Episode 91

Mastering Difficult Conversations With Your Staff

Published on: 22nd March, 2026

Hello and welcome to this weeks episode of The Australian Small Business Show.

In this episode we dive into a topic that so many small business owners struggle with, having difficult conversations.

We unpack why these conversations are often avoided, how that avoidance can actually make things worse, and the hidden cost it can have on your team, your time and your overall business performance. We also explore the reality that difficult conversations show up in many forms, from underperformance and behavioural issues through to pay rise discussions, promotions and even interviews.

We share real examples of the types of conversations that come up in small business and why putting them off can lead to bigger problems down the track. In particular, we discuss how delaying these conversations can create confusion for team members, impact team culture and even make your eventual response seem like an overreaction. We also touch on the importance of setting clear expectations early, especially during the hiring process, to avoid difficult situations later on.

A big focus of this episode is giving you practical strategies to approach these conversations with more confidence. We talk about the importance of getting clear on your objective before going into the conversation, understanding your team members communication styles, and tailoring your approach so your message is actually heard. We also highlight the value of being specific, prepared and aligned, particularly if you are working with a business partner or leadership team.

Finally, we share some simple but powerful tips to help you take action, including why you should not delay these conversations, how to structure them effectively, and the importance of following up afterwards. If this is something you find challenging, we also share details of an upcoming workshop designed to help you prepare, script and confidently handle your next difficult conversation.

Want to join Kristy-Lee’s upcoming workshop on this topic? Get your free seat here:

https://www.peoplepoweredbusiness.com.au/handled

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Disclaimer: The information shared on The Australian Small Business Show is general in nature and does not constitute professional advice, legal or otherwise. We recommend consulting with your advisors on your specific circumstances.

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About the Podcast

The Australian Small Business Show
The Australian Small Business Show has been created by small business owners, for small business owners.

Your hosts Matt Heighway and Kristy-Lee Billett, who have both been running businesses for over 15 years, will bring our first hand experiences to offer insights, advice and inspiration to help you build a successful small business.

Each week we’ll discuss one specific strategy, topic, resource or tip that’s relevant for every small business, and we’ll be inviting along some amazing guests and friends in business to share their expertise with you.

Whether you're starting out, scaling up or a seasoned small business owner, this Australian Small Business Show is the show for you.

About your hosts

Kristy-Lee Billett

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Kristy is a nationally recognised HR expert, passionate small business advocate, podcast host, mum, wife, beach lover and runner.

She has spent more than 20 years now working in the field of Human Resources, People Management and Recruitment.

For the last 10 years she has dedicated herself to exclusively supporting small to medium sized businesses, those who employ less than 100 staff with all aspects of their HR, recruitment, people management and resource structures.

She founded her first business in 2006, and today she continues to direct this business, which is now known as People Powered Business.

Today She loves working with businesses inside our People Powered HR community to help them gain the knowledge, tools and resources to handle absolutely anything when it comes to their teams, with complete confidence.

Matt Heighway

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Matt is a CPA who has been working with business owners in multiple capacities for well over two decades. After commencing his career as an Accountant and Business Adviser, his own national start-up won numerous business awards and was featured in BRW fast 100. Since the business sold, he has been working with small-medium business owners helping them with business growth strategies and holistic business coaching.

Matt also is the Director of Lifetime SMSF, an accounting practice that specialises in Self-Managed Super Funds. Helping Australians manage their retirement nest eggs has been a lifelong project for Matt and he continues to get joy from helping.

Matt is a lifelong learner who loves to chat with other business owners. he is passionate about small business and always wants to see them win. He is at his best when things need turning around though, and gets his motivation helping small business owners come back from a set back.