Welcome to Caroline Kennedy's Blog
The AI Sycophancy Leadership Crisis No One Is Talking About By Caroline Kennedy AI sycophancy leadership, the growing gap between how seriously leaders believe they are thinking and how seriously they actually are, is now the subject of landmark peer-reviewed research. And the findings should stop every senior leader in their tracks. I want you…
Why Your Leadership Team Might Be Your Biggest AI Problem By Caroline Kennedy AI leadership Australia – we are at a crossroads, and the problem isn’t the technology. Every week, another Australian CEO tells me the same thing. They’ve invested in AI tools. They’ve run the pilots. They’ve sent their CTO to the conferences. And…
What Does the Third Wave of AI Mean for Your Business & AI strategy 2026 ? By Caroline Kennedy Do you get that feeling – the one where you open your phone in the morning, see another headline about AI, and think: didn’t we just do this? Me too. And I want to tell you:…
AI Leadership Lessons from Deloitte’s $440K AI Report Failure By Caroline Kennedy AI Didn’t Fail Deloitte. Thinking Did. The $440K lesson in what happens when speed is a priority over critical thinking. Can you imagine refunding your client, the Australian Government, because your AI tool made up facts, and no one noticed? That’s exactly what…
Am I the Bottleneck in My Own Business? By Caroline Kennedy Let’s cut through the noise.The same habits that got you to your first million, to $10M and beyond, might now be choking your growth. I see it every week. A CEO who built their company through sheer grit suddenly finds themselves stuck. Not because…
Why High-Performing Teams Plateau, and What Great Leaders Do Next By Caroline Kennedy When your team is strong, the numbers are solid, and the business finally has a rhythm, it can feel like you’ve made it. You’ve built the right systems, brought in the right people, and moved out of firefighting mode. Things are good.…
AI Keynote for Leaders: What CEOs and Organisers Must Know in 2025 By Caroline Kennedy Most leaders are drowning in complexity, overloaded with decisions, and falling behind without even realising it. They don’t have a strategy problem. They have a thinking problem. While most of the noise around AI focuses on tools and trends, the…
The importance of strategic planning really cannot be underestimated when it comes to business growth. Having a clear vision and strategic plan in mind is one of the major cornerstones to any business’s growth strategy, which is why it is so important to ensure that you are completely clear about this before you embark on…
For businesses who are looking to maximise their growth, the decision to scale may seem like an easy one to make. However, this can often be easier said than done. Research shows that around 70% of businesses find it difficult to scale, particularly when it comes to startups. In fact, one study by Startup Genome…
As any entrepreneur knows, entrepreneurship is very rarely a straightforward journey to success. Instead, entrepreneurship is often more like a rollercoaster ride, with lots of highs and lows and bumps along the way. Although every entrepreneur’s journey will be different, there is one thing that is for sure: you are almost guaranteed to come up…