This Might Not Go Well: The reality of coaching through change with Jason Leunberger

Georgina and Allard are joined by Jason Leunberger, sharing his powerful insights from a six-month team coaching engagement within a large, complex organisation. At the heart of his story are key learnings about subgroups, the courage to experiment at different levels of the system, and the time it takes for a team to truly come together as one. We also explore the value of co-coaching in navigating this journey.

Jason, with a background in tech, consulting and leading GRC globally at Starbucks, now coaches leaders and teams through Kinkou. He shares a pivotal moment when a divide between longstanding and newer leaders surfaced, and how facilitating a direct dialogue helped unlock insight and provide a way forward.

You’ll discover:

• How subgroup dynamics can shape (and stall) team effectiveness. 
• Why courageous experimentation at different system levels matters. 
• The importance of staying present when discomfort and division arise. 
• How co-coaching strengthens support during complex interventions. 
• Why patience and timing are essential for lasting team alignment. 

This episode offers rich, real-world insight for team coaches and leaders working with change and complexity, highlighting that true transformation takes time, courage, and a willingness to stay with what’s emerging, even when it’s uncomfortable.

Brought to you by Team Coaching Studio - The world’s leading academy for team coaching. To find out more about us visit https://teamcoachingstudio.com/

Transcript

SPEAKER_03 0:01

Welcome to Teams Transformed, the podcast of people who want to see real team transformation.

SPEAKER_01 0:07

For courageous coaches, curious leaders, and anyone passionate about unlocking the true power of Teams.

SPEAKER_03 0:13

We're your hosts, Jordina and Al Art. Here's a journey with you through transformational insights on how to coach teams with presence, depth, and emergence.

SPEAKER_01 0:23

Let's explore not just the tools, but the art of transforming teams. Hi there everyone. In this episode, we are joined by Jason Loyenberger, who began his career in tech working for a VC-backed startup, then held consultant roles for multiple firms, including Ernst ⁇ Young, working with Bootstrap founders to Fortune 10 leaders and teams. After leading governments, risk and compliance globally for Starbucks, where he was recognized for his coaching and leadership development, he founded Kinku to focus on coaching leaders and teams, a work that he loves more than anything else. And in this episode, he shares with us a story that happened not too long ago. A piece of work with a rather large team, clearly divided into the old guard and the new guard. So lots of learnings here about subgroups and courageous experimenting with different levels of the system and the time that it takes really for a team to uh come together as you know, one voice, one team. And we also touch upon the value of co-coaching along the way. So, anyway, an absolutely wonderful story to listen to. Hope you enjoy it as much as we did. We've called it This Might Not Go Well, in reference to uh those very specific moments in team coaching and that we've all felt, I'm absolutely sure. This might not go well, but it went very well. So here you go, Jason.

SPEAKER_03 1:45

Hey Jason.

SPEAKER_00 1:46

Hey, Georgina and Al. It's so good to see you and hear you. I've missed you.

SPEAKER_01 1:52

Miss you too. Where are you still in New York, Jason?

SPEAKER_00 1:56

Or I'm very far away from New York. I'm in Seattle.

SPEAKER_01 1:59

Oh, in Seattle. Why was I thinking you were in New York? I don't know. I don't know, but yeah, Seattle. Yeah, same country, different coast. Yeah.

SPEAKER_00 2:08

Yeah, different coast.

SPEAKER_03 2:10

Yeah. Oh, well, thank you for joining us today in this Moments of Emergence series of podcasts, Jason. And uh look forward to getting to the conversation. Um, before we start, what what what do you want the listeners to know about you?

SPEAKER_00 2:27

Well, I think uh maybe something to know about me is that um I love learning and I love learning through this whole um team coaching experience. And I definitely am uh learning as I go, for sure.

SPEAKER_03 2:49

Yeah, that makes sense to me. It's a never-ending learning experience, isn't it? And I think team coaching at its best teaches us as much about ourselves as about the the art of team coaching. Yeah. Yeah.

SPEAKER_01 3:06

Yeah, it really resonates with me too, the uh the never-ending, the never-ending desire to to learn more and to understand more and to and to make sense of what's happening and and um and reflect on what's happened. And and maybe, and maybe that's part of what this podcast is about too, on you know, reflecting on on what has happened and why it happened the way it happened and and learning from how we showed up in the moment. And yeah, so let's maybe we could dive just in, uh straight in. You know, this so this series of podcasts, as Georgina mentioned, is really it is about moments of emergence. So it's uh as you well know, we love we love to work emergently. We love to work with the warm, the warm data, as Nora Bateson would call it, that that that that's apparent in the relationships between people in a team. And uh and and quite and more often than not, when we do that, you know, we we discover new things. The the we're open to the unexpected, and we're not we're not defining the team as a uh as a frozen kind of entity that we define as the team and therefore we kind of have a handle on it. But we stay open to the fluctuating relationships that that exist in the moment. And and so we were wondering with Georgina in as we were talking about this podcast just before we hit the record button, if if there is such a moment, Jason, that stands out for you where you go, gosh, I remember when this or that happened, and maybe maybe I wasn't really prepared for it. Maybe I was, and uh, but this happened, and it seemed like a rich enough moment to unpack with the team and make sense of.

SPEAKER_00 4:45

Yeah, so I'll I'll give you a little bit of context and background into the moment. So the context and background is um I was working with a team and I had a uh great co-coach with me, and the team was rather large. It was like what they would consider it an extended leadership team. So it was made up of a core leadership team and then an extended leadership team. So we were coaching both teams, so one is a core and then one all together. So when we got together as an extended team, it was it was pretty big. But like what are we talking about? 16 people or 16 people, 16, 17 people in a room, very large conference rooms. It's tough to find large conference rooms that fit that many people. And um so it's a very large team, very diverse, at an organization that has been around for a very, very long time, and they're very large. And about six weeks into a six-month engagement, there was a massive re-org. And so when when you said that you know, working with a team not as a locked structure, like it was very, very real to us after six to eight weeks of being with this team to where the makeup of the team had completely changed. So people who were peers uh the day before were now uh reporting to people that were previously peers. So relationships had been were relationships were being challenged. The team makeup had completely changed. Uh, there were some members that were no longer with the company and had been there for a very, very long time. So the the energy just changed in a matter of a week within the first third of this uh time that we had together, this engagement. So leading up to this moment, we get so we dealt with all of that. We um we sat with that, we worked with that together, my co-coach and I. But the moment the moment of emergence didn't happen until probably five and a half months in to a six-month um bit of work together, a six-month engagement together. So the moment of emergence happened uh uh far ways into the work that we were doing. And the the way that we had built this work is that we wanted to have what we were calling um a team development day in the beginning and a team development day at the end of our team coaching work. And it was a time for us all to come together to be in person, and we focused on uh a light agenda. And um, and we we had in mind something that I've um I've I've heard Al refer to many times and minimum viable structure. Yeah, which I love. I love that. Um, so we had a light agenda, team development day. This is towards the end, so about five and a half months in. And we're working through half the day. So I'm in person, and for a number of reasons, my co-coach couldn't be there in person. So they were she was on teams. So she was with just one other person remotely, and then the rest of us were all physically in person. So that was that was challenging in and of itself, just my co-coach not being there with me. And and um, somatically, I couldn't, I couldn't see or like even visually with our eyeballs checking with each other, just to kind of sense what's going on. But what had happened in the room that day was, and we were get we were getting a sense of this over the course of months, is that, and maybe this is this is similar to many other large organizations that have that are established and have been around for a very long time. But there is this sense of what I would consider an old guard and a new guard. So we had these um the strong members of what I would consider the old guard, not to say that the their contribution wasn't valuable. They had just been there for a very long time, so they understood the culture, the systems at play, how things got done, the way people made decisions, how money was spent, all that sort of thing. And then we had this new guard that had this very different energy, and they challenged the old guard. And then what we ran into pretty often was this just this wave of uh resistance, like this this energy that would not allow anything to happen once they got going, because they would both generate their own resistance, and then what we got to was this wall, and we would get stuck. And so, in the moment of emergence, when we were working through a specific situation, a challenge that the team was experiencing, what emerged in the moment was what felt like two mayors of each town represented themselves, and they didn't call themselves out as like I represent the old card and I represent the new card. It just it became very apparent after all these months that there was one voice that was representing uh those leaders that had been at the company for a long time, and one voice that was representing the new leaders.

SPEAKER_03 10:31

Yeah, sounds like it's got quite tribal in the moment.

SPEAKER_00 10:37

Yeah. And so what happened in the moment was this emerged, and both of them started essentially representing their side of the challenge. And it was very specific to them because it was a tension that they were dealing with specifically, but you could almost feel the rest of their tribe standing behind them, supporting them. So in in that moment, because it would it felt like almost a one-on-one with spectators in a room of 15 or 16 people, yeah. Uh I had um I had asked in that moment, um, would everybody be okay if we experimented with something for just a few minutes? So I kind of I I intervened because it was getting getting a little focused and exclusive. So I felt in the moment like, okay, if this is feeling exclusive, how about we just make it exclusive? And then maybe we can learn, maybe we can learn from it being an exclusive conversation and we can all learn from it. So I I asked the two of them, and this is something that my co-coach and I had even talked about through debriefs. So, like, what if this happens? Like, what are we going to do? If it if it gets heated and there's tension, like what what should we do? So we hadn't necessarily rehearsed this, but it's something that had crossed our minds. So, like, what what if this happens? So I asked them if they'd like to experiment in the moment. And they said yes. I said, How about how about we just listen to the two of you work through this challenge and we'll sit back. We won't intervene, we won't ask questions. We just we want to we want to hear from you and and have you work out this challenge just one-on-one. And and maybe, maybe I'll step in from time to time to just ask some clarifying questions. If I'm noticing something that maybe um maybe feels stuck or maybe feels a little more tense or tight, would that be okay? And they said yes. And then what was interesting is the room is everyone at the table, for whatever reason, just moved their chairs away from the table. And they literally became an audience looking in on these two people working together. And we worked through a challenge for about 30 minutes, and they they worked through this tension, this specific challenge together, and they um uh there were definitely some moments where they um got a little tense, yeah, and and a little little more little more tight. And the challenge for me was to just like let let that happen, let tension happen, don't intervene when I when I felt that there was some tension because they could they could work through it together. I asked a few clarifying questions, but when we got to the end, it felt like they had fully worked through something that had been pent up for a long time. And we we debriefed in the moment in front of everyone. So it was just the three of us. It was the two of them, and then it was me, and then our again all the people from the teams. But it um maybe shifting to what it taught me is that being brave and being brave in the moment when you sense something is happening, to to one, let it happen, but then maybe try to shine a little more light on something that's happening that you're noticing as a coach. And and trying to be okay with that. Be okay with calling calling that out because even though it was this moment of emergence happened so late into the engagement, it was it was pivotal. I don't know what ripple effect that conversation had long past that moment, because we were only with them for another few weeks.

SPEAKER_02 14:39

Yes.

SPEAKER_00 14:41

But after that, on that day when we sat with it when we were debriefing, even wrapping up the the day together, you could you could sense almost like a like a sigh of relief.

SPEAKER_03 14:54

Yeah.

SPEAKER_00 14:55

Like everyone took a uh they let their breath out.

SPEAKER_03 14:57

Yeah.

SPEAKER_00 14:58

Like they'd kind of been holding their breath, and then they like something got unblocked.

SPEAKER_03 15:04

Had been blocked energetically, some tension in the system got released. Jason, I'm I'm I've got a uh curiosity there about in in the story. So uh there's 15, 16 people, the it became tribal between two people two people, you um got an experiment with those two people in the spotlight with an ex an invitation to work through this topic in front of them. And then after you had a debrief, did you at any point include the people who'd been observing in that in that experience? Because I could imagine for half an hour they're on the outside or for more than half an hour.

SPEAKER_00 15:48

Yeah, we um we had asked at the at the end what what did anyone else notice as they were working through this together? And we had a few people chime in with uh they they definitely lent their leadership styles and got pretty they got very prescriptive as to what they felt the one person should have done versus the other person, who was right, who was wrong. So in the in that debrief, it it got a little got a little messy. I see people people were people were leaning in and kind of sharing uh like their hard opinions as to what they saw. But then there were some comments that were that felt a little more personally impactful.

SPEAKER_02 16:32

Yeah.

SPEAKER_00 16:33

They shared what did what they noticed or what what was happening for them, or thinking about a challenge that they need to work through with someone else. And maybe this was a little insightful to them, and just watching them take the time to work through this. Because things are happening, what one of the things that was happening with this team that happens to so many teams is they're working so quickly and they're pushed to work even faster. And many, many of their conversations are so transactional, and there's the conversation is mainly focused on speed. How quickly can we resolve this? And taking the time to do this was something that they had not done very often to just let it let 30 minutes go by and like what what could we do together? Um, but yeah, so to answer your question, there were there was a bit of debrief. There was probably more debrief when the when we had dispersed. And so like small hallway conversations after that.

SPEAKER_01 17:29

No, it's interesting that this happened like so relatively late in the in the six-month engagement that this had. It goes to show that uh sometimes the things that really need to be said need a very, very strong container for it to finally be okay to be said. And that uh and and the reason I say that is because you know, many teams that you work with, there'll be this underlying kind of desire to uh to get to one voice, one team, you know, or or something to that effect. And uh and uh especially in the kinds of teams that you describe, Jason, you know, that work really hard and that want to move towards resolution as quickly as possible. There's often a real a real pressure on both the team and whoever it is that's working with the team to get to that stage of one voice, one team. Um, and um which may lead to completely, you know, situations of of a very superficial or artificial kind of kind of harmony. And so um it really pays, I think, in a lot of these assignments to not rush towards one voice, one team, but to understand what makes reaching one voice, one team so difficult. And and when I hear you speak, it's it's it was really a whoa, you know, five and a half months down the line. No, but let's really now finally take the time to understand what makes reaching one voice one team so hard for us. And and uh and you get that sub that subgroup kind of dynamic. You n you called you called it the two mayors, you know, the two towns that stood face to face. And uh um and that that subgroup work um must have generated so much awareness, so much insight for the rest of the team. So what what what a wonderful example of working with that one level of the system.

SPEAKER_03 19:19

Yeah.

SPEAKER_01 19:20

The two mayors.

SPEAKER_03 19:21

Yeah. And and Jason, one of the things that strikes me in your story is um this wasn't on your on your agenda. It's not like you're saying, you know, at uh 2 p.m. we're gonna take two people and spotlight them and get them to work through an issue. You you grabbed a moment and made space for it because the energy was there. And this was what was this was the dynamic playing out in the room. And that's what we mean by moments of emergence is taking the opportunity. It's not it doesn't it's not always that the whole team program is is um without any structure. Uh I mean it might be, but there's so much magic if you if you look at the dynamic and you track what's there, there's so much magic in in the dynamics that are happening. Um and and oftentimes the pre-planned agenda means we we we ignore that. You could have ignored the tribes, the two mayors, and so okay, we've run out of time for that now. Now now let's get on to the next pre-planned activity. Yeah.

SPEAKER_00 20:33

Yeah, so so true. We actually um disregarded, we skipped past the rest of the agenda for the afternoon.

SPEAKER_01 20:43

Yeah, it's it's it it's such a danger, right, Georgina? Like you're saying, in those, in those, in those agendas, and and in a lot of that discovery work that we like to do up front or that the team likes us to do up front. Because when we do that, we we think we understand the team, as if the team were, you know, like at a conceptual level, when we talk about the team, somehow we've we've frozen it, we've turned it into an entity that is, oh, I understand the team now. But the dynamics that you describe too, Georgina, mean that the team is um is very fluid. And so when we come up with, like everything in life is fluid, right? But but when we when we come up with these agendas, or when we do too too much, maybe pre-work, we attempt to freeze, to freeze, freeze-frame the fluid. And we miss out on what's really happening in the moment. So yeah, well done, Jason, and and and co-coach.

SPEAKER_03 21:49

Co-coach, coach. I mean, that's a that's a very complex environment with you in the room and um with your co-coach joining virtually. when you couldn't read the somatics when you've your co-coach. Um could you speak a little bit about that? About how that played out in that moment? How did you contract for what you're what direction you're gonna take or signal to each other? Do you remember?

SPEAKER_00 22:17

Well uh maybe I blacked out in the moment. I I don't I don't remember the specifics but I I do remember my co-coach she was on Teams and she starts direct messaging me immediately and I I only caught glimpses of it um but she was she was being very encouraging yeah so when I did glance at the chat it was like okay she's with me like we're in on this together so I I I feel like I can just go because she's she's ready to she's been watching this entire time yeah and listening so she will she will help I mean we were together she will help if if we get we get stuck so I felt fully supported by her in the moment because it felt it felt a little scary yeah it felt a little scary um there were some very strong personalities in the room uh there was also in the moment I remember thinking like this might not go well and one of these strong personalities might feel intimidated they might feel like this is off the rails and not the direction that they want to take this and they might grab the reins from me as and just kind of intervene on our intervention. Yes so I was a I was a bit nervous about that too because there were there were some some strong voices in the room that had had opinions about the way things should and shouldn't be done.

SPEAKER_01 23:55

I like I like no I I like I can so identify with this notion of this might not go well. Yeah I think we've all we've all been there yeah and we'll continue and we'll continue to go there and and I think that's a real sign of our our our growth no as interveners that this might not go well but let's try it anyway because even if if it doesn't go well whatever well means if even if it doesn't go well then there'll be something to be learned from it and is there anything that you remember Jason about how you managed your inner state to support you in going for the moment what did I do to support my inner state I tried to remain calm.

SPEAKER_00 24:45

Yeah I recognized that my energy was probably through the roof. Okay um I was I was charged um ready to go so in in moments like that just with the the practice of of team coaching and and working on yourself I had I had been practicing a bit to just when when I felt an energy spike like ooh here it is let's jump in and and and do what we think needs to be done or do what I think needs to be done in the moment or to to raise the awareness of the team in the moment my energy went up so that was a signal to me to like time to get really calm put your feet on the ground you know make sure my I I think we were all at that point we we almost it almost felt like we were in a in a circle in chairs. So we weren't there was no table separating us it was literally the three of us almost in like a small circle so we were in pretty close proximity to each other and I I remember trying to get calm and it doesn't mean that there weren't like nerves and like lingering like a lingering sense of like you know anxiety yeah about it but I just tried to remain calm and and let it go and stay in the moment maybe I said to myself like stay here be here because I I tend to say that in my head at times when things are tense stay here be here.

SPEAKER_01 26:21

Stay here be here no I'm still sitting a little bit with and then I'll that'll be my last kind of thing I want to throw in here but I'm I'm still struck by the fact that it took five and a half months you know out of six months to for this to service. And and things happen when they have to happen right I'm absolutely convinced about that and you we knew from the beginning you knew from the beginning that that this was this was an old guard new guard kind of setup right and I and then part of me is always wondering well is there something that we could have done you know to make to make that this particular kind of epiphany uh to make it happen earlier on uh and I I really don't have the answer to that but if you were if you were if you were to work it with a similar team again or a similar similar kind of setup would something you would do differently or oh my gosh I don't think we have enough time to talk about all of that. We're gonna invite you back.

SPEAKER_00 27:22

Oh you're so right I mean just my my co-coach and I had talked so often can I just say for a second having a co-coach is such a beautiful thing. Oh yeah and I am so I'm so happy that the two of you introduced that to her and I yeah because that was so useful to be able to debrief and talk through what we were both experiencing and being able to listen in different modes and things like that. That was just by the way if if she listens to this we say we we we send you know big warm hug to her yeah yes I I'm sending a big warm hug to her too she's probably warm because she lives in a warm place and I'm cold it's cold here. But anyway yeah big hug to her um it was so nice to be able to debrief but when we were we debriefed often and to your point Al there was there were so many moments where we where we looked at each other and we're debriefing afterwards and just saying like this is so hard this is so hard and they are being so resistant to everything to each other to us to the world like they no one wants to change at all and the leader is not making it any easier the top leader was making it much more difficult. So maybe if I just add one thing that we would do differently is we would have a very intentional and slow one-on-one with the leader before we started this work and maybe it was a bit too rushed and really front load what this work could be like not to say that it will be like this but this is what it could be like and this is what we really really need from you for what could be possible because I I I think an intentional conversation with this leader might might have changed things a a bit but then again maybe it wouldn't have I we just we just don't know.

SPEAKER_03 29:34

But if if we were to go back and do it again we would we would have like a very intentional close conversation with this team leader just yeah almost one-on-one I'm a big fan of um conversations with and also coaching team leader alongside the team coaching I do and I often find myself saying you know what this work's going to need of you leader is to be the change that's needed in the team you're you ultimately have more power and influence than anyone else in the room and when you be the change it creates the conditions for others to change um and and that they might nod to that but it takes time to work that through in coaching um because they've they've got perhaps some fears or resistance to change um that is deeply embedded in in what it means to be a leader deeply bedded in the past we don't we never know what those barriers might be so there's there's often some human developmental work for leaders to do to be able to let go of the positions that they've adopted to make more space for something possible. So I'm with you on that I think that's a great insight yeah you you're bringing up some things that we had heard from this leader often which was my title precedes me and they would say that out loud and they would say that in front of the team my title precedes me I walk into the room my title precedes me and the that work of the leader being so important for for them to be willing to do the work not only within the team but on themselves because as as you mentioned we we all carry a bag with us and the bag is full of stuff and we don't we don't know what's in each other's bags unless we get really curious and and and get interested in knowing what someone else might be carrying and being a team leader is hard it's high pressure and exposed you know people feel oftentimes quite exposed feel the pressure of all that's not that's not quite right and not quite working often gets pushed up to the team leader. Uh I often feel that team leaders you know benefit from more support to process it all. Yeah so it sounds like you did a great job there with lots of learning for the team and lots of learning for you and your co-coach. And for anyone who's listening to this absolutely thank you so much for sharing your story Jason is there anything you'd like to say in closing off a final reflection today?

SPEAKER_00 32:34

Yeah the thing the thing that comes to mind and maybe just reshare resharing this story because I don't think I've I've talked about this story is that being in the middle of of this team coaching work that we do being okay with something happening or something not happening is really important because in that in that mode of being team coach sometimes you want something to happen so badly and sometimes it takes so long for something to emerge and being being patient and just trusting that when the time is right it will more than likely happen and then be brave enough to go for it.

SPEAKER_03 33:18

I noticed Jason you used the word being three times there and I want to put highlight a pen over it that's the being a team coach isn't it it's being energetically available for whatever's wanting to emerge rather than our own drive for pace or performance or results or impatience. That's a really sounds easier than it is it's an ongoing practice the being of a team coach and um and that's being with what's often uncomfortable until it's ready to change.

SPEAKER_01 33:54

Thank you so much for your time and bringing that and sharing it with everyone Jason I'm sure um listeners will greatly appreciate yeah thanks thanks for having me thanks for letting me share this man thanks for thank you for for agreeing to be here and and sharing sharing your insights the way you did it's great to reconnect with you Jason.

SPEAKER_03 34:17

Looking forward to the next time yeah absolutely looking forward to seeing you again soon bye for now thanks for joining today's journey of Teams Transformed if this sparked a new insight or a deeper question we invite you to sit with it not to solve it but to let it unfold for resources community and reflection prompts visit teamcoachingstudio.com Until the next time stay present stay curious and keep leaning into the art of emergence