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I'm Elizabeth, and simply put, I design brands and websites. I mix in marketing strategy, personality galore, and tons of fun to create custom brands, custom websites, and website templates. These designs convert lookers into buyers and take the headache out of the design process. I believe your brand should be a knockout. I'll help you create a captivating + profitable online presence! Join me, won't you?!

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Navigating Conflict in Your Business with Confidence: Expert Tips for Handling Tough Team and Client Conversations with Jillian Dolberry

Reading Time: 16 minutes

Today we are talking about boundaries and difficult conversations with team members and clients, and while that might not sound like the most fun conversation, I promise that it absolutely is (and it’s so important too!). Nobody ever wants to be navigating conflict in your business. Whether you are like me and work with a small team of contractors or you are looking to hire your first contractor, this episode is for you! And hey - even if you don’t have a team yet, we are talking about difficult conversations and setting boundaries with clients too, so this absolutely still applies. I’ve brought Jillian Dolberry onto the podcast today because she is a pro at teams (she specifically works with VA’s and OBM’s through her membership “Serve Your Heart Out”) and she also works with CEO’s on team-building, hiring, and leadership. So basically - she’s seen BOTH sides of this! 

We cover everything from:

  • The difference between a VA and an OBM
  • How we should be setting and enforcing our boundaries
  • How can we show grace to our team through difficult conversations
  • What conflict in your business really is
  • What we need to be doing BEFORE we let someone go
  • Whether or not you should treat your team like family
  • And so much more!

Join breakthrough brand all access group

Before we dive in - are you in the Breakthrough Brand All Access Facebook Group yet? It’s free to join, and it’s where we take conversations like the one I had with Jillian today further. Pop in and ask questions, share insights, and even peek behind the scenes of my own business and what I’m trying lately. You might even meet your new work BFF or team member in there! I’d love to see you inside!


Listen & subscribe on your favorite platform:  Apple Podcasts  |  Stitcher  | Google Play  |  Spotify  | iHeartRadio

Search for episode 218!

Who is Jillian Dolberry?

If you haven’t come across Jillian yet, here’s her official bio:

Jillian Dolberry is the founder of Serve Your Heart Out, a community that provides personalized coaching and training for VAs and OBMs. While devoting her heart and time to the members of her community, she helps online business owners set boundaries, get unstuck, and reach goals that honor the reason they started their businesses in the first place. As a wife, mom, and business owner, Jillian has become a master of setting boundaries, allowing her to serve her community, family and her clients well.

But on a personal level? I chatted with Jillian for 30 minutes before this interview and she asked me questions like: what’s happening in your business? What’s not working now? What are you looking for? And let me just tell you - she had all the answers! She clearly knows her stuff, and I’m so excited to bring this interview to you today!

an interview with Jillian Dolberry about navigating conflict in your business and having tough conversations with your team

First, what is a VA? And what is an OBM?

A virtual assistant is a VA, and then an OBM is an online business manager. An OBM specifically can have many different job titles, but at the end of the day, it's really someone who's coming into your business and managing the day-to-day operations. They're executing less and planning more. They have a hand in the strategy of your business as well. 

Basically, a virtual assistant is going to be executing all of the tasks that pop up and the administrative side of things, while an OBM is in a position to guide, train, and equip the VA so that they have everything they need to be successful. A virtual assistant can often move into an OBM role fairly easily (and, in fact - that’s how I got started!). 

As business owners, how can we better set ourselves up with our team members or clients to lessen difficult conversations and pain points in the relationship as we start working with them and ongoingly? Is there a way to avoid conflict in your business?

In order to set better boundaries, we have to teach people what we will and won't tolerate (I don't love the word tolerate, first of all, but for all intents and purposes, it works). We have to communicate what our boundaries are to people. We also need to remember that it's a continual conversation. For example, if you tell me that your office hours are between 9-12 am, and I email you at 1 pm, you should be waiting until the next day to email me back. We are the ones responsible for communicating and holding our boundaries. It’s not up to the client or team member to remember to email you during your office hours, it makes sense for them to email you when they think about it. But it’s YOUR job to say that you won’t email me back until you are back in the office. 

In order to set better boundaries, we need to learn how to communicate them and really respect them ourselves. I think we have this idea that people should know what our boundaries are because we've like put it on our email signature or website or something and it shocks us when people don’t “respect them”. We can't expect people to remember those things all the time. We can't expect people to abide by them because they're not their boundaries. Our boundaries exist for us to respect them first and foremost. When we respect our own boundaries, it removes us from being reactionary to what our clients need and positions us to respect our own limits and live life accordingly in that way as well.

EM: Yes - I teach this in Booked Out Designer, but I think so often we put our boundaries in our contract, but then we don’t actually communicate them outside of our contract. I’ve learned in my own business that we teach people how to communicate with us. 

Exactly. First, we have to figure out what OUR non-negotiables are. What do we have to protect? What do we not want to do? We also have to know what our values are. A lot of people have an idea of what their values are but putting them on paper is completely different. Decide what your values are, and what boundaries you need to create to protect what it is you value. When it comes to setting better boundaries, start there.

Read More: 4 Questions That ACTUALLY Help You Get To Know Your Job Applicants



If we have been too lenient with a team member or client, what should our first step be and how should we navigate these situations?

First of all, I just want to approach this with empathy because it's really hard. It's not an easy thing to approach when you care about somebody and you've made the choice to bring them on your team and you've invested in them and you've poured time and financial resources into them (as well as emotional and mental resources). 

Approaching these situations can be really, really tough. So the first thing that I would say to do is give yourself grace. And I know that that sounds a little like, “okay, fine, sure” but I think that that's the most important thing because you will not be able to approach any sensitive situation properly (and kindly and clearly) if you haven't given yourself grace first. A lot of times when these situations arise, we're thinking, “oh man, I've really screwed up here” whether that’s because you feel you let this go on too long, or you've overlooked too many things, or whatever it is. So we put that pressure on ourselves to be perfect and to get it right the first time. And yes, could we have done better? Probably so. But just because you're giving yourself grace doesn't negate the fact that you can take a step to make a wise choice and move forward in that direction.

EM: That’s so true - as business owners, you're wearing a thousand hats, and it’s easy to miss something. I find that then there is almost like this impulse issue where you go from “Okay, this isn’t working, but I wasn’t doing anything about it and now I am and I want to deal with it right now”. 

How can we avoid going from 0 to 100 when something isn’t working?

Yes - so, I don't know if I actually recorded a podcast on this or if it's still sitting in my queue as an idea, but I like to call it leadership courage. And basically, what that means is you're willing to be clear with your team as things arise. Very rarely are you going to bring someone on your team that you're just setting loose to do the things and you're not tracking what they're doing or you're not seeing the work that they're doing in some capacity. I'm not talking about micromanaging, please don't do that. But you should have a pulse on what kind of work this person is doing. 

Personally, I like the phrase clarity is kindness. If you're not being clear, you're not being kind. And sometimes clarity looks like providing them with feedback. And ultimately, nobody likes conflict. I think that the biggest thing with conflict in your business is we have this idea that it's an argument or it's this negative thing, but really it's just saying, “we are here and we want to be here”. 

So if we approach conflict in that way, we can then say, “okay, I just need to provide feedback to this person to try to get them from here to here”, it feels less like conflict in your business and more like a roadmap. I don't want to oversimplify it  - that takes courage. It takes courage to be able to say, “hey, this isn't what I had in mind exactly, so let's bridge the gap in communication so that I can be clear with you, which is ultimately being kind, to bring you from here to here”.

navigating tough conversations with your team

How do we make sure we're showing grace to the team member or a client through a hard conversation while still holding to our expectations? And what setting is appropriate? For example, it a team member is underperforming.

It definitely varies. I think that if you're letting someone go, that needs to be face-to-face out of respect. But as far as providing feedback to people, I don't think that we need to overcomplicate it. I think that the sooner we can communicate it, the better everyone's going to feel.

I know that we think about grace as this big spiritual word, and I am a Christian (I run my business on faith-based gut and heart and all of those things), but I do feel like grace is so applicable in day-to-day life too. Grace is being able to be kind and be clear. It's not letting people get away with things. It’s communicating things in a way that makes them feel seen and heard, while also being honest. I think it’s less about the medium in which you communicate (ie. via Slack or Zoom) and more about the feeling behind it (and how you communicate that).

Start with a script - it’s okay to draft something to say. It doesn't make it less personable or emotionless, it actually helps you remove some of those things that you're feeling that are maybe not healthy to project or put on other people before you start communicating with them. Emotion is not bad, it's important to be yourself, but I like to say, “we need to affirm the gray and act on the black and white.”  What this means is: in every situation, whether it be internal dialogue or dialogue with a team member, we need to affirm the gray (the feelings). The gray is the feelings. We need to say, “Okay, I understand you may be feeling XYZ”. But we also need to communicate the black-and-white facts like, “This task wasn’t done in the way I had expected it to be.” 

EM: To add to this - one thing that’s helped me is communicating what the BUSINESS needs versus what I need. As a personal brand, it can be tricky because you have likely been running the business by yourself for a while, but I personally prefer saying, “The business needs THIS” vs. “I need XYZ done this way”.

I completely agree. It’s about the betterment of the business. It’s a good way of reminding them that we all have the same goal here.

In the online space, it feels weird to say “fire them” because often we are working with contractors, but what advice do you have when you do need to end the relationship between you and a team member or client?

I don't want to say this flippantly because I want people to understand that these situations are really difficult, and they are impacting people's lives (and livelihood), and your team member may not have the same perspective that you do about business or faith or all of those things. Sometimes it can be hard to communicate really hard information to people who may not have the same perspective as you do, and we need to remember that their reactions are not a reflection on us or our business. It's a reflection of what's going on in their hearts. I think remembering that will help you release a level of pressure or a level of responsibility that we can internalize as business owners when letting someone go does not go well.

I will say that the last person that I had to let go was an employee, and that was probably the hardest one because I had invested a lot of time and a lot of care into them. When you work with someone over Zoom, you see their family and you get to know them to a certain extent and it's just really difficult to cut ties in that way when you've built that personal relationship. And I don't think that I do this perfectly. It never feels like you've mastered it in the moment, but the most important thing is that you walk away knowing you've made the right decision for the business. Ultimately, you've made the right decision for that person as well, because I think if it's the right decision for your business, you can trust that God's going to take care of them, and it's going to be the right decision for them too. 

I am a very empathetic person, so I also have to say, if this is something you're going through or are considering, I see the struggle in that. It's not going to feel easy. It's not going to feel good. No one's gonna walk away saying, “Thank you for being so honest with me”. 

As leaders, we also need to make sure we are not ambushing people. 

Let’s go back to that leadership courage - we've got to have conversations BEFORE the toughest conversation. Before you say goodbye, there needs to be prior conversations with clear facts of where the conflict in your business lies. Because ultimately, we started working with this person for a reason. And we need to honor that by seeing if it's something we can work through (by making things clear and by identifying the conflict), and see if we can take steps to get to where we need to be. And if it's not going to work out, that's okay. You can still honor both people and move on with respect, even if you disagree.

Read More: My Team Building Story: Hiring, Outsourcing, Terrible Hires, Delegating And More!

avoiding conflict in your business before you fire someone

How do we balance being friends with our team members AND leading well?

Listen - I love hard. And when you run a business that is based off of what you're good at and what you're passionate about, your business is your baby. And as you bring people into it, it does feel like a family. Beyond the team, a lot of my clients have become really good friends. My virtual assistant has become a really close friend (like we've gone on retreats together!), so it's really difficult when you have to have these hard conversations and when you have conflict in your business or potentially have to let them go or anything like that. Or even when they have a hard day in their personal life or in their business, I find myself wanting to fly across the country and just like treat them to lunch. I like to send them Starbucks gift cards to let them know I’m thinking about them.

When you have someone working in your business, they're investing their heart in your business, too. So there's naturally that connection of friendship and that family-type feeling. Ultimately, my advice is not to conform to what the culture or traditional business advice would tell you. I have heard a lot of “you have to be hard” or “don’t get emotionally involved”. And I'm not saying that that's not applicable in some cases, but I guess my belief around this lies within what I feel like God calls me to, and that is to love and honor people well. I feel like he has personally equipped me in specific ways to do that for people. And so if I feel that gut feeling to pray for my client or pray for my team member, I will do it. If I know my virtual assistant is having a hard time, I can step in and take care of things for her. I can be sensitive and empathetic to that. 

Elizabeth McCravy works with family and gets to know her team

It’s important to be yourself in leadership too

Every situation is different and I think that is why it's super important to be yourself and to lean on who you are as a person. A huge reason we start our own business is so that we can build the narrative of our lives to honor what we feel called to and what we feel passionate about. So if you're ignoring that because of the fear of being hurt or hurting someone, then you're doing everyone a disservice. We've got to show up as our imperfect selves and serve well. That's the only way that we serve well, by showing people that we're human too, you know? And when we don't hit the mark every time, that's okay. We just have to accept grace that's freely given to us and extend that to other people.

EM: I think that’s such a good reminder and honestly, it kind of reminds me of the book Traction, which I love, and I feel like a lot of people in the online space love, but it doesn’t always work for our kinds of businesses either. It’s easy to get caught up in what the big corporations are doing (for everything - not just handling conflict in your business) and think “I should do that too” but the truth is we can run our businesses however we want.

Read More: 8 Keys To MORE Freedom In Your Brand And Website Design Business


What would you say to the business owner listening who doesn’t feel that close with their team right now?

f you are not meeting with your team on a regular basis, you need to be. It doesn't have to be every week and it doesn't have to be for a full hour. It could be 15 minutes once a month. But you have to connect with them and be willing to ask important questions. 

If right now you are thinking, “How do I even orchestrate a team meeting?”, I know it can feel nerve-wracking. Not all questions have to be business related. You can ask questions like: 

  • What is a win for the week (or month)? 
  • What's a challenge for the week (or month)? 
  • What's a question you have for me right now?

Don't limit it to business stuff, either. Allow it to be personal. One thing that I like to do is when someone starts working with me on my team, or on other teams that I help manage, I have them fill out this onboarding form that actually asks them questions about themselves. I ask them surface-level things like, “What’s your favorite store” and I also ask them things like “What’s your love language” and “How do you like to be rewarded?”. You can actually learn quite a bit about a person by asking those questions and then that will help you cater the way that you talk to them as well. I have a podcast episode on this as well. 

Ultimately, what we're doing by asking these questions is bridging the gap. If we think about conflict, if you don't know your team at all, but you do want to get to know them, then you're at point A and you want to be at point B. So, what are the steps you can take to get there? Asking these questions is going to help you. 

You have to be able to open that door and know that it starts with you. It starts with that leadership courage and being able to take the step and say: I want to get to know you. I care about you. Even if you are just in my business to check my inbox, you're still a human being, and that matters.

EM: I totally agree - it IS so important (and so hard) to meet consistently at times. One thing I did at the end of last year which has really helped is scheduling all of our team meetings and one on one meetings MONTHS in advance. I put everything in Clickup so they have it on their calendar. Then as it approaches if we don’t have anything to discuss for whatever reason, it can always be canceled or moved, but the date is set so we can be PROACTIVE instead of reactive. As another tip: we do a Slack check-in every Monday where everyone says what they are working on, what they might need this week to get their job done, and what’s going on in their life that week.

What would you say to someone that doesn’t feel like a leader right now?

First, it’s a myth that anyone feels like they are perfect at setting boundaries. 

I feel like there are people who think that I'm really good at setting boundaries, and I have worked on this a lot for myself and my business, and so it has become easier for me, but does it feel like I've gotten it perfectly? No, it never does. So if you're feeling like you're doing it wrong, at least you're doing it. Give yourself some credit there. 

Leadership and setting boundaries is a muscle that you have to strengthen in your business and in your personal life (both to feel confident and also have the courage to do it). So the advice I have there is to be willing to just stick it out through conflict in your business. I also want to encourage people that if they set a boundary and they get a little bit of pushback from that, then it's probably a sign that it's working.


Rapid Fire Questions with Jillian Dolberry

What would you say to someone considering an Elizabeth McCravy website template?

How much time do you have? I went to college to be a graphic designer and then by the grace of God, have just moved into a completely different space but because I have that background, I feel like I can't “unsee” good design or bad design. What I have loved about the Elizabeth McCravy website templates is that I have like the hardest time choosing between them. They all have ready-made professionalism for you but are also incredibly versatile. They also feel really intentional. 

Elizabeth, you are so good at doing this in all aspects of your business but for example, when I come to your shop saying, “OK, I need a website template”, you don't just give me your website template. You also give me a coupon code for your website template and you give me a quiz so that I know which one's the best fit for me. Then you give me a course on how to actually do the thing. You feel very well cared for throughout because you came for one thing but you ended up with everything you need. Not only do they look amazing, but it also just feels good because I feel empowered in customizing it for my business.

In the last few years, what have you gotten better at saying NO to?

I'm a recovering people pleaser. I'm honestly in a season of quitting because I'm a two on the Enneagram. I'm always volunteering for things because I love people and I just want to help them. It's just a part of who I am as a person. I would say that the muscle I have strengthened the most as far as saying no is saying no to meetings on specific days. I protect my Mondays with everything I have because I know that especially as a two, if I get moving and helping other people, I've lost myself by the end of the day. When I think about what I need at the top of the week, it's giving my business the oxygen it needs. 

It's giving me as the business owner the oxygen I need to be able to fulfill all the needs of other people too - and I'm not just talking about business. I'm talking about my family life too. Mondays and Tuesdays are... chaotic in our house. There's soccer, there's small group, there's taekwondo, my husband is a teacher and a real estate agent, all the things. So there's got to be a priority around making sure that I have given myself and my business what I need on Monday because by the time the week takes off, it is on its own track.

Connect with Jillian Dolberry

Definitely check out my new website here, or tune into the Grace Filled CEO here. I’m also on Instagram all the time @jilliandolberry and I’m in my DM’s a lot if you want to come say hi!

Did You Know Jillian Uses the Gabby Template For Her Website?

The Gabby template has been a best-seller here at Elizabeth McCravy for a while and when people ask me what template I would choose for my OWN business, the Gabby template is often my answer. The Gabby template is a FULL Showit website template, with the option to add on both a sales page and podcast pages. The vibe of the template is polished and professional but with a lot of zing as well through colors and fun typography. The Gabby template also won FIRST PLACE among 30 other templates in a Showit design contest when it launched. Don’t forget to use code BBPODCAST for 10% off as a special gift for tuning in.

Best Showit Website Templates for coaches-gabby

Links Mentioned:

Watch this episode on Youtube

Join my FREE Breakthrough Brand All Access Facebook Group

Shop the Elizabeth McCravy Website Templates 

Check out Booked Out Designer

Connect with Elizabeth on her Instagram

Connect with Jillian on her Instagram

Check out Jillian’s website (the Gabby template IRL!)

June 13, 2023

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listen to the podcast!

I'm Elizabeth, and simply put, I design brands and websites. I mix in marketing strategy, personality galore, and tons of fun to create custom brands, custom websites, and website templates. These designs convert lookers into buyers and take the headache out of the design process. I believe your brand should be a knockout. I'll help you create a captivating + profitable online presence! Join me, won't you?!

Hey there!
of the year


Let's be friends, yo.