Become a pro at having hard conversations.

5 Steps to Making Hard Conversations Easier

Business Tips

5 Steps to Making Hard Conversations Easier 

If you’ve been in business for very long you’ve probably had your fair share of hard conversations. I want to make these conversations less painful for you, so here’s my five steps to making hard conversations easier. 



The hard conversations I’m talking about are not the ones you need to have with your spouse, your mom, or your friend. I’m talking about the ones you need to have with an employee, client, etc.

Maybe there’s someone who sent you a disrespectful email or is copying your work. Maybe there’s someone you need to let go or talk to them about doing something differently in their work for your business. 

These are the hard conversations I’m referring to when I list out my five steps. There’s tons more examples of hard conversations you will have as a business woman, and these five steps will help you in whatever that conversation needs to be. 


Make your hard conversations easier with my five steps.


Before I get into the five steps, I want you to know that having hard conversations is a sign that you are growing your business. It’s a good thing! Remember, even good things are hard. 

When I first started my business, I would put off these hard conversations for months before I handled them. And when I say handled, I mean I would give in and do what’s easiest for the other person and what’s most inconvenient for me. I thought I was being compassionate and understanding of their needs. Now I realize it was the worst thing I could’ve done for them and me because I was avoiding growth for both sides. Growth is always what we want, even if it’s uncomfortable. 


Here’s an Example 

Let’s say you had a client who didn’t like the style of graphics you made for her, but she never said anything because she didn’t want to hurt your feelings. A few months down the road she decides to leave you and now you’ve lost a client over some changes that could’ve been made.

It would have been MUCH more beneficial for the client to reach out to you in the beginning and list the changes she wanted made to the graphics and you would have continued working together! Instead, you are left with a loss in clientele and your client is left with a loss of service. 

I get it. Hard conversations are SUPER uncomfortable to have. Maybe even to the point where you will never have them. But it’s worth it! When you have the hard conversations it helps you grow your business, your business relationships, and your confidence. 

You just need to learn the skills in having a hard conversation and then be brave enough to use them. And if anyone is brave enough to have that hard conversation, it’s you! Because you care about your business and your why more than having an uncomfortable conversation or possibly (hopefully not) hurting someone’s feelings. 

It’s important to note that someone’s feelings can still be hurt even if you have no intention of doing so. It’s up to them how they receive your message. You can do all the preparation on your end, but it’s up to them on how they receive it and how they respond. And that’s OK. 


Learn how to have hard conversations like a pro.


Where Most of Your Hard Conversations Come From

When someone is not meeting your expectations is probably where most of your hard conversations come from. I’ll be direct on this–it is your fault if you have clear expectations and have not communicated them. 

Are we now having a hard conversation? Just kidding! 

But it’s true! It’s important to ask yourself these three questions if someone is not meeting your expectations:


  • Have you identified what your expectations are for that person?
  • Have you told them what those expectations are?
  • Have you clearly identified them and reminded that person what they are?


No one can correct what they don’t know is wrong. This is not an emotional thing. This is a business and we want to do and serve the very best. 

Are you making corrections a part of your business? There needs to be space for correction and growth, because this is how you will grow your business and business relationships. Correction is part of the process, not a part of punishment. 

Let go of the fear, caring too much of what others think, or whatever it may be that is keeping you from having these hard conversations. It doesn’t have to be awkward or personal. Remember, correction is part of the process, not a part of punishment. 


Make correction a part of your business.


5 Steps to Making Hard Conversations Easier 

Before I give the five steps, let’s set this up with a scenario. It’ll make more sense that way. 

Scenario: You have a social media manager you’ve told once to include certain hashtags on each Instagram post, but she won’t do it. You aren’t sure why and you’re starting to feel frustrated that it’s not being done. How should this hard conversation go?


Step 1: Wait until you are calm and collected. 

I’m not saying wait three months to say anything. That would just build up your anxiety about it and make you more upset. Not to mention the three months’ worth of posts that would be posted without the correct hashtags. 

However, when you have the hard conversation, make sure you are neutral and level headed. You need to be driven by the circumstance and facts, not by your emotions. Especially if those emotions are sad or mad. 

Calm and collected is the best way to go.


Step 2: Go in with a plan. 

Do what works best for you. If writing down a plan will help you state your thoughts more clearly, do that. If running through your points in your head is enough, do that. As long as you thought about it and did a little planning about what you want to cover before you start the conversation, that will make it much more effective. 

Having a plan will also make it more clear for you and for your employee. Clear is what you’re going for, especially when talking about expectations.


Step 3: Focus on actions, not attributes. 

Hard conversations are never a time to attack someone’s attributes. Be very careful and aware of the words you use in the conversation. Focus on the actions you want changed, not on the attributes you can’t change. Commenting on attributes will only hurt her feelings and not provide any solutions. Focusing on the actions will help you and your employee have a better understanding of what’s wrong and how to fix it. 

In the conversation, you could even ask your employee her ideas on how to fix the problem. Don’t feel like you have to provide all the answers. Asking your employee for her advice will help her see you care about what she has to say and will therefore make her more loyal to you.


Step 4: Sometimes less is more. 

Do not overcompensate or over complicate. Sometimes we use too many words because we’re nervous and don’t want to hurt feelings. But then the message becomes unclear. Just be straight and simple and the feelings behind your words will show through. 

Other than not being too wordy, it’s also important to be silent.

Do you know the teacher silence? Where a teacher will ask a question and have to wait an awkward amount of time before someone answers? Yeah, that’s what I want you to be OK with. It’s OK to have silence. Giving that moment–or moments–will help her really think about the questions you’re asking and hopefully you two will be able to come up with a solution together. 


Step 5: Be kind, but professional. 

There is a professional line to stand by once you realize you are doing a legit business, and that you’re legitimately paying people and legit businesses are paying you.

By the way, one of the best things you can do when you start hiring employees is to get a contract. I use Brittany Ratelle for my business contracts. You can download a template from her website and use it over and over again. Use “Michelle15” to get 15 percent off your purchase. 

Believe me, a contract is totally worth the investment. The contract makes it less messy and less personal, which is what we want in business. Both of you signing the contract leaves it at the clear expectation that this is what you get from me and this is what I get from you. 


Learn how having hard conversations can help grow your business.


Ok, biz sister. I feel like this post was a hard conversation! Whew! Believe me though, having hard conversations is one of the best skills you can learn and my five steps on making hard conversations easier will help you get there.

If you want more tips and tricks on how to grow your business, follow me on Instagram @iammichellegifford.    

You can check out my website here to see the courses and services I offer to help grow your business too! 

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