The HR Challenges Guide for Leaders Doing It All

The HR Challenges Guide for Leaders Doing It All
Published on
August 19, 2026
Contributors
Jessica Trumble
Founder / CEO

Feeling like HR is the hat that never quite fits?

You’re not alone. For most founders, COOs and CFOs we meet, the people part of the business silently creates the most uncertainty. You're managing it because someone has to, but there's often a nagging sense you might be missing something especially as legislation shifts and your team changes.

Across 100+ businesses and six years at We Are Charlotte, we've noticed the leaders who navigate people challenges best aren't the ones with the biggest HR teams. They're those who recognise the signs early, understand what's going on beneath, and know how to approach it in a way that fits their size and stage.

We created this guide to bring together the HR challenges we see most often, so you can make decisions with more confidence and less second-guessing.

Inside you'll learn about:

  • Getting your work model right at different stages
  • Assessing talent objectively and setting clear performance expectations
  • Providing genuine career progression inside a smaller business
  • Defining your culture non-negotiables and protecting an entrepreneurial mindset
  • Expert perspectives from legal and finance specialists, Burch & Co and Future Advisory
  • Real-world case studies of other Australian SMEs overcoming HR challenges

Whether you're putting HR foundations in place or rethinking them for your next stage, our guide will help you spot the signs early and know how to think through what comes next. Get your copy below.