Tricky Conversations at Work: 8 Phrases Leaders Can Use
Updated: Aug 13
By Stephanie Bickel
Most leaders know when a difficult conversation needs to happen.
You notice a pattern in someone's performance. A meeting doesn't go well. A colleague says something that concerns you. A client relationship starts to feel strained.
You know you should address it, but you hesitate.
Maybe you aren't sure how to start the conversation. Maybe you don't want the other person to become defensive. Or maybe you're hoping the situation will resolve itself.
Usually, it doesn't.
Learning how to have difficult conversations at work is an important leadership communication skill. The longer you avoid an issue, the more opportunity there is for frustration, misunderstanding, and resentment to build.
The good news is that a difficult conversation does not have to begin with confrontation.
Often, the first few sentences determine whether the other person becomes defensive or is willing to work through the issue with you.
Why leaders need to have difficult conversations
Leaders sometimes avoid difficult conversations because they want to preserve a relationship.
But avoiding the conversation can actually create more damage.
When expectations aren't discussed, people are left to make assumptions. When concerns aren't raised, small problems can become patterns. When feedback isn't shared, people lose the opportunity to adjust.
Your team is also paying attention to what you address and what you allow to continue.
The goal is not to become comfortable with conflict for the sake of conflict. The goal is to become comfortable raising important issues early, clearly, and respectfully.
Leaders mature quickly when they learn to raise concerns instead of avoiding them.
How to start a difficult conversation at work
One of the hardest parts of a difficult conversation is simply knowing how to begin.
You don't need a dramatic opening. In fact, approaching the conversation with curiosity rather than accusation can make it easier for both people to participate.
Here are eight phrases you can adapt to different situations.
1. "That meeting had some highs and lows. I have some ideas for next time."
Use this when something didn't go as planned and you want to debrief without immediately placing blame.
Starting with an observation creates room to talk about what worked and what could improve. It also signals that the purpose of the conversation is to make the next experience better.
2. "I have a few ideas about our next client meeting that I'd like to discuss."
Not every difficult conversation needs to sound difficult.
This approach works when you want to address something that happened previously while keeping the conversation focused on what you can do differently going forward.
It shifts the discussion toward preparation and improvement.
3. "I'd like to talk about ______ with you, but first I'd like to get your point of view."
This is one of the most useful ways to begin a conversation when you know there may be different perspectives.
You may have information the other person doesn't have. They may also have information you don't have.
Ask before you assume.
Giving someone an opportunity to explain what they experienced can change the direction of the entire conversation.
4. "I need your advice on ______. Is now a good time to discuss it?"
This can be especially effective when you need to raise a sensitive issue with a colleague, client, or someone more senior.
Asking for advice invites the other person into the conversation rather than immediately putting them in a defensive position.
It also gives them an opportunity to choose a better time if they aren't able to give the conversation their full attention.
5. "I received your email. Could we talk about that soon?"
Some conversations should not continue over email.
If tone is becoming difficult to interpret, the issue is getting complicated, or several messages are going back and forth without resolution, move the conversation.
A five-minute conversation can sometimes resolve what another five emails will only complicate.
6. "I think we may have different views on ______. I'd like to understand yours better."
You do not need to pretend that you agree.
Strong leaders can acknowledge disagreement without making the disagreement personal.
This phrase makes your position clear while also demonstrating that you are willing to listen. That combination can help keep a disagreement productive.
7. "Your comments about ______ were interesting. We may have different information. When would be a good time to discuss it?"
Use this when you believe a disagreement may be based on different facts, assumptions, or experiences.
Notice the difference between saying, "You're wrong," and saying, "We may have different information."
The second creates an opening for both people to examine what they know before deciding what should happen next.
8. "I've noticed a pattern in our meetings that I'd like to discuss with you. Would you be open to trying something different?"
Patterns need to be addressed.
Maybe someone regularly interrupts colleagues. Perhaps meetings consistently run off track. Maybe decisions are being revisited after everyone thought they were settled.
Describe what you have observed and invite the person into the solution.
This gives you a way to address recurring behavior without turning the conversation into an attack on someone's character.
How to prepare for a difficult conversation
The words you use matter, but preparation matters too.
Before you begin, get clear on what actually needs to be discussed.
Ask yourself:
What have I observed?
What assumptions am I making?
What information might I be missing?
What outcome would I like from this conversation?
What does the other person need an opportunity to say?
What needs to be different after we talk?
Be particularly careful about the difference between an observation and an interpretation.
"You interrupted three people during today's meeting" is an observation.
"You don't respect the team" is an interpretation.
Starting with what you actually observed gives you a much stronger foundation for the conversation.
What leaders get wrong in difficult conversations
One of the biggest mistakes is waiting too long.
Leaders sometimes tolerate something repeatedly and finally address it when they are frustrated. By then, what could have been a relatively simple conversation carries months of emotion with it.
Address concerns while they are still manageable.
Another mistake is entering the conversation determined to prove a point.
You should know what you want to communicate, but you also need to leave room for information you don't have yet.
Listen carefully. Ask questions. Be willing to adjust your understanding of the situation.
And don't overcomplicate the conversation.
Be specific about the issue. Explain why it matters. Listen to the other person's perspective. Then determine what needs to happen next.
What if the other person becomes defensive?
Even when you prepare carefully, you cannot control how someone else will respond.
If the conversation becomes emotional, resist the temptation to match the other person's intensity.
Slow down.
Ask a question.
Clarify what you heard.
You might say:
"Tell me more about how you're seeing this."
Or:
"It sounds like you experienced that situation differently. I'd like to understand that."
Listening does not mean you have to agree. It means you are making sure you understand the other person's perspective before moving forward.
That is an important distinction for leaders.
Difficult conversations are part of leadership
The strongest leaders do not wait until every conversation feels comfortable.
They learn how to communicate when the situation is uncomfortable too.
That might mean giving feedback sooner, addressing a pattern you've been noticing, asking a question you've been hesitant to ask, or acknowledging that you and someone else see a situation differently.
Each time you practice, you become better at separating the issue from the emotion around it.
You also show the people around you that concerns can be raised, disagreements can be discussed, and difficult subjects do not have to damage relationships.
Think about one conversation you have been postponing.
You may not need to have the entire conversation today.
But you can decide how you're going to start it.
Frequently Asked Questions About Difficult Conversations at Work
How do you start a difficult conversation at work?
Start with a specific observation or issue rather than an accusation. Explain what you would like to discuss and invite the other person to share their perspective. The goal is to create a productive conversation rather than immediately putting someone on the defensive.
What should you say during a difficult conversation?
Use clear, neutral language. Focus on what you have observed, ask questions, listen to the other person's perspective, and explain what needs to change or be resolved. Avoid making assumptions about the other person's motives.
How can leaders handle difficult conversations with employees?
Prepare before the conversation, address the issue specifically, and give the employee an opportunity to respond. Focus on behaviors, expectations, and outcomes rather than making the discussion about the person's character.
Why are difficult conversations important in leadership?
Difficult conversations allow leaders to address concerns before they become larger problems. When handled well, they can create clearer expectations, strengthen working relationships, improve performance, and build a culture where people are willing to communicate openly.
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