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Column | Leadership

Jill Geisler: 9 ways difficult conversations go south and how to keep that from happening

Column | Leadership

Jill Geisler: 9 ways difficult conversations go south and how to keep that from happening

Image of Jill Geisler

Jill Geisler

No one likes to fail. That’s why so many people avoid having “difficult conversations.” They fear they won’t be effective, or they’ll make a sticky situation worse. For leaders, such avoidance can cause problems to fester, even multiply. That’s unhealthy.

Here’s a reality of leadership: We are responsible for telling people things they’re not happy to hear. It could be a performance review that’s less than stellar. An assignment they’d rather not take on. A freeze in pay or benefits.

Other tough conversations include announcing changes staff didn’t ask for, telling folks who applied for a promotion that the job went to someone else, nudging good employees to break some minor bad habits and confronting bullies to ensure they don’t harm others.

But  to maintain a healthy organization, such conversations can’t be mishandled or neglected.

So what are the most common ways to mess up a tough conversation? Here are nine missteps that can derail your best intentions.

1. Fail to prepare.

The more important the issue, the more important it is to approach it with a plan. If you’re discussing tardiness, document it with facts. If you are announcing a change, list the questions you’re most likely to hear in advance, especially those from the biggest skeptics on your team. Have your answers ready so you aren’t fumbling for words.

If you’re telling a good-but-not-quite-ready person they’re not getting a promotion right now, practice that talk with another manager so you can get feedback. If your goal is to ensure that the employee doesn’t give up on your organization, you need to find  the right words and say them the right way.

2. Neglect to look up and around.

Does your boss need to know you’re about to have a tough conversation with someone? If the person you’re talking with is a favorite or a friend of your boss, it’s not a bad idea to loop your leader in. You want your boss to be knowledgeable about the what and the how of the conversation you plan to have in case the other person complains about you or attempts an appeal with your boss.

Who else might be affected by the tough conversation you’re about to have? Could there be a ripple effect if they share the information with others? Is there a union issue involved? Always consider other stakeholders in the process.

3. Engage without emotional intelligence.

The best leaders approach difficult conversations with empathy. Even if they are firing someone for cause, they respect the dignity of that person. When discussing a performance issue with a person who starts raising their voice or using profanity, they don’t respond in kind. Emotionally intelligent leaders understand the importance of keeping cool, because it enables them to think more clearly and never regret what they said in anger. If someone cries during a conversation, they pause and give the individual the space needed to collect themselves. They think about the relationships they want to have in the future with staffers and work to ensure their tough conversations achieve that goal.

4. Use ineffective language.

Tough conversations require focus and clarity. Don’t use hyperbolic language (e.g., always, never, worst) because you could be asked to provide detailed evidence to support those over-the-top words. It’s better to be specific: You’ve been unreachable for more than two-hour stretches on three occasions over the past week.”

If you’re unsure exactly how to focus your conversation, try this mental exercise in advance: Assume you are addressing the other person and say to yourself, “The purpose of this conversation is to tell you … ” and then fill in the blanks. “The purpose of this conversation is to tell you we went with another person for the job opening, and how I want to help you prepare for the next opportunity.” This isn’t a script for all occasions — you’re not a robot. But it does help you focus, frame and phrase.

5. Duck responsibility.

Too often, managers who want to be liked will put the onus of the conversation on others. They hide behind language like: “People are complaining to me that you … . ” It’s better to lead with your own observations: “I’d like to talk with you about some things you’re doing that are getting in the way of your effectiveness.”

Now, it’s very likely that you’re bringing those things up because people are complaining to you. And it’s equally likely that the person you’re talking with will say, “Are people complaining? No one has said anything to me!” Your answer can be: “This conversation is about your actions, irrespective of who’s complaining. Let’s focus on that together.”

6. Debate for the love of it.

If you’re a person who loves to debate and needs to have the last word, you risk going down way too many unproductive rabbit holes. People often respond with deflections during tough talks, as in: “Are you having this same talk with Joe? He does the same thing and worse.” Or “I can’t believe you’re talking about this when we have a staffing shortage that no one is taking seriously.”

Your love of debate can lead you to take the bait rather than staying focused on the subject at hand. Learn to respond with: “This is a conversation about you, not Joe.” Or: “Staffing is very important. And you are my focus right now. ” Then, proceed on track.

7. Expect an unrealistically happy ending.

Tough conversations sometimes end with the other person seeing the light and shaking our hand. But more often, people need time to process negative information. Don’t feel you’ve failed if people say, “Okay, I heard you. I still disagree, but I get it.” That may be the best you’ll get in the moment. Rainbows don’t follow every storm, but the sun eventually returns.

8. Fail to follow up.

The most serious tough conversations usually require paperwork to document what transpired. It’s even more important to follow up after everyday challenging chats. Reinforce the positive behavior of the person who’s now coming in on time. Give feedback to the person who’s learning the new skills you asked them to acquire. Let people know that the rough patch you just walked through together doesn’t define your relationship permanently.

9. Avoid having the conversation in person.

Remember that distance adds to the difficulty of tough talks. If you are upset, step away from the keyboard. Talk face to face. Pick up the phone. Zoom.

To keep difficult conversations constructive rather than destructive, be fully present, fully prepared — and don’t hesitate to practice.

About the Author

Jill Geisler

is the Bill Plante Chair in Leadership & Media Integrity, Loyola University Chicago, and a Freedom Forum Institute Fellow in Women’s Leadership.


Do you have questions or topics you’d like Jill to address in a future article? Email Crystal Milazzo, HFMA senior editor, at

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