“There’s power in failure, you know, so I’m not afraid of failing, I’m not afraid of making mistakes.” Anna Oakes […]


“There’s power in failure, you know, so I’m not afraid of failing, I’m not afraid of making mistakes.” Anna Oakes and her love for humanity with 20+ years of corporate experience as a leader, coach, and strategic business advisor. She’s passionate about everyone leveraging their strengths and maximizing their impact. Throughout her work, she’s dedicated to helping organizations and leaders honor their NOW and get to where they want to go NEXT.

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Leadership with Anna Oakes

I’m excited to bring on our guests. She actually is a consultant, and kind of known as a Kate caretaker of humanity, which is something really cool to talk about. She combines her love for humanity with her 20 plus years of corporate experience in over four years. As an entrepreneur, as a leader, coach, and strategic business advisor. She and her team are currently focused on their work on inter intrapreneurs. Those changemakers innovators who choose to work within organizations, she’s currently writing a book to help intrapreneurs maximize their impact in their role and organization while helping organizations lead and leverage their valuable resources. Well, she gave her first TEDx talk in April 2019, to help individuals leverage their current role to get their best next step coming on. So we’re gonna talk more about that. So please welcome Anna to the show. And how you doing?

I’m doing great. How about you?

I’m fine. Yeah, that intro was always a lot there. But I’m excited to dive into all of it. So. But would you start with just giving our listeners a little bit about your background and your current focus?

Yeah, so background 20 plus years of corporate experience, the last five-plus we’re at a wealth management firm. So I haven’t heard that term capital gains tax and in a while, but I’ve like brushing myself off there. So the first half of my career in corporate was really in management and leadership. And then I found myself by being curious and opinionated, leading the strategic side of people operations, and so really passed up that C suite role to be the Chief Human Capital Officer in order to go out on my own and help more organizations. So a lot of what I do is one on one coaching of high performing either intrapreneurs people working within organizations who are trying to make a big impact, or entrepreneurs working on their own a lot of founders at a C suite, coaching there, as well as consulting.

Awesome. So you say the financial advising, so were you or a financial advisor or walk us through that or you worked within one?

Yeah, so I worked within, so the last corporation that I worked with before I went on my own for years ago was Robert W. Baird, so wealth management firm, a lot of financial advisors, a lot of that speak, their corporate headquarters here in Wisconsin, as well as Northwestern Mutual so.

Okay, so I’m picturing the show billions and if anyone who’s seen that and there’s a gal and billions who basically like runs the show, by helping to coach and inspire and make these high performing equity managers successful? Is that what you did Anna?

Pretty much you know, I always call it, Do you know what a consigliere is in the mob? Okay, so it’s the guy behind the guy like you don’t see him as often, but he’s really the one like influencing a lot of the strategy and direction. And so I had the honor of being at the table with the executives and even in our lines of business, whether it was investment banking, private equity, being with them as they were making these strategic decisions for their business, and not only considering the people operations, really but just helping them make better decisions as individuals. And as collective teams.

Oh, I love this, this is gonna be even more fun than I thought. So that’s like my wife and I saved her show and, and I forgot her name right now. But she’s like our favorite character. So before we get there, though, I’m curious, who is Anna growing up? Right? And not so much? Who but more. So I want you to think about that time period. Okay, and what was that gift that you were given? I believe we’re all been given certain gifts in this life. And what was that one gift that you were given? And how does that connect how you bless or help people today?


Leadership with Anna Oakes

Leadership: A Leader is is the one who knows the way, goes the way and shows the way.


Yeah, so I joke that I was raised by hippies. And my parents like to stop telling people that because, I mean, they did grow up in the 60s, they did have a little bit of that hippie stint. But what I really mean by that is that I grew up in a house that was very committed to our community, right? You served the people that you lived with. And it wasn’t just about you. And so I grew up with a high school teacher, mom, and I grew up with an attorney, dad, but one who really did a lot of service, a lot of pro bono work with the city attorney for the small town that we grew up in. So I would say, Gosh, looking back, who was Anna, I mean, I was a big talker, always the one who liked the social side of school, and maybe not the academic side. So I think that love for people took me to where I am. But I’ve really leveraged this natural skill set or the strength of strategic and futuristic thinking. That’s just where I live, like, Where could we go? And then how do we get there individually and collectively, and I take that as my social justice work, I take that into my one-on-one coaching and then obviously, in my business too.

Beautiful. I love that. That is so cool. So when did you become fascinated and or obsessed with building teams and helping people think, you know, the vision of the future? And the strategic part? When it clicks in like, say, Yep, this is what I was, you know, created to do. This is what I’m supposed to be, this is my calling?

Yeah, I think in terms of this is my highest and best use was probably when I fell into the people operations or the Human Resources side of business. I was on the leadership side growing up at companies like State Farm Insurance, and a lot of other organizations where I had the privilege of learning from, I think some of the best in terms of large systems, right, large systems, and how those worked, and how they invested in their people and their leadership. So it’s kind of spoiled. And then when I get into other organizations, I’ll give you an example. I worked for an organization here in Milwaukee, a leading supplier of equipment for the long-term health care industry, the right company called direct supply. A great company was going to work in leadership over their supply chain area, but started to have conversations. This was about 15 years ago, with their CEO and with other leadership, once I got on board. And they had huge growth goals. Obviously they had to write the baby boomers are retiring. It was a great industry to be in and I was so fascinated by that. But was a little bit worried honestly, about how we were going to actually grow like that. What, what talent were we going to bring in? How are we going to build the right talent? And then what talent did we need to buy in order to achieve those goals? Right, that expertise that we would need to bring in? So honestly I just started being curious. And it wasn’t very long, probably a couple months before they were like, do you want to just help us with this? Like, do you want to help us build our employer brand in the area, because at the time, the CEO, Bob wanted to be the best-kept secret in the area. And I thought, well, we can’t be the best-kept secret in the area and grow like we’re not going to attract the right talent. So I did that with him for a few years and got recruited to go to manpower global. And it was probably at that point that I was like, Oh, I’m really naturally good at this. It fits with my interest in growing the business but also in this humanity space of like, how do we treat our people really well as humans? Because without them we really have nothing. So it was a nice balance. I think it was probably at that point where it clicked for me that wow, I could do this for a living I could make a living out of this.

Right and you mentioned your parents like all those you know the social talkative you know high schooler it’s all like I told you, he’s gonna be a star here, right?

I’m not kidding. No brat when I got into this part of my career, my parents, I remember my dad saying, Wait, what do you do?  You’re at the table with the executives like the people running the whole company and you’re telling them and you’re giving? And I’m like, yeah, and it wasn’t that he didn’t believe in me. I think he’s just still envisioning me this like really talking to a little nine-year-old. And I’m, you know, I’m still that person. I’m still young 29-year-olds right now and they’re reminding me of that inner child and reconnecting with that side of myself. That is our natural strength. 

It’s the best, I love that it is so cool. So let’s dive into some of the strategy here right and so thinking of the business professional, you know, the business broker, the financial advisor, the luxury real estate or the commercial Real Estate syndicator operator broker and then also the high net worth entrepreneur performance sort of our audience. What’s the best kept, I guess, secret, if you will, right to unlocking vision and strategy for them? Like, what’s the biggest blind spot is maybe they put it like, what are they missing? And what’s actually going to come and be like, okay, step number one, do this or.

Alright, so first of all, let me preface that y’all are gonna roll your eyes when I say this, but it is, it is the secret. And it’s not a big secret. But it’s a strategy. And if you practice it, because I do think it’s a practice, I think you’ll get further and make a bigger impact. And that’s self-awareness. Right? So I think it was Cornell who did a study, what was the number one predictor of success for CEOs. And it wasn’t charisma, it was strategic thinking. It was self-awareness. So how do we build this awareness of who we are, who are natural, what our natural strengths are? And how do we then leverage those for personal impact? And you could put, you know, 10 of these, these listeners or you know, high impact financial advisors, whatever they are next to each other, and ask them to do the same types of tasks, but they’re going to approach them differently. And that’s okay. But what I see happen for these high performers, because remember, I care about the high performing teams, but in order to do that, I actually have to get high performers first. So in order to coach the high performers, we start by asking them to slow down, because they’re moving so fast, they’re doing so many things, they’re trying to build wealth for themselves, or trying to build wealth. For those who are trying to build their business, they’re trying to make a brand, they’re trying to do all these things, serve on a board, do these things. And I get it as a business owner, I get it. And if we move too fast, we actually miss the growth. And we will stay stagnant, or we will go backward. And I don’t want that to happen. And so it’s not a huge ask that I’m making Brett. It’s an ask that says, For like 10 minutes a day, do a little bit of reflection. Maybe you don’t want to journal, use a calendar, maybe you don’t want to write, use your computer, maybe you don’t want to type, do it audio, but spend time thinking about what I do today? What could I have done better or differently with what I did? Who did I meet? Right? They’re good, they’re pretty good at that I’m not, they’re probably pretty good at keeping track of who they met. But then nurturing those relationships over time. And I think when we actually pause, whether it’s that 10 minutes or one hour, whatever you want to take, you’re actually the ROI on that investment is so huge, you’re going to get that back. And not only personal impact with your personal relationships and your work, but in the growth of your business.

Okay, I’m gonna try to calculate that in a minute. So Self-awareness is the number one way to predict success for high achieving CEOs, executives, entrepreneurs, it's understanding our strengths Share on X And then leveraging that not being anyone else we’re not, you know, the strengths, the gifts we’ve been given were used, those events leverage those to accomplish a result. But in the process, you need to slow down. And we need to, if we move too fast, we risk either going backward or just missing the growth altogether. Correct. And the application is simple. 10 minutes a day, and reflecting on what I do today? What could I have done better? What can I improve? Who did I meet? that it gets those? Correct?

Yeah, you did? You did? And I think, you know when we do that, and we consider where I have been? And where am I going right? That just helps us become and come across as more authentic because remember part of what I did in corporate America, right? I helped transition CEOs into Chairman roles, I help pick new CEOs, I help understand what these high performers did. And they have a lot of coaches, right. They have a speech coach, they have like handlers, they have a team of like five or six people who are helping these people be successful. And one of the things that we always talked about was when you can show up your most authentic self, even if you consider that, you know, kind of gangly and awkward. People respond to that authenticity so much better. And I and I have seen high performers, especially in that wealthy area, become distracted with the hustle and forget that they are in the middle of that is really the key.

Excellent. So how do you show up besides self-awareness and practicing this reflection and having coaches? How do you show up as your most authentic self?

Leadership with Anna Oakes

Leadership: The true test of leadership is how well you function in a crisis



You know, I mean, I think you have to use tools around you and use the people around you to ask for feedback. If you don’t have a personal Board of Directors, you should form one, you know, like that, that group of people who’ve known you for quite some time, and maybe not everybody on there does, right because they all serve a purpose. But you know, I can tell you about mine for example, you know, I have somebody who’s been on there and known me for 15 years and has acted as a mentor and a friend and we served on a board together, you know, and she will always push me to one charge more, when she reviews my proposals for me, she’s like, ah, more more, you know, she’s always that one, we need that one that will push us. And then I have another person on the board that when maybe I get too big for my britches that will pull me back and say, like, Hey, remember, a little bit more humility or whatever, right? So they’re able to give you that feedback. And as high performers, the higher we go, the less feedback we get. People are either intimidated by us or think we must already know, right? Must already have somebody telling us those things. Or they don’t bother with it at all right? Like, oh, that’s not my place to tell them. So one thing that I typically hear, so we’re not going to get that feedback on a regular basis. And so seek that out externally. And as you build your team, you need to set that tone from day one, when you hire that first person, right? My first hire was a role called an integrator, do you use that term ever in your roles? Okay, so an integrator for me, it’s kind of, you know, from an entrepreneurial perspective, a lot of coaches and consultants use it, it’s really that person who wrangles me in and who says, okay, Anna, you’re this huge, futuristic, strategic thinker, you have all these ideas, literally every day, thank you for that, here’s what we said, we’re gonna focus on what’s now not important. And now what’s more important, and she sort of keeps track of those ideas, and then brings them back up and plans out how we’re going to execute everything so that I can live in my strength area and continue to build the business if I had to stop and do that I wouldn’t be building the business. Or if I was building the business, nothing would get planned and executed effectively. And so not only am I seeking external help, I’m building a team that from day one, I have the tone with her that she’s there to hold me accountable, and I’m there to hold her accountable to and so we’ve had some tough conversations about what she could do better or differently. But remember, I asked every one on one that I have with her, what could I be doing better or differently, and when she doesn’t have any suggestions, I make sure I come with them. Sometimes.

I love that I can think of my executive assistant who has been like just a rock star for about a year now. And it’s exactly right. Like, I’ve got to the point where I’m like, Okay, so I’m going to have this vision, and I have these thoughts and I have the strategy. But I want you to design this and organize it and implement it. Okay. And as more the more that I that I’m more, you know, the strategy and the vision and the more that in we can design kind of both of us are kind of designing, but the more that she can organize that and then start to implement, even if it’s just the first draft of something, right, the first part of the system or the first draft of the ebook, or the first draft of the proposal or whatever we’re working on. Right? Then I can go back and kind of you know, but if I had to try to start from A to Z, I’m not gonna get dizzy, because I’m still stuck up in the you know, the vision part of if that makes sense.

Yeah. And I think we overcomplicate leadership, you know, and we over complicate parenting, you know, are you a parent?

Oh, yeah, we have five kids. Yeah.

Oh, lordy. five kids how old?

Two to nine

Two to nine.  Okay,  So I think parenting and leadership are a lot of like, and I think we overestimate and we underestimate in some ways, right? The ways we underestimate is that I think we forget that it is an honor to be both. And we made a choice to be both right? We could get into the parenting thing and accidents and all that but we want as a leader, you for sure make a choice. Okay, you have taken on this role of influence and impact for other humans. So you have to take that seriously. That’s where I think we, you know, underestimate and I think where we overestimate is sometimes we think it has to be very complicated, that building these connections has to be complicated. It doesn’t. It’s a routine connection. It’s communicating clearly and consistently. It’s calling yourself out when you need to for high performers, honestly, it’s often that we need to say like, Hey, I got ahead of myself, hey, I forgot to do that for you. You know, I have a podcast of my own. And I gave feedback to one of my team members earlier this week about Hi, one of the show notes to come out. And she did them. And it was sort of vague feedback. And I looked at them today, we had a new episode drop on talking about race and other taboo topics at work. So I read the notes. You know, that just doesn’t flow well. So back to her. And I can’t be afraid to say things like, Hey, I know I said that. I said that you did it. Let’s actually do it this way. And let’s do it this way going forward like you did, you didn’t do anything wrong. It’s on me. Here’s how the agreement that we’re going to make is we are learning to work together on this new thing because it’s a new task for her.

Yeah. So we’ll say sometimes I’m saying like, I’m thinking out loud here. And as I think out loud, and then she can ask me questions. And I’m like, Yeah, you’re kind of right there. I see what you’re saying and The key is communication and collaborating, creating a safe place Share on X, right, where we’re both humble enough. We’re both working together. And I also oftentimes say, hey, you’re just as much valuable team members I am and your strengths in a lot of ways are more valuable than mine are right, but in different ways, and that’s okay. Like it, we’re all in this together. And let’s, let’s have an open dialogue. And, and, and again, that’s why I think she’s, she’s my number one executive system because she is she’s willing to like and she asks questions in a way that’s really thoughtful and, and then also straight to the point too. So I love everything you’re saying. So how does somebody find that Rockstar, team member? executive assistant? You know, coach, walk us through that process?Yeah, what do you think?

Yeah, so a lot of experience in hiring, I oversaw talent, acquisition, diversity and inclusion and all that good stuff from an HR perspective. So I can give you a little bit of that wisdom, but then also just on my own building teams internally, both for the teams that I ran in HR, but also remember hiring executives hiring high performing investment bankers throughout the time. So I think when it comes to hiring, a lot of people want to know like, what assessment can I use? It’s going to tell me this person’s profile. Most assessments out there, for example, I like Strengths Finder, which is actually Clifton strengths. Now, they highly encourage you not to use them for hiring and so do I. So I’ll put my HR hat on for just a minute, right? That could somehow eliminate people who actually could be at the role. So I think don’t use assessments in hiring, you have to use your best judgment, you have to have performance-based conversations. So give me examples when, here’s an example, when we have something that comes up in my business, can we talk about how you might handle that, right? Really giving and working through those scenarios is going to help you understand and not getting too distracted? Right? Like they might talk like you. So you’re obviously going to like them. But is that really what you’re looking for? Right? For example, my integrator talks very differently than I do in an interview. But she’s super high in her strings of organization and linear thinking and plan fullness, right. She’s that Yin to my Yang. And that’s what I needed. So I had to dig deep in the conversation of the interview to know if she was going to do that or not, I looked at her experience, right? She’s led teams, she’s been a leader, all that good stuff. So you look at the interview. And then I think once you set that tone, in an interview for the open and honest collaboration that you’re looking for, you start to have really honest conversations when they come in the door. How is this working? What could I be doing better differently, here’s what you could be doing better differently, right. And that trust is formed, I always tell the leader, like, it’s our job to tether the person to the organization like a hot air balloon, right? Like think about, I’m the basket, they’re the balloon, they can easily float away. And someday they will. And that’s cool. But for now, I’m investing in them. And I’d like them to stay. So it’s my job to put the ropes on. Right. It’s my job to tell them through those trusting conversations through the flexibility that I show. And in order to get the right skills match that you’re talking about, I have to be very clear on the scenarios and the expectations. And then just like we just talked about a very minor example with the podcast, I have to be ready to say, not exactly what I was looking for. Even if it was a misunderstanding for me, I can’t go like, Oh, I should have been more clear, I’ll just let it go. No, I really wanted to know, this is my brand. This is how I want the podcast to be represented. And in order for you to perform to my expectations in this part of the role looks like this. Right? So we have to be very clear from the time we interview. And every time we talk to them, we’re setting that example. And so it goes back to maybe where we underestimate. It’s just our responsibility, but we don’t have to overcomplicate it, it’s as simple as consistent communication.

I love it. I read a book, Patrick Lencioni on and it talks about the ideal team player that talks about three traits: humble, hungry and smart, right. And so the hungry part is, you know, being willing to work extra hard. And in your year, you’re just naturally, you know, internally motivated, generally speaking, not external, the smart part was like emotional intelligence being able to connect with you. But the most important one he said is, if you don’t have this one, it’s really a big fat. It’s the humility part, right. And I think what you’re saying, you got to Lead with humility, you got to lead, you gotta get out and pull the rope not but not push the rope. You got to tether them to your values, but you got to show that you're humble enough to receive the feedback Share on X. And likewise, they need to be as well, right? And so excellent. 

So Okay, one more thing,

Please, please, please,

Your listeners, I’m picturing your listeners, and I want to get really tactical with them. That, you know, they’re in the same boat as me building these teams. I’m not talking to corporations who have layers and layers and thousands of employees. I’m talking to small business owners and founders and, you know, small leaders. So what I want to say is that when you’re looking at your team, and you’re building out that team, we don’t have to, I guess that you know, where I’m going with that is we don’t have to overcomplicate that we have to have somebody different in each type of role. We have to have, you know, this skill set here, this skill set here, it’s your job to set the tone, and that’s why I talk about intrapreneurs. I want them to think about creating a culture of intrapreneurship within In their group, because you people who work for startups typically are a little bit higher risk-taking deal with changing and fluctuating demands are more flexible, that’s the person that we’re looking for, because a lot is changing and growing as we change and grow our businesses. So because we’re looking for that person, we might think, Oh, well, they want to own their business someday. Or even they say they want to own their business someday, quite, because they have similar characteristics to us, except they’re choosing to work within an organization, let’s leverage the printer in them, bring out those characteristics, coach them and grow them, get them where they want to go. And I think they’ll stay longer. In fact, I know a lot of business owners who created that intrapreneurial culture, saying you’re not the entrepreneur or you’re not the one whose name is on the lease or paying the paychecks, but you are operating with as closely as we can get, I think, to an ownership attitude, ownership thinking, but it’s my job to set that tone, that it’s appropriate to have those goals and to be hungry, and I will get you connected with people you want to because a lot of these entrepreneurs who do that, the person ends up staying longer and becomes maybe their right-hand person, or I’ve had somebody who owns a coaching business, that person who wanted to go out and own their own business actually ended up staying with them for over 10 years and really helping them build the business even bigger.

Yeah, I love that. Right? Don’t put yourself in a box or the employee in the box. And, and, and celebrate the things that make somebody ambitious, right and entrepreneurial. And, and just really pour into them, give more to them. Right. And yeah, and don’t try to box them in or set a certain role. You want them to grow and flourish because that’s ultimately going to help you grow and flourish. And if someday they do go away and, you know, graduate, let’s say to their own business or something else, hey, that’s what it is. But hopefully, you’ve had a chance to build a culture when you bring someone else in, and they’re doing the same for somebody else that what you’re saying, Yeah,

Yeah, don’t keep them small. And I know you think you don’t do it leaders, but you do I watch you and you do. And if I didn’t watch myself, I would too, because I want to keep every my integrator so bad that I’d be like, well, maybe it won’t give her exposure over there. And it happens in the blink of an eye in the back of my head, that then I’m like, Oh, I’m not gonna share it. Nope, I’m pulling that back up. And I’m going to share that idea. I’m going to give her exposure to that side of my business so that she can learn and grow. And she will stay and perform better.


Love that. Love that. So let’s shift a little bit into an example of your service. Okay, so I want you to now. Okay, great. I’m like, Anna, I need your help. I need you there. Like, what are the steps to like, get about going to becoming a leader that I need to become?

Yeah, so are we talking about just a leader wanting to be a better leader or a team?

Yeah, leader better? Lead better leader, right, or building a team? Right? Just essentially, you know, walk us through how your service helps to get there, like, you know, the steps that go in that process involved?

Leadership with Anna Oakes

Leadership: The key to a successful leadership is influence, not authority.


Yeah, I mean, you know, I think if we had to layer it out, it would start with you, right? If the leader says, I really want you to come in, I have organizations reach out like, we have a performance issue. I know we could be doing better. I think we have a culture issue too. Can you come in? The answer is always like, okay, we start with you. And I know they don’t want to hear it. But if we don’t, nothing I do, it will just waste your money. So let’s not even try. So we have to start with them to say like, what are you doing that you can stop doing or pause so that you can create capacity? Because I think there’s two problems that almost all leaders have: capacity and capability. Like we are pushing ourselves too hard. We don’t have breathing room, right? We’ve already talked about the value of the pause. So you’ve got to stop and pause and things to create capacity for new things. What could you be doing better or differently as an individual? What could you be doing better differently as a leader? And so we start there by creating that capacity? And then we talk about capabilities? How often are you living in your strengths? Are there any areas where you need to improve, and PS, there’s always areas that all of us need to improve? So let’s be humble enough to admit that. And I’m not saying I’m going to send you away for some four months training or something or that it may not even be official training, because I’m actually not a huge fan of official training without any other supplement, I’d rather have the hand to hand combat of like, what are you going to do to perform differently over the next two weeks over the next one month over the next quarter? Let’s just start there, to shift some of those behaviors. And I’m not trying to make you somebody different. I’m actually trying to bring out your natural skill sets that maybe somebody didn’t see. Or you had a model that had different strengths than you and so therefore, you tried to emulate that model. Good. Now, let’s take what we want out of that model. And then let’s get back to you, how do you lead? How do you operate? What’s been the most successful things that you’ve done to grow your business today and let’s do more of that. Right? So we really start with the individual and once we get them into, like I say under control because it’s sort of an overlap. Once we get that part cleared out, then we can start working with the team to say like how do we collectively that leader and each of those team members want to grow the business because they can share their vision. But we got to hear what the vision of the whole team is. Do you buy into that, you know, I think, to business owners, and this is probably not going to be two leaders that your readers are looking at. But I would invite them to look at Rachel Hollis and Dave Hollis. And the company they built called the house go, H-O-L-L-I-S I truly admire, and you know what they built for an organization. And if you watch what the Hollis company is doing, you don’t have to look at Dave and Rachel, individually if you don’t want to. Although they’re very successful in their own right, look at how they built this team, to say that it isn’t about the Rachel or Dave brand. It’s about the Hollis company and what they want to do as a group. And so it really, really matters for you to bring your people along, especially if you want them to stay, they’ve got to feel part of it. And we as small business owners and leaders have a bigger advantage in that area than big corporations do. Because we’re small enough, we’re nimble enough that we actually can make them part of the story. Right, your VA my integrator. They’re a huge chapter. I tell her all the time, I would not be here today, if it weren’t for you. And I know that to be true. And I have to repeatedly tell her that so we’ve got to help them make them part of the story.

That’s incredible. I love that you start with yourself. What are you doing, maybe trim transfer, or trash, you know, stuff that’s getting in the way that’s holding you back from your capacity, holding back from the gifts that you’ve been given your sweet spot, what you should be you should be using. And then once you get that kind of settled, and you’ve created some space there, start to grow and improve those other parts of yourself. And then number two, though, work on your team, right and help bring the team in and help them become a part of the vision right? Not just yourself, right? Maybe the vision be a team vision versus an individual vision fair summary,

It is a fair summary. And then I would say and then we go back to you, as we’re continuing to work on the team. Now we used to layer in and now I actually do get to work with you on a different version of your leadership with your team. Right? Because you probably were leading differently. Now let’s lead differently and better going forward. So now that you know what you know about you now that you’ve collaborated with the team in new and different ways, how can you lead even more effectively, efficiently, and impactfully? To your team, so that we can get really tactical?

So amazing. I love it, Anna, and were you ready for the lightning round over and I tell everyone how they can connect with you. Hey, let’s do it. Alright, cool. So Anna, knowing what you know. Now, if you go back to your 25-year-old self, what’s the one Golden Nugget that you would make sure you knew or something you would do?

Oh, man.I honestly, I’m a person who lives with very little regret, Brett. So it’s hard for me to think about something I would do differently. And I would say, Oh gosh, I don’t think I really don’t I mean, the good, the bad and the ugly got me to where I am today. So I love it. I could say maybe don’t drink as much advice, but it did impact me at a younger age. 

So there you go. That’s honest, I have a yes. Honest. Absolutely. What is the one book you’ve recommended or given it the most in the past year?

Leadership with Anna OakesHmm, Let Your Life Speak. It’s by a guy named Parker Palmer. And here’s my hippie coming out. He used to be a Quaker and he was a leader. I can’t remember what university in California. But he’s just a really wise guy in the way that he talks. It just gets to me in terms of like, how can I live to my highest and best use, it’s not too religious or not to anything, it’s pretty straightforward. And so I gift that a lot to the people that I coach,

I love it. Give me a digital or mobile resource you recommend for your business.

Something that I’m offering or that I use for my business?

Could be a digital mobile resource that you recommend for your business.

Okay, digital and mobile resource. Um, you know, I’ll recommend somebody else so Desiree Adaway is a consultant and coach and she has a course right now called Whiteness At Work. And I think race in our workplaces and equity and fairness is a topic that is going to be at the foremost of our brands as leaders over the next few years and beyond, I hope and so I would recommend her work, Deseret Attaway, She’s got some workaround whiteness, whiteness at work as leaders.

Awesome, favorite leadership quote or theme you try to live by.

Oh man, you know, my mentor. He’s my longtime mentor and friend, Alonzo Kelly, told me about 15 years ago I think I was talking about going back to get my, because I found myself at the table, I had a communications undergrad, I didn’t understand all of the financial conversations going on. And I really wanted to say so, I think I’m gonna go back to my MBA. And he said at the time, you know, don’t expect a huge raise after this. And don’t expect this, expect that you’re going to ask better questions. And that advice rings true. It’s still his advice today that It's not the amount of questions that you ask. It's the best question that you can ask. Share on X

Love that. What are you curious about right now? Hmm.

Honestly, a trauma in the workplace. It’s a passion topic of mine, as much as I’m writing my book on intrapreneurs, and how, you know, companies can leverage and lead that talent better. I really, really, that’s the thing, I always come back to the micro traumas that we as humans bring to the workplace and how that affects our performance. And then the micro and even macro trauma that can happen in the workplace and all that affecting our humanity, which is obviously, you know, my personal calling, and then performance was my professional calling.

Excellent. Last question. How do you stay centered? Anna after all, your success, all your coaching, you know, all of the education, all of the inspiration, you’ve helped coach people and leaders that you’ve influenced, how do you stay centered personally in your values, Anna? And how do you stay encouraged to reach for new goals?

Yeah. Well, let me tell you something that another good friend of mine says is like, There's power in failure, you know, so I'm not afraid of failing, I'm not afraid of making mistakes. Share on X And so I want everybody to hear that like that, that owning a business and being an entrepreneur, or solopreneur, or an owner, whatever. It’s not easy. It’s hard work. It’s very heavy lifting and entirely different ways than I’ve ever had to do before. So for years, and I’m like, Ooh, this is no joke, right? So the way I stay centered in that is, I mean, I honestly have that board of directors who keeps me really strong. I’m constantly auditing how I’m spending my time. This is my highest and best use, right, I just resigned off of a board because I didn’t think that I was making the impact that I could, and I didn’t think we collectively were moving as fast as I needed to. So then that means my time there is done. And I’m not going to make that decision lightly. But I am always aiming for auditing to my highest and best use both of my time and my values. Because we kind of get ourselves into these situations where it sounds really good. And we kind of get into it. And this is not a commentary on that board. This is a general comment, we get into it. And then we there’s we’ve made assumptions or everybody kind of thought it would look or feel like this. But then does it look or feel like that six months later, one year later. And I think too many of us, especially in the Midwest, got Midwest nice that we stick with it. When I’m telling people all the time, like think about it like a patchwork quilt where there’s not one thing on there that you know, don’t expect to be fully fulfilled by your career, have a lot of different patches on your quilt and swap them out when they don’t work, give yourself permission to do that. We don’t do that enough. And then and when we do that, then we’ll have capacity to think about what is our highest and best use and get to our best next whatever that might be.

So powerful and there’s so much wisdom there I want to thank you for being on the show, and sharing your gifts, your talents, your inspiration, your expertise, so much content. Keep doing what you’re doing, keep blessing others, keep using the gifts you’ve been given to make a difference in this world. And that being said, one last thought from you and remind the listeners where they can find you and reach out to you.

Yeah, I think the best place is our website buildhighperformingteams.com you can find us on social or podcast everything links to there. Yeah, I just would love to be connected. I’m happy to serve in whatever capacity that is. My biggest wish for all of the listeners is peace and progress. If we can all have that and strive for that every day we’re going to be better.

Love that. And I want to thank our listeners for listening to another episode of the capital gains tax solutions podcast.


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About Anna Oakes

Leadership with Anna Oakes

Anna Oakes is the Founder and CEO of Oakes Co.. Her main goal in this life is to restore humanity back into our work and workplaces. Raised by hippies to believe she can change the world (without a cape!), With 20+ years of corporate experience as a leader, coach, and strategic business advisor. She believes we (as leaders and employees) can do better, be better, and make a positive impact wherever we are.

Shes passionate about everyone leveraging their strengths and maximizing their impact. Throughout all of her work, shes dedicated in helping organizations and leaders honor their NOW and get to where they want to go NEXT

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