12-Sep-2025 by Allison McMillan

Read Time: Approx. 5 minutes

The Secret to Creating Professional Development Experiences That Actually Matter

A Leadership Retreat. For. Women. Let's break this down.

We've all seen a thousand of them.

The women's leadership retreats that focus on how busy women are. We balance so much. There's so much mental load. We do all the work things, then we come home and do all the house things, and then you add the kid things on top of that. Often women's leadership retreats are promoted as a chance to take a breaks and for self-care.

Or you have leadership retreats. Experiences that are meant to put you in the room with other peer leaders. There are many of these too. Learn X framework, meet others, talk shop, and more.

These are great. And they all serve a purpose. AND most people know that the best part of these experiences is the hallway track. It's those people you happen to meet. Did you sit at a good table for that one dinner? Were you stuck in the bathroom line with someone who you really vibed with and exchanged business cards? It's happenstance. It's serendipitous. And it's the reason people sign up for these kinds of experiences.

But what if the serendipity was intentional? What if instead of having 5 minutes to chat about who you are and what you do in the bathroom line, you had 50 minutes to understand more about where and how your lives and experiences intersect and how to leverage that in a meaningful, non-transactional way.

I hate calling Extraordinary Machines a "Women's Leadership Retreat". Because those words are so loaded, and the space is so crowded, and there are so many assumptions about what that kind of thing is.

It'll be different, because it's what is needed by so many women looking for that mix of personal development, professional development, and camaraderie. But enough about Extraordinary Machines and how amazing it will be (hey you, have you signed up yet?!?! You gotta to it before October 1st).

Let's zoom out a little bit. Thinking about your next professional development experience, how to convince your manager or company to pay for it, or thinking about planning something? Out of hundreds of professional development sessions, conferences, and experiences, what makes a really good one?

1. The Right People

There are a variety of ways in which organizers get the right people into the right room. I know we live in a world of AI, but I'm hesitant to say that an algorithm can make this magic happen (although it can potentially be a start). There's a human touch here that is super important. I often think about this in the same way that I think about putting teams together, hiring, or creating effective smaller groups of people. It's a puzzle, where some of the pieces are obvious, and some are a little more challenging. Every puzzle piece belongs to a puzzle, and every puzzle needs all it's pieces to be complete. This can often be done through a recommendations-base or vetted network (for example, needing to be recommended by someone who's in the network or has done the experience in the past), in addition to some sort of application or conversation.

2. The Right Opportunities to Actually Meet Those People

Ok, I feel like if you've been following this blog for any period of time this is one of the things that I post about the most. A gathering is NOT just about putting people in a room (even on the surface, it seems like that's all that's been done). It's about giving people opportunities, easy ins, and fun ways to actually get to know each other. Think about it this way... a handful of times a day someone asks you how you're doing. And most often, people respond with "I'm good" or "I'm fine" even if they're great! or awful! It's because most times people don't actually want to, or feel comfortable enough, giving the real answer. And that one time a day or week where you can actually, really, truly tell someone how you're doing, it feels so refreshing.

3. Content That Makes You Think or See Something In a Different Way

Let's not fool ourselves, we also go to these experiences to learn something. Maybe that's learning about something practical and tangible, or maybe it's learning something about ourselves that feels like a lightbulb moment. When you are presented with new knowledge or understanding of something, a new viewpoint or lens, that leaves you continuing to think about it beyond that session, that's gold.

4. Having Something You Can Immediately Put Into Action

Yes, the above-mentioned perspective shift or idea that you're left with is important, but, just as important is to have something you can actually do within a few days. I have notebooks upon notebooks upon notebooks of notes and information. And I'll refer to them, but in order to feel productive and really give me some momentum post-travel and settling back into my routine, I need to be able to quickly and easily take action on something.

5. That Just Right Feeling

Yes, I'm always looking for that Goldie Locks moment. These experiences can feel too advanced, or too basic, but what's just right? I often recommend one of the best ways to spend your money is with coaching but that leaves you without the people and camaraderie. If you can put one through four together, then it's likely to hit all those high-points that help people walk away with that "just right" feeling.


I'm building the experience I wish existed. The room I want to be in and that I want to share with you. If you've been looking for that same room, maybe we should talk. Book a quick chat with me today.

pixar style women in conversation and post-it notes

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