Crossing the Threshold Leadership Podcast
Life and leadership are full of threshold moments, those spaces between what was and what’s next, when we’re ready to move forward and want to do it well.
Crossing the Threshold helps mission-driven small business and nonprofit leaders navigate what’s next in life and leadership—without losing what matters most.
Through honest, practical conversations drawn from their own journeys, James and J.C. guide you from knowing what matters to actually living it.
Crossing the Threshold Leadership Podcast
Nobody Told Me Leadership Would Be Like This
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Leadership looks a lot different from the stage than it does on a random Tuesday afternoon.
Most of us step into leadership thinking about vision, impact, influence, and changing things for the better. Nobody tells you about the repetition, the hard conversations, the decisions people may not like, or the weight you sometimes have to carry quietly.
In this episode, James Wilson Jr. and JC Fowler talk about the side of leadership nobody really prepares you for — and why some of the hardest parts may not mean you’re doing it wrong. They may simply mean you’re leading.
IN THIS EPISODE:
- Why great leadership is often surprisingly ordinary
- The power of repeating what matters most
- Why doing the right thing doesn’t guarantee everyone will be happy
- Where people-pleasing and leadership eventually collide
- How to weigh feedback without letting every opinion define you
- Why leaders need the right people and places to process what they’re carrying
CROSSING THE THRESHOLD THIS WEEK:
Ask yourself:
- Where do I need to embrace the boring?
- What part of leadership have I been treating as evidence that I’m doing something wrong — when it may simply be part of carrying responsibility?
- What am I carrying that I need help with?
Leadership does not mean carrying everything alone.
LEADERSHIP MOMENTUM ACCELERATOR
Sometimes the hardest part of leadership is being too close to everything you’re carrying to see what actually needs your attention.
The Leadership Momentum Accelerator gives you two coaches focused on you for 70 minutes, a personalized roadmap, and 30 days of continued support and accountability.
Learn more:
→ https://www.cttleadership.com/leadership-momentum-accelerator
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Threshold Thoughts:
→ https://cttleadership.kit.com/thresholdthoughts
Crossing the Threshold Leadership Podcast
Real life. Real leadership. One threshold at a time.
You don’t have to stay stuck leading from reaction. This week, take one honest step toward the leadership, team, and life you’re called to build.
Subscribe and share this episode with a mission-driven leader who needs language for the weight they’re carrying.
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The Dirty Jobs Leaders Do
SPEAKER_01What's up, y'all? This is James Wilson Jr. I'm here with my man JC Fowler. Um, we are jumping back into crossing the threshold leadership. And I want to ask you a question, JC, as we step into this. What is the least glamorous thing you've ever had to do because you were the leader?
SPEAKER_00Dude, we started this meeting just a fledgling couple of us, four to six people, and it's a 12-step group. And uh, we want to bring something different to the area, a bunch of young guys. It was a cool time. Our dream was that it would grow. Guess what? It grew amazing. We can't take credit for it. It's a total team effort. And uh, you know, people at 12-step groups like smoking cigarettes. Okay. Well, we were at a church, and which was first of all, you know, between you and I, it was uh no smoking. Uh, but that didn't that didn't stop these folks. Um, and uh yeah, man, every night after the meeting, I would pick up about 50 cigarette butts. Yeah, yeah, that's leadership, right? That's leadership, man. And I I remember thinking, I this is not what I pictured.
SPEAKER_01Yeah, that's good. What about you? What about you? The one the one that just keeps uh blowing my mind is so we were in Norfolk, Virginia, and where you are in Norfolk, uh, I believe it's because of the sea level and all these other things that uh they've got these things called water bugs. And water bugs are just another word for cockroaches. Um, and so what's interesting, man, is we've just launched this campus building campaign. We've got all the stuff, we've got I've got staff, we got this, all of these great things happening, and I'm the leader of these this team and et cetera. And uh man, we we get in the hallway, and leadership for me was um everyone was terrified to pick up the dead water bug. So I'm now my leadership for me was a Sunday morning, um, swiftly grabbing the uh cockroach on the floor, making sure nobody had to deal with it, smashing it, all of the nasty sounds and throwing it away. But it was like that was uh I I I didn't know when I signed up to be a leader that I was also a bug killer uh and a cockroach cleaner.
SPEAKER_00So, anyways, all I heard, all I heard was that if you call a cockroach a water bug, it sounds way less threatening.
SPEAKER_01That's it. So it's all about language, right? It's it's it's all about language. Oh man. So what we know is that leadership looks uh a lot different from the stage than it does on a random Tuesday afternoon or after Sunday afternoon or after a meeting. It looks different. So most of us enter leadership thinking about vision, impact, influence, and changing things, making things better. Nobody really tells you about the weird middle, making decisions uh that will impact people, things that they won't like, carrying information you can't always share, repeating yourself for the fifth time or the seventh time, having hard conversations with people you actually love or people you just met, and sometimes wondering if you know what you're doing at all. Like, do I even have a clue of how this is all working out? So,
Why Great Leadership Feels Boring
SPEAKER_01today we're gonna talk about a side of leadership that nobody really prepares you for. I was not prepared for it.
SPEAKER_00Yeah, there I think three movements we'll walk through. The first one being this uh a lot of leadership is ordinary, or we could say boring. Yeah, great leaders are boring in a lot of ways. Leadership is follow-up, it's repetition, conversations, checking details, explaining the vision. Again, again, again. We talk about leaders are the CRO, the chief reminding officer. Oh man, come on. Vision leaks, organizations drift. It's about resolving misunderstandings that keep coming up, sitting with people and doing the things nobody applauds. Yeah. I just like before we even get into that kind of the necessity and fruitfulness of repetition. Yeah, what did you picture leadership would look like?
SPEAKER_01So crazy, man. I always had this vision. I've told my wife this. Um I grew up in Philly, so I've always had this vision of being downtown um in uh a suit of some sort in this high-powered, in this, you know, penthouse of an office overlooking the city. And man, that I would have a secretary that buzzes me in, or you know, when I somebody wants an appointment with you, hey, Mr. Wilson, or Dr. Wilson, depending on my my speed. And I just had this vision of a leader being in this high-powered environment, making the cool decisions and traveling to the coolest places, having you know, on stages. That that's just that was my vision. Um, and the challenge was I just realized really quickly that um I don't like heights. So being in the penthouse, being in the penthouse, the top floor is like, yeah, that would kind of make me anxious. Um, I also realized that I don't want anybody buzzing me in and out. I also realized real talk, man, I don't actually like being behind a desk all day. Like I really don't, I actually prefer to be out and about. Like what the best setting for me has been lunch meetings. I enjoy being out and talking to people. So yeah, man, it it is uh, but that was my vision of leadership early on. Like lunch meetings and Thai food. That's it, man. That's that's that's that's real leadership, man. Lunch meeting and Thai food. Come on.
SPEAKER_00I think I pictured mine, it was way less more simple. I'm liking the vision though. I just pictured a stage with thousands of people and me speaking and people cheering and applauding, and and then maybe me signing books afterwards, you know. Like, like now, you know what I discovered is I'm happy to get on a stage and do a keynote, like, and that will bring me real joy and energy. But to me, it's actually not even a necessary ingredient. No, like to actually be with people and and help shape some of the shape some of the initiatives behind the scenes is actually where I feel like the greatest impact happens. Yeah. Um, so yeah, I think keynotes like that could be part of a recipe for creating that momentum. But I'm like, huh, my vision for what it was and what it is now. Yeah, it's just it just changed so much.
SPEAKER_01It just changes.
SPEAKER_00Yeah, go for it. What do you think great leaders do repeatedly? Period. Question mark.
SPEAKER_01This is probably gonna be like a left field one. Um but I think that leaders do this repeatedly, they say the words that matter most. Um, and what I mean by that is I've found that good leaders are often the ones that say thank you the most. Um the ones that say I'm sorry the most. Um, they are the ones to let you know, hey, I care the most. Like good leaders, I think, are always saying the things that matter most. Um two word sentences.
SPEAKER_00Thank you, I'm sorry, I care. Yeah, I care. I learned about this one the other day. Uh conferences listening to uh the phrase I like you. Mm-hmm. Mm-hmm. People want to be liked. Dude, it's crazy.
SPEAKER_01Like wow those those simple I I I think you can, you know, you there's so many things that I've experienced in leadership from leaders, even done myself, but those words are like they are game changers. Yeah. I like you. Um man, I'm sorry. Yeah, please forgive me. Please forgive me. I forgive you. Like those are right simple words, but leader good leaders do those things repeatedly.
SPEAKER_00Yeah, definitely. I think good leaders uh correct and celebrate repeatedly. Yep. Like uh ongoing accountability and feedback that flows both ways, yeah, open that up and to celebrate. I'm not great at celebrating, so I gotta leave myself a little note. You know, I want to be a great leader, and I know I so that would mean celebrating. And so I'm like, oh, wait a second, don't just move forward. Yeah, a lot of leaders are forward thinking, which is great. Yep, awesome. I would get things done, right? But if we're not celebrating, we're almost like we're missing the soul food. And like, what's the point? Right? It's like, well, I'm thinking about my next birthday. Like, what? Right here. We got some life right here. Dude, I also I think the number one would be uh a reminding of the why. Yeah. Or a different way to say that would maybe be that's good, uh, what's at stake? Hey, what's at stake? Why does this matter? What's the why? And yeah, we think, uh I don't want to, I don't want to sound stupid and repeat myself again, or they're getting tired of hearing that. Yeah, yeah. Listen, until your people are mocking you and can repeat you verbatim, you are not saying it. You ain't said it enough. Like literally, um, the the idea that, well, I said it once, so they should know it, is like a stubborn, weird human quirk. And we know it takes like seven or eight times for something to even stick. And so let's say you say it once every staff meeting, your staff meetings every week, you're gonna be repeating that at least eight weeks, and I would say just repeat it every time.
SPEAKER_01But yeah, you you you just uh to that example, it's that you just believe your own hype, right? Like we just believe, oh, I I'm such a great communicator, right? I'm gonna say this and they're gonna get it. It's like that's cool, but they're not you, and that's not even that right, you they're not great communicators, it's that you've had this scenario and you've lived this thing in your head that they don't have, they have they weren't privy to, right?
SPEAKER_00Yeah, yeah. They're inspired. Like, no, people need to be reminded more than they need to be instructed. Yeah, people need to be reminded more than need to be instructed, yeah, man. So, yeah, a lot of great leadership uh impact happens through very ordinary faithfulness, repetition.
SPEAKER_01Yeah, yeah. Let's do it,
When Doing Right Still Hurts
SPEAKER_01man. I I want to switch gears to this one as this one feels uh a little bit nobody ever tells you that leadership can be so personal. Yeah, um, and one thing that we found is that you can do the right thing and people still get upset, yeah, right? So the the reality is that you, as a leader, as much as you want to, you're not in control over anybody else's response. And so you can communicate clearly and somebody still misunderstands you. You can make the right call and somebody still dislikes you. You can care deeply about somebody and still have them be disappointed by you. Um where's that showing up for you?
SPEAKER_00Yeah. I mean, I if everybody likes you, you're probably doing it wrong. Or you're lying to somebody, or you're doing nothing. I don't know, you know. Um that's a good one. I think that's I think that's real. Where's that showing up for me? Yeah, I don't think I realized how much that trying to lead well and effectively would require like clarifying things that you thought were communicated perfectly and owning it. Like, even simple, it could be as simple as the other day someone said to me, like, Oh, I didn't know that was happening. And I'm like, Oh, well, that's interesting because I talked to you about it personally. Uh, we sent out a mass text, we sent out an email. Actually, there were three emails. It's only been a month. Yeah, it's really going. We give an announcement at the all call. Um, and so it's easy to get defensive and be like, Well, that's on you. Yeah. Rather than say, okay, that's helpful. Let me oh, you didn't see any of the emails, or you didn't see all, and then oh, I found out they switch emails, they don't have the email anymore. You know, it's like, oh, okay, so easy, easy to get defensive. But I think understanding the idea that leaders aren't just responsible for what they say, they're responsible for what people hear. And I don't mean responsible like you can control the outcome, meaning uh after that discrepancy is created, it is your responsibility to help bring that person on board. And hey, maybe just to apologize, I wasn't wrong. Okay, I didn't ask if you were wrong. You want to be right or you want to be happy?
SPEAKER_01Yeah, there it is. There it is. I I love the the the thing is that you can be right and still ruin a relationship. Um there's there's you you've gotta be able to navigate some of those things. So as we kind of think about this, man, uh a little bit more, why because it sounds like at some of the core of this, why do people pleasing and leadership eventually collide?
SPEAKER_00Yeah, and I I can't speak for you personally, but I know I felt that, and I feel like earlier in my leadership, it was like I must be doing it wrong if someone's unhappy. But the truth is you're not gonna please everyone, yeah, and a lot of times that's like the uh clarity is kindness and to say, hey, I know you want to go this way, but it didn't go this way. And I think that leadership gets heavy, burnout comes fast for people for leaders who don't try and elevate above the sort of internal desire to be people pleasers, because the people will always need more pleasing, and you will always be stuck in this tension of um these people want X, these people want Y. Who do I disappoint? Yeah, I heard it this way leadership is disappointing people at a rate they can handle. Yep. That's like change management, right? Yep. What about for you? How has people pleasing showed up in your own life?
SPEAKER_01Man, I mean, it showed up in so much of uh I was, you know, not to go back to back in the day, it was like, nah, I was, I was, I was um a shy kid and really shy growing up, always to myself. Um, and so to step on stage or to step in an environment where that needed leadership, I usually would like that's where people would um actually show up and like, oh, respond to me. So I started learning early on that you know, performance equal love, right? Right, right. Performance equals or pleasing people, performance equals people. So all of those things. And so where it shows up for me then is I have to constantly say, like, I'll give a yes to something, and then after giving that yes, because I want to please this person, then I'm stuck with like, yeah, but I didn't really want to say yes to that. I only said yes to that because I was trying to to please or appease them and keep keep things from getting friction. And so I just started assuming that, all right, well, leadership is because you've got to move things forward, leadership is about people, right? And so I just assume that because it's about people, then it's about meeting the needs of the people all the time.
SPEAKER_00All the time, yeah. Yeah, always gonna be more needs too. It's always gonna be more needs, and competing needs. Yep. And yeah.
SPEAKER_01Hmm. I heard someone say that was really helpful that the idea of leadership is leadership is influence, right? And and John Maxwell, leadership is influence, and the reality of leadership is that you are taking people from where they are to where they're meant to go. Yep, right? So there's there's transformation, yeah, that's different. Yeah, that's so it's not just meeting their needs, but it's saying, hey, I'm taking you from where you are, yeah, where you're meant to go.
SPEAKER_00I love you too much to leave you there. Yeah. And that's you know, we gotta be careful with that and hold that humbly because you know, who are we to decide on? But you know, careful thought and discernment and and and some of these truths that we've uncovered. Where so how does feedback fit into this, right? Because we can control people and what they hear necessarily. I mean, we can we can communicate effectively and and repetitively, um, but then we get that feedback, but feedback and people pleasing can be a dangerous mix, right? If we can't separate so what, yeah, what do you think about that?
SPEAKER_01So, man, I have so many thoughts on this, and um trying to get it clear. I I think that we live
How To Weigh Feedback Wisely
SPEAKER_01in um at some level, we live in an unjust feedback culture. Um, everything, everybody. Okay, I didn't ask for like everybody's got something to say about everything. And so I think for feedback, it is important in those relationships. It's important in leadership, it's important for feedback. I think how we do it is really what the the the sticking point is. It's not always what you say, it's how you say it, right? And so for me, some of the best feedback I've gotten was feedback that I was able to discover. Um, and what I mean by that is sitting with a leader, um, and I just finished doing something, and they put me to the side, hey, okay, cool. That was great, great. I mean, I love how you led that meeting. What would you have done better? Yeah. Totally. Naturally, I'm already gonna be because I'm uh I'm always I'm already thinking about how could I improve? Blah blah blah blah. And so to hear that leader say, Okay, cool, and the leader, a good leader is gonna say, Let me tell you what you did great. Like before you beat yourself up, yeah, let me tell you what you did great. Here's what let's let's think about how we can improve on this. And I think feedback, I mean, we can get into a whole lesson on that, right? But I think that feedback has to be contextual. Um, I think that feedback has to be specific. Um, I think I also, this is personal, I think feedback has to be earned too. Um, I don't really receive feedback well from people um who haven't really who we're not either in deep relationship with or we haven't really you haven't gone to that place. So you may just have a feeling or a sense of like this needs to change. I don't mean it needs to change, that's just what you feel. But does it actually does the whole picture and and that's I as I'm as I'm navigating it, it's like it's feedback is I've got so many thoughts on it.
SPEAKER_00What I'm hearing you say is that don't the weight you assign to feedback should be proportionate to the person. That's good. I couldn't you you you said it better. Yeah, you said it better. The way you assign the feedback should be proportionate to the person, and yeah, so like if you give me feedback, it's it's heavy and light at the same time. It's light because I know you have my best interest. Yep, it's heavy because your words carry weight with me. That's it. But leaders, you guys are gonna receive feedback, and you already know this, from all sorts of people, brand new people on the street, especially in the in the digital space, right? And it's like, oh, this person said I wasn't good. And we have a negativity bias, right? Psychologically, well, we'll find the bad thing, 99 good things, one bad thing. Oh, I remember the bad thing. Yeah, it's so interesting. Yep. Um, but yeah, so I think to be humble enough to receive it and learn from it, but to have enough self-worth and awareness that, oh, that doesn't define me. And the feedback that I'm really gonna allow to sit heavy should come from a select few who actually know what they're talking about. And we can learn from everybody. We can learn from everyone. I'm totally yeah, man. Okay, yeah. Yeah, I like what I like what we had here. Mature leadership requires enough humility to listen and enough conviction to still make the call. That's good. That's good. All right. Uh, last last piece of uh leadership being not what we expected it to be. Uh, is a lot of times
What Leaders Carry And Share
SPEAKER_00you guys are carrying a lot more than people know. Maybe it's information, maybe it's pressure, responsibility, some sort of uncertainty. There could be personal issues, financial issues, organizational tension, might be family stuff. Maybe you're about to let someone go, and no one can know but you and good old HR. Yeah. Right? So we oftentimes are carrying more than maybe we expected to, or certainly than people know. Yeah. So what do you think? How honest should leaders be with their teams about what they're carrying?
SPEAKER_01I think that there are there are some things that your team um doesn't need to carry, but that is to still say you need a place where you can unload it. Right. And so so it is it is to say that if I'm doing a great job of unloading with the right people, then I think I'll have a better sense of what my team can carry. So, so if in fact, often what happens, right, is that your your your leadership, the organization, the assignment, whatever it is, becomes all of your identity, becomes all of your identity, becomes all of your community. And so now when you're trying to process something or you're needing to navigate these hard things, you just feel like I gotta spit it up on these people, I've gotta throw it on them because this is my family, this is my team, these are the people I'm running with. And it's like, yeah, but they were not that that's no, you actually, I hate to say it, you're abusing some of your power. Um, and this is this is a weird. Kind of codependency. So I'm answering the question in that I almost want to take a step back and say that I'll know how I need to have another place I can be fully and completely honest. And then from there, after processing, then I can bring some of that to my team.
SPEAKER_00Yeah, I like that starting there rather than yeah, just working it out. Team should never be your therapy session. Yep. Yep. I do think over time, and everybody's wired differently. For me, I earlier in my leadership would pull all the punches and not share anything. Like, oh, I don't only the strong survive. I don't want to see me. I don't want to.
SPEAKER_01Yeah.
SPEAKER_00And or or here's like a weird kind of lie we often hear is uh, well, I don't want to burden them. Yep. It's like, yep. Oh, so you'll just be totally isolated and distant from them. And so, like, where's that middle ground? So I like what you said. We need to start with having a safe space, coach, mentor, spouse, you know, therapist, the whole deal, uh, whatever it is for you. And then from there we can kind of navigate, okay, here's what I can share. I feel like just again in real time, I have received the anxieties of the leader as being part of that team well when there's either been some uh like uh like a verbal awareness, uh a statement of like the leader says, Hey, I'm processing through some things, can I process with you guys? And I'm like, Oh, now we're in processing mode rather than me feeling like the ship is sinking, you know, or or to say, yeah, to name it like, hey, here's what I'm anxious about, but I I think I do want to hear from the leader, and this is where this third party is so important. I do want to hear from the leader, and it's gonna be okay. Yeah, and we'll figure it out together, and we've survived worse, yeah. And yeah, you know, like yeah, I almost need that.
SPEAKER_01You need that. We all I think we all do, like somebody, I don't need certainty, but I do need clarity. And that clarity comes in that you spent some time already like saying that language itself, hey, I'm processing some things. Can I process this with you? Oh, I feel so ready. Okay, great. I'm like, yeah. Because it means that you're not just throwing this up on them. Yeah, you've actually gone ahead and said, Right, I could probably say it this way, I could probably say it that, or this is not really an issue. That really is, it's a tornado in a Tika, right? Like so, so I think you're right, man. It is, it's the having the right structure. I hate to belabor it, but for me, it is we're gardening, right? So we're just getting rid of the new season, blah, blah, blah. And we look at um the things that survived were the ones that were on the trellises, they needed structure. The the fruit, the the plants needed structure. It's defined. Yeah, it's defined, and I needed a place to everything can't hold the weight. Yeah, and so I need to determine who's gonna hold most of this weight. And so I think that if you're a leader and you don't have a trusted mentor, a trusted coach, uh, a trusted, trusted relationships where you can process things, you you need to do that immediately.
SPEAKER_00Yeah, and that's gonna require some risk. Yep. And so like, well, I don't have anybody. I'm like, yeah, go in to find someone is gonna require some risk. And there's someone else that feels like they don't have anybody.
SPEAKER_01Yeah, man.
SPEAKER_00Um, and yeah, reach out to us, we'll help you get connected. Yeah. I the the power thing you said just really resonated with me because it almost just articulated something I've experienced where because the the one with the the person with authority in the room, when they talk, uh people shut up.
SPEAKER_01Yep.
SPEAKER_00And so if they start dumping something on you, it's almost like a you know, if the definition of trauma is like helplessness, it's like a little traumatic. And again, I don't mean to get uh dramatic here, but it's like I can't do anything about this because you're the leader, and so I just have to carry this thing you're dumping on me, and I don't even know where it's going, rather than like, hey, we're processing, and I'm like, oh, thanks for bringing me with you. That's it. That's cool. That's it, man. So leadership does not mean carrying it all alone, but it does require wisdom about what and where you share it. So leadership is not always what we expect it to be. Sometimes it is repetitious and boring. Other times we learn that we cannot control people's reactions and the way they hear things and outcomes, but we're still responsible. And finally, that oftentimes it means caring more than we expected andor than people realize. Yeah. Bring it home, man.
SPEAKER_01Yeah, let me do it. Let's the three questions in order for us to cross the threshold. Uh, where do you need to embrace the
Three Questions To Cross Thresholds
SPEAKER_01boring? Number one, where do we need to embrace the boring? Second question I I would have for you is what part of leadership have you been treating like evidence that you're not doing something or that you are doing something wrong when it may simply be part of you carrying responsibility? And then question number three is Is there anything you are carrying that you actually need help with? So I think as we think about some of this stuff, is that you as a leader, we've said it all often, like you're not a robot. Like you actually, in order to move things forward, you're gonna need some help. So if this is you, um, I want you to take a deep dive, listen to it again. We were just sharing our thoughts, but I also would love for you to send this to a leader who may need to hear yeah, this part of leadership is real. Weird but real. Weird but real. All right, y'all. I'm James. I'm J C.