989: 5 Questions That Make Difficult Conversations Less Terrifying | Leadership Strategies

Shameless Leadership

Sara Dean

Self-improvement, How To, Business, Management, Education

4.7 • 800 Ratings

🗓️ 28 April 2026

⏱️ 26 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Difficult conversations are something most of us avoid, delay, or overthink. I get it. Who wants to get super uncomfortable - on purpose?! But what if you could reframe difficult conversations as a massive opportunity to grow your leadership skills? In this episode, I share how I approach these conversations through a simple 5-question framework that centers on emotional intelligence, intentionality, care, and self-leadership. In this episode, we explore how quickly our assumptions can shape a conversation before it even begins, and why separating fact from story is such a powerful communication skill for leaders. I also talk about what it looks like to create common ground intentionally, even when tension exists, and how that changes the trajectory of conflict resolution. One of the most important parts of having hard conversations is not just what you say, but how you show up. I walk through how to ground yourself before speaking, how to choose your tone and energy, and how to anchor into the leader you want to be in the moment. This is how we start to shift from reacting to leading. If you’ve ever wondered how to speak up at work or in your leadership without overexplaining, shutting down, or escalating tension, this episode will help you. These five questions are a practical tool you can return to again and again to strengthen your communication skills and build more trusting relationships through honest dialogue in your personal and professional life. Links Mentioned: Hire Sara to speak: saradean.com/speaking Coach with Sara: https://saradean.com/executive-coaching-services Connect with Sara on LinkedIn: https://www.linkedin.com/in/saradeanspeaks Watch Shameless Leadership episodes on YouTube: https://www.youtube.com/@saradeanspeaks Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

Click on a timestamp to play from that location

0:00.0	This episode is brought to you by Expedia and Visit Scotland.
0:04.6	Start your story in Scotland.
0:06.9	Experience the pool of wide, untamed landscapes and fresh cuisine that feels rooted in place.
0:13.6	Discover castles steeped in legend.
0:16.6	And feel the genuine warmth from locals you meet in a place that will stay with you long after
0:22.2	you leave. Start planning your own Scottish holiday today at Expedia.co.uk slash visit Scotland.
0:34.0	Welcome to shameless leadership. I'm your host, Sarah Dean. This show is for women, transgender people, non-binary folks, as well as allies, who are committed to advancing their leadership while also advancing the leadership of those around them. In each episode, we will offer practical tips, leadership strategies, and inspiring stories to help you become a more confident, compassionate, and
0:55.2	inclusive leader. The truth is, you were born to lead. What might happen for you if you were to
1:00.9	wholeheartedly embrace that part of yourself? So let's start now, together. Hello, shameless leaders.
1:07.9	Today we're going to talk about everyone's maybe least favorite subject,
1:11.3	which is difficult conversations and how to make difficult conversations less terrifying
1:16.3	by asking yourself five specific questions before you go into a difficult conversation.
1:21.5	I want to acknowledge that while most of us don't love difficult conversations as great leaders, if you can get more
1:29.7	comfortable with the discomfort that comes with tough conversations, this can be such a
1:34.6	leadership advantage. I think that the reason most of us struggle with difficult conversations
1:39.6	is because we care a lot. We care about the people that we're engaging with. We care about
1:44.7	things going a certain way. We care about outcomes. And so with that care, the stakes feel higher.
1:50.7	And so giving yourself permission to acknowledge that when you need to go engage with someone in an
1:56.2	uncomfortable way, it's because you care. It's not because you're bad at something. It's not because you're not
2:01.6	qualified or ready to have a difficult conversation. It's just because you're invested and emotionally
2:06.4	invested in most cases. And so as we're talking through these questions today, and we're talking
2:11.6	through how to approach conversations in different ways and how to really get yourself well prepared,
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from Sara Dean, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Sara Dean and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.