“What is the single greatest characteristic of a leader?”

Without hesitation, once Kade posed this question, he got a lot of responses.

Empathy. Curiosity. Decisiveness. 

And so many more.

In this episode, Kade chats with Primitive’s Chief of Staff, Annie, to discuss your answers while exploring his reasoning behind what he believes to be the greatest character of a leader.

Connect with the folks behind the episode: Annie Gilbert and Kade Wilcox

• Annie Gilbert

• Kade Wilcox

• Primitive

Kade Wilcox: Hey, everybody. Welcome to The Primitive Podcast. For the next several weeks we're going to really kind of switch it up. We're going to have some conversations with Annie, our chief of staff on all things leadership - different things we're learning, different things we're experiencing at Primitive. Also, we're going to have another episode where Annie interviews another, kind of, equivalent of a chief of staff at another local company. And so we're excited to hear from him and just continue to give you insight into how organizations utilize the chief of staff role, or roles of its equivalent. And so it's really changed our company. And so anytime we meet someone who's doing similar work, we really want to feature that as a way to help you kind of think through different ideas of how you could implement a similar strategy in your own company. So that's kind of what you can expect of the next four to five weeks. As always, thanks for listening to the podcast.

Annie, thanks for joining me and for you know, like the rest of our team that I get them into just kind of suggesting things and y'all are always so willing to kind of help out. So thanks for doing this.

Annie Gilbert: You bet. I'm excited to dig in. So this first topic that we're going to talk about is leadership qualities practically applied. And the idea from this came from a post on LinkedIn of Kade's that where he just asked people, "What's the number one leadership quality, in your opinion?" and got a lot of responses. And so we've kind of broken those responses down into some broader categories and want to just ask Kade to share what does this look like as a leader.

Relational Leadership...When You’re Not Relational

And so the first one is, what does it look like to be relational as a leader? And some of those responses were: authentic, being a servant leader, compassionate. And I think the response we saw most often was empathetic. And so, Kade, just tell us about how you do that; how you apply being relational to leadership.

Kade Wilcox: First of all, I think it's a really unfair question because you know, as the chief of staff, you know that relational CliftonStrengths, you know, if you look at the CliftonStrengths and there's like 30 something of them, you know, that relational strengths are typically at my very bottom. So I find this to be an unfair question. But a good one. And so there are a couple of things I think about from my own leadership. And then I'd love to hear your thoughts, given your understanding and dynamics of our leadership team. And then also you have a lot of relational strengths. And so I'll answer kind of what I think is important from my perspective with our team and the way I approach leadership. And then I'd love to hear some of your thoughts as well.

Authenticity = Credibility and Trust

So the first thing I think of when I think of like, what does relational leadership look like, is that first point you made. And we saw it several times in my LinkedIn post was just being authentic. I think that it is a - that's like a really critical thing to be able to do amongst your team. I was just like, be really authentic and it creates a level of credibility and trust amongst your team because they know whether things are high or whether things are low or whether things are going good, or whether they're going bad, or whether a company or organization is going through a challenging time. They know, you know, because of your authenticity, that what you're sharing with them, and what you're saying to them, is true. And so I think being authentic, it really lends itself to being trustworthy and having credibility.

And so I feel like your point about what we saw in my post about being authentic is really, really critical. I think the other thing that I try to think about related to being a relational leader is trying to really understand my own weaknesses as a relational leader. And so I know that my, you know, my bent, you know, my disposition, my personality, my leadership style, is not real strong as it would be defined in terms of relational strength in CliftonStrengths. And so I try to find ways to be consistent with who I am and my strengths, but kind of cultivate and nurture being relational. And the way I do that is really a couple of things. First of all, I know that that is not my strength. And so I try very hard to lean into people whose strengths are very relational.

I think that is a really obvious and true in you and also in Jess, our COO, and then certainly other people in our company. But the first thing I do related to that is realizing my own shortcomings and my own gaps and try to surround myself with people who are really, really good leaders and are very good at relationship. I would like to say, I don't think that excuses me from nurturing, you know, relational gifts or relational skills. I think it's something that, you know, if you're a leader and you're not overly relational, or it isn't exactly, you know, your strengths zone, for example, I don't think it justifies being poor at relationships or neglecting leaning into that. But I do think it's really important to be able to have people on your leadership team and in your organization, who are anchors, you know, who are real, real strong there so that when things do kind of come and go relate to your team and, you know, hard conversations and hard seasons, is that you have people that can raise their hand and say, "Wait a second, wait a second, wait a second." This is how that's going to feel to someone, or this is how they're going to hear that, or this is how it's going to impact, you know, their life.

And so I find that to be really, really powerful. So I guess, just to summarize, you know, when you say, what does it look like to be a relational leader? I think what I try to be is really authentic. Like you're going to get exactly, you know, who I am all the time; good and bad. So I think that level of authenticity creates hopefully credibility and trust. And also a little bit of predictability. I always crack up when people ask me a question, but they already really know the answer because I'm pretty predictable. So I think being authentic is one. And then I think second is certainly leaning into growing relationally as a leader.

Intentionally Surrounding Yourself with Others Who Are

But even more importantly, if it's not your strength, really surrounding yourself with people who are really strong there. And the last thought I thought about when I saw this question that you posed was I had a job one time, and I remember the leader talking at a staff meeting and he made this comment. And he said you should always seek to understand before being understood. And I probably fail at that more often than I succeed, but it's really stuck with me for, shoot, almost 20 years now. You know, that in any situation, in any circumstance, whether it be with a client, whether it be with a teammate, whether it be able to spouse or a friend, you know, that if you start out a conversation or you start out a situation where you're really trying to seek to understand before making yourself heard or making yourself understood, that it goes a long ways, I think in creating empathy and understanding. And then, you know, helps you navigate whatever conversation or whatever situation you're in. So those are the kinds of things I thought of when I read your question.

Annie Gilbert: Yeah. I think that's all really great. I have some responses to some of that and then a couple of my own things to add as well. So when you talk about authenticity I think your self-awareness really feeds into the authenticity. And so just like you were talking about knowing that this is not your natural area of strength helps you be authentic because you're not pretending that it is, you know? And you just, you can't be fake with people and get away with it; not these days. And so I think that being aware of it, and then, like you said, being willing to grow into it, and then also leaning into those around you, that that is their strength. And making sure that you have people alongside you who have different strengths than you do. All of that's really, really valuable.

I think along with that, for me, it helps me build trust to build relationships with people which is obviously really important in working with a team and being able to really be honest with each other, push back on each other, encourage one another. There has to be that foundational trust. I think that even though, you know, you're not naturally relational, some things that I see you do, and the way that I see you lead with relational aspects is that you share, personally. Because you're so authentic, because you're so comfortable in your own skin, you share things. And that gives other people permission to be who they are as well. And so I don't even know if you realize that you do that, but that's a relational area that you're really good at that is natural for you. And I think it just helps people know he's just being himself so I can be myself at work, too.

And that's really important. And then the last thing that comes to mind for me and just how I apply my relational strengths in leadership is just knowing that I'm going to always be working with people who are so different from me. Everybody's individual and unique in their values, in their worldview, all of those things. And I think of Jess and her strength of individualization, and how she can look at a situation and the individuals involved in that situation and really problem-solve, strategically, in a way that at the same time cares for those people. So I think you're right in saying that she has those relational strengths as well. And then I think that just really being a learner of people and understanding what makes them tick because that's going to be different for everyone. And that takes time and investment. I think about Bob Goff and how he talks about just noticing what's adjacent and just taking a genuine interest in people. And that can go a long way in helping them feel safe and helping them have the ability to be themselves.

The Art of Knowing Who You Are, and Aren’t

Kade Wilcox: Yeah, that's really good. Maybe before we move on to the next question, there's just one more thing I would say to leaders, and I've really learned this mainly through failure, is you have - I feel like it's critical to really, really spend intentional time understanding who you are. And that requires both strengths and things that you're not naturally inclined to be strong at. And I think most people intuitively understand that. And would acknowledge how critical it is to really know who you are and be self-aware, and be honest in that, right? Like it's super easy, you know, to create your own false narrative, because it's what you aspire to be, which is good. It's good to aspire to be better than you are and, you know, to grow, but to be really, really frank and honest with yourself, I think most people agree with that. But I think the thing that oftentimes gets forgotten, not intentionally, but just because it's not intentionally done, is understanding those you're working with.

And to me, one of the most powerful things about the CliftonStrengths finders that we really focus on in our organization is that, you know, I don't know our team's strengths perfectly by like a long margin, but I feel like I know our leadership team fairly well. And when I am being my best self you'll notice I said when, which is not always, I pursue conversations, or challenging conversations, or casting vision, or whatever, with an understanding of the people that I'm trying to either lead or to work with or to move forward. And so I think it's really critical that you not just know who you are, but you really understand the people that you're working with the most are. And that by its very nature is relational and creates a tremendous amount, I think, of trust and credibility. So I think it's been really helpful for our organization to do these things.

Annie Gilbert: I agree. And that's a great segue into our next question, which talks about honesty and being ethical. We saw the word integrity come up quite a bit on the responses as well. So how would you say that you practically apply integrity to leadership and why is it important?

Kade Wilcox: Yeah, so really I love it. The first thing I thought of when I saw this was one of my favorite interviews I've ever got to do on The Primitive Podcast was with Drayton McLane. And at one point in the interview, he talked about how you have to write down your integrity. Like you have to define: who are you? And like, what are these moral, you know, principles and anchors that you're never going to leave and let go of no matter the situation. And then he pulled out of his coat pocket a note card and it literally had his integrity on there. And so the first thing I think I want to think of integrity and leadership is like, you know, defining what your integrity is, right? Like knowing where your bounds are, knowing where, you know, what your anchors are and you know, just, yeah, just establishing that in your own mind.

Good Leadership is Not Accidental

I feel like good leadership really often boils down to intentionality. It's like, there's a lot of things that good leadership means, but I feel like it's hard to say, you know, if anything, good leadership is intentional; it's not accidental. And I think of that idea when I think of integrity specifically that you don't just wake up one day and have integrity. Like it's an intentional exercise, it's an intentional effort. And like, you know, any good thing is tested and tried and true. Right? And I think there are going to be so many opportunities where your integrity is going to be, you know, tested and you better have those things deep, deep, deep into something, right? That anchor analogy or else, you know, or else you're going to find yourself tossed to and fro based on the situation and based on the circumstance.

And so I love, I love this question and I think integrity is really critical. And it's interesting, I've spent a tremendous amount of time thinking about integrity because I've thought a lot about politics lately. And, you know, it's the one thing that I feel could really differentiate and separate leaders in the 21st century from pretenders. And that is you make very clear who you are, what you're for, and why you're for those things. And just making those things really clear would go a long ways in establishing yourself as a genuine true leader. And so everybody has to define what integrity is for them. But I think this is really, really important and is absolutely a necessary part about good leadership.

Now, the thing that makes what your question - how you stage your question so interesting for me is this word of application. You know, this word apply. It's like super easy to get out of, you know, a little note card, or however you like to take notes and write down three or four cute little words that make up this is my integrity, and it sounds good and it looks good. And if someone asks you, "What is your integrity?" You know, you could like roll through it. It's kind of like a organization's cultural document, right? It's like really easy to create one. What's really hard is to apply it and to live by it. And so, you know, when you say, "How do you practically apply integrity to leadership?" I don't know how to answer that question, honestly. Like it's really good, but here's a stab at it.

Three Ways to Evaluate Your Integrity

First of all, I think going back to self-awareness and like, self-evaluation - something I appreciate about you, and frankly, there's just really, a couple of people, is that you'll give me feedback, right? And you'll say, "Hey, this was really good", but you also say, "Hey, that was tough". Or, you know, "Next time you might consider doing it this way." You'll push back, right? Like you'll give me feedback and it's really critical, but I think most leaders might be in a similar situation where they're not always naturally getting a lot of feedback. And so the reason I bring that up is because when you think of how do you imply your integrity, if you're not self-aware and you're not constantly evaluating your own leadership, then how do you know if you're applying these principles of integrity that you've defined for your leadership? How do you know if you're actually applying them? There's a couple of ways. One is being self-aware and evaluating your own character and your own integrity. Two is surrounding yourself with people who certainly believe in you, affirm you, support your leadership, but more than anything, will look you in the face and say, "That sucks You, really shouldn't do that." Or challenge you, right? And then third, it's a fruit of your integrity. What is the fruit of your integrity? And so other than being in - defining your integrity and intentionally trying to apply it in every level of your leadership, I'm not for sure how you apply it.

But I do think one way to know if you are applying it is that those three steps, you know, evaluating your own integrity and the progress you're making to surround yourself with people who will be honest with you, even when it hurts. And then three, what is the fruit of your integrity in your life, in your marriage, in your children's lives, in your friend group, you know, in your leadership team, in the culture that you're trying to create and strive in your organization and your client relationships? Like, are your client relationships toxic and always going off the guard rails, or do you see the fruits of like clear convictional integrity and all these different areas of your life? And so I think, you know, I don't know if that makes sense, but those are the ideas and the thoughts that come to my mind when you said integrity applied, which I think is really an interesting way of understanding it.

Annie Gilbert: I do think integrity is one of those things that is really abstract. And so I love what you said about looking at the fruit. Sometimes that's the only way to evaluate if this is being applied is what is the result? What is the outcome? So I love that picture of, you know, that's how you can measure something like integrity is by the fruit. Something that comes to mind for me for integrity, when I think of that word, is just consistency. And so along the same lines of what you said about being intentional. I think it means those daily deposits, first of all, at the very beginning, early on, establishing what are my non-negotiables and where am I going to refuse to cross the line? We always think that we never will compromise, but there's opportunities that come up and it just becomes easy sometimes to consider that. So I think establishing that firmly in the beginning, but then those daily deposits of consistency and living it out and thinking about why I'm making the decisions I'm making and how do they point back to my integrity. So I am exactly in line with everything that you talked about

Being Anchored in Something is Really Attractive

Kade Wilcox: Yeah. I think one more word of encouragement here before we move on to our last question is, you want to talk about an opportunity to be different in the 21st century? Be man or a woman of integrity, of strong principled, clear, you know, moral principles, right? What an amazing opportunity we have to be anchors to people, right? Like to be this lighthouse for a culture and for society that is just being tossed to and fro right now, you know, by all kinds of all kinds of different things. But you - I mean - I just, man, you want to talk about an opportunity, be a man or a woman who has thought through what your principles are, has tried and true integrity because you've been tested by fire, and you will have an opportunity to lead because you will be different. You will be different and people will be attracted to you because you are steady and stable and not perfect, but you are anchored at a time where so many things are completely unhinged.

Something that is anchored is really attractive right now. And that's really what good leaders do, right? They create strength, and clarity, and hope, and direction for people. So that's just, man, I guess we can talk about that for a long time. I love this last question so fire away.

Annie Gilbert: All right. So I feel like there were a lot of different expressions of the same sort of vein of this next question. People said sense of purpose, inspiring, decisiveness, passionate, and curiosity. And so I think that the theme here is about vision. So what helps you cast vision for the people you lead and then how does grit or resilience contribute to staying on track with that vision?

Kade Wilcox: Hmm. Do you want to talk about a softball? Listen, people, if you ever go on in an interview, have someone like Annie who knows your strengths and knows where you love spending your time and have them just serve up that softball question.

What It Looks Like To Cast Vision

Okay. Here's what I think of the first part of your question. First of all, vision has come easy to me my entire life. Like literally my entire life. Futuristic is obviously one of my top five CliftonStrengths, and I can see expressions of that as far back as my memory will go. And I think those who know me the best, the longest, could attest to that - that I've just always been vision-oriented and into the future, right? I'm futuristic. And so I think the thing that helps me first is I it's literally how God created me.

Like I can just see things. I can just see them, and that sounds super silly, but I just think it's a real strength. But one thing I do to nurture that, you know, coming to the practical, and this is, I think, something people can do whether they have futuristic in their top five or not, is like put yourself in a position to nurture that component of your leadership, right? So like everyone is inspired in different ways. And so here's some ways that I love nurturing this component of my leadership that helps me create vision. I love to travel. So that has a huge impact on my ability to create vision. I mean, even just practically, like while I'm recording this right now, I'm in Arthur, Nebraska, population 80. My wife's grandmother lives here.

It's in the sandhills of Nebraska, one of the most beautiful places on earth. It's remote. It is quiet. It is pristine. It is beautiful. I'm on a run this morning for 50 minutes and I wish someone could just run beside me and jot down, you know, all these things going through my brain. But those kind of - doing those kinds of things puts me in a place that helps me create vision, right? So when you think about how vision is so critical even the scriptures talk about where there's a lack of vision, people will perish. And it's so true. Like if you look at it in a family unit, if you look out at a school, if you look out on a community level, if you look out at a level of government, if you look at it in a small or large organization, nonprofit, or for-profit, it doesn't matter, like every level of society where there is no vision, people will suffer.

And so when you talk about what helps you cast the vision? One is nurturing that strength, nurturing that doubt, that ability to create vision, and to think about vision, and to understand vision. And so doing things that help you be in that frame of mind. So for me, it's traveling, it's running. You know, running is so powerful because you're just alone in your head. And so you have to think about something. And so just creating these environments where you're nurturing this ability to create vision.

But then another thing is understanding how critical it is; understanding how powerful a healthy, meaningful, robust vision is for people. And so if you are a leader, then the essence, the definition, the entire purpose behind what you're doing is for the good of people, right? And so if not having a vision is bad for people and having a vision is good for people, and you're a leader, then you have to have a vision.

And so I think the other part of that first part of the question is understanding how critical it is and understanding what fuels that for you and what puts you in that frame of mind, you know, that can create vision. So when you say what helps you cast the vision, it's that it's understanding, you know, how I create it. And so putting myself in position to do that and for a leader, that means not being overly busy which is a challenging thing because most leaders tend to gravitate towards busy-ness because there's some false affirmation about busy-ness that actually thinks you're doing something. When in reality, that's not necessarily the case. So you have to have space for vision. You have to know where are you at your best so you can create vision.

But then yeah, the other part of it is really acknowledging and always remember, you know, that vision in many respects is one of the core elements, or lifeblood, you know, to what's good for your people, but the people that you've been entrusted with to lead, and you are a steward over that leadership. And so I think those are the things that help me cast vision.

Does Grit and Resilience Matter?

And then I can't wait to hear your feedback on all this, but you know, your second part of the question, how does grit and resilience contribute to staying on track with vision? I mean, I think it's everything. I mean, honestly, even someone who has no vision for their life, or their family unit, or school, or whatever it is they're doing, even people, you know, who aren't prone to being futuristic or having vision, you know, can come up with ideas related to that, right?

Like it's fairly easy to come up with. You know, if someone says, "Where do you want to be in five years?" You know, it's fairly easy to come up with two or three things that sounds really great and sounded like you would really enjoy them. What's really hard is to actually do those things. Like being a doer is way harder than being a dreamer. It's easy to say, of course, I want to run a marathon or I want to lose that weight, or I want to be out of debt, or I want to buy that car, or I want to start that business, or I want to run for that office. All that stuff is easy. Frankly, anyone can say anything, but when you talk about resilience and when you talk about grit, to me, it is one of those singular factors that differentiate you from other people, you know, because everyone can talk, very few people do.

And so I think the ability to persevere, the ability to demonstrate resilience, the ability to have grit, oftentimes is the difference between success and failure, you know? Because everybody related to their vision or their aspiration or whatever they're trying to accomplish is going to experience resistance. You know, experience setback, experience people who think they're crazy. I mean, I got back from my run this morning and I - there's a section of land. It's probably several sections. And as this epic farmhouse on it, huge old hay barn, it's out in the middle of nowhere and I got home and I'm like, "Hey, babe, when we're like 50, and the kids are out of home. Like we should buy that." It's like, we go live here in the spring and summer when the weather's so nice. And it's like, you know, she thinks I'm crazy, you know? But anyway, so I could give you a million examples, but I think that is the difference between people who actually accomplish their goals and objectives and their vision and people who don't. So when you say, you know, how does grit and resilience contribute to staying on track with vision? I think it's like almost everything. Clearly, I can talk about vision and stuff all day long. I love that stuff. It's where I feel like, at least I'm at my best. I mean, that might be wrong, but my point is, I love it. And so what are your thoughts related to vision and that whole topic.

Annie Gilbert: Yeah. So this question is kind of, for me, the reverse of the first question for you, because futuristic for me is dead last in my list of strengths. And I think the second part of that question really speaks to your focus in staying focused on the goal and seeing it through and being a doer. So those things are not things that come really naturally to me, but I love what you said about really it's about nurturing, what inspires you and that's how you find your vision and your purpose. And so even if you don't have these strengths, that seem like it's easy for you to create vision, you've just got to find what it is that inspires you and really gives you that drive because we all have something, right, that does that. And so I think what you said about people who don't think that they have vision, they really do. They've just got to figure out what it is and what brings that out in them. And I think, you know, creating space, like you talked about, really just provides that motivation and ideas about what they want. We all want something from life and from, you know, our careers and the things that we're pursuing. And so we've just got to identify it so that we can go hard after it.

Kade Wilcox: Yeah. That's really good. Yeah. Well, this was good. I think that's a good wrap on this one. I really appreciate you doing this and I feel like my last comment to those listening would be so much of this boils down to intentionality and creating space to like think through these things and figure out what it means for you. You know, we shared a little bit about what it looks like for us and our organization and in my own leadership, but the biggest piece of advice I could give is just, what does it look like for your leadership? Who are you and how do you tick? But it boils down to being intentional and acknowledging that it's really, really critical. So Annie, thanks for teaming up with me on the podcast and for those listening, as always, thanks for listening to The Primitive Podcast. We'll see you next week.

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