Michael Hunter: This is the Uncommon Leadership Roundtable where we bring smart people together to discuss interesting topics and maybe have a little fun along the way. I’m your host, Michael Hunter with Uncommon Teams, and joining me today are, in no particular order:

Kevin Wilkins. Raise your hand, Kevin, so we all know who you are.

Kevin is founder, CEO of Trepwise, a strategy consulting firm whose mission is to unlock the potential of purpose-driven organizations by aligning people, process and vision. Trepwise has been named one of the best places to work by City Business for the last seven years. Pretty impressive. He went to Dartmouth College, Harvard Business School, has over 35 years of experience in nonprofit, corporate and private. So pretty much everywhere. And his company teaches putting people at the center of work.

Viveka von Rosen: Nice.

Michael Hunter: Kevin, quick, what’s a fun fact about you?

Kevin Wilkins: A fun fact about me. I have three boys and they’re now 28, 24, and 22. When each one of them left to go to college, I replaced them with a girl dog. So now I have three girl dogs that live with us and I’m very fond of them and they’re very fond of me.

Michael Hunter: That’s great.

Viveka von Rosen: And those bitches are easier to take care of.

Kevin Wilkins: I’m telling you. I’m telling you, they actually do what they’re told. It’s crazy, crazy, I say. And my boys actually liked them once they got over the shock of it all.

Viveka von Rosen: Well, that’s good. I love that.

Michael Hunter: And next is Viveka von Rosen, who is a—raise your hand Viveka, so we know who you are. Viveka von Rosen is a celebrated LinkedIn expert with over 19 years of experience in LinkedIn marketing and sales. She empowers successful executives and entrepreneurs with their brand and business pivots.

Her core message of “Women’s words will change the world” succinctly summarizes her mission of helping her clients bring their legacy dreams to life. Fun fact about you, Viveka.

Viveka von Rosen: Well, I learned how to hang glide when I was 15 years old I still kind of do it. I’m actually gonna take up paragliding because I’m old and they’re much lighter. But the really cool fun fact is that my dad is the one who got me into hang gliding when he was 55 years old. And an even funner fact is that he is still in the Guinness Book of World Records as the oldest hang glider pilot. So he was flying until he was 92. So I have years and years ahead of me.

Kevin Wilkins: That’s awesome.

Michael Hunter: Is 92 when he passed or did he stop for some other reasons?

Viveka von Rosen: No, 92 when he stopped because he needed to, he was 92, because he was 92. He was 96 when he passed.

Kevin Wilkins: Good gene pool.

Viveka von Rosen: Good gene pool.

Michael Hunter: And then we have Muness. Muness Castle is a data and engineering leader with over 20 years of experience. He specializes in data engineering, strategy management, organizational design, and architecture.

Viveka von Rosen: Wow.

Michael Hunter: Muness has led or consulted with teams at Shopify, Zapier, JPMC, LivingSocial, Staples, and way too much more to list them all here.

Fun fact about you, Muness?

Muness Castle: I forgot to prepare a fun fact, but Kevin’s fact leads me to one about my  journey with dogs. So I finally got my first pet ever,

Kevin Wilkins: Nice.

Muness Castle: Alvin, he’s, wandered off. I’m in my forties and now I feel like I, that last step towards becoming an American, now I’m a dog owner.

Viveka von Rosen: I thought you were gonna say an adult.

Muness Castle: An adult. Well, no, I’m hoping that one never comes.

Kevin Wilkins: That’s great. I love the name.

Muness Castle: Yeah. Yeah. He’s a sweetheart.

Michael Hunter: And I am Michael Hunter with Uncommon Teams. I’ve spent 35 years helping leaders across six continents greet change like an old friend, and create and inhabit their legacy, leveling up themselves and their teams in a way that is safe for them and for everyone else. You could say that I started out my career debugging code, and then I switched to debugging people. I realized that was inflicting help, and now I help people debug themselves.

Viveka von Rosen: Nice.

Michael Hunter: And a fun fact about me is I have been a reader for as long as I can remember, including reading the entire library the summer of my third grade year, which got me a special award from my librarian, which was a great way to be introduced to my brand new school in third grade, the first day, for the librarian showing up, giving me an award for being a total geek.

Viveka von Rosen: I love that.

Michael Hunter: So we’re here today to talk about learning from success, and this is meant to be a safe space. So let’s treat each other like humans, as I know we all will. And this is about connecting and learning, not pitching.

I have said so many times and have heard from other people so many times that we can only learn through failure. And I was thinking about this one day recently and I realized, well, that can’t be true because surely we can learn from everything. So how do we learn from success? Let’s start with Muness. We’ll each get up to three minutes— you don’t have to use the time—to say what you wanna say, you can ask questions, thoughts, whatever you’d like to say, and then we’ll go into some open discussion time.

Muness Castle: So just sort of like opening thoughts, Michael, for now?

Michael Hunter: Yeah.

Muness Castle: As I was thinking about learning from success, um, I think the biggest thing that came to me, the first is the idea of learning from the process and not just the outcome,

Viveka von Rosen: Yeah.

Kevin Wilkins: that’s good.

Muness Castle: The outcome is often out of our control.

There’s a lot of randomness in the world. There’s serendipity that sometimes makes up for our mistakes  and gives us successful outcomes even when we didn’t necessarily apply the right processes. So there’s a disconnect between the outcome and the processes we applied.

And one thing we can do is focus on what did I know at the time? Did I make the right choice given what I knew then, given what was going on then? Not necessarily on how it turned out. So that’s a lot of the ideas I had really focused around this and the disconnect between outcome and processes that we used.

Viveka von Rosen: I like that.

Muness Castle: That gives us an avenue for learning from both successes and failures. I’ll stop there.

Michael Hunter: Great. Thank you. Let’s do Kevin.

Kevin Wilkins: Yeah, I like the idea around the process. We often tell our clients that they’re gonna get as much out of the journey as they will in the ultimate destination. I think people are so often focused on the destination and they lose sight of the steps needed to get there. So if we can help train people how to think through making a plan, understanding how they can, what they can control, and what they can’t control. I agree that it’s hard to say that you can control the outcomes, but you can have specific goals and you can have specific strategies to try to get you to those goals. And how you develop that in a kind of human centered way is what we focus on.

Michael Hunter: Great. And Viveka.

Viveka von Rosen: You know what I think is interesting? I love this question because yes, I mean we always talk about what we learned from failure. What I learned from success is that it is so much more than an end goal and, to what, Muness and Kevin were saying, it really is about the process.

But not only that, I think when we achieve success, there can be a kind of a, “Oh, is that all there is?” And that’s a really good indication that maybe we weren’t doing enough. Iliterally my whole business Beyond the Dream Board is about that. I found a dream board during COVID when I was cleaning the garage as one does, and I pulled up this dream board and literally I have everything on it. I had done it, I had created it in the early 2000s and I literally had the car, an upgraded version of the little Mercedes convertible. I literally had a castle, married, speaking career, books, like all the things.

I was just not happy. So that, using success to measure are we doing enough and is there something beyond success and should we maybe be making bigger goals for ourselves? It’s a good measure against that.

Michael Hunter: When I started thinking about this, I sat down and said, “Okay, well, so how can we learn from success? Learning through the process, as we’ve all said, was one. Comparing when we’re getting the outcomes we hoped for versus when we’re not, what was the same, different, what might have been present that helped one thing happen versus the other was another.

But in the end, for me, I realized, it comes down to viewing everything as experiments. When we frame things as experiments, experiments don’t succeed or fail, you just execute and then provide data that then we can use to decide what to do next. And so if we take that frame, then it takes the idea of “This was successful or not” out of the picture, and it’s just, “Well, what happened? How surprised were we at that outcome and what does that lead us to want to do next?”

Viveka von Rosen: Yeah. I feel ya.

Michael Hunter: Now we’re in the open discussion time. Where do we want to go from here?

Kevin Wilkins: I like  what Viveka said around having achieved what she had dreamt, but not necessarily being happy about it. And I think that’s really interesting and really insightful and incredibly vulnerable. So thank you for sharing that.

I think that in my situation, I define success based on what society defines success. My career path after business school and financial services, I was in financial services for 20 years. And I often talk about the fact that how to succeed in financial services was pretty clear. They laid out a path for me and if I just continued on that path and did what I was supposed to do, I would get ahead. And the benefits would be title and money and power and prestige and whatever, whatever else society says is really good. And I was a workaholic on top of it. So that was a helpful driver in terms of me going down this path.

Viveka von Rosen: Yeah.

Kevin Wilkins: But it wasn’t necessarily my path. It was a path that was given to me, that I totally bought into, that I chose to be on.

But nevertheless, I didn’t define the path. I would go back to my business school reunions and people would say, “You’re still in financial services? Like, that’s so weird.” Once I got over the insult of it all, I understood what they were saying. I understood that they were like, “You’re more the creative. We thought you’re more the marketing. You being more technical seems a little bit different.”

I’m like, “Yeah, but I like it.” That wasn’t I love it, but I like it.

And then 20 years in, I was president of a financial services firm that we ended up selling to another firm. Suddenly the path went away. I had a contract, but then the path was just gone.

And I loved what Viveka said. You reflect. I’m like, “Okay, I guess I’ve achieved what I’m supposed to question mark. Why aren’t I more happy about this?” And it wasn’t till I started to really examine my life and what drives me and getting my self-worth from within versus my self-worth from external

Viveka von Rosen: Exactly.

Kevin Wilkins: factors that things became a little bit better for me personally in terms of just life satisfaction.

The work that we do today and the work that I’ve been able to do for the last 15 years is unbelievably different than what I did in financial services. I’m not making nearly as much money as I used to and I have never been happier.

Success, making sure that success is defined by you and your self-worth, comes from within you, versus success being deemed by society and your self-worth coming from titles, money, organizational names that you work for, et cetera.

Viveka von Rosen: I am curious. I love that. It occurs to me, and so I have a question for everybody. I work with mostly women and mostly people, women, 50 or older. To some extent, we’ve achieved success, to Kevin’s point, and gone like, “Okay, now what?” I wonder if it’s even worth having this conversation with people in their twenties and thirties? I know it wouldn’t have been worth having this conversation with Gen Xers when we were in our twenties and thirties. ‘Cause we were strive, strive, strive, right? Get, get, get. And accumulate, accumulate, accumulate. And do, do, do.

I’m really curious because I don’t work in this arena, could we bring the fact that success really is an inside job, would the youngins even believe us? Muness, you’re in your forties, you’re the youngin here.

Kevin Wilkins: A child, a pure child.

Muness Castle: The thing that stood out to me as you were asking that question and as Kevin was talking was that this comes up a lot for me when I talk to people about do they want to become managers or not.

And I put it right in front of them: “Success will be incredibly difficult to quantify. You won’t be able to quantify it. You will have to trust yourself that you are doing the right thing. Oftentimes the outcomes will be divorced from what you did, from what your reports did, and all that.”

And so I do talk about that to youngins, as you said. And it is interesting that it does seem to change their mind and give them pause.

“You know what? I would rather have the very clear signals of success that as an individual contributor I can get. I accomplished ‘X’ the outcome is ‘Y’. 

Progress equals actions is much clearer. Whereas as leaders, as managers, that is much harder and it is something that I try to bring up.

People do seem to hear it, and it does help guide them, at least for a while. That’s my experience with your question, in terms of does this resonate with others.

I think it’s a really good point that Kevin and you brought up that it is a really important thing for us to face. I myself, after years of management, have realized, “Why is this so much harder than being an architect? Why do I keep going back to the other side?” Well, this is why. Because success is so hard to derive from, because it has to be meaningful, it has to be something I believe, like Kevin said, not something that is really easy to see.

That’s my take.

Viveka von Rosen: Yep. Mm.

Kevin Wilkins: Yes. Yes. Right.

Kevin Wilkins: I love that. I also think that there is  a new generation here, like the Gen Zers, they’re looking for conscience. They wanna work for organizations that have a purpose more than just a paycheck or more than just a product. They wanna really try to change the world. So they have a level of, I would call, emotional maturity in some ways.

That they realize that it’s bigger than them and that they wanna be part of something or someone, or some organization that’s really making a difference.

I see that with my children. It’s not necessarily about the paycheck. They like to be paid, but it’s not necessarily about the paycheck. They would be willing to make a little less if they work for a name that means something, and an organization that does something, beyond just making money.

So I would argue maybe the pendulum swung to a little bit more idealism and the answer’s probably somewhere in the middle. But I don’t see this current generation defining their success by the name of the company that they work for, or the amount of money that they make.

Viveka von Rosen: I find that really interesting and true. What’s interesting to me, and now we could be going down a rabbit hole, so you’re welcome to reel us back in, but I also see, and I noticed this with my first intern. She was a Millennial, to be fair, but I’m definitely noticing it with Gen Z, that you have this subset that fails to launch and then you have this subset that is massively, massively successful to levels that because of how we brought up, we couldn’t even achieve. And it’s so interesting that there’s such a disparity between the two groups of people. So what you were saying, both of what, what all of you have been saying it, it’s really ringing true to me.

And I’m wondering how do we even get the Millennials and the Gen Zs who are failing to launch, like how do we even get them excited about success? Whatever success actually means.

Michael Hunter: I talk with youngins all the time about these things and from small children up through twenty-something straight outta college or the first few years of their career. And I find they always have an idea about what success is. It often changes pretty frequently. The way I can be most helpful to them is to ask a lot of questions about why they believe what they believe, to help them explore that. Because all of us here have had enough life experience to know that our beliefs change and deepen, and we throw off all the beliefs that other people have put onto us. We start digging through that, understanding what’s really ours. The youngins haven’t had as much of that experience, often, and so one way we can help them understand what success might mean or where they might want to head is by helping them, asking some of those questions to them.

Kevin Wilkins: Hmm.

Viveka von Rosen: Yeah, absolutely. I really am fascinated. Again, I don’t have as much interaction, so I’m fascinated to hear from everybody else who does have more interaction, what have you noticed that’s the difference what makes our Gen Z and our Millennials successful and I’m gonna say successful in the eyes of society because my failure-to-launch stepson might feel like he’s successful. I don’t know. What have you seen? Is there a common denominator between those who fail to launch and those who are experiencing massive success at a young age, other than TikTok?

Kevin Wilkins: It’s an interesting question. Massive success. Not sure what that means technically. I think you could talk to lots of people who feel like they have been successful thus far. I’m not sure many in that generation would say at a young age that they’ve had massive success.

But if success is being defined on making choices, learning from the choices, making new choices, living an intentional life that you own, then I think that that could be defined as success. When I hear “failure to launch”, again, that’s large language. So we would need a clarity around definition.

Oftentimes you’ve got helicopter parents that take care of the situation that the kid’s in, making sure little Bobby and little Susie are being fairly treated and then they helicopter. That’s a hard model. It’s a common model and it’s a hard model. The generation where everyone gets a trophy, right? No hard feedback.

Failure to launch may be a bigger risk in that population because if you’re used to mommy and daddy taking care of everything for you, then what path do you really own? Are you just owning your parents’ path versus your own identity, your own choices, your own intent?

It makes it maybe a little bit easier not to be a failure to launch.

Viveka von Rosen: Yeah. That’s great. So then it’s a matter of how do we bring that forward? Especially to the kids who have the helicopter situation going on.

Michael Hunter: Do you have a thought here, Muness?

Muness Castle: That question is hard for me to answer. I think there’s a selection bias, right? Most of the young people I work with are people I work with. So I think there’s an aspect of, well, they are on the success track. They’re at work. They’re showing up every day. They’re doing some cool data sciencey or data engineering things in my case, for the most part.

And so, I’m not sure. I do see a lot of them are getting internships, right? It wasn’t just about learning at college or university. But also going out there, experiencing multiple jobs, knowing that they’re not the best in the room.

So that does seem like a theme. But again, there’s a selection bias. Like do other people also experience that but fail to launch? Perhaps, I don’t know.

Viveka von Rosen: I love that about internships because that gives people an opportunity to keep it interesting, to really feel what it’s like. I feel like I went through a series of unintentional internships, because I kind of bounced around trying to find what I wanted to do, because what I found success in didn’t even exist back then. So, internships just seem like a real blessing because it really does allow someone to dip their toe in, get an experience, see what drives them, have the multiple experiences until they can find a thing that they really do love and want to excel at.

Michael Hunter: When someone is failing to launch, that’s one, a sign that we may be using a different frame than they are, and so asking questions to understand what their frame is, can be really helpful.

Viveka von Rosen: Yeah.

Michael Hunter: Maybe they don’t care about anything as long as they have some form of sustenance and then all that they’re doing all the time is gaming.

Viveka von Rosen: Yeah.

Michael Hunter: That can be perfectly fine. However, they haven’t always had, as we’ve been saying, the opportunities to have all the different experiences to understand what something else might feel like and that something else might feel more fulfilling. And so helping them understand how other possibilities and to at least help them be aware that other things might be, feel better to them, so that they’re at least making a conscious decision of, okay, I understand there’s these 1800 other things I could be doing right now, and directions I might be headed towards in my life. And right now, I am consciously choosing this for whatever the reasons are.

That making something conscious is maybe the biggest thing in pretty much every conversation I have with anyone of any age and amount of experience.

Viveka von Rosen: Yeah.

Michael Hunter: So it’s, we often can’t see for ourselves what we’re not seeing and so,

Viveka von Rosen: Yeah.

Kevin Wilkins: Definitely.

Michael Hunter: Like, we can’t see our own back. We need someone else to tell us what’s going on there, or we need to use mirrors or other forms of technology. And if we need to see our back to pull out a splinter or a thorn, then even with all the technology, our hands are probably gonna go mirror from what we need to.

So it can be complex. Where someone else can just make that a much more simple process.

Viveka von Rosen: I just had a visual I really don’t want in my head.

I was talking about, ’cause of course I was thinking about my stepson, but it’s interesting, I think about my women, who’ve been super successful in the corporate world and now they’re starting their own thing and they don’t have, to your point, Michael, they don’t have all of the systems in place. They don’t have a marketing team, they don’t have a sales team, they don’t have a customer success team anymore. They don’t have hundreds of thousands of dollars of

Kevin Wilkins: Yeah.

Viveka von Rosen: sales and marketing stack to rely on anymore. And so yeah, it’s funny ’cause after three or four months, that’s usually when they hit the first wall. They go strong ’cause they’ve launched into something new and they’re super excited about it. And then about four months in they’re like, “Oh.”

And so it’s interesting.

Kevin Wilkins: Yeah. Yeah, definitely.

Michael Hunter: So we’re about at time. Let’s go into final thoughts. Each of us, what are you taking away today? What are you gonna experiment with based on what you’ve, how you’ve maybe shifted your thoughts today?

Let’s start with Viveka.

Viveka von Rosen: Well, I’m gonna have more patience for Mitchell and I’m gonna start asking him more questions. My generation is very much set a goal, achieve the goal, that’s success. So the first question is, “What does success mean to you? And are success and joy the same thing? What would make you happy?” How can I support him to find that joy and success in his life?

I will start asking my stepson more questions as, as I will also ask, as I do ask my own clients questions; I can take my technology and my skillset and apply it elsewhere.

Kevin Wilkins: That’s awesome.

Michael Hunter: And Kevin.

Kevin Wilkins: Yeah. I love your concept around experimentation. The world is not binary, although oftentimes we treat it like binary. Nothing is forever. Testing things out and doing well or not doing well is just a moment in time and then you test the next thing out.

I also like what Viveka was talking about in terms, didn’t use these words exactly, but this is what I thought when she was speaking and that’s the importance of being agile.

We’re living in a very uncertain world right now. Every day there’s more chaos to try to understand and get through. Chaos that actually is directly impacting people’s lives and people’s work.

So how do we maintain the agility to adapt and to pivot as you need as you’re dealing with some uncertain content that’s surrounding you, and the chaos and how can you manage chaos?

I think you can manage chaos through iteration. I think you can manage chaos through agility. So that’s what I’m gonna be taking away.

Michael Hunter: Thanks. Muness?

Muness Castle: My takeaways are largely around curiosity. Where are you coming from? How are you approaching this situation? What does success mean for you? ‘Cause they are different for all of us. And we’re all coming to  that from a different angle. And not to assume that my idea of success matches up with other people’s.

Kevin Wilkins: It’s good.

Michael Hunter: Thank you.

I am first of all reminded why you are three of my favorite people.

Kevin Wilkins: That’s kind.

Michael Hunter: The ways you have adjusted my thinking, the different viewpoints you’ve each brought today and helped me inhabit for this short period of time has been really useful. I forget that not everyone has daily exposure to the breadth of age of people that I do. So thank you for that.

Kevin Wilkins: Be careful there,

Michael Hunter: This is perhaps one advantage of doing everything remotely,

Kevin Wilkins: right?

Viveka von Rosen: True.

Michael Hunter: I hadn’t thought about it, that all this work that I’m doing with my 8- and 10- and 17- and 15-year-old nieces and nephews is exactly the same as I’m doing with the 20- and 30- and 40- and 50- and 60-year-old people that I’m working with in my coaching practice.

Viveka von Rosen: Nice.

Kevin Wilkins: That’s great.

Michael Hunter: Thank you all for your time today. And what is one word you’d like to end with? Muness.

Viveka von Rosen: I’m stealing Kevin’s, which was agile. I loved that.

Michael Hunter: Okay, great. Thank you.

Kevin Wilkins: Intentional.

Michael Hunter: And Muness

Kevin Wilkins: Curious.

Michael Hunter: And I’ll say awareness.

Kevin Wilkins: Awesome.

Viveka von Rosen: Fantastic.

Michael Hunter: Thank you Viveka, Muness, and Kevin for spending this time with me today.

Viveka von Rosen: Thank you.

Muness Castle: Thank you. Bye