Jade Boyd Co.

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3 Ways to Avoid Awkward Conversations with Systems

3 Ways to Avoid Awkward Conversations with Systems | The Business Minimalist™ Podcast
I'm Jade!

MBA | Business Strategist | Business Minimalist | I help busy creatives bring order to chaos with an intentional business strategy and simple systems.

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Have you ever heard the lines, “sorry, it’s company policy” or “I don’t know, let me transfer you to my manager”? If I’m being honest, as a business owner, whenever I hear these lines, there’s a part of me that gets really jealous. I mean wouldn’t it be nice if we could all just forward tricky emails and requests to our “manager”? Or tell those over-demanding clients, “Sorry, there’s nothing I can do about that, it’s company policy.”

As business owners, we get a lot of random requests and questions ranging from over-the-top exciting to excruciatingly uncomfortable. But I have some good news! You can create many different types of systems and automations in your business to eliminate a lot of those awkward situations virtually overnight! In this episode, I’m sharing three examples of systems that my coaching clients and I have used to avoid some really awkward situations.

3 Ways to Avoid Awkward Conversations with Systems | The Business Minimalist™ Podcast with Jade Boyd


Has someone ever asked you to speak at an event (or do some other favor/collaboration) and not mentioned how much they would pay you? I noticed this happening a lot with speaking requests for me and my clients. Instead of responding to their request with, “How much are you going to pay me?” I created a speaking questionnaire instead! This not only helps me stay organized and collect all the information I need in one place, it also means I get to respond to their inquiry with excitement and clarity on what the next steps will be.


If you’re like me, you get a bajillion cold pitches daily. And let’s be real, most of them can be deleted immediately. But what about those pitches that deserve a response but still aren’t the right fit? I wasted so much time responding to emails from people requesting to be guests on my podcast who just weren’t the right fit. Instead, I created a template email response telling them exactly what I WAS looking for and pointing them to fill out a podcast questionnaire with more information if they had a specific (and interesting!) topic that matched what I’m looking for. As a bonus, it’s the same form I have all of my guests fill out, so I’m two steps ahead if they come up with a good topic to share.


Let’s be real – no one wants to get the email that says, “we need to talk”. And it can be really hard to communicate constructive criticism to contractors and employees over email. Instead, think about scheduling set times for check-in meeting where regular feedback (good and bad) is expected and welcomed! This makes it easier and more natural to broach the harder conversations without turning into a big thing.


I truly believe that there are few awkward situations that systems can’t solve in your business. Dealing with any other awkward situations you can’t stand? DM me on Instagram @jadeboyd.co and I’d love to brainstorm a systems solution with you!

Links and Resources Mentioned in This Episode


Click here to read the full episode transcript!

Jade Boyd: As business owners, we can’t have the line of, sorry, it’s company policy because we are the business owners.

Today, I’m going to share with you three different systems that I use to avoid awkward conversations in my business because let’s be honest, as a business owner, we have to interact with a bunch of different people on the internet and sometimes things can get a little bit awkward and there’s lots of ways that systems can help us set up our business in a way that makes things more structured and gives us an out to get out of some of those awkward conversations or situations.

I always think about employees recently, I was at Staples and printing out templates, some prototypes for my wall calendars for the planner, the planner line that I’ve been working on for 2 years, and it’s finally coming to fruition, but I went to pick up my order and it printed absolutely horribly. And he gave me the line of, oh, sorry, the printer is broken.

There’s nothing I can do about it. Corporate, corporate, blah, blah, blah. And as business owners, we can’t have the line of, sorry, it’s company policy because we are the business owners. So it’s like, sorry, I don’t want to help you. Or sorry, I don’t want to do that for you. And that can be awkward and it can be uncomfortable, especially if you’re a person who doesn’t like confrontation.

But naturally, as business owners, we’re going to be asked to do a bunch of different things for a bunch of different people. People are going to ask us for favors and time on our calendar. And there’s lots of ways that systems can help you be kind to those people, be empathetic, but also be professional and stick to your boundaries.

So I’m just going to give you three quick examples today of things that you might be able to directly implement the way that they are or adapt the strategy and implement it in a different way in your own business.

So my first system is a speaking questionnaire. Whenever somebody asks me to speak, I send them a questionnaire to fill out. And this came up recently with a client because she was asked to speak at an event and they basically told her everything except If she would be paid or not, and it’s hard when somebody is giving you this great opportunity to speak to be like, well, are you going to pay me?

It can present kind of an awkward situation, but really, like, I want to be paid for this, this event. If I’m going to travel and speak there, right? Because she has been paid to speak at other events as well. And so. I recognized this last year after speaking at a larger summit. I was asked several times after that to speak for people who’d either seen that talk or been on my email list and watched it, and I found myself coming up with this problem for the first time too.

Like, there’s so much information that I need to have in order to know if this is a yes or a no for me. And so I created a speaking questionnaire in ClickUp that asks all the information that I need to know in order to make a good choice for me and my business in terms of, is this going to be the right audience for me? Is my topic going to make sense for them? Is this a paid speaking event? How much is your budget? Is there travel? Is this virtual or is this in person? What location is this at? To not only like streamline having everything that I need to know. In one place, if I say yes and show up to the event, it would still have everything I need to know to prep and go to the event as well, but also to help me make better decisions in my business without having to have a back and forth conversation and DMS that seems really unprofessional or to straight up ask somebody, well, are you going to pay me or not? Because it can feel a little bit uncomfortable in a one to one situation, not that that’s a bad thing to do, but having the system in place makes it super seamless.

So if you want to see exactly what’s on that form, it’s a public form that’s on my website. So if you go to my contact page, www. jadeboyd. co backslash contact, you’ll see a link for my speaking inquiry form and you can copy and paste all those questions and use them. If you do speaking events or if there’s some other situation in your business that you could apply that to, of course, client inquiries of any form, you’ll want to have a questionnaire similar to that, but for this specific instance, that If you want to grab those questions and make this part of your business a little bit easier, feel free to go over there and do that.

The second thing is a podcast guest questionnaire. If you have a podcast, You will quickly be inundated with podcast guest pitches in your inbox. I feel like I get multiple every single day at this point. And it’s really honestly exhausting. And a lot of them are just really terrible. Like, why would you pitch this person to be on my podcast?

They are talking about topics that make absolutely no sense for my audience, and they have no experience in small business ownership. A lot of crappy pitches, but a lot of pitches that are like, okay, I could maybe see that, but… the pitch isn’t super clear or I’m not sure what topic they would actually focus on. They seem like a great business owner and they could provide value, but I need like a spicy topic for them to pitch me on, right? So another system that I set up because I found myself, there’s so many of these pitches that I just found myself deleting them because I didn’t have enough time to read through their entire website and read their entire pitch deck and make an informed decision, you know, three times a day.

It’s not the best use of my time. So I created a template email to send to people that basically says, hey, I really appreciate your interest in being on the business minimalist podcast, here’s a bullet point list of the things that we’re looking for right now. And if you’re listening to this and are interested in being a guest, I’m specifically looking for people who are experts in specific evergreen marketing strategies or system softwares. So that’ll give you a little. Bit of a preview of what’s to come in 2024. And then after I give them that bulleted list of what we’re looking for so that they can kind of self diagnose if they’re a good fit or not. I say, hey, I have this form. If you’re interested in being a guest, you can fill it out. We’re booked for guests for 2023, but if you fill this out, I will review it and consider you as a guest for 2024 with no promises that I’ll get back to them. So it’s a short and sweet template. It gives them all the information they need. It puts the onus on them to fill out the form and then I don’t have to do the mental thinking of how am I going to respond to this person nicely because they seem like a really nice person, but I don’t want to tell them that what they want to talk about is not valuable for my audience, right? It’s a little bit awkward. So having this form solves that problem for me.

And then, of course, you can just delete it, which I said I was deleting a lot of them. But some of these people are tenacious and they will follow up many, many times. And so it’s worth my time just to send a template email so they stop, emailing me. There’s so many of them. If you’re a podcaster and you experience the same problem, you should DM me because we can commiserate about this.

I don’t know how they find me. I’m sure it’s because they’re searching through podcast directories and searching for business or something like that. But a lot of them is just like, why, why did you pitch me this? It makes no sense. So anyway, I’m definitely dedicated if you’re a listener to only providing you the best of the best guests. And I hope that that’s been your experience so far. And if you have people who would be great recommendations for guests, always open to hearing that. But that’s one system that I have to avoid those awkward conversations of anyone and everyone wanting to be on this podcast.

And my third and final system for you, a tip for avoiding awkward conversations in your business is to have scheduled times for feedback meetings with employees that you have or with contractors that you’ve hired to work with so that there is a set time and place to give them feedback. So that you don’t have to send them that email that says, hey, we need to talk because nobody likes getting that email that says, hey, we need to talk. And usually it’s not as scary as people assume it’s going to be, but having a set time for feedback and to check in on how things are going, either congratulate them on things that they’re doing well, or let them know ways that you want to see them improve or ways that you can help them make those improvements makes it a lot easier and more natural to broach the harder conversations if they do end up coming up without turning this into a big thing.

I was working with a client, a service provider recently, who was realizing that she doesn’t have the right people in the right seats in her business. And it wasn’t a matter of training. It was a matter of giving people who are already doing incredible work more of the tasks that they’re naturally good at, but she was having a hard time knowing how am I going to tell them this and how to transition that work off their plate and onto someone else’s plate.

And so we talked about exactly this scheduling check ins regularly, whether for you, that might be once a week. If you’re working with somebody 1, really in depth, or it might be once a month or once every quarter. The frequency is going to differ based on what type of contractor it is and how much feedback they need.

It also varies with how long they’ve been with you. I just onboarded a VA at the end of the summer. And initially, we were meeting more frequently. And now that she’s onboarded and kind of knows what’s happening, we’re meeting a lot less frequently. So set a schedule that makes sense for your employees or your contractors and when you need to have those conversations.

But if you’re already doing that consistently, one, it’s not scary. And It’s not awkward if you do end up needing to give them feedback because it’s a rhythm that they’ve already been in. And two, it’s also a little bit of accountability for you if it’s hard for you to again, engage in those conversations that might be a little more awkward. It’ll give you the accountability because you do have a set time and it is your job as a leader, as the CEO of your business, to be investing in your people and to be leading them well. And part of that is giving them feedback and constructive criticism sometimes.

And planning ahead makes it a lot easier to schedule. So that is number three. Having set meetings to give feedback for your employees and for your contractors and allowing them to give that feedback to you too. Because maybe they’re holding on to some awkward feedback that they have wanted to tell you and don’t have the right time or place to say that. So it’s a good time to ask them for feedback as well.

So to sum this all up, the three systems that we talked about today were a speaking questionnaire for speaking events, a podcast guest questionnaire, and set times for employees and contractors to give feedback. I hope that this episode gave you some new ideas on how you could create systems in your business to not only streamline things, but avoid some of the awkward situations that you know that you procrastinating on or just straight up avoiding altogether, like deleting those emails and instead have the opportunity now to turn them into systems that help you move your business forward without the messy, uncomfortable conversations that we all want to avoid.

So I hope you take what you learned today and get 1 percent better this week.

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Hi, I'm jade!

Ready to simplify and scale your services?

From MBA to Brand Photographer to Business Coach, I learned the hard way how to build a life-first business that allows me to work part-time hours without sacrificing profit. Now I help service providers simplify and scale their businesses so they can earn their dream income while living life on their schedule. If you're ready to build a sustainable, profitable service business (without the burnout), apply for the Business Edit Group Coaching Program today!

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Business + Productivity Coach | I help busy creatives bring order to chaos with an intentional strategy and simple systems.

Hi, I'm Jade!

Jade Boyd Co.