Gone Is Here: The United States, Central America, and the Making of a Crisis,’ by Jonathan Blitzer. About immigration policy and reform in the United States, it's just shocking how undeveloped it was: immigration policy. So that is just a book. I'm learning more than I wanted to. It's overwhelming and depressing and very illuminating. I also want to plug a lovely little book called ‘Course Design and Assessment’ by Kathy Lund Dean, our colleague, and her associates. It's been really helpful as I think about my course and its objectives and what I could be doing differently.

 

Scott Allen  40:30 

She's awesome. I just really respect her work. She's a good friend too. Kathy, I want to give a shout-out to you for your good work. Tim, so much appreciate your time, and thank you for the good work that you do. Always a pleasure to check in with you. And again, congratulations on this article. I think it's moving things forward, and I think it's just a really wonderful perspective on the work that we're doing. I'm going to put a link in the show notes to your article so that people can, at least, know where to access that. You know what? I hope you have a wonderful fall, sir.

 

Tim O'Brien  41:04  

Thank you. Likewise, look forward to seeing you. 

 

Scott Allen  41:07 

Take care. Be well. 

 

 

[End Of Recording]