The Small Business School Podcast

Business Builders (Pt.31) How to Have Hard Conversations in Business

Staci Millard Episode 328

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0:00 | 17:49

Having tough conversations is part of leadership — but that doesn’t mean it comes naturally. In this episode of Small Business School’s Business Builders Series, I’m breaking down how to handle those sticky situations with clarity and kindness, so you can lead with confidence instead of avoidance. You’ll learn how to stop spiraling, avoid resentment, and actually strengthen relationships through honesty and respect.

Key topics covered:

  • Why hard conversations are a leadership skill (not a personality trait)
  • The three key questions to ask yourself before you speak
  • How to check your tone and timing so you don’t react from emotion
  • A simple 3-step framework for navigating tough conversations
  • Common pitfalls like over-coaching or over-owning — and how to avoid them

Challenge

Pick one hard conversation you’ve been avoiding.

Ask yourself:
What outcome do I actually want?
What emotion am I feeling, and how do I want to show up instead?
Is this about them, the situation, or me needing to lead more clearly?

Write out the 3-part structure:
What have you noticed?
How does it affect the business or person?
What do you want to ask or suggest next?                                                                                                          
Then book the time and actually have the conversation this week.

Mentioned in this episode: If you are running a business in Canada and you need help with all the things accounting related, but more importantly understanding the numbers I invite you to check out https://thriveaccounting.co/



Staci's Links:
Instagram. Website.

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