Navigating Hard Conversations: Scripts and Strategies for When It's Awkward, Emotional, or Personal
Hard conversations suck. They just do. They're awkward, emotionally loaded, and personal in all the worst (and most important) ways. If you're in any kind of leadership or ownership role, you’ve either delayed one, over-explained one, or completely bailed on one. This guide is for the moments when you know you’ve got to say something, but the words just aren’t coming. Let’s fix that.
Understanding the Messy Middle
Most hard conversations have at least one of these ingredients:
awkwardness
emotional charge
personal tension
And no matter how many leadership books you've read, they never stop feeling ick. The goal here is to give you scripts and strategies that actually help—not more theory, just real-deal language and ways to move through it without spiraling or steamrolling.
Types of Conflict Moments That Deserve a Script
Giving feedback on underperformance: necessary, rarely fun, and often derailed by nervous rambling
Calling out behavior that’s rubbing people wrong: tricky balance between protecting others and avoiding gossip or triangulation
Noticing cultural misalignment: vague but impactful, and hard to name without a clear script
Following up after a tense moment: underrated move that builds trust and emotional safety when done well
How to Start the Conversation Without Panicking
Try these openers when you’re gearing up for a hard convo:
“Hey, this is hard to say, but I care about you and your role here, so I want to talk about something that’s been coming up.”
“I’ve noticed something lately, and I want to bring it up before it becomes a bigger issue.”
“Can we talk about something I’ve been sitting on? I think naming it will help us move forward.”
Holding the Space Without Losing Your Sh*t
Always close the loop with a concrete next step, even if it's simple.
“What do you see as your next steps?”
“Is there anything you need from me to make this shift?”
“Let’s schedule a follow-up in a couple of weeks and make sure we’re both on the same page.”
Clarity at the end helps keep resentment, confusion, and weird vibes at bay.
Your Two-Part Action Plan
Pick one hard conversation you’ve been avoiding. Ask yourself why it’s felt so hard to bring up.
Choose one of the starter scripts above. Schedule the conversation and commit to showing up clearly.
Want help navigating this kind of stuff with non-cringey support and real-time feedback? Join the Culture Focused Practice Membership. We talk about real leadership growth, practice culture, and all the messy moments that come with being the one in charge. No fluff, no corporate Kool-Aid, just real tools for real leaders.
About the Author
Dr. Tara Vossenkemper is a gently-candid consultant who’s been in the trenches of group practice ownership since 2017. With a hearty blend of depth, irreverence, and a solid dash of humor (or so she hopes), Tara helps practice owners navigate the can-be-messy process of hiring, culture-building, vision generating, people-y issues, and all the other things that keep you up at night. When she’s not consulting, she’s probably wrangling her animals or homeschooling her kids—because why not add more chaos to the mix?
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