Leading with Heart and Edge: Coaching in a Complex World

Rachel Cossar: Everyone and welcome to another episode of conversations in the future of work. I am your host, Rachel Kosser, and I am really excited to get into some pretty alternative coaching, mechanisms today with our guest, Mike Sweeney. Mike, welcome. Hi. Great to be here.

Mike R. Sweeney: So nice to see you and so nice to have you.

Rachel Cossar: Would love if you could share just a a few tidbits about your background and what it is that you’re working on today. Sure.

Mike R. Sweeney: Usually, I’ll I’ll tell people that I’m a military officer turned girl dad, and everything in between. Most of my work today focuses on working with high performing executives, intact duos, like cofounder duos and high performing teams. And I enjoy playing in the space between things. So when two things might be true at the same time in a polarized world, that tends to be where I spend a lot of my time. Awesome. Let’s get into it.

Rachel Cossar: So, you know, I was thinking about where we could take this conversation today. You have such an interesting, background and, obviously, evolution into the work you’re doing today. But I’d be curious to hear if you could summarize your current approach to coaching and really getting to some of those deeper topics with your clients. Sure.

Mike R. Sweeney: My my main focus usually is on building a sense of agency, courage, and freedom with clients or helping them bring that out, playing in the space between opposites and helping people move toward fulfillment, which is, I’d say, the next level beyond simply success. And, I did mention kinda work one on one, work with intact duos and teams. And I find that we’re facing more paradoxical situations. So I’m often working with clients on balancing work and life. Not moving like a wrecking ball with more work and then more life, but finding a way to balance artfully, accountability and empathy, especially with teams, focus and flexibility, especially with start up teams, with organizations that have very smart people, you know, decision speed and decision quality. My approach, I’d say, is usually, you know, not everybody has a saber hanging behind them. So I’d say I’m pretty direct. Like, I like to cut through and say charge every now and then. Typically high accountability. And I also love to play in the space in between coaching sessions. So a lot of coaches just send they do their hour. Two weeks later, they do their other hour. I like the heartbeat in between. And I’m very focused on helping clients build capability and not dependency. So I like at the end of our six month time, they now have new capabilities. They might hire me in the future for something else, but they have now elevated their skill sets. So that’s a bit of, how I, approach coaching.

Rachel Cossar: So you mentioned, I I just feel like this, like, work life balance one is one that a lot of people struggle with. So, like, how do you can you give us more of a concrete example of how you might help someone dynamically meet that balance? Sure.

Mike R. Sweeney: So, this gets into often values and boundary work. It’s like, what are people’s values and in what order? And sometimes achievement is very high on the list Mhmm. At the expense of other things. I lean on some of the work from, positive psychology. And one of the frameworks in the book flourish is PERMA, you know, positive emotions, engagement, relationships, meaning, and achievement. And if somebody is pegged on the a at the expense of the other things, like not a lot of friends, not a lot of time for home, not doing work that matters to them. Sometimes it’s a matter of reorienting the values and reordering things. Mhmm. There’s also especially with high performers, I find a lot of, insecure overachievers, And I wouldn’t necessarily call someone that, but people who feel like I’m not quite enough. And the answer to is what is enough is a little bit more, always. So we talk a lot about boundaries. And usually, the first thing I’ll say to someone is, the most important part about boundaries is believing that you deserve them. Mhmm. I kinda let it sit there. And then I I love a quote I read once. It says, the the only people who are bothered when you set boundaries are those who benefit when you don’t have any. Yeah. So sometimes work and life, it’s about, not the wrecking ball, but a tight rope walker. Like, what does balance mean for you? What do you really want? So balance for me means being able to pick up my daughter on Wednesday at 02:30 from school. Mhmm. So come hell or high water, that’s what I wanna make sure I do. Balance for me means being able to travel for client work and then mix in some fun stuff on the side, either adventure, hiking, or going to plays. So that’s what balance means to me. And balance is a verb, so it’s like a constant tweak. So, really, it’s figuring out what are the values, in what order, what are the boundaries, and then, how do we make commitments to ourselves and others that allow us to hold to those boundaries. And I find a lot of people say yes to a lot of things that they kinda wanna do. And for me, there’s hell yes, and then there’s everything else. Right. And that doesn’t mean that there aren’t times that we have to negotiate boundaries, especially in relationships. But very often the the trick is values are unclear, making decisions that are not aligned with them, and then not having, not deserving, or not holding to boundaries. Yeah.

Rachel Cossar: I feel like that framework can be applied to so many different kind of tricky situations. Right? Like negotiating on behalf of yourself. Right? It’s the same thing knowing what those boundaries are. And if it falls below that, you’re like, okay. So no deal. Right? Doesn’t that’s I think that’s a powerful framework and certainly being able to stand by your values and boundaries is a math, like, massive life skill. It is, and it’s not something that comes easy.

Mike R. Sweeney: And, also, there’s especially people who are, who perform very well tend to honor their commitments to other people, sometimes at the expense of themselves. And it’s very much sometimes you literally have to put on the oxygen mask to have the capacity to support others. And, that’s one of the things that I encourage people to to do, you know, have, rituals or practices that help you ground. Yeah. Anticipate what your capacity might be in advance. Identify and have triggers to know when things feel out of balance. And I like to do things that, get people out of the neck up thinking. So sometimes using artistic expression, like drawing what balance might look like for you. I had a a great example of working with a client and she traveled a lot, and she, used to dance. And so she drew a picture of herself, like, on point on top of a car with, you know, work on one side and life on the other. And through the the description of that diagram and what we noticed in the diagram, we kind of had some fun and some playfulness with it. It’s like, when will you know you’re leaning left? When will you know you’re leaning right? And sometimes bringing that subconscious and, like, the body work up through an artistic expression can, add a little bit more color to the situation rather than I feel out of balance when I think this. So trying to get out of the robotic. Right.

Rachel Cossar: And do you feel like it’s an it’s, I feel like the ideal is when you have sustainability in maintaining that balance or, you have, like, daily practice, like, daily practices of whatever whether it’s your prep work or your meditation or your yoga or your walk or your, like, picking up your daughter, whatever. Like, if you have those things, you can maintain balance a little more sustainably. Obviously, nothing’s ever perfect, but that’s something that I feel like, sometimes in our culture, there’s, you know, okay. I let me just, like, grind, and then I’ll have, like, a weekend or, a few extra days off. Right? And it’s like that, to me, always feels a little, like you’re missing the ideal kind of ability to meet what you want to meet from a family personal perspective and also a professional perspective ongoing, right, sustainably. That’s a great point.

Mike R. Sweeney: I think what my my approach to sustainability kinda comes from a few different sources. One is I was a tank officer when I first got into college in the army. And so we always had a routine of PMCS, preventative maintenance checks and services. So before you went to the field, to maintain your operational readiness of your vehicle and maintain your combat power, you did things in the field to maintain that vehicle. And even when you were out in the field, you had to do some things to maintain that vehicle every day. I remember when I worked in manufacturing, you couldn’t just run a labeler on a bottling line all the time. You had to take it down for preventative maintenance. And, when I think about my life as a runner, I have to balance the paradox of activity and rest. Yeah. And if I over index on activity, I get hurt. If I over over index on rest, I don’t perform to the right amount. So I don’t know what the sustainable balance is, but sometimes it’s, like, maybe maybe an eighty twenty, you know, self care versus performance. But I think having those practices and also identifying, what they call keystone habits. Like, for me, if I’m reading, if I’m running, and I’m meditating, everything else is probably gonna be okay. I still have my, you know, daily rituals, but, like, I have some of those key, those keystone habits that make everything else work. And I know if any of those three are off, sleep is a really important one too. Yeah. Like, identifying those key that lead to everything else, those are the early warning systems you can put in place. Like, if one of those three are off, something’s gonna go wrong, and I have to make adjustments. But I think sustainability and being able to perform at a high level level over a long period of time is the goal. And, like, grinding yourself to burnout, I I don’t know. Like, usually, you lose if you if you miss out on multiple days of work or you can’t go to commitments or you end up sick. So what do you think about this new what is it?

Rachel Cossar: 996? Oh, what? Tell me more. Okay.

Mike R. Sweeney: So I don’t know enough about it.

Rachel Cossar: I was hoping maybe you would know. Like, is there, like, a West Coast, like, kinda grindy, yeah, origin? I think everyone figures out what works for them.

Mike R. Sweeney: So, I know back in maybe ten years ago, so people talked a lot about, like, Pomodoro technique. Uh-huh. Like, you do twenty five minutes of work on, five minutes of rest. Mhmm. I’m I found that, I’m more of, like, a fifty two eight kinda guy. Like, I’ll do almost like a school period of fifty two minutes, and then I’ll break and take eight.

Rachel Cossar: But I had to find my own tweak.

Mike R. Sweeney: So what whatever, like, all those little secret things are, you know, often people talk about, like, what’s the best time management, or, you know, daily task management system?

Rachel Cossar: What’s the one that works for you? And you have to experiment a lot to find it.

Mike R. Sweeney: So whatever is coming out of the West Coast, if you’re talking about six working six days, I always thought that the that the goal was I will provide a client or an organization Yeah. My talent, my skills, and I will help them get results. And if I can do that in the smallest amount of time possible, Mike Incorporated wins. Yeah. Yeah. And I still wanna deliver the value, but I don’t necessarily want to make time or how much time I put into things the goal. I would rather, have more time for family, for fun, and find a way to balance. And that doesn’t mean that I don’t have weeks that I have that I grind. I just don’t do them week in, week out, and I hope that clients don’t do that longer. But, so what do I think of that? It’s probably another different style that might work for some people that were will require personalization and tweaks to figure out if it’s healthy for the individual or the child. Right.

Rachel Cossar: So I pulled up nine nights. That’s awesome. So it actually like, I think it references, a work work ethic or work structure from China, and it’s actually 9AM to 9PM, six days a week. I mean, if that if you if okay.

Mike R. Sweeney: So if you feel like that’s balanced for you and you have this, like, massive goal that you’re after and it’s, it it feels like you stress, not distress, and it feels like flow, and you’re building something great, and you feel like you’re still getting sleep, and you’re eating well, and you get a chance for exercise, and and it’s the time in your life when you want to make a difference, then by all means, do it. I I don’t know if that’s how our bodies and our, society was built. Yeah. And that in in some ways, that feels very, you know, work centric. Yeah. Yeah.

Rachel Cossar: I’d rather have more time for, like, walks with my dog personally, but, to be on my own. Right? Yeah. I guess Gen z is redefining it because I think it it usually is, rep built, aligns with, like, corporate slavery, which, obviously, it’s not good. Do you wanna work those hours, Rachel? No.

Mike R. Sweeney: I’m like, no. This sounds awful.

Rachel Cossar: But I think that there’s something anyways, maybe we can, like, footnote it and and circle back in the comments. But, I think some people are trying to redefine it. But I I think it also is actually, like, an intensity that’s connected to winning the AI race in The US. You know? So people are, to your point, like, it’s like the the the moment. Right? The defining moment. So I don’t know. But, anyways, I guess we’ll follow-up on that one later. But crazy interesting stuff. I wanna you had mentioned a a number of really interesting analogies you brought over from your past. What other either I know you’ve already mentioned a couple. So if there are others that really, you know, inform your current present day perspective, would love to hear those and or, how you think about bringing experiences from your past to the present in general.

Mike R. Sweeney: I I would describe myself as a as a pretty good architect, but a very poor resident. So I think sometimes we have to figure out where we work in organizations, the type of organizations we work well with, and when we are at our best. So I’m good in the in the in the build days, and I’ve discovered that over time figuring out what my peak moments were in work. Mhmm. I’ve also spent a lot of time in learning and development, and I’ve noticed that, you can’t just build a skill in a four hour session or an eight hour session. It requires performance support, things that will help you on the job. It requires reinforcement, and it requires practice. And I think practice is something that we don’t do enough of. So I have a a client who was working on, pitching this new program, for the first time. And, my advice to him was to do some repetitions. He ended up doing them to his teddy bear. And he recorded a couple of them, so we called them teddy reps. Yeah. And he would just do them, and they got better and better. When I was preparing for, a TEDx recently, I did 50 reps in a week just to make sure that I was ready. I would also, say that my experience in the army was a was a really big influence. Specifically, I was 24 years old, a brand new second lieutenant, and my partner was a 48 year old platoon sergeant who had been around the block. So he’s twice my age. He has all this experience, and yet every morning he says, good morning, sir. It was so strange and unnerving. So I had the book knowledge, maybe the strategy, but he had the the the, you know, will and the mood of the people, the experience, the the repetitions. And so together, I felt like that was a very powerful combination. And it doesn’t really exist in corporate. When I left the army and went to corporate, I was like, wait. I gotta lead on my own? Yeah.

Rachel Cossar: I don’t have my platoon sergeant with me, so it would stretch for me.

Mike R. Sweeney: That’s one of the reasons I like to work with cofounders is because I think that that that balance, that complimentary pair, the dynamic duo can be really fun. And I did not learn to lead on my own. It took me a while to figure out that it’s okay that I’m not well rounded. I have three or four signature strengths. I’m gonna lean into those and then find other partners to help me do the other things, but not try to be this perfectly well rounded pair. I think being a father of girls definitely was an eye opener for me. I started my career at an all male unit, and I moved into, being a girl dad. And, you know, I don’t wanna paint with broad brushstrokes, but they had some empathetic skills out of the box that I had to learn when I was 40. Right. And, having the experience of of being a girl dad, you know, going to their dance recitals, walking, holding hands with a little girl, having conversations with them, I think that softened an edge a little bit and gave me the ability to both, you know, come with presence and power and directness and then also, you know, empathy and, genuine connection. And, I think everybody probably has different types of energies in them, and they gave me, a more well rounded approach to being a human that I think maybe I didn’t have when I was very achievement focused and and direction focused early on. So there were a few. Yeah.

Rachel Cossar: That’s, I mean, that’s wonderful what like, it’s incredible how you can be stretched in so many surprising ways, right, as you kind of evolve through your life and with children and, you know, the the the great educators. I mean, I can tell you one one moment.

Mike R. Sweeney: Middle daughter, she was crying, and I was mad at her. And I and I said something like, you still haven’t cleaned your room. And she said, but, daddy but, daddy, I’m highing because she didn’t say crying at the time. And and it was almost like disbelief. Like, how can you be angry when I need to be consoled? Like, you don’t understand how this works. Right. Right. And, that gave me the ability to to really stop, pause, see the mood, the attention, and and focus less on what message I’m delivering and, like, kinda what’s the temperature in the room.

Rachel Cossar: But, like, that’s something I always felt like, oh, maybe I could’ve learned that earlier. Right.

Mike R. Sweeney: It was a powerful message to receive from someone who’s just trying to explain, like, I’m in a mood that needs to be consoled before you deliver that message. So, like, come here and give me a hug. Yeah. And that’s a very natural thing that that maybe I was missing. But then, you know, when you look your your little kid in the eye and they’re, you know, four or five or so Yeah. That tends to soften you a bit. Right. Right.

Rachel Cossar: That’s, I always think it’s powerful, the different experiences we have in completely different sectors or parts of our lives, whether they’re just, you know, happening over here at the same time or from our past, you know, in a completely different world, so to speak. And, you know, I have a my in my TED Talk, it’s like, your current self is built on the shoulders of past identities and past experiences you have, which I’ve always liked that idea. Because I remember when I left the ballet world, I just assumed that nothing I’d learned would be relevant. Right? And, obviously, that has not been the case. But, it can be easy sometimes, I think, to turn your back on past selves because it might feel not relevant, or maybe it’s something you don’t even want to remember. But it’s all such an important part of, like, where you go next that, being able to flexibly bring aspects of different experiences forward is really powerful too. I think that’s the unique stuff. Yeah.

Mike R. Sweeney: Like, when you have the same ingredients, you’re gonna make the same thing that tastes pretty much the same, but those are the spices that make us unique. Yeah. And sometimes those are the distinguishing strengths. Like, if someone says, oh, how did you learn to do that? Like, oh, I learned my approach to sustainable, you know, sustainable work and work life balance from maintenance on a tank. Not everybody has that. Right?

Rachel Cossar: And it makes sense for me, but I think the same thing for you.

Mike R. Sweeney: If you have the the discipline, certainly had to have, you know, stretching and taking care of your body, you know, the ability to to read music. There’s probably lots of applications for that uniqueness. Mhmm. And a lot of the times that I’m working with individual coaching clients, it’s figuring out, you know, who were you? You know, what was the journey to now? Who are you now, and then who are you becoming? And there’s maybe some direction, some choices that you have on that. But those baseline foundational experiences are what make people unique, and I like sometimes the best conversations for me are people who are coming from areas that maybe aren’t a specific ladder. You just followed a certain Oregon Trail track to land in this job. I like people with a little bit of spice. Yeah. Totally.

Rachel Cossar: Speaking of spice, so you really like working with founders, and and and and with founder relationships. I feel like that’s you know, those can be pretty spicy sometimes. But, what, yeah, what is your pull towards that cofounder relationship and coaching people within that? Usually, they’re doing something great.

Mike R. Sweeney: They have a vision or a mission or they’re trying to solve some sort of challenge, and they’re in the building stages. So that fits with my idea of being an architect versus a resident. So if a a company’s been there, they’re doing the same thing, probably not the right place for me. Mhmm. And it’s sometimes it’s cofounder, sometimes it’s CEO, CEO combos, anytime you have a duo that needs to work really well. And and in usually, in situations where they’re, someone’s building a company, you’re dealing with things that came up in the founder’s dilemma. Right? You’re talking about the power of the relationship. You’re talking about roles and responsibility, clarity as things evolve, and rewards, how those get discussed and negotiated. And there are constant negotiation because the organization continues to change and evolve, and they’re seeking congruence and alignment between two people. And sometimes that requires, a balcony view. Some founders are able to do that, pull up to the balcony, see how the organization and their relationship is going. But sometimes when you’re in it, it’s really, really difficult. Both my parents were therapists. Not when I was born, but they grew into that role. I did have a relationship in my life that ended through divorce, but I went to multiple marriage counselors. And I remember learning some of the skills of of fair fighting and some of the skills of setting those healthy boundaries that, I was learning but maybe not applying in the first go round. And there’s a ton of research from the Gottman Institute on marital relationships that can be cross applied to founder relationships. So I think I feel compelled to try to help people, do it better. And I think there’s a little bit of, you know, sadness and guilt at not being able to do it right the first time. That’s why I went back and got my degree in organizational psychology. That’s why I like to help create dynamic duos. And, also, I read somewhere that, a duo is the smallest atomic unit of a team. And, usually, if there’s conflict within the team, it’s showing up in the duos. So if we have powerful duos, we have powerful teams. So I think at the individual level bringing out your best, duos bringing out each other’s best, and then that can create a great team environment. And most people experience their work life through a team. So if it’s a really positive environment, we can impact, the quality of someone’s life, of the entire team’s life, and how effective that duo or that team is at accomplishing their big mission. So I I just find it’s really, really rewarding. Yeah. And I think maybe it’s, a little bit of lament at not being able to do it right the first time. Yeah. Absolutely.

Rachel Cossar: The I I wonder, is there something you see, like because I’m assuming you also have cofounder partners who just at the like, end up splitting up. Right? Like, it’s just there’s not there’s something missing there. Do you ever see something, like, that you’re like, oh, if I see this with founders, I’m like, I am concerned about them being able to, like, move through it. Yeah.

Mike R. Sweeney: Probably, I’d go to, like, the the the kind of four horsemen of marital relationships. So Yeah. Good thing to Google on Gottman. But one of the things I, I I guess two things I’d look for is, subterranean conflict. Mhmm. It’s not safe to share the real thing Right. To the other person. And the opposite of that, or or I guess maybe a positive sign is, when they’re telling a story of a success in the organization, like, they almost are interrupting each other with, like, pride, one upsmanship. You You know? Like, oh, yeah. But then you, like, told the guy that. And, like, you remember when and I think you have to find that in marital relationships also when it’s, like, a funny story or a celebratory for you. There’s almost, like, a a battle for the good. Yeah.

Rachel Cossar: And then and then you told them, like, you’re not we’re not taking that for blah blah blah. And they and they almost, like, correct each other Yeah.

Mike R. Sweeney: In a strength based way. Mhmm. So, subterranean conflict, I’d say, is a is a big warning system. Like, if I find sometimes I’ll do two on ones then one on ones. And if the one on ones are not about the future, they’re just complaining about the other person, then another. Then I find myself kinda monkey in the middle a little bit Yep. Where there’s a lot of complaints, criticism that have not been shared because it’s not safe to or, you know, something bad that happened or one person is volatile, that subterranean conflict, where it’s almost like, corporate nice or perform performatively nice. Right. Usually a a pretty bad sign that people have moved away. Those can be addressed. Yeah. That that that is definitely something that is a a danger sign. Yeah. Wow. Fascinating.

Rachel Cossar: I just feel like the cofounder relationship is such a fascinating one. And it is, like, very much runs in parallel to any kind of intimate relationship. Right? Especially when you’re working on something so new and risky. So, fascinating stuff. What, like, what are your top like, looking ahead, Roy, in such a kind of disrupted dynamic space. So what are your predictions for the next six months? Well Or longer or shorter?

Mike R. Sweeney: I I think, we will continue to have paradoxical situations pop up that require more than an outrageous response. Right? So I have all these situations where people are frustrated because, we should focus. We should have clear strategy. Like, we need to be adaptable and flexible to the market. Like, both things need to be true. Yeah. As a, relatively pacifist liberal democrat who grew up in New England who also served in the military, I have a lot of conversations in the middle Yeah. About a lot of different things. And in The US, like, we just don’t seem to have the, the endurance to engage in the difficult conversations that we need, as a country, as a company, as, you know, individual relationships. So I think being able to get past outrage. So So I guess the prediction is, like, we will continue to have pretty significant conflict Yeah. And this wrecking ball left, right, left, right. So we have to be prepared to find ways to get over this or that thinking and move into the middle. I think and I think with that, staying curious for longer. Mhmm. Humor is built on incongruity when things don’t make sense and it’s ambiguous, and we kinda don’t understand that it’s a little dangerous. So using humor and play, can be really powerful and allowing that to happen and not getting kind of too serious. Mhmm. I think the other prediction I have is that we will find out as much as we’ve kinda moved back from diversity. That’s what makes teams and organizations perform better. So I think that we’re gonna come back to a place where speaking about DE and I, speaking about diversity is okay again, even though it kinda doesn’t feel like it. We’ve kinda, like, swept some of those programs under the rug. We’re gonna realize that, those are very important, and the things that we started learning kinda post George Floyd are still important to keep learning Yeah. Especially as kind of the most privileged class. So I feel like that’s gonna make its way back. And and, as people are approaching the world of, augmenting their work with AI, we’re going to realize that there’s always someone getting on the highway at Exit 1. Mhmm. So as much as we figure it out and how are we using ChatGPT and have our own agents, we still have people who have never been fried. And so there’s going to be, a societal conversation that needs to happen about how we use these things, what they mean, what the risks are, but there’s still people who have never tried it before. Yeah. We’re recognizing that, we’re gonna have a lot of people really smart, really fast that have the curse of knowledge that need to be able to bring everybody else along because this could cause a significant societal shift in how much work there is available to people. Mhmm. Will it happen in a year? No. Will it happen faster than we think? Probably. So those are a few, but I I I think the primary prediction is we’re gonna continue to be polarized until we can find a way, to get past outrage and engage in, difficult, healthy conflict conversations. Yeah. Well said. I mean, that’s why that’s why my TEDx was called, you know, how to find common ground when there is none. Yeah. And I I found some really good research on paradox theory and polarity management that helped me, figure out. Because sometimes I can dig my heels in, and I’m very convinced that I’m right about something, but just my point of view. Yeah. Yeah. Yeah. Totally.

Rachel Cossar: Thank you for sharing that. Usually, I have a thank you slide, but I’m seeing now that it’s not there. So, Mike, it’s been such a pleasure to have this conversation with you and get to share it with our audience. Is there anything else you’d like to share before we sign off? No. Just my pleasure.

Mike R. Sweeney: I think I think the the one thing that you said about, sustainability, finding what makes your life sustainable, is a wish and a hope that I have for everyone. Yeah. Amen.

Rachel Cossar: Where can people connect with you, follow your work?

Mike R. Sweeney: LinkedIn is a great place, and then, sabrecoaching.com is my website. So if you wanna find about, you know, coaching, work with duos, or work with teams, you can find me there. Awesome. Great. Well, thanks again, Mike.

Rachel Cossar: And, thanks everyone for joining. We’ll see you next time.