Hard conversations are often defining moments in your career.
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.
Look, hard conversations are inevitable in any workplace, but they’re also an opportunity to stand out.
When handled properly, these types of conversations can actually transform and improve your relationships, build trust, and pave the way for meaningful growth.
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. Let's get into it!
Key mistakes to avoid
Hard conversations often fail before they even begin. Not because of the topic, but because of how they’re approached, making it harder for everyone involved. There's 5 mistakes I see happen far too often and I don't want you falling into these traps, including:
→ Diving in unprepared: Hard conversations require careful thought and intention. Rushing in without a clear message or goal often results in rambling or miscommunication. When you don’t know exactly what you want to say or achieve, the conversation can veer off track, leaving both sides more frustrated.
→ Getting defensive: It’s natural to feel the urge to defend yourself when you're getting challenged or criticized. However, reacting emotionally can escalate conflict and shift focus away from resolution. It will also cause much more friction making the situation worse than need be.
→ Avoiding accountability: No one is perfect, but placing blame or deflecting responsibility weakens your credibility and diminishes trust. Acknowledging your role in a situation, even if it’s minor, sets the tone for a constructive conversation together.
→ Focusing on the person, not the problem: Shifting attention to someone’s personality or character rather than the issue at hand can make the conversation feel like a personal attack. This triggers immediate defensiveness, lessening your chances of coming to a mutually agreed upon resolution.
→ Ignoring timing and environment: Bringing up a sensitive topic in the wrong setting, like during a high-stress moment or in a public space for others to witness, can make the other person feel blindsided or embarrassed. As much as possible, address these conversations 1:1 as it garners more respect for the other person, despite the frustrations you may be feeling.
3 ways to make hard conversations easier
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 member for a hard conversation she was initially hesitant about having. In leading with empathy, it helped her employee to be much more receptive to the feedback she 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. This approach not only builds trust but also increases buy-in for the changes or solutions you propose.
→ 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?”
How will you address hard conversations?
Hard conversations may never feel easy, but they are some of the most powerful tools for growth, trust, and impact in your career. Every hard conversation you navigate builds your confidence and strengthens your leadership skills. The more you practice, the better you’ll get.
You've got this!
Your mission this week is designed to practice having hard conversations, even ones you may have been avoiding altogether. Set aside some time to reflect on the prompts below and take intentional action.
1/ 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.
2/ 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.
3/ Evaluate and improve:
- After the conversation, take 5 minutes to note down what went well and what you could improve for the next time.
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