In the first article of this series, we explored why difficult employee conversations feel so uncomfortable, and why avoiding them can create bigger problems. The next step is preparation.
One of the biggest mistakes leaders make when entering a difficult conversation is failing to prepare. The quality of the discussion is often determined long before the meeting begins. Thoughtful preparation increases clarity and keeps leaders focused on solutions instead of reactions.
Understand the Situation Clearly
Preparation begins with understanding the issue. Keep a written record of employee performance and behaviors, including dates when possible. The goal is to document facts — not assumptions or interpretations — by listing what happened and when. Conversations grounded in observable facts are much easier for employees to hear and understand.
A helpful habit is taking notes at the end of each day or week. When you’re immersed in daily operations, it’s easy to miss patterns in behavior or performance, but writing things down helps you step back and see the bigger picture. In many ways, this practice is a gift to your future self when situations like this arise.
Technology can make this process easier. Many leaders now use AI tools to organize their notes. For example, you might spend a few minutes each day using voice dictation to capture observations, which the tool can summarize into brief notes that you can review later.
Plan What You Will Say
Once you understand the situation, the next step is planning the structure of the conversation.
A helpful framework for delivering clear and objective feedback is the SBI model, which stands for Situation, Behavior, and Impact. Start by describing the situation, then explain the observable behavior, and finally discuss the impact that it had on the team or the business.
Be prepared to clearly state the change you want to see. Employees are more likely to improve when they understand both what happened and what success looks like moving forward.
Practice How You Will Say It
Hard conversations tend to go best when a leader enters them calm and prepared. Taking time to think through how you want to communicate can make a meaningful difference. The goal is to remain professional and neutral, setting aside any personal feelings so the discussion stays focused on improvement.
It also helps to approach the conversation with curiosity rather than accusation. Be open to hearing the employee’s perspective. Progress is more likely when both sides feel heard.
One helpful technique is to role-play the conversation with someone you trust. Practicing out loud can significantly improve your delivery and calm nerves. AI tools can also help you think through scenarios and responses. When in doubt, put yourself in the employee’s shoes and consider how you would want the message delivered.
Choose the Right Time and Setting
The environment matters. Difficult feedback should always be delivered privately. In most cases, it’s best to schedule a dedicated meeting so both parties can focus on the discussion.
The best time to provide feedback is shortly after the situation occurs — ideally within 48 hours. The longer you wait, the less impactful your feedback will be and the more likely you’ll forget to give it.
There are times, however, when feedback should be given immediately. If a behavior is clearly inappropriate — such as sleeping at a desk — it’s important to address it in the moment. Even then, discretion matters. The goal is never to embarrass or shame someone.
Prepare Yourself Mentally
Finally, preparation includes your mindset. Shift your thinking from “This is going to be uncomfortable” to “This can help someone succeed.” As mentioned in the first article of this series, most employees want constructive feedback. They want to improve, grow, and advance in their careers.
When leaders handle these conversations thoughtfully, they help create a culture where employees feel supported and valued — fueling stronger performance, greater engagement, and higher retention.
Preparation Makes Courage Easier
Preparing doesn’t eliminate the discomfort that can come with difficult conversations. But when leaders take time to understand the issue and think through the discussion, the conversation becomes less intimidating and far more constructive.
In the next article, we’ll focus on what actually happens inside the conversation, including practical techniques that help feedback land clearly and effectively.
Originally published in Small Business Monthly’s April issue of 2026 by Julie Tuggle-Nguyen, EVP of Human Resources.
Part 2 of the Series: Making Hard Employee Conversations Easier