Difficult Conversations Matter

Has it ever happened to you?

Feeling uneasy or anxious because you have to talk with a team member who missed a deadline, a client who doesn't agree with your proposal, or even with your manager for a raise?

Even though these conversations can be uncomfortable, you can't avoid them. But there's good news! If you follow these steps, you can approach these moments with confidence and empathy while maintaining professional relationships. 

Step 1: Prepare

Before starting a challenging conversation, take a moment and ask yourself:

• What do I want to address?

• What am I hoping to achieve?

• How do I want the other person to feel at the end?

For example, you want to discuss a salary increase. Your goal is a 10% raise, and you want the other person, your manager, to feel you are worth it. Another goal can be to ensure the conversation remains professional and collaborative, even if the answer is “not now.”

Preparation also means gathering facts. If it’s a performance issue, note specific examples. If you’re negotiating, research salary benchmarks or industry standards. The clearer you are, the more confidently you’ll communicate.

Step 2: Choose the Right Time and Place

Timing can make or break a difficult conversation. Intercepting someone in the middle of a busy day or during a team meeting isn't ideal.

Instead, consider a private and neutral setting where both parties can focus. If it's virtual, check that there aren't any distractions on either end and test your tech in advance. If possible, give the person a heads-up (“Can we set aside time to discuss [topic]?”) to set the tone for a productive and calm discussion, rather than blindsiding anyone.

Step 3: Use Empathy

It’s easy to let frustration or nerves take over, but applying empathy can transform even the toughest conversations. Start by acknowledging the other person’s perspective:

• “I know you’ve been juggling various projects lately…”

• “I value the work you’ve done on X, and I want to make sure we’re aligned moving forward.”

This way the other person feels heard and respected, and they’ll be more receptive to what you have to say.

Step 4: Focus on Solutions

When it’s time to address the issue, stick to facts and avoid emotions or assumptions.

Rather than saying, “You’re always late with your reports, and it’s making things harder for the team”, try, “I noticed the last two reports were submitted after the deadline, which delayed the timeline. Let’s discuss how we can avoid this in the future.”

The goal is to convey a constructive message that leads to solutions.

If you’re negotiating, demonstrate how your request can benefit both parties: “Based on my contributions to [specific projects], I believe a 10% raise reflects the value I bring to the team. I’d love to discuss how this aligns with company goals.”

Step 5: Listen Actively

Difficult conversations are a two-way street. After you’ve shared your thoughts, give the other person a chance to share their perspective. Practice active listening techniques like:

• Nodding or giving verbal cues like “I see” or “That makes sense”.

• Paraphrasing what they’ve said to ensure you understood: “So if I understand correctly, your concern is X?”

Even if you don’t agree, showing that you’ve listened fosters trust and makes it easier to find common ground.

Step 6: Follow-up

A productive conversation doesn’t end when the meeting does, so you must reach out afterwards. To ensure clarity, summarise any action points or agreements in writing: “Thanks for our discussion earlier. As agreed, I’ll start [action], and we’ll check in again on [date] to review progress.”

If the answer to a negotiation question isn't immediate, ask for the next steps: “Can we revisit this discussion in a month?”

Difficult conversations can feel like navigating a delicate balance, but they’re also an opportunity to strengthen relationships, solve problems, and advocate for yourself. With preparation, empathy, and clear communication, you can turn even the toughest talks into a positive outcome.

And remember, if you need extra support navigating workplace challenges or mastering negotiation techniques, Ni-Cons is here to help you take the next step in your professional journey.