The Business Owner's Guide to Confrontational Conversations

September 6, 2023

Many times, that next level of success in your business is just on the other side of a confrontational conversation.

Like most people, you might be thinking, “Ahh, I hate confrontation!” And we understand, these conversations are not always fun to have, but they are crucial to moving your business forward. And good news! Today we’re going to help you seamlessly have 3 of the most common confrontational conversations you’ll likely have to have as a business owner.

The Top 3 Confrontational Conversations We’ll Work Through Today Are:

  1. How to talk with employees about their performance
  2. How to communicate with difficult customers
  3. Conversations you’re afraid to have with yourself


Because all people are imperfect and we all have room to grow, chances are, you’ll find yourself in a position where you’ll need to address an employee about their performance. We recommend that you develop the habit of regularly complimenting your employees on what they’re doing well. This creates a positive work culture, builds their self-esteem, and makes feedback and critiques more well-received.

To give performance feedback, one tool that we highly recommend using our Employee and Self-Evaluation Forms. We’ve created templates that you can download and use here! Give a copy of the Self-Evaluation Form to the employee and have them fill it out themself. As the employer, you fill out the Employee Evaluation form as well. Then, set a meeting for the two of you to go over the evaluations together. If you both rated the employee’s performance similarly, then you are both on the same page and you can discuss opportunities for next-level improvement. If not, this provides a great opportunity to talk about where the differences are. You can offer the employee feedback and inspire them during the conversation by making suggestions for future growth. It’s an easy way to get an uncomfortable conversation started and give both of you to share from your individual point of view.


No matter how exceptional your products or services are, you’re bound to run into dissatisfied customers. On one hand, negative feedback and reviews can be helpful for pointing out legitimate areas of your business that could use improvement. However, there are some people that are just plain unhappy, and your business can become a target in the crossfire of their negativity. Sometimes customers will complain about your prices being too high, or they’ll complain that they don’t like the way your business is run, or they’ll make inaccurate complaints about key employees. As a business owner and leader, one of the best things you can do is develop a strong backbone. Be humble and flexible, but also believe in your business so strongly that a few misguided complaints won’t sway you from your core mission. It’s okay to say no. It’s okay to stand up for yourself and your employees in a respectful way. For example, if a customer complains that your prices are too high, you can kindly respond with, “Thank you for your feedback! This is the price that we’ve found to work best for our business. And we appreciate your business if you decide it works for you too.” Practice being in the habit of communicating your boundaries, while still being respectful to others.


It’s important to be honest with ourselves and evaluate what’s working and what isn’t working for us in our business. We like to break it down into these two questions:

  1. What do you need to stop doing? – What are the tasks you’re doing that aren’t getting you anywhere? What is your top priority, and what are the side-projects distracting you from achieving that? What can you streamline or automate? What can you delegate to an assistant or other employees?
  2. What do you need to do more of? – What are the daily steps you should be working on to reach your goals? Is it reaching out to more potential clients? Are you willing to do more things that are out of your comfort zone? Minimizing tasks that don’t provide you results, and learning to discipline yourself in knocking out one project at a time? Whatever it may be, commit to doing less with more intention.

We hope you find these practical tools helpful! Rather than avoiding confrontational conversations, make them a fun challenge for yourself! Start today, watch yourself grow, and watch your business grow right along with you.

Read more: Entrepreneurship 101: How to get a Startup off the Ground Quickly

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CA, 95825, United States


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