Elite Virtual Assistants

EVA Blog Article
Courageous Conversations
November 1, 2021

Updated: Oct 26, 2022

Courageous Conversations by Laura Licursi

Courageous conversations. These aren’t easy for most of us, but they’re essential if you’re going to thrive in today’s world. If you can’t or won’t stand up for yourself, or your beliefs, who will? If you’re unhappy or unclear about something and don’t speak up, who will know? If you feel you’re being taken advantage of and don’t let someone know how you feel, how will things change? There are two ways to deal with problems: mask it or fix it.

When you mask it, it’s like sweeping dirt under a rug; it really doesn’t have anywhere to go, so it just keeps piling up until eventually, you can’t hide it anymore. And then, you guessed it, the sh*t hits the fan.

When you fix something, you deal with it head-on. It might not be pleasant, it might be uncomfortable, it might be scary… but it’s handled.

Every successful person I know understands there is one common denominator to be the best you can be… and that’s to always have open communication with everyone in your life. And many times, being able to have that type of communication is led by the ability to have courageous conversations.

Let me start by saying that it’s taken me years to truly understand this concept. When I was younger, a courageous conversation to me was basically telling people EVERYTHING that was on my mind. You know that saying, “Wear your heart on your sleeve”? That was me. Work, play, it didn’t matter… whatever I was thinking just came out. And that’s fine for some people, but to really be successful in this life, I knew that I had to rein it in and learn to articulate my feelings in better ways. And, even though I was better at it in the business world, I wasn’t so good at it in my personal life. The two are really intertwined; you can’t be one way at work and one way at home… your communication style needs to be reflected in all the areas of your life.

Age does funny things to people. Some become more laid back. Some more uptight. Some learn from their mistakes. Some don’t. For me, I’ve become more self-aware. Not that I don’t fall back into bad habits now and then, but I make a truly conscious effort to communicate openly, honestly, and effectively with everyone in my life. I try to remain calm and see things from the other person’s perspective. I put myself in their shoes. And do you know what I usually find? They have no idea how I’m feeling! Maybe that’s the way they’ve always done things and no one has ever told them otherwise. Maybe they’re having a bad day or a bad week. Maybe something is going on personally that’s filtering through to the current situation. Whatever it is, you’re not going to know until you open up that conversation.

In today’s virtual, fast-paced world, where there are more ways than ever to communicate with each other, we, as a society, are worse than ever at it. We’re busy, overcommitted, distracted, and without meaning to be, unaware of how we’re coming across to others. We give short answers, send quick texts & unproofed emails… we’re so busy worrying about what’s next that we don’t stop to think about the “now”. We like to just move on instead of trying to work things out. And sometimes things can’t be worked out, but how do we know unless we consciously try?

And the best way to dig into the root of any problem is to be willing to lead a courageous conversation. This may make you uncomfortable. That’s okay. We can’t grow if we stay in our comfort zone. This may scare you. That’s okay too. Scary isn’t always bad. It means you have to be brave enough to overcome your fear and strong enough to have the conversation.


Over the years, I’ve followed a few steps when I’m feeling like it’s time for one of “these” conversations:

  • I never address anything in a frenzy, while I’m upset or angry. This is a recipe for disaster and can cause even more problems down the road.
  • I walk away until I can calm down, no matter how busy I am. Getting some fresh air can do wonders for a quick cooldown.
  • I always write out my thoughts, even if it’s just an initial brain dump. And it’s usually not pretty… but I get all of my thoughts and feelings out first, then work on what I need to prep for that conversation.

Then, I write the answers to these 3 questions:

  • What’s the purpose of the conversation?
  • What do I hope to accomplish?
  • What are my intentions?

Now, I craft my conversation. These are always best addressed either in person (if possible), on Zoom, on the phone, or, if all else fails, a nicely-written email. Even if the conversation happens in person, it’s best to write everything out (it’s even okay if you read it, I’ve done that before!). Do what works for you to keep your emotions in check and keep you on track. And, I always watch my words. I try never to accuse, because many times, the problem has more to do with our perception of the situation.

Let me give you some examples of some experiences that can warrant that courageous conversation and what it might look like:

Let’s say you’re working with several people at the same company. They begin the relationship by throwing anything and everything at you from all different directions and reaching out to you on multiple channels. You’re frustrated and overwhelmed and want to cry (or walk away altogether). What do you do?

A big part of being professional is knowing how (and how NOT to) handle a situation like this. There’s almost always a solution to be found, but your approach is imperative to your success.

So, if you follow my steps above, then you would quietly walk away so you can breathe & reflect.

Then, you’d answer the 3 questions listed above and write out your answers, which could look like this:

  • What’s the purpose of the conversation?
    • To let the people you’re working with know that the way things are going is not working and you’re overwhelmed by the disorganization of the current situation.
  • What do I hope to accomplish?
    • To find a more streamlined way of presenting work that has to be done.
  • What are my intentions?
    • To find a solution that makes it easy for your client to give you work, easy for you to receive the work and get it done in an efficient manner.

Now you can sit down, write out all of your thoughts, and put them together in a format that makes it easy for you to start this courageous conversation. You can start by saying something like, “(Name[s]), I’d like to set up a time for us to talk because I’m struggling with our current situation and workflow and have some ideas and suggestions on how we can work in a more efficient and effective manner that will benefit all of us”.

Now you’re ready to address the current situation and your solution to the problem. Let me tell you, most people will applaud you for taking the initiative to resolve this problem, and as I mentioned above, they may not even be aware of how it’s affecting you or others around you. Solutions could be as simple as:

  • Implementing a project management software where all communication stays within one platform.
  • Setting boundaries as to when you’re available and when you’re not, especially if work is being thrown at you at all hours of the day and night. These can include things like:
    • You’re free to message me anytime, but I can only respond between the hours of 9am-5pm, Monday-Friday. Anything sent to me outside of those hours will be addressed on the next business day.
    • Set up the response time expectation. Usually, 2 hours gives everyone on your team ample time to work with.

Here are a few other examples of bottlenecks that would require communication and a courageous conversation that you can apply the above method to:

Communication Bottleneck: You want to say NO to something

It’s okay to say no. If you’re meeting with a client and you’re a far-right-wing and they’re a far-left-wing and you’re not okay with that… let them know! If you’re religious and they’re not and you believe it will affect your relationship… let them know. You’ll be far more respected for being upfront about your feelings and beliefs, along with the fact that you won’t be wasting your time or a client’s time by getting yourself set up to work together. People are too busy these days. Be strong, be brave, be you.

Communication Bottleneck: You Don’t Know Everything

It’s also okay to not know everything. If you have a potential client with a list of six things they’re looking for help with and only you know four of them, would you turn down the job? It’s okay to confidently say, “I can definitely help you with the top four items, but I would need some time and/or training to learn the other two, which I’m willing to do on my own time”. People respect that. You’re being honest, you’re taking initiative to learn something new (that you’ll be able to add to your resume), and you’ll be giving yourself some grace during the learning process.

Communication Bottleneck: You Don’t Like Everything About A Job or Project

Not every client will check every box you have in your head. This also goes to the fact that there may be a task or two a client wants you to do that isn’t really in your wheelhouse, meaning, you don’t “like” to do those things. If the entire job consists of this type of work, then, of course, you would turn it down. But if it’s one or two tasks out of 10, then suck it up buttercup! Life is full of doing things we don’t like to do, it comes with the territory. I’ve never heard of anyone saying, “I love changing a poopy diaper”, but does that mean we leave our kids in dirty diapers because we don’t like doing it? I sure hope not. My point is, there are parts of everyone’s lives that aren’t 100% pure enjoyment. But that’s life. I like to look at situations like this using the 80/20 rule: as long as I enjoy 80% of the work, I can handle the 20% I don’t enjoy. For that 20%, use the “Eat That Frog” approach: make it the first thing you do and get it out of the way!

Communication Bottleneck: You See An Opportunity To Offer More Assistance

Let’s say you’re looking to work more and you know there is more work to be done. Chances are your client is too busy to even think about how to offload more work (most entrepreneurs think it’s easier to do it themselves). Think about this: how do you know that your unwillingness to reach out and tell your client that you’d like more work or more challenges isn’t perceived as you being uninterested or too busy, which is why you’re doing the bare minimum? Again, this one goes back to not opening a line of communication with your clients, and when that happens, people dream up their own reasons why things are or aren’t happening. Don’t make people wonder, let them know where you stand at all times.

Communication Bottleneck: You Want To Stop Working With Someone

Don’t. Go. MIA. I’ve seen this happen before and it floors me every time. If you’re overwhelmed or need a break… tell someone! And, be prepared to help transition someone else in your place. Even though the world is a huge place, the world of business is smaller than you think. People talk. People speculate. Everybody knows someone that can relate back to you. And that’s not always good depending on how you handle situations. If there’s an emergency, there’s still no reason you can’t reach out via text or email to let someone know you’re unavailable and stay in touch until you have a solution for them. As a professional, it’s your job to make sure that if you can’t complete a task or project for someone that you help find a replacement or solution for them. It’s professional. It’s courteous. And it’s exactly how you would want to be treated yourself.

Communication Bottleneck: You need clarification

Many times small business owners are pulled in 100 directions and their instructions are clear as, well, mud. Don’t be afraid to stop them and use this phrase from Brené Brown from her Dare to Lead book, “Paint done for me”. This simply means to have them take a step back and explain to you what their end result looks like to them when the task or project is complete. Knowing the expected outcome of what you’re working on will help you to work in the most effective and efficient manner to ensure you’re delivering the results they require instead of just checking that box as “done” off a list of to-dos. Chances are if you’re not clear about what to do, and you’re afraid to ask, then you’re going to end up doing it… again. And this time, at your own expense.

My best advice is this: instead of being afraid to communicate with a courageous conversation, think of it as the foundation of building a strong relationship, and a testament to your dedication to handling your responsibilities as professionally as possible.

Stop thinking small. Stop worrying that you’re bothering people because you want or need answers. You are as important as the next person and deserve to be treated in a respectful manner. But remember, no one will know how you feel if you don’t speak up, and be prepared to lead a courageous conversation!


Ready to have your own courageous conversation about your business? We’re all ears!

Schedule A Call!


3 Critical Steps to Take Before Hiring a Virtual Assistant

Don’t Waste Anymore of your Time!

We have a simple process; learn what you need to get you started with a VA!

Download our handy Action Guide that will walk you through the 3 Critical Steps To Take Before Hiring A Virtual Assistant.  When the time is right, you’ll be prepared!