5 Tips for Navigating Difficult Conversations

3 min read
Aug 2, 2023 11:04:42 AM

There's no time like the present to tackle something that most of us avoid at work (and in life): difficult conversations. ❌

Just the thought of them can make you want to sink down into your chair.

But here's the deal: difficult conversations don't have to be something to fear. When done well, they're our greatest opportunities for growth. When we approach them with intention, magic happens. 

Most of us have to learn this lesson the hard way. Typically after years of avoidance or after being on the giving and receiving end of many difficult conversations. Here's just one example from our SVP of Growth that she agreed to share to show you're not alone in this journey.

But the truth is, difficult conversations are a must if we want change. Uncovering the uncomfortable is how we experience growth and improvement.

So let's overcome that fear of difficult conversations with these 5 simple tips:

1. Timing and context matter. Choose a focused and distraction-free space to engage in these conversations. Maybe you even have a repeating agenda item in your weekly 1:1 where you offer feedback each week, both good and constructive. That way, your team expects it, and there are no surprises.

2. Be clear, objective, and specific. Address the behaviors causing concern, fostering accountability and a culture of learning. It's important to address the behavior rather than the person and come to the table with support and suggestions.

For example, something like "Joe, I've noticed you've shown up late every day this week. Is everything okay?" instead of, "Joe, you're always tardy. That's unacceptable," shows you care about the other person and doesn't target their character.

3. Active listening is key. Embrace diverse perspectives without interrupting or assuming. Curiosity brings innovative solutions. Like the situation above, asking probing questions can help uncover the "why" behind an issue and allow you to coach the team member into better habits or support them to grow in new ways.

4. Collaboration is magic. Shift from confrontation to problem-solving. One of the best ways to de-escalate a challenging conversation is by getting on your team member's level. 

Look at their personality assessment data to learn the best way to approach the conversation. For example, do they prefer direct feedback or is it better to back into the difficult conversation? Here's what that looks like in Leadr. 

Dan Cogswell Care Card

5. Follow up. Send a feedback request after the meeting to ensure you're aligned on the outcomes and next steps. Then, continue to provide guidance and support after the conversation. This shows your commitment to finding meaningful solutions together.

If it applies, create goals and offer resources that help the person improve so you don't lose sight of what you planned together in the meeting. When they make progress, be sure to recognize their growth.

Leadr's recognition feature is a great way to celebrate individual and team wins.


Following these steps is a great start but when it comes to real people facing real challenges, there isn't always a formula.

We put together an on-demand webinar to walk you through some of the nuisances and sticky situations you face day-to-day. The webinar offers even more practical tips like these in greater detail to help you turn every challenging conversation into a growth opportunity. 

What conversation have you been avoiding? Try using these tips to make it happen today.

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