Tough Topics Challenging Office Conversations

Engaging with Empathy: How to Help Employees Through Challenges

As we reformat the new normal for the pandemic era, you may have wanted to tell your team, “It’s going to be fine. Cheer up!” Or perhaps you want to encourage someone to return to the office and think that the right directive is to say, “Don’t worry. You can manage it. We will all wear masks.”
Andi Simon, PhD

Instead of causing your friend or colleague to feel better, your sympathetic comments may create a negative response in them. They walk away upset with you and feeling worse. You know that you want to help others feel they are being heard. You do care about them. But what should you say?


On a very simple level, sympathy involves the feeling of being sorry for someone but understanding from your own perspective. Empathy, on the other hand, involves putting yourself in the other person’s shoes and understanding why they may feel a particular way. The difference seems subtle, but it is key to saying the right thing at the right time.

If you fall into the sympathy trap (the “cheer up, it will be OK” conversation), you are expressing how you feel, but you sound like you are disregarding the seriousness of the person’s feelings.

Try not to say things that:

1. Change the subject.

When that problem turns into a conversation about how the Lakers did last night, you have deflected the conversation away from their concerns to another topic. It might make you more comfortable, but the other person is going to feel hurt and discounted, suggesting that you really didn’t care at all.

2. Look for a silver lining.

“At least we didn’t lose the entire account” sounds like it might be a good comment after a bad situation. Your instinct is to provide optimism. Or perhaps you compare this event to that of another person and say, “Allen lost the entire case.”

But a silver lining makes the person you are trying to support believe they have no right to feel the way they do. Moreover, comparing your colleague’s situation with another person’s might sound fine, as if this is all a norm-referenced world. But you are diminishing their pain relative to someone else’s.

3. Dismiss their pain.

“Forget about it,” “cheer up” or “smile” are not statements you should think or say. You should not tell them to calm down or say they are overanalyzing the situation.

When you say this, it sounds like you don’t think it is such a big deal, which makes them feel worse. You are telling them that they are making it into something bigger than it is. Perhaps you are right — they may be brooding over something that to you is not worth their time and energy. But to them it is a big deal. When you dismiss it, you are acting as if you don’t care about their feelings or them as a person. Their experience is less real to you.

What should you say?

“Spoken with thoughtfulness, your words can help make a situation easier for someone who is struggling with pain, challenges, uncertainty and even mental health issues.”


Here is where that empathy training becomes essential. Spoken with thoughtfulness, your words can help make a situation easier for someone who is struggling with pain, challenges, uncertainty and even mental health issues. When someone shares something difficult with you, they are looking for you to support them, not cheer them up.

Here are some things to consider:

1. Keep it in their zone, not yours.

Begin by affirming your appreciation for their trust in you. Try saying, “Thank you for sharing your pain with me. It means a lot to me that you trust me.” Recognize their courage and vulnerability. Share your understanding that choosing you as a confidante is very important to you. Then ask how you can be of help. You “feel their pain.” How can they use your support? Reaffirm that it will stay in your complete confidence, not become a topic for gossip.

2. Ask for clarification.

Before you jump in with ideas or help, make sure they can clarify what is really bothering them. It’s difficult to be of help when things are unclear to them and to you. Be an interested inquirer, not a person with ideas ready to suggest to them, whether they are the right ones or not. Try to restate the problem. “So this is what I hear you saying. This is why you are feeling so frustrated or depressed.” As you restate the reasons for why they are feeling as they do, they can hear your sincerity and concern.

3. Boost their self-worth and character.

Try to point out their courage. Emphasize their personal strength in dealing with complex problems, be they in the workplace or in their personal life. Help them understand that they have shown a lot of talent and strong character in the past. Encourage them to see their own power in overcoming what they are going through. Don’t diminish their pain or the problem. This is a time to recognize their ability to cope with it and overcome the difficulties.


Think carefully and then tell them that you understand. Ask what you can do to be of help. Assure them that you are here when they need you. “What is it we can do together to help find the right solution?” might be a great approach to build on their trust.

If you see your efforts to comfort others backfiring, pause and regroup. While you think you are saying the right thing when you urge someone to “cheer up,” those words trigger negative responses — not hope. It takes a remarkably simplistic understanding of the mind to believe that you can simply issue commands — “feel better!” — and expect it to oblige. Hope creates positive mental energy but comes from actions that engage the person, not directives told to that person. Focus on how to engage, embrace, empathize. Watch and see your caring efforts turn into help for others.