Business Builders (Pt.41) From Doer to Leader: How to Know You’re Ready for Your First (or Next) Leadership Hire Artwork

The Small Business School Podcast

Ready to leave the small business struggle behind? The “School for Small Business” podcast supports small business owners in scaling a business that is profitable, purposeful, and doesn’t leave you burnt out. No matter whether you run your business online or you own a brick-and-mortar, you can expect our world class experts to support you with mindset, tactics, and everything in between so you can have the business you dreamed of. Based on our lived experience, we know that small business CAN be easy and we are here to show you how.The “School for Small Business” is hosted by Staci Millard, a CPA by trade with over 15 years of experience seeing the behind the scenes of thousands of small businesses. After growing and selling her first 7 figure business, Staci has been on the ground running - mentoring small businesses and working to increase success rates. Staci strongly believes you don’t need to have gone to business school to be successful so you can expect nothing but simple, impactful advice. Tune in each Tuesday for a new 30 minute or less episode of nothing but valuable advice to help you grow your small business. We are so excited for you to be on this journey with us!

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The Small Business School Podcast

Business Builders (Pt.41) From Doer to Leader: How to Know You’re Ready for Your First (or Next) Leadership Hire

November 11, 2025 • Staci Millard • Episode 351

In this episode of the Business Builder Series, I’m diving into one of the biggest growth milestones for any small business owner — making your first or next leadership hire. If you’ve been wearing all the hats (COO, CMO, CFO…and maybe even floor sweeper), this episode is for you. I’ll walk you through how to recognize it’s time to expand your leadership team, what roles make the biggest impact, and how to set those hires up for success, even if you’re starting small.

Key topics covered:

How to know when you’re ready for a leadership hire, and the signs it’s time to step back from the “doing”
Why fractional roles (like fractional CFOs or CMOs) are a game-changer for small business owners
The difference between a team member and a true leader, and how that impacts your energy and focus
Why you should be cautious about hiring a Director of Operations too soon
My top 5 tips for successful leadership hires, from hiring for how they think to giving them space to truly lead

When you hire leadership, you stop being the whole engine and start being the driver, and that’s when your business really starts to move forward.

Challenge:

Audit your leadership gap. Ask yourself:

What am I holding on to that someone else could lead?
What role would let me step into my CEO-level work?
What would “done really well” look like for this person?

Staci's Links:
Instagram. Website.

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