Let’s say the quiet part out loud.
It’s always the people.
Not the strategy. Not the tools. Not the project management platform that some people on your team still refuse to use correctly. The strategy may be fine. The tools may be fine. It’s the people. Specifically, it’s the way the people relate to each other. That’s where thing gets complicated.
Maybe you’ve done on offsite retreat before. Let me guess. Things at the office didn’t magically change because you put folks in a different room, flew them somewhere nice, or made them write stuff on big Post-it notes. Because the problem was never that you didn’t have enough Post-it notes. It’s the people.
The boss that everyone manages upward. The so many of you talk about on Slack and in texts. One or two people who slow everything else in the company down, and the six people who have silently organized their workflows around them. The great new hire who has been “almost fully onboarded” for eleven months. The meeting that could have been an email, but you did it in person hoping putting people in same room would make things smoother.
None of these things get fixed by proximity to a flip chart. When these things get fixed, if they get fixed, it’s by someone who understands how human beings actually relate to each other. I know what it takes to make it safe enough to tell the truth, and how to hold a room through that part where telling the truth gets uncomfortable.
For some teams, the problem is that they share an office and still don’t work well together. For others, it’s that they work together well, but several members of the team don’t even know how tall or short anyone is because they have only ever seen from the shoulders up on video calls. They’ve never all stood together in the same room.
So, the question isn’t whether to take your leadership team somewhere. It is where, and with whom.
Why A Work Retreat in Portugal
Getting your team to Lisbon may not fix every problem. But putting everyone in a facilitated context where it is possible to name the problems, work through them, and leave with something different than what they arrived goes far. Very far.
Take a direct flight from New York, Washington, or most major European cities. Settle into the language, the light, the pace, and the food. I’ve lived here for nearly five years. I speak Portuguese, and I know the venues that work for the kind of deep, focused work a leadership retreat requires.
And, let’s face it. When the work is done, you want to know the off-the-beaten-path restaurants, neighborhoods, and experiences that will make your time between sessions as valuable as the sessions themselves. I’ll take you to lunch spots that you might never find on your own, and I’ll introduce you to the city the way a local does. Because I am one.
Lisbon is home base. For the right engagement, I travel.
Why Me
Most retreat facilitators come from organizational development, HR, or executive coaching. I come from 20 years of studying how human relationships actually work. I’ve spent my career at the intersection of behavioral science and culture, researching, teaching, writing, and performing about the trust dynamics, communication failures, power imbalances, and unspoken needs that shape every relationship. Including the ones on your leadership team.
I’m also a trained performer. Sundance Creative Change alum. Writer and performer of two sold-out one-woman theater shows reviewed by The Washington Post. A veteran of Washington Improv Theater. That training? How to read a room, hold attention, navigate unpredictability, and make people feel safe enough to be honest. These are core facilitation skills that AI and most organizational development frameworks cannot teach. What I bring to a retreat is a natural way of being in a room that makes other people more honest, more present, and more capable of doing the work they came to do.
Who Is This For
Bring me a leadership team of 8–25 people who are working on something that cannot be solved in a meeting.
We’ll likely get the most out of working together if you’re navigating one or more of these challenges:
- A values-behavior gap: The culture you describe in your mission statement doesn’t actually show up at work. Everyone knows it, but nobody is saying it.
- A trust deficit: Something happened, or didn’t happen when it should have. The silence has compounded, and it’s made honest communication harder. Decisions are slower. Conflict goes underground. Good people are quietly disengaging.
- A creativity block: The same people in the same room are producing the same thinking. You need to break out of the mold to help your organization grow. You want a genuinely different environment to generate genuinely different ideas.
If your situation is one of these, or even if it’s something that you’ve not yet found the language for, we should talk.
What To Expect
Every retreat, just like every good relationship, begins with a conversation. You tell me your team’s current state and what a successful retreat would look like. During our video call, I’ll ask questions, and together we’ll figure out whether a Lisbon retreat is the right move and what it would look like for your specific team. If we’re a match, I’ll send you a custom proposal for approval. Expect a lot of pre-retreat work (anonymous survey, conversations with key leads, agenda co-design). Because, yes, Lisbon is a good time. But, we’re also coming together to make sure we resolve your specific situation. Every retreat ends with a set of deliverables: decisions made, priorities ranked, commitments named. Memories of a good few days? Sure! But, you’ll also have a plan to keep you accountable when you return home.