Four Ways to Make Difficult Conversations Easier

One of the biggest barriers to leadership success is learning how to initiate a difficult conversation. New leaders have confessed to me in private coaching sessions that they are afraid the employee might cry or, if it’s a high performer, the employee might quit. Others have told me that they don’t have the confidence or skills and are afraid to ask for mentoring because they don’t want to appear to be incompetent. As a result, conversations that need to take place are put on the back burner, waiting for an explosion. (In fact, time and time again I have observed that the conversation avoided today becomes the lawsuit a decade later.)

Here is a four-part process new leaders can take immediately to make the difficult conversation doable.

Set Your Intention
Leaders are human too. If you are still angry about a situation, you may be unaware of competing motivations: the intention to embarrass someone versus the intention to help the employee course-correct.

Practice saying, “My intention is…” before you take any action or hold any conversation. See if what you say equals how you feel. If there’s a hint of blame, or a sting of sarcasm, you have some “energy management” to do to align your intention with your action.

Talk Observable Behaviors, Not Assumptions
Consciously speak about the observable behaviors, not your feeling or assumption about what’s going on. Look at the difference between saying, “You have a bad attitude and don’t care about others” versus “Yesterday I saw you slam down the phone and leave work early.”

It’s difficult to measure someone’s attitude, thought process, or motivation, but you can definitely ask for a specific behavior change that is observable and therefore measurable.

Speak to the Vision
Ask for what you want instead of asking for what you don’t want. A big mistake leaders make is talking about the past–about what didn’t work and about what should not have happened.

See the difference here: “I don’t want you to miss your sales numbers this month,” versus “I want you to easily make your sales numbers this month.” Every time you catch yourself saying “I don’t want…,” finish the sentence and then say, “What I do want is…” You will change the habit after about a dozen consecutive practices.

Connect the Dots
Bad behavior affects the business. For example, the Queen Bee doesn’t get along with the team, therefore teamwork is non-existent. The rude boss makes the environment miserable, so absenteeism increases. Lack of proper documentation puts the company at risk for litigation.

When you give performance feedback, help your employee connect the dots to see how their behavior affects the business. For example, “When you come in late, it sends a message to the entire team that punctuality doesn’t matter. In addition, others have to pick up the work-load, and they start to get resentful. So, it affects productivity and teamwork.”

Conclusion: Difficult conversations are difficult because of three things: internal resistance, external resistance, and lack of skill. As a leader, you have the power to increase your skill and reduce your internal resistance. Once you befriend the uncomfortable emotions associated with helping others to course-correct, and you communicate with the right intention, you not only elevate your leadership, you elevate your life.

Disclaimer: This article first appeared on AMA Playbook

Marlene Chism is an executive educator, consultant, and author of Stop Workplace Drama, (Wiley 2011) and No-Drama Leadership (Bibliomotion 2015). She works with executives, and high-performing leaders who want to transform culture in the workplace. To explore opportunities please email