Peak Performers by Tiffany Uman

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How to handle hard conversations without fear

July 28, 2025

Thank you for joining my Peak Performers newsletter! Every Monday, we share practical tips and scripts to help you land the roles you want, thrive with confidence at work and grow faster.

Handling hard conversations isn't easy and can feel uncomfortable.

But they build character and resilience which are essential as you grow into more senior roles.

Whether it’s giving tough feedback, addressing a conflict, or advocating for yourself, these moments test your emotional intelligence, communication skills, and leadership.

This is not the time to overthink or pretend that things will simply get better on their own.

The truth is that avoiding the conversation is often more harmful than navigating it imperfectly.

The key is learning how to approach these communication moments with confidence and strategy, shifting away from potential conflict into constructive dialogue. Here's how.

3 ways to handle hard conversations without fear

1. Lead with empathy

Hard conversations often feel adversarial, but they don’t have to be.

Leading with empathy shifts the dynamic from confrontation to collaboration. When you acknowledge the other person’s perspective or feelings, it builds trust and disarms defensiveness.

It's not about agreeing with everything they say or diminishing your own arguments. Rather, it’s about creating a dialogue where both sides feel respected and heard. This way, you can find common ground to move forward together.

→ When giving constructive feedback:

Communication example: “I really appreciate the effort you’ve been putting into this project. I also noticed [specific issue], and I’d like to work with you on finding a way to address it together.”

​This is exactly what our client did with her team for a hard conversation she was initially hesitant about. In leading with empathy, it helped her employee to be much more receptive to the feedback shared. Since that conversation, she's already noticed clear improvements in her employee's behaviour.

→ When addressing a team member’s missed deadline:

Communication example: “I know the past few weeks have been especially busy, and I appreciate all the juggling you’ve been doing. I know how tricky that can be. That said, I'd like to better understand what happened with [specific task] and how we can prevent delays moving forward.”

→ When raising concerns with a colleague:

Communication example: “I really value our working relationship and want to make sure we’re aligned on how to approach this situation. For instance, I’ve noticed [specific behaviour] and I’d like to better understand where you’re coming from so we can address it together.”

→ When advocating for yourself with a manager:

Communication example:“I really appreciate the opportunities I've had to work on X, Y and Z. I also want to make sure I’m contributing best towards my [goal]. I’d like to discuss [specific concern] and how we can ensure I'm set up for the most success in that this year.”

2. Be direct, not abrasive

While empathy sets the tone, being direct ensures your message is understood without confusion or misinterpretation. Don't feel the need to sugarcoat your points, as this runs the risk of leaving your message unclear or diluted.

The key is to balance honesty with respect by addressing the issue head-on without attacking the person.

People appreciate clarity, especially in high-pressure moments, and it demonstrates that you respect their time and role enough to communicate effectively. Remember, directness doesn’t mean being harsh. It means being clear, concise, and focused on the issue, not the individual.

→ When addressing underperformance:

Communication example: “I’ve noticed that your recent report missed some key data points which has caused delays in our submission. What would you suggest we integrate to ensure your future reports do not miss this level of detail?”

→ When dealing with disruptive behaviour in meetings:

Communication example: “I’ve observed that during our meetings, there’s been a tendency to interrupt others while they’re speaking. Your points are valid. That said, it’s important for everyone to feel heard. I know it would be appreciated if you gave others more space to share their ideas before cutting in. Do you see where I'm coming from on this?”

→ When addressing missed expectations with a colleague:

Communication example: “While we agreed on splitting responsibilities for this project, I noticed that certain tasks you committed to were left incomplete. It’s important we align moving forward to meet our deadlines as I wouldn't want it to reflect badly on either of us. How can we ensure this doesn't happen again?”

[Check out my free LinkedIn Learning nano-course on Nano Tips for Handling Difficult Work Situations]

3. Nail the "what's in it for them?"

A hard conversation isn’t just about addressing your concerns. You also need to frame the discussion in a way that highlights how resolving the issue benefits the other person.

People are more likely to engage and collaborate when they see a direct connection between the conversation and their own goals, values, or success.

Shifting the focus to “what’s in it for them” transforms a potentially defensive interaction into a shared opportunity. It shows that you’re invested in a positive outcome for both sides.

→ When giving feedback to a team member:

Communication example:“Improving the accuracy of your reports will help showcase the depth of your analytical skills to leadership, which could lead to more high-visibility projects for you in the near future.”

→ When addressing a peer on a different team about collaboration issues:

Communication example:“Aligning on our approach now will save us both time and ensure the final submission reflects both of our strengths, making the presentation stand out even more.”

→ When discussing workload with a manager:

Communication example:“Reprioritizing some of these tasks will allow me to focus on delivering higher-quality work on the initiatives that matter most to the team’s success. I'd love to be able to orient more of my time towards that this quarter.”

→ When proposing a process change:

Communication example: “By adjusting the timeline by 2 weeks, we will ensure the final product meets the highest standards we've set, which will reflect positively on your department. Does that work well for you?”

This is the strategy I coached one of our clients on recently when she was facing a delicate situation with her boss's boss. It helped her transform a tense conversation into a thought partner discussion.

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This week’s mission: Use these 3 strategies to better handle hard conversations.

• Reflect and prepare. Identify 1 upcoming hard conversation you’ve been avoiding. Write down the key points you want to address and the outcome you’re aiming for. Practice your opening statement, ensuring it starts with empathy and sets a positive tone.
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• Put it into practice. Schedule a time to have the conversation in a private 1:1 setting. During the discussion, prioritize being direct but respectful. Use 1 of the communication templates shared above to guide your approach so it feels natural for you.
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• Evaluate and improve. After the conversation, take 5 minutes to note down what went well and what you could improve for the next time.

You've got this!

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