7 Ways Leaders Can Make Difficult Conversations Easier


Throughout the years, I have had dozens upon dozens of difficult conversations.  From laying people off, to discussing attendance issues, to conversations on performance.  None of these conversations were easy.  There were conversations that ended up going smoothly and those that left me feeling like I missed the ball.  The best ones were those where the recipient ended the conversation by thanking me for the discussion and where the performance issue improved.

What I noticed was that there were common patterns in what drove those successful conversations.  Key steps that when followed, increase your likelihood of a successful outcome.

What is the successful outcome of a difficult conversation?  Mutual understanding and agreement of two conditions:

  • What is the variance between the desired outcome and actual outcome?
  • What the next steps should look like.


Here are 7 Ways Leaders Can Make Difficult Conversations Easier


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

My last blog post was titled, “6 Reasons Why We Avoid Having Difficult Conversations”.  Procrastinating on having those 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.


Seek First To Understand

Understanding 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.


“People almost never change without first feeling understood.” ― Douglas Stone


“The single most important thing [you can do] is to shift [your] internal stance from “I understand” to “Help me understand.” Everything else follows from that. “ – Douglas Stone


Use “I” Statements

The simple switch from “you” to “I” can positively impact the outcome.  The use of “I” statements minimizes making the other person feel guilty and resentful.  It is also the most 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”.


“I feel overworked and would appreciate some extra help”.


“Simply by changing your own behavior, you gain at least some influence over the problem.”
― Douglas StoneDifficult Conversations: How to Discuss What Matters Most


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 question.  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.


What is the End Game?

While you shouldn’t over prepare for the conversation, some preparation would be beneficial.  Try and figure out before you engage in discussion what the end game looks like.  Remind yourself what you want the end result to look like and use that as your guide.  It can also help keep your emotions in check and keep perspective if the recipient becomes angry.

Keeping the conversation focused on the future keeps the discussion positive. Although looking at facts is important in order to make critical conversations successful, the goal should be to change behavior and not just to present information.


Pick the Right Setting

I was shopping for groceries recently and when I arrived at the cash, the cashier was being coached by her supervisor.  Needless to say, I am not convinced of the effectiveness of that conversation.

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.

Which things were even simpler?

Click on the image below, enter your information and receive your FREE PDF guide on 6 Steps to Follow During Difficult Conversations.  I have even included some phrases that can be used as an example.

Click Here to Download