In this episode of his AI Success Starts with Leadership mini-series on the AI Agent & Copilot Podcast, host Shawn Dorward, Microsoft MVP and COO at Innovia Consulting, discusses the evolution of AI, specifically Copilot Cowork,  which shifts from task-based AI to outcome-focused work.

The Podcast is hosted by Dynamic Communities, the home of Summit NA!

Click here for the full video or the audio file from Spotify.

Key Takeaways

• Innovation may happen from the bottom up, but the risk still sits at the top. Some of the most interesting AI experimentation happening inside companies right now isn’t coming from leadership. It’s coming from employees who are trying new tools, automating workflows, sharing prompts, building agents, and figuring out better ways to get work done. That’s a great thing—but there’s an important tension here. The people experimenting aren’t necessarily the people who ultimately carry the legal, financial, security, or brand risk. Leadership does. Ignoring that tension doesn’t make it go away. It usually just creates fear on one side and frustration on the other.
• Make the experimentation visible. Leaders should be actively asking, “What are you trying? What worked? What didn’t? What surprised you?” There is probably far more AI innovation happening inside your organization than you realize. The problem is that much of it is happening quietly. You want those people sharing what they’re learning, not hiding it because they’re unsure how leadership will react. And frankly, your most curious employees are going to want to work somewhere that values that curiosity. If you don’t create that environment, somebody else will.
• Guardrails should create confidence, not kill momentum. Be very clear about where AI can be used—and in some cases, where you actually expect it to be used. Then identify where human judgment is required and which actions need review or approval. Good guardrails don’t eliminate accountability. They make accountability clearer. And when employees know where the boundaries are, they’re usually much more comfortable experimenting inside them.
• Curiosity may be one of the most important leadership skills in the AI era. The strongest leader in the room doesn’t have to be the person who knows the most about AI. In fact, there’s a pretty good chance someone on your team knows more about a particular tool, model, or use case than you do. That’s not a threat. That’s an opportunity. Ask questions. Let them teach you. Learn in public. Leaders who are willing to invite knowledge upward while providing direction downward are going to get much further than leaders who feel like they have to pretend they already have all the answers.
• You don’t have to out-AI your team. Leadership isn’t about being the person who knows every prompt, builds every agent, or clicks every button. You don’t own the clicks. You own the conditions. Your job is to create an environment where people know what’s expected, understand the boundaries, feel safe experimenting, and have a way to turn good ideas into something the organization can actually use. That’s where leadership shows up.

The big takeaway for me: Your job as a leader isn’t to be the smartest AI person in the room. It’s to create an environment where the smartest ideas can surface, the right risks are managed, and your people have permission to learn, experiment, and move.

Click below to listen to the Spotify audio version

Thanks for reading!

Shawn Dorward

Microsoft MVP, Business Applications

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