Ep 37: Courageous Leadership In Online Business: How To Be The Best Leader For Your Business

September 27, 2023

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Episode Notes

In this episode, Jillian explores the concept of leadership courage in online business. She shares personal experiences as a supervisor and emphasizes the importance of addressing challenging topics, communicating clearly, and admitting when you're wrong. She also discusses the significance of being open to learning, challenging one's perspective, and honoring everyone involved, even in difficult situations. She encourages listeners to approach conflict with curiosity and a willingness to learn and offers her assistance in navigating difficult conversations.


Read the Transcript:

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Jillian Dolberry (00:00:00) – I'm Jillian Dolberry, your fellow business friend and host of the Grace-Filled Podcast. When you tune in with me every other week, you will get practical steps in growing your business gracefully while juggling all the other amazing or challenging things going on in your life. I believe in building deep connections, building your business on strong values, serving our clients really well, and approaching boundaries and conflict in our business with a whole lot of grace. If you are ready to grow your business your way with ease. Stick with me, friend. It's time to be a grace-filled CEO. Hey friends, welcome back to the Grace-Filled Podcast. Today we're chatting about leadership and AI. There are so many elements of this, right? There are so many leadership books out there. So much for us to learn and grow in and leadership podcast, all the things. But today specifically, I want to talk about having courage as a leader of your online business, what this actually means and how you can make some really positive changes and how you lead your people, whether it be clients or whether it be your team to create a really trustworthy environment.

Jillian Dolberry (00:01:08) – So I'm kind of just going to jump in here. I've got a couple of points and really this topic has been sitting on my idealist for quite a while because I had an experience where I was a supervisor and not the official top leader of the company, but just in a supervisor type role. And what I experienced really impact and how I handle leadership moving forward in my own business, but also on the teams that I have been fortunate to manage. So I want to share that with you. So the first thing that I want to kind of address is what leadership courage is not leadership. Courage is not avoiding hard conversations. It's not not telling your team members when you have feedback for them. Leadership. Courage is not when you avoid people or conversations because you're afraid that. You might be called out or disrespected in some way. Leadership. Courage is not being unwilling to admit when you're wrong. Leadership. Courage is not disrespecting people by being combative or defensive. And lastly, leadership. Courage is not being vague.

Jillian Dolberry (00:02:38) – I wholeheartedly believe that clarity is kindness. And if we are able to be clear with people, then we are being kind with people, even if they don't like what we have to say. So with that said, let's jump into these elements of how leadership courage transpires in online business and what that actually looks like, because obviously we have some different challenges than people who work in person, meaning we work online. We're not face to face all the time. We are face to face on Zoom. Occasionally we chat via Slack or messaging or hear each other's voice on Voxer, but we don't always have that like face to face accountability, to be honest with people or to be clear on what our expectations are, what needs to improve, or giving people positive or negative feedback. So let's now talk about what leadership courage is. Leadership. Courage is being able to communicate with your team or people in general in business about hard things. This could be personal, hard things. This could be part feedback to provide.

Jillian Dolberry (00:03:47) – This could be anything. And ultimately, so many of us veer away from these hard conversations because yikes, they can be uncomfortable and nobody likes to be uncomfortable, truly. So we look for ways around that. We look, we maybe put it off too long or we just avoid the conversation altogether. Or maybe we just say like, Oh, well, we'll talk to you about that some other time. We put it at bay and then we never address it moving forward. But having the courage to step in and say, I need to have this conversation and I just being transparent, I'm uncomfortable about it, but I know that it needs to happen and I want to honor us both by having the hard conversation. You just don't understand how valuable that is. People will see the authenticity of your heart in that, and that is the way to approach those hard conversations. Now the next thing is being clear, even when it's difficult. I worked for my church in the last couple of years and did a lot of their media type tasks and some administrative ones as well.

Jillian Dolberry (00:04:57) – And one thing I loved about my supervisor there was that he every time we had a conversation and we had quite a few deep, hard conversations that had to do with like sticky things like money and time and family balance and how to do things better, and me providing some feedback on things. And every single time we had a conversation, he let me say exactly what I needed to say. And then he came back and he said, okay, I just want to make sure I fully understand you. So if I don't, please correct me, but I want to make sure that I am clear on what you're trying to say. And then I will try to be clear in my response. And he always opened the door to have further conversations, to provide clarity. And if for some reason we weren't seeing eye to eye, it just kind of kept going around and around until we did or until we understood each other at least. And that was extremely valuable because that is the supervisor saying, I have time for you, I hear you.

Jillian Dolberry (00:06:04) – I want us to understand each other. I know that I may not be in the right here, and I'm humble enough to understand that and absorb that. And you can't break me. Right? One thing that we hate doing is we hate having hard conversations with people where we're afraid to hurt their feelings. And if we're able to be clear with someone on something that might be hard to hear, we also need to feel strong and stable in the fact that we can't break them. So whether you're on the delivery end or the receiving end, we need to have that stability in us that wants the clarity even when it's difficult. So working to bring that clarity in difficult conversations is extremely courageous. The next thing is being open to being wrong. And there are some things that we know were right on. There are things that we feel convicted about. There are things that aren't. It's not black or white. It's just gray. And you might feel differently about something that I feel differently about. And that's okay.

Jillian Dolberry (00:07:15) – It's okay not for it to be black and white, clean slate, clear as day, but we need to be open for someone to challenge our way of thinking and our way of doing things and even our perspective. The most valuable thing in working with people in these hard conversations and coaching them through it is being able to say, You and I are on an equal playing field where both human, we're both imperfect and honestly, we both need Jesus just as much as the other one. So we both have a lot to learn and that is a way of approaching a conversation. It doesn't matter if you're the CEO or the virtual assistant or the online business manager or the copy editor or who you are on the team. If we all come to saying you're a human being and I'm a human being, and we're going to have this conversation and respect each other by being willing to see the other person's point of view. You are going to be building man, you're going to be breaking generational ties that are toxic.

Jillian Dolberry (00:08:23) – You are going to be building community, you're going to be building respect and building an environment that people want to be a part of. Next Leadership. Courage is prioritizing, honoring everyone involved, no matter how difficult they are being. Now, I want to kind of put a preface there that. People aren't difficult. We don't want to call someone difficult, but the experience with them may be very difficult. And so it's our duty as a leader who has courage to prioritize honoring that person regardless of how they're acting. I have been in a situation before where I was basically breaking up with a contractor and we were. Talking through some things and figuring out like what would be the best way to move forward. And ultimately I decided it's not the best fit to move forward. And I felt like I delivered an email that was respectful and just providing clarity. Well, she read my clarity and came back with a lot of defense and felt like I was minimizing what she had provided in the first place. Now, that to me was a complete misunderstanding because I greatly appreciated the work that she did for me.

Jillian Dolberry (00:09:53) – And ultimately, maybe I worded that wrong. Maybe I said something that triggered her. I don't know. I mean, again, being open to being wrong, I'm just kind of like opening up that perspective for her to provide me with feedback and trying to see her side of things. But ultimately, the conversation just did not de-escalate on her end and therefore it was just really difficult. But I tried to do my best to honor her every step of the way. That is something that has felt very, very important to me. It's a huge piece of my business. It doesn't matter what people have done or who they are or how bad things are. Every single person that you come in contact with deserves to be honored, and that looks differently in different situations. But ultimately in this one, I by honoring her, I really tried to share my appreciation with the things that she had done for me in my business, regardless of how things were ending or how we were moving forward or not. And therefore, that's what I want you to take away from this, is it's not that we have to be a doormat for somebody or it's not that we have to be silent in sharing our convictions or how we feel about things or our perspective.

Jillian Dolberry (00:11:13) – The ultimate goal is to honor everyone in the room. That means the person that you're speaking to and that means yourself. And lastly, leadership. Courage is approaching conflict with the goal of learning something new and seeing the positive. I read this book one time called Conflict Without Casualties, and when I read it, I was working for a company where there was a lot of conflict, and unfortunately I was the only one who felt very off put by it. Everyone else was. I think it was kind of a standard for the industry for there just to be all kinds of conflict. But I could not it just did not sit well with me. I felt like there was an opportunity and conflict besides just disagreeing and the energy in the room to be very negative. So I started reading this book called Conflict Without Casualties. And the idea of it is that we can have conflict. And with people in business situations or personal situations, and we can all walk away from that conflict being better people, better understanding each other and something positive coming through it.

Jillian Dolberry (00:12:26) – Now, conflict is really you probably hear that word and you're like, Oh, conflict. I don't want to touch that with a ten foot pole. I'm right there with you. But I want to challenge that definition because I believe conflict is we are here, but we need to be here. The conflict is simply the gap between two different places or things. And so as we approach those conversations, oftentimes people can feel defensive. I have felt defensive in those conversations before. I have not handled myself properly in all situations. We are all learning. We're all growing. We're all imperfect human beings. So we have to be able to give ourselves grace in that. But approaching conflict with the goal of learning something new. So what can I learn about this person that I'm communicating with? What can I learn about this situation that we're in, about the program that we're using, about the application that we're using, about the way that this person communicates? I mean, you could go on and on, but there's always an opportunity to learn more, even if it is as simple as learning how they're feeling in that moment, because that is something new that changes from moment to moment because we know this feelings are crazy.

Jillian Dolberry (00:13:43) – Feelings are they have their own mind. They just go off the hinges. Sometimes we can't control them, sometimes we can. But ultimately that is something that will always be different in every conversation and it's something worth learning about. And then the last thing is seeing the positive in this book, Conflict Without Casualties, which I will link in the show notes because it's excellent. There is a section about for every. Negative trait or negative situation or negative action or emotion. There is something positive behind it. Every time somebody does something that is negative, there is something behind it that is motivating it, that is actually positive. A good example of this is anger. When someone is angry, it's actually because they're they're passionate about it. There is some some level of care and love behind that anger that is motivating them to anger. Right. So we have to be willing to see both sides of that. Peel off our own glasses of this is my way, This is how I feel. This is the biggest thing in the room right now, being able to take a step back, look at all of the pieces, respect and honor the other person's feelings and say, okay, where is the positive trait in the negative trait that I'm seeing? Some good examples of this are maybe someone is coming off very passive aggressive or un assertive I guess, and that kind of feels negative.

Jillian Dolberry (00:15:24) – Like you want them to like stand up and say something, but really they may have like this sense about them that is like they want to be nice, they don't want to be unkind and they're afraid of communicating something that could come off as unkind. Or maybe someone is very stubborn. But the positive trait of that is that they're strong willed and they're persistent. Or maybe someone is easily upset in a conversation. But the positive of that is that they're sensitive and they're caring and they're empathetic. They feel things deeply. For years of my life, decades even, I thought the fact that I was empathetic was actually like a curse, because sometimes it can feel negative, emotion can feel negative. And that's what the world tells us a lot of time. But that's actually a superpower because I have the ability to be face to face with you. And if you're telling me one thing, I can see what's going on in your mind on the back end that sounds a little like supernatural, and I promise it's not.

Jillian Dolberry (00:16:31) – But it's definitely a spiritual gift to be able to feel what other people feel and be able to be present in that with them. You know, another negative trait is insensitive or maybe like brutal in conversation, when really the positive side of that is that they're very honest and can be communicative and trustworthy. We can trust those people to tell us the truth. So it's just really important to make sure that we're not just seeing the negatives, but we're also looking at the positive elements of whatever is coming up in the conversation with this other person. As you listen to this today, I really want you to think about how you can increase the level of courage in your leadership, whether it be to your clients or your team, or maybe it's inside your four walls with your family. I want you to think about ways that you can leverage your positive traits, how you can create watch areas for those positive traits, and how you can communicate better with people about some of the tougher things that we go through and that we deal with.

Jillian Dolberry (00:17:36) – There is a lot on our plates on the regular and we can get stressed and overwhelmed. And so to have this foundation of courage in online business as a leader is truly imperative. I can't even articulate fully how important it is. And most importantly than that, we don't always get it right. Yes, that's an important note to remember. We don't always get it right. And when we don't, we need to be willing to be wrong. Like I said before, and improve. Learn from our mistakes, Apologize if necessary, give ourselves grace. Forgive ourselves for being imperfect. Because even though that sounds silly, it is definitely a real issue with us. Sometimes we have to be willing to move forward well and that when you choose to do that, when you are able to take a step back, forgive yourself, give yourself grace, ask for forgiveness, whatever it is, when you're able to do that effectively, you're already being courageous. And that is what I want to leave you with today.

Jillian Dolberry (00:18:48) – I know that you've got it in you. I know that you're here for a reason, and I know that you are going to impact people positively with your leadership skills and most importantly, with your courage and grace. If you are preparing for a hard conversation or you feel like there is something upcoming that you need to address and you're just not sure how to word it, I want you to pop over to Instagram and message me in my DMS. I weirdly, I love helping people walk through these things. I guess that's weird. I don't know. I've always thought that that to be strange when I explain it to people like, Oh, I like conflict and I don't really like conflict. I love conflict resolution and I love doing it in a way that honors everyone in the room. That is very important to me. And if that is important to you too, I encourage you to reach out to me if you need some assistance in crafting a response or supporting people by having these hard conversations in your business.

Jillian Dolberry (00:19:46) – Until then, I hope you have a great rest of your day and I'll see you soon. All right, friends. That's it for this episode. I'm so grateful you're here and would love to connect with you. After you subscribe to the show, come hang out with me on Instagram at Jillian Danbury. See you there.

Be sure to subscribe wherever you listen to podcasts or at You can also continue the conversation with me on Instagram at @jilliandolberry.

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