In this episode of the AI Agent & Copilot Podcast, Shawn Dorward, COO Innovia Consulting, welcomes Lisa Crosbie, Microsoft MVP, Copilot Lead, Barhead an Akkodis Company. The two discuss how Microsoft Copilot Cowork changes work from prompt engineering to effective delegation, review, and human judgement. Lisa is a well known content creator, if you’d like to learn more, specifically about her YouTube channel, you can find it here.

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

• Who is Lisa Crosbie? Lisa Crosbie is an Australian-based YouTuber, Microsoft MVP, and Copilot Lead who spends a lot of her time learning, experimenting with, and teaching people about Microsoft Copilot and AI. One of the things I appreciate about Lisa is that she shares the learning journey—the good, the bad, and the frustrating—not just the polished end result.
• Cowork changes the way we think about prompting. One of Lisa’s biggest observations is that using Copilot Cowork feels different from the prompting we’ve gotten used to. It becomes less about perfecting the magic prompt and more about learning how to delegate work effectively. You need to be able to explain what you’re trying to accomplish, provide the right context, and clearly define what you expect back. That’s a very different skill. As Lisa put it, the human effort involved in effective delegation becomes a major part of successfully using these tools.
• We may do less of the work, but human judgment becomes even more important. This was probably one of my favorite parts of the conversation because there is a real tension here. If I have to spend time reviewing everything AI creates, at what point would it have been easier to just do it myself? Lisa’s perspective is that AI changes our role. Instead of always being the person doing the work, we increasingly become the person directing it, reviewing it, challenging it, and making it better. I think that’s incredibly important. AI can generate the work, but there still needs to be human judgment behind the outcome. At the end of the day, I still believe people choose people—and that human element can’t disappear just because AI did some of the work.
• Learning Cowork is equal parts fun and frustrating. Lisa described her experience with Cowork exactly the way I think a lot of us are experiencing AI right now. Sometimes the result is incredible. Other times you’re wondering what in the world just happened. The quality can depend on the model, the instructions, the context you provide, and frankly, how good you are at directing it. But when it works well, the value isn’t simply that AI does something faster. It can organize research, create resources, help structure your thinking, and allow you to take on work you may not have attempted before. One of the harder questions is simply, “What should I use Cowork for?” That’s also where colleagues and the community become incredibly valuable—seeing what other people are doing gives us ideas for our own use cases.
• We’re nowhere near the end of this AI wave. Lisa doesn’t see the pace or intensity around AI slowing down anytime soon, and I agree. She sees part of the next wave of AI being more “autopilot” experiences—AI working in the background without us constantly initiating every interaction—along with much more voice interaction. The challenge for all of us isn’t going to be keeping up with every announcement. That’s probably impossible. It’s figuring out how to manage the speed, the noise, and the overwhelm while still learning enough to take advantage of what’s actually useful.

The big takeaway for me: Cowork isn’t just another way to prompt AI. It starts changing our role from doing the work to delegating, directing, and judging the work—and that may be one of the most important AI skills we have to develop.

Click below to listen to the Spotify audio version

Thanks for reading!

Shawn Dorward

Microsoft MVP, Business Applications

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