Get expert insights delivered straight to your inbox.

Skip to Main Content

How to Handle Difficult Discussions

In the world of awkwardness, difficult situations, and just plain don’t-want-to-do-it, almost nothing ranks higher than having to tackle a tough conversation with a team member. And when that person’s a family member, it only gets worse. No one wants to tell a son or daughter they’re just not cutting it. The easiest solution is to put it off.

So how do you handle these tough situations when your natural instinct is to totally avoid them? Here are a few dos and don’ts of dealing with conflict.

Don’t put it off. Revenge may be a dish that tastes best served cold—at least according to Don Corleone—but if you are having an issue with one of your team members, it needs to be handled as soon as possible. Procrastination not only hurts you and the person involved, it also hurts your whole staff as they watch incompetence or bad behavior go unacknowledged. Like Dave says, “If you allow people to misbehave, underachieve, have a bad attitude, gossip and generally avoid excellence, please don’t expect to attract and keep great talent. Please don’t expect to have an incredible culture.”

Do get it on your calendar. Schedule an appointment for a meeting with the person who is having an issue and block out enough time to get the problem solved. It’s not fair to either of you if you rush and wind up without a resolution.

Don’t be cruel. Nothing is ever accomplished by being a bully or being mean, even when you are justifiably upset. In this situation, you have power and control, and they have neither. Plus, the idea of the meeting is to course correct and teach—not to embarrass and demoralize the person or lose your cool.

Don’t lose focus. For most of us, the first response to an uncomfortable conversation is to shift to a different subject. But as a leader, it’s the last thing you want to do. You have to concentrate on the problem at hand and keep on course.

Do be prepared. The easiest way to stay on track is to be ready before the meeting. Write down the preferred outcome and the talking points you need to cover with the team member to accomplish this goal. Keep the list close at hand. If you feel yourself starting to drift, grab it to remind yourself of what you need to cover.

Being a leader is never easy, especially when it comes to hard conversations. But to be able to unify your team and move your company forward, you have to deal with them. The best way is to set a time, extend grace, and be prepared beforehand. And then the one thing you were dreading the most suddenly becomes easy.

Learn what it takes to become a great leader. Our weekly newsletter includes tactical advice and resources that will propel your business and leadership skills to the next level. Sign up now!

Did you find this article helpful? Share it!

Ramsey Solutions

About the author


Ramsey Solutions has been committed to helping people regain control of their money, build wealth, grow their leadership skills, and enhance their lives through personal development since 1992. Millions of people have used our financial advice through 22 books (including 12 national bestsellers) published by Ramsey Press, as well as two syndicated radio shows and 10 podcasts, which have over 17 million weekly listeners. Learn More.

Related Articles

Best Business Podcasts

Best Business Podcasts

Use this list to find a new favorite from the best business podcasts out there, then start listening and unlock new levels of business and leadership success.

Ramsey Ramsey
best small business quotes

Best Small-Business Quotes

Need some wisdom to conquer your business and leadership mountains? These small-business quotes will guide and encourage you. Stay focused and climb on!

Ramsey Ramsey