Organizational change / Jun 27, 2025
9 Techniques Leaders Can Use During Difficult Conversations
4 min read

Summary
Nine ways to expertly handle tough conversations in the workplace.
9 Techniques Leaders Can Use During Difficult Conversations
A common thread that I have seen in many leaders is their hesitation when it comes to having difficult conversations. It doesn’t matter what management level they are; I have seen people struggle with this many times. The good news is, this is a skill that can be trained and improved upon.
By being intentional about what you want the outcome to look like, you can improve the probability of a successful conversation, no matter how difficult.
9 Techniques Leaders Can Use During Difficult Conversations
Prepare
The first step is in determining what you want the end result to be. While the conversation should allow for authenticity, you should loosely plan the topics you want to discuss. What are the key messages you want to get across and what would you like the outcome to be? If emotions get high, keep your end game in mind. This will help you get back on topic should the conversation get sidetracked.
Communicate the Topic
It can be frustrating for an employee to have their leader ramble on without knowing what message the leader is trying to convey. Start the conversation by summarizing the topic. For example, if the conversation is meant to address punctuality, you may start the discussion with, “Today I would like to address concerns with your punctuality.”
Take Responsibility
As a leader, you have a responsibility to manage your employee’s performance. If an employee is not meeting the company’s expectations and you do nothing, you are effectively accepting the poor behavior. Before you can judge an employee’s performance, ensure that you are judging your actions taken to improve your direct report’s results.
Address Conflict Directly and Promptly
There are several reasons why you may hold off having a difficult conversation. Most of them are not for the benefit of the employee nor the company. Procrastinating on having these types of discussions happens too often. Once you have identified that there is a need for that important conversation, address it directly and do not put it off. By doing so, you are not only elevating the problem but doing your employee a disservice.
Not a One Way Conversation
Avoid making the conversation a download of what you want to communicate. Difficult conversations should be just that, a conversation. This means that to spark a two-way discussion, ensure you are asking the employee questions. Asking questions to understand the “root cause” of the problem can make the discussion go a lot easier. If you can find the trigger to the undesired outcome, together, you and your direct report can find a solution.
Use “I” Statements
The simple switch from “you” to “I” can positively impact the outcome. The use of “I” statements minimizes the chance of making the other person feel guilty and resentful. It is also an appropriate way to inform someone that their behavior is causing a problem.
Here is an example of the difference between “you” and “I”:
“You never help.”
Vs
“I feel overworked and would appreciate some extra help.”
Pick the Right Setting and Time
If you have ever witnessed someone being coached in front of an audience, you know it can be uncomfortable. If you were the target of this “public coaching,” how much of the message would you retain? Chances are that the recipient of coaching in front of others would be mostly thinking about how they wish it would stop rather than the message itself.
While it is important to address issues as soon as possible, it is also essential to pick the right setting. It should be in a private area, where no employees have the chance of “dropping in”.
Keep Your Body Language in Check
Keep a conscious thought on your body language. No matter what your words may be saying, your body language may be “shouting” something different. Eye rollers not required.
The Follow-up Feedback
An important step every leader should keep in mind is the importance of follow-up. Your goal in having these types of conversations should be to inspire positive changes in behavior or improve results. Your effectiveness in having difficult conversations will depend on your follow-up after the conversation is over. This step is critical if you want to have a lasting impact.
It can be discouraging for an employee to have a performance conversation with their manager, then work hard to improve their results and get no recognition. The opposite is also true. If an employee’s behavior or performance does not improve within an appropriate time, you need to follow up with another conversation to help the employee course-correct or enter performance management.
If you need more ideas on having these difficult conversations, I have prepared a guide, “6 Steps to Follow During Difficult Conversations”.
Elita blogs about Leadership and Personal Development including a weekly #5MinMotivation series. For more leadership articles, click here.
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