The Primitive Podcast: Developing and Mentoring Leaders

Posted by Kade Wilcox | June 7, 2021

developing leaders

Every high-performing company knows at least one fundamental rule: 

Profitability and productivity boil down to how thoughtfully you invest in your people. 

In this episode, Kade chats with Primitive’s Chief of Staff, Annie, to chat about how to intentionally invest in creating leaders within your company, and the one thing you have to know to ask for if you’re the one being led.


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

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, the equivalent of a chief of staff in 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.


Welcome to The Primitive Podcast. I'm joined again this week by our chief of staff, Annie Gilbert. Annie, thank you so much for being willing to do this as we kind of talk through a couple of different issues related to leadership. So thanks for joining me.

Annie Gilbert: Yeah, I'm excited to do it.

Kade Wilcox: So maybe tell everyone kind of what we're going to talk about this week and we'll jump in.

Annie Gilbert: Okay. So our topic this time is developing leaders and mentoring others. And so we tend to talk a lot about ways leaders engage in self-development and growing. Most leaders are really motivated to do that and do it well, but I think it gets a little tougher and there's some gray area whenever we are talking about developing other leaders. We have control when it's our own development, but we don't have as much control when we're trying to grow others and give them opportunities. So that's what we're going to talk about this time.

The Importance of Investing in Talent and Development

So the first question we'll dive into is how important is it to invest in the development of the entry-level roles and rising stars of your organization?

Kade Wilcox: I think the first thing I think of when I think about this, really this topic that we're discussing today, in the first place is really how hard leadership development is. I honestly feel inept and incapable, and oftentimes struggle at developing my own leadership, you know, being accountable for my own growth and my own development. And so it's a bit intimidating, honestly, when you start thinking about, for me specifically, the responsibility I have for the development of our leaders and the responsibility that our leaders and myself have for the development of our teammates, and things like that. And so this is really hard and I don't honestly feel like I have any answers. But I'll share what I can think of when you say how important it is to invest. Like it's critical. Like you're only ever going to be — you know, an organization is only ever going to be as good as the weakest individual on its team.


And something you shared a couple of weeks back about culture is like your, you know, your culture is only good at that thing that you tolerate — that, you know, that thing you tolerate the most. So, you know, you look at a teammate or you look at an issue in your organization, you tolerate it because it's easier to tolerate, you know, than to fix or to address or to, you know, to move on from, and really your organization isn't any different when you think about like leadership development, right? Like we're all leaders in some way, we're all leading something. Even if it's like, you know, the most minimal thing in an organization on some level, we're all leading something. And so if you're not striving or doing something to elevate everyone's leadership, then you're not just impacting that individual negatively, you're impacting the very organization that you're trying to help succeed and to lead forward.


And so that's — that, I think, is among, you know, one of the most critical reasons why develop — leadership development for everyone is critical. Look, regardless if you're the CEO, you know, or whatever in your organization may be considered kind of, you know, entry-level or, you know, bottom of the barrel or whatever other terrible analogy there is for a person that might be deemed, you know, that entry, entry level role. And so I think it's just, it's critical. I mean, it's essential. Now how you do that and the different things that exist in order to facilitate that growth and to be intentional about it — I know we're about to talk about that — but that's, to me, where it gets, you know, really difficult. 

The Risk of Not Investing Is Too High

I think the second thing I think of in terms of its criticalness is, outside of what I just shared, which is being, you know, everything for your organization to continue to progress and to accomplish your goals and objectives is how hard it is to recruit new employees.

You know, like I don't know what the cost to Primitive is. Every time we lose a new employee or like to lose a teammate and have to replace that. But it's a lot, you know? It's a lot of time and energy on you and others who recruit and interview. It's a drag on the teammates to have to pick up that slack, you know, to replace that person who's left. You know, it's a ton of time to onboard a new team member and help them, you know, get situated and settled in with their client and with the team and with our culture. And so, you know, the reason I bring that up is because when you think of developing your people, like, you know, I don't know, I'm sure there are two or three things that are really important to people when it comes to employment and their vocation, their work.


But I feel like 10 years in, one thing that we've for sure seen is that, you know, they want to grow, you know? They want to know, "What does my future look like?" Like, “Where is this going?” Like, “What opportunities do I have here?” You know? “And how can I get better?” And, you know, everyone expresses that in different ways and everybody's kind of motor, so to speak, runs at different speeds. But it's natural I think as people, as humans, to want to know that and to want to get better. And so if you're not doing that in your organization, if you're not investing in talent, if you're not investing in development — and there's all kinds of ways to do that, right? — but if you're not doing it, I feel like people will go somewhere where they can get that. And it has a huge negative impact on your organization. So I think those two things immediately come to mind when you think about how critical it is to really invest in the development and leadership development of everyone in your organization, regardless of what the role is.

Annie Gilbert: I agree with that. I think about my — one of my top strengths is developer. And so it's about this. It's about helping people grow and pouring into people. I think what I've found as the biggest challenge of that is being sure that I'm asking the right questions of those people. Because sometimes you can identify talent and potential, but if that person does not have the desire to grow in that direction and the drive and the motivation it's really a waste of time and energy to try to want it for them. And so that's what I found to be true. And sort of one of the basements of that developer strength is wasting time on low potential people. Not low potential because they can't grow but low potential because they don't really want to. And so I think that in addition to identifying the talent and the potential that's there you have to really get to know what matters to that person, that individual — how do they want to grow — and then determine the logical path for growth for them based on all of those things together.

Kade Wilcox: Hmm. Yeah, that's really good. I mean, let's jump in. I feel like the second and third questions are really simple. Not simple, they're the opposite of simple, in my opinion. But they're similar in nature. And so let's talk now about how we try to do that at Primitive. So there's a couple of things that immediately come to my mind and then you can fill in the gaps and, and share some of your thoughts as well. The first thing I think of is my own responsibility in contributing to leadership development. And this one's really hard for me. Like I think about it all all the time, because I feel so inadequate at it. You know, you read leadership gurus, like, you know, John Maxwell or, you know, like Craig Groeschel and all these other really significant leaders in, you know, in the leadership development niche — books, podcasts, things like that. And they have such a, like, an intentional system and process of developing leaders.


And they talk about it in such a way that just seems so natural, and not scripted in a negative way, but like very scripted. And it's like, you know, very, very organized. And I don't have that at all. Like when I think of my responsibility to lead you or Jess or Heather, or, you know, whoever, I don't have any roadmap whatsoever about helping you develop as a leader. And so I question that a lot. Like, how do you make leadership development so intentional that there is really a process or a program, for lack of better word, for that development? So I feel really weak there and I don't think I excel at it in that way. So then what does it look like? Well, it's a lot less formal than that, but I do think it's important and I try very hard at doing this.

Modeling Good Leadership

And there's a couple of things that immediately come to mind. One is I try to model it. Like the first thing that I tried to do in terms of leadership development is model at least what I hope and what I aspire good leadership to look like. It doesn't mean it's complete, or it doesn't mean it's perfect, for sure, but I try to go, okay, what does good leaders — like, what do I think good leadership looks like? What, you know, what is good leadership in such a way that helps other people thrive and succeed and accomplish their own goals and objectives? What are those things? That's what I want to be. And so I aspire, you know, to model leadership in a way that helps everyone grow in their leadership, because hopefully, as imperfectly as it may be, trying to model good leadership.

So the first thing I try to do related to leadership development for those I'm entrusted with, just in relationship to, is model it like, real practically. Like don't ask someone to work hard if you don't work hard. Don't ask someone to be prepared for a meeting if you don't show up prepared for a meeting. Don't ask someone to really buy in and believe the core values of your organizational culture if you yourself are not bought in to those core beliefs and values of your culture. And so I really, really want to model the — you know, for our team and for our organization, what I hope leadership looks like in our culture. So that's the first thing.


And then the only other thing I can think of like real practically speaking that I try to do really hard, is be accessible. Like, I don't know all the answers to good leadership. I don't know what you need to be a good leader. I don't know what Jess needs. I don't know what Tim needs, you know, whatever, whoever it is. I don't know exactly what that looks like, but I do know that I want to be accessible to have those conversations, to provide feedback when possible, you know, to be present; just to be present for you and with you, so that as you're going through your own leadership journey, I can even know what you might need or what you may desire or what you would ask for, you know, in order for you to accomplish your own leadership journey. And so those are the only two things I can think of. Model it, which I try to, and then to just be accessible to those that you're leading so that you can be in relationship with them, be present for them as they're going on in their own journey.


And then I think the third thing that comes to my mind, and it's really closely related to the second, is just doing everything possible when aware of a need to meet that need. So if you ever came to me and you said, "Hey, there's this course. I would like to take it for part of my, you know, my ongoing counseling continued education." Absolutely. Like we're going to go all in on that thing, right? And so just being willing, you know, to hear someone who you're leading with and working with, say, “I have this need,” or “I have this desire,” — hearing it, and then doing everything to fulfill that if you have the means. And so that's how I try to do it, but I have to be honest, I find myself all the time wishing there was like a script, you know, a plan, a model, a method to say, this is how we do leadership development. So before we get into how we do this for the rest of our team, because we do have some structure and we do have some things that we do to help that, what are some of your general thoughts on that and what, what kind of feedback or pushback would you give there?

Providing a Psychologically Safe Space

Annie Gilbert: I think that's really great. Just describing it in that way. I — what I wrote down and just wanted to expand on a little bit is something you alluded to, as far as anticipating needs. Like, we don't necessarily know what an individual needs or wants if they don't express that. And so I think our role in that becomes let's create psychological safety. Let's encourage people and consistently remind people that it's safe to ask for what they need, whether that's a course they want to take, a conference they want to go to, whatever that looks like. Because we really depend on people to know what they need and to have the freedom to ask for it. So I think our job then becomes, okay, we're going to provide the opportunity or many opportunities for growth, but then we're going to let people select the ones that matter the most to them that, you know, make the most sense for them. I think something that you mentioned too about just investing in it. You know, setting aside an intentional budget for growth and development, which is something we're, you know, being so much more intentional about.

Kade Wilcox: Yeah, that's really good. You know, man, you created a thought in my mind. My encouragement — let's say you're listening to this podcast and you're being led. Like you're a part of a group or whatever, and you're being led and you want to be developed. And you know, this word is always interesting what it means to different people, but you want to be mentored. I think my biggest encouragement to someone who has that desire — and I have that desire for me. Like there, I mean, there are a countless number of people that I admire that I respect that I would love to learn from. I mean, the whole reason The Primitive Podcast exists in the first place is because it was a great platform, you know, to be introduced to, and to ask questions of, people you admire, right? And it's that right there. It's identify what you really want.


Like, what is it you want to be developed in? Like, specifically, not like, oh, “I just want to be a better leader.” Well, that doesn't mean anything. Like that — there's no, there's no clarity to that at all. It's like, you know, a better thing would be, is like, “I want to be better at managing meetings. I want to learn from you on how to manage meetings.” Or, “I'm not entirely sure how to define my integrity and my principles. Can you help me think through what yours are and help me think through what mine is?” Or, “I don't know how to create a vision script for our organization,” or “I don't know how to hire,” — whatever it is, right? If you want to be developed and you expect the leaders leading you to do that — I think that's a fair expectation — but I think in return you should be able to articulate clearly what it is you actually want.


Like, you know, if any came to me and said, "Hey, Kade, I don't feel like you're doing a very good job developing my leadership and I'm disappointed by that. Like, that's really why I wanted this role.” You know, I would be like, "Man, I'm sorry." But then my very next question would be, "How can I help you? Like, what is it you specifically want to grow in?” And so if you're listening to this and you have that desire for development, then I would just encourage you to be very specific, as like, what do you actually want to grow in? And then that's going to help someone, you know, help you be successful when you have clarity and your own mind where you actually want to grow. Does that make sense? I felt like that was really wordy, but I think it's important.

Annie Gilbert: Absolutely. I think it's very clear and important as well. And I — that was another thought that came up for me, something that you mentioned, like there's always someone that's going to be more advanced than me that I can go to and learn from. And at the same time, there's always going to be someone that is, you know, further behind me, whether in their career or their growth or wherever they want to go to. So there's never a shortage of people to learn from and then people to turn around and teach. So I think sometimes, like we talked about earlier, we get busy and we don't intentionally take the time to teach others. But if we do that in our organizations and we neglect this, then we're not going to have leaders who are being raised up and developed to then take on more responsibility and keep the organization in a good and healthy place. So going back to that initial question, it — that's why it's so important.

Creating Space to Connect

Kade Wilcox: Yeah, it's really good. Maybe we can shift to talking about how we try to do this for our team. So I think there are some things over the last 18 to 24 months that we've implemented as an organization that really facilitate growth for our teammates. Again, not perfectly. And we have a long way to go. But I feel like we have a real clear structure in place that helps facilitate it. And here's some things that immediately come to my mind, you know, for the leaders out there listening who sit in a similar seat as mine. Here's some things we've done that I feel like it made a huge impact on our organization. And then, Annie, you can fill in the gaps and maybe speak into it from your perspective.


I think there's a couple of things just on an organizational level that the leaders do, and it's a couple of things. First of all, we facilitate opportunities to be together. So when you think about learning from people, when you think about being developed as a leader, when you think about being mentored, a lot of that comes down to presence. Like, are you together? Are you even being present together? And so I think we have a really good cadence of connectivity you know, between our all-team meetings, between our annual all-team that we have where, when possible, we do that in person. We, you know, we have a lot of like community-oriented things where we'll do happy hours. We have our community cohorts that you facilitate. We'll do our donut meetup. Like there's things that we do as an organization that facilitate these normal cadences of just being connected.


And so I think that's a huge component. That's very systematic. Like we have normal rhythms there that facilitate being present that facilitate growing from each other, learning from each other, talking about culture and facilitating these learning opportunities. And so it's like, that's something that we do really well and absolutely contributes to the overall development of our teammates and our organization. I think another thing that's really practical that you and others have done a great job facilitating, particularly our direct supervisors, people who are leading people, is we have annual reviews where they're very specific, very intentional, very helpful opportunity for a teammate, for an employee to get feedback on the progress of their work. And it comes from multiple layers, which I love. Like it's not just one person on their team or not just from their supervisor. So you get feedback from your supervisor, you get feedback, collected feedback, from the people that you most — you'll work most consistently with.


And then you get to do a self-assessment, which I think is really fair because I've been a part of some evaluations in the past where it's like, first of all, it's anonymous. I despise that. I think anonymous employee reviews are totally unfair and a total load of crap and don't do anyone any good. And so ours are not and I really appreciate and value that. But it's coming from multiple viewpoints and I think that's really important. And then there's really clear action-oriented items in those reviews that shows them not only where they are and how they can grow, but where they can go from here, right? And we've kind of learned that the hard way; not, in the past, been really good at creating a clear vision of like, "Hey, if you want to be here a long time, you can do that. And here's how you can grow in your role you have now. Here's what your next role could look like." And it's not like we're promising things because every organization is, you know, kind of only has the knowledge of where they're going in that moment. But casting that vision and spelling out for them, like, "Hey, here's a roadmap for really what your growth could look like and your career trajectory could look like at our organization." And that kind of clarity where they fit and where they can see themselves in a few years, to me, is part of their development, right? It's helping them see here's who I have to continue to become to not only excel in my current role, but also who I have to become, you know, moving forward. So those are the things I think we do really well and are growing in and getting better at every time we do them, and every year as we think about how to do it.


But what did I miss? And, like, what do you think from your experience? Because you've really helped architect this whole thing and certainly help manage it and make sure stuff gets done.

Annie Gilbert: Those are great examples that I really hadn't even thought of. So I'm glad you shared those. Some other ones that did come to mind for me are really just the opportunities to work across teams. In fact, we have two questions on our review that say, you know — that asks how well did this person work across teams when they had the opportunity and did this person go above and beyond? And those are real indicators for us of, okay, if someone constantly likes looking for ways to step outside their comfort zone and maybe their norm and go the extra mile, like that's someone who's ready to move up to what's next. And so I think that is huge just to create those opportunities for people. We've brought in people to do training for our copywriters. We've started doing stand-up design meetings so that these designers who are working on all different kinds of things can share what they're working on and learn from each other and get excited about what they're getting to do.


So that's been really good. Bringing in people for our Primbound in January, like Bob Goff and Dan Mall, was just huge. It was inspiring. It was just investing in bringing someone that has a different perspective than, you know — they hear from us all the time. And so sometimes that just gets us in a little bit of a rush. So just having a fresh perspective and someone coming in and answering questions and talking about you know, how to grow is important, I think. And providing accountability. I think that's the other thing is that we're just checking in regularly enough and giving that feedback, even if it's hard, even if it's constructive, but consistently pointing things out and we don't wait until the annual review and then tell them for the past year what we wish they would have done differently. It's immediate feedback so that they can apply it and so that they can grow now and not in six months. So I think we've gotten better at that.


And then finally, the internship program is huge from what it started out as, which was really just sort of maintaining people who came in and kind of worked on things every once in a while, to developing into this mutually beneficial program where we are not providing only this amazing experience for interns who want to learn more about, you know, whatever role they're in, but the mentors — we have a mentor program, too — who have the ability to practice and kind of test out some of their own leadership skills, and managing someone, and they read through a book together, and there's accountability there. And so the internship program has become this opportunity. Like, "Hey, you want to be a leader? Be a mentor and get a taste of what it's going to be like on this level." And then we can kind of look at, are you ready for the next level of responsibility and, you know, managing people because that's a big part of leadership. So those are some ideas that came to mind for me.

“The single greatest thing…”

Kade Wilcox: Yeah, it's really good. And you know, the last thing I would share on this before we wrap up this episode — the single greatest thing that we've done as an organization to really focus on this is hiring for Annie's role. So as I've said multiple times, Annie's our chief of staff and she has a lot of responsibilities, but her responsibility is people. And, you know, she doesn't have operational or client responsibility. She has no financial responsibility in terms of revenue or anything like that. She doesn't have any responsibilities really outside of people and culture. And in committing to this role and leaving that role alone — I mean, I think some people strive to do this on some level, but then they end up adding on two or three other hats and, so, it gets watered down and they can't focus on it.


And certainly you do a lot of work, you have a lot of responsibilities, but all that energy and all your creativity and all your focus is primarily on, you know, our people and culture. And what that allows our organization to do is to never forget what we're really about. And that's our people. And if you're really about your people, then you're going to do what's best for them. And what's best for them is to help them grow and to nurture them and to lead them in the direction they want to go for their own life and their own vocation. And so the single greatest thing we've ever done as an organization is hire Annie and create this role. And so all these things we've shared are very practical. 


And I think, you know, that they're very likely to spark ideas and people who are listening to this episode for their own organization. You know, but if you're an owner or a C-suite type person listening to this then the things that you could do that would serve your people the best - more than you'll ever be able to do on your own. It'll serve them better than any amount of money you will ever be able to pay them, or any amount of benefits you'll be able to provide them — is to hire someone like Annie whose role is to look at your organization critically in terms of how we are doing, or how we are not doing. And she's really our pulse. She's our conscience when it comes to, are we really doing what we say is important to us? Or are we just doing it in lip service? And leaders out there, if you're anything like me, I fundamentally believe everything I'm saying at the very core of my being, but where I struggle would be in the implementation and the support of that conviction. So if you were a leader and you, too, share in my conviction that your people are the most important thing you could ever have, but you don't have the ability, like I don't have the ability, to implement these things and to think about them critically and to do them well, I would never do this on my own.


I would say it was important, but I would have no framework and I don't have the leadership skill or the aptitude to truly create things that nurture people in the way they need. Then you have to find someone who can do that, and that is the single greatest gift you could ever give your organization. And so, man, I could — well, we have. We've thought — had whole episodes where we talked about the role of a chief of staff. And I have other videos where I've shared why I think it is so critical. But when you think about our team and developing leaders it is, it has been and will continue to be a huge way that we, though imperfectly, continue down this journey of really trying to do what's best for our people, which includes leadership development.


So I'm super grateful that, you know, the — Annie Gilbert, who's on this podcast, belongs to Primitive and Primitive belongs to her. And not to somebody else's organization. But my — yeah, I would highly encourage you to go find your own Annie because it will transform the way that you see your culture and you focus on it for the good of all people. So it really does work. What do you think, Annie? Should we stop there?

Annie Gilbert: I think that's good.

Kade Wilcox: All right. Thanks for listening to The Primitive Podcast. I really appreciate it. I hope this content and you know, I hope it brings you value. I know we certainly, our team certainly enjoys, you know, creating these podcasts and trying to contribute, you know, in this way. And so for those who listen consistently, thank you. We really appreciate it. If you're a new guest, go back; we've had some remarkable people on the podcast I'm confident you could learn from. So thanks for tuning into this week's episode and we'll look forward to connecting with you next time.

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