Best. Surprise. Ever.
This is Rachel from Kristen’s team, coming to you with an unexpected twist: Kristen didn’t write today’s blog post . . . our team did!
Last week, Kristen shared that we crossed a big milestone—the one-year anniversary of transitioning our company—and that the team flew to Houston to surprise her and to celebrate this special moment together. We wanted to tell you more about how that surprise came to be and why it was so important to us to make it happen:
Back in March, Amanda, our Chief of Compassion, threw out a crazy idea: What if the four of us (Rachel, Amanda, Monique and Cheyenne) all flew to Houston to surprise Kristen?
The one-year anniversary of transitioning our company was coming up on May 9th, and Amanda wanted to plan something really special to honor and celebrate such a huge turning point in our lives. Kristen has always been so intentional about celebrating each of our work anniversaries, and Amanda thought it was about time that we returned the favor: Not only would this be the one-year anniversary of the transition, but it would also mark 15 years since Kristen officially started Student Maid. It was only right that we went BIG on the celebration.
While some of us had been able to see each other in person recently, it had been two and a half years since all five of us had been in the same room together (thanks, Covid). In that time, two of us had gotten married. Two others had their first children and bought their first houses. As a team, we had paid off our debt, successfully transitioned our company, and survived the pandemic. Had we been able to, we would have celebrated each of these things together in person. But that wasn’t in the cards for us, and we were all feeling the loss of those special moments. While we love the flexibility of being a remote team and we work hard to keep our relationships strong, we’ve learned over the years that there’s really no substitute for being in the same place together. It’s the little, casual moments that we miss the most: having meals together, chit-chatting before meetings, dropping by each other’s offices to say hi. Before Covid, we did our best to get together once or twice a year, so we were long overdue for an in-person catchup. For all of those reasons (and more), we knew that a surprise, in-person visit was exactly the right way to celebrate this moment.
When Amanda first mentioned the idea of traveling to Houston, we were a little skeptical. Could it really work? A lot of things would have to go right for it all to go off without a hitch—not the least of which was figuring out how to block off Kristen’s calendar so that she would actually be in town that week instead of flying out for events. There were a ton of moving parts: We would be coming from three different states—Florida, Virginia, and South Carolina—and Monique would need to bring along her 7-month-old son, Atlas. We also knew that Kristen would have several virtual events and lots of meetings during the week we would be in town, and there was nothing we could do about that. We talked briefly about waiting for a better, less-busy time for our trip, but when we really thought about it, we realized that there would probably never be a perfect moment to get together. There would always be obstacles and reasons not to do something like this. If we wanted to see each other in person, we just had to go for it. Some time together was definitely better than nothing.
Within an hour of Amanda’s initial pitch, we were all on board, and we had a plan: We knew that Kristen had a self-care spa day planned for the Saturday before the anniversary. We decided that we would coordinate our flights so that we would arrive in Houston at around the same time that afternoon, and we would go straight from the airport to the spa. After the surprise, we would pick up Kristen and head to dinner, and then after that, we would go to the AirBnB we had booked for the next five days. Other than dinner on the first night, we didn’t plan any kind of agenda for our time together. We knew we’d have to get our regular work done, but we could at least count on having meals together and soaking up the joy of seeing each other in real life.
We booked our flights and the AirBnB on our personal credit cards (because we knew that Kristen would notice the charges on the business account), and we put a giant “DO NOT BOOK” on Kristen’s calendar for Sunday, the day after we would arrive. We wanted at least some guaranteed time together, so we told her we had planned a surprise for her that day, and she should keep the day open. Then, we made a quick call to our CPA to make sure we could reimburse ourselves for the business expenses post-surprise, and we made secret Slack and WhatsApp channels so that we could stay in touch about the trip without notifying Kristen. We even talked to Spiros, Kristen’s husband, to let him in on the secret. It was so hard to keep such a big secret from Kristen for almost two months—especially for a team that tells each other pretty much everything going on in our lives.
When the day finally came, everything went as smoothly as it possibly could: Our flights were early; little Atlas handled his first flight like a champ; and we made it to the spa to meet Kristen right on time. When we got there, we went to the front desk and asked them to tell Kristen that she had a delivery she needed to come pick up from the front desk. Then, we hid in a corner of the lobby and waited for her to come out. And when she finally did . . . priceless. You’ve got to see her reaction for yourself:
(Kristen is wearing a bathing suit under that towel—we promise!!)
It was the best feeling. Not only had we pulled off the biggest surprise ever for Kristen, but we were finally together again for the first time since 2019.
We know that this whole situation probably sounds unusual: We all voluntarily flew across the country on a Saturday and took five days out of our lives to make our boss feel really special and loved and to spend some quality time with our coworkers.
But we truly wouldn’t have it any other way.
The week together was just as special and cup-filling as we’d hoped. While we still had plenty of work to do, we took advantage of all the casual moments we had missed so much. For some of us, this week was the most time we had ever spent in the same place together, even though we’ve worked together for years. It wasn't like any kind of retreat we'd done in the past: There was no big-picture planning or team review. We didn’t even plan activities or outings like we normally would. We all just did our regular, everyday work (and took the opportunity to help Kristen cross off some big, personal to-dos she had been putting off). But we didn’t need a packed agenda to make the time count. Just being together reminded us that we don't have to wait for a special moment to do something special. We left feeling more connected and closer than ever.
It wasn’t just a conspiracy of love that made this trip possible, though. There were two other major factors: our company’s financial transparency and a clear understanding of our decision-making power as a team.
When we say financial transparency, we mean that each person on our team has access to our company’s financial information. We know each other’s salaries—even Kristen’s—and we know where Kristen and Monique allocate every single cent of revenue we bring in. We have a budget for team retreats (which is what we decided to call this surprise), so we knew that we had enough in the bank to cover our flights and an AirBnB without having to check with Kristen.
You might be thinking: Sure, you knew the money for a team trip was there, but how could you use that budget without even consulting Kristen?
While Kristen is at the top of our team hierarchy, we make a lot of big decisions (such as where to go on a team retreat) together. No one person is in charge of those things. And knowing Kristen well as we do—thanks to all of the work we have put into building our relationships—we knew that a surprise visit to Houston would not only be okay with her, but VERY welcome. Not everyone would appreciate four people and a baby dropping in on them after a day at the spa, but we knew that Kristen would be thrilled. And we were right!
We realize that it’s not every day that you come across a team of coworkers who would be willing to go to these lengths for their leader. But it’s important to note that leaders deserve to be celebrated, too. Kristen told us she would have never in a million years expected us to do anything like this but that it felt so good. It was a good reminder that any person, no matter what their role is, can make people feel valued and cared for. And it’s often our leaders who need to feel that the most.
We are so passionate about sharing what we have learned about team communication, relationship-building, and working efficiently because we want everyone to feel how we feel at work: Valued. Supported. Empowered. Fully engaged. Working in our “sweet spots”—where our talents and motivations meet. It wasn’t easy—or quick—for us to get to where we are today, but it was worth every hard, vulnerable moment to have what we have now.
We also realize that reading something like this blog post when you’re not in a supportive environment can feel demotivating. If that’s you, we want you to know that you are not alone. There are so many workplaces that don’t yet embrace human leadership, that don’t understand how important it is to value and empower their people to be the best humans and leaders they can be. But with your help, we can change that. We can make human leadership the standard instead of the exception.
Big hugs and lots of love,
Team KH
Rachel, Monique, Cheyenne & Amanda
