Work On, Not In


My executive team and I just returned from a weeklong offsite in Mexico. It was reflective and challenging and inspiring and fun and a million other amazing adjectives. We left the clearest we’ve ever left a retreat, knowing exactly what our goals for the company are for the year and how we’re each going to contribute to them. We left feeling the closest we’ve probably ever felt as an all-remote team. And we left feeling more connected to our company’s purpose than ever before. It was, dare I say…the perfect offsite.

Now, if you know my work and you’ve read my book, you know I don’t do perfect. I screw up a lot. This offsite was only perfect because we’ve had years of imperfect ones to learn from. I wrote this piece not to brag about how good we are at offsiting now—that would be lame—but  because I want you to learn from our journey and create similar amazing moments with your team. I’ve found that offsites (when done right) can be the most profound thing you’ll ever experience as a team. They don’t have to be in Mexico and they don’t have to last a week, but they do have to happen if you want to build a team and a company that can withstand anything.

And now I’m going to do that thing where I take you back in time to how it all started for us.

Years ago—at least a decade—a wise mentor gave me the best advice I’ve probably ever been given: He told me that in order for my company to have any chance at real success, I had to find opportunities to work on the business instead of in it.

It sounded good in theory, but I had no clue how to be anything but “in” my business. Student Maid was just a baby startup, and I was leading it solo. I found myself wearing all the hats one wears when bootstrapping a company: I answered every phone call, interviewed every job candidate, trained every new hire, scheduled every client, replied to every email, sent every invoice . . . you get the idea. I was working 60+ hours a week and drowning in to-dos.

I wanted so badly to take my mentor’s advice and step away from the day-to-day to focus on Student Maid’s growth, but I felt like I was stuck in a hamster wheel: If I stopped running, everything in my company would come to a screeching halt. (Anyone else know the feeling?)

It wasn’t until I made my first key hire that I was forced to make the switch from “in” to “on.”

When I hired her to help me lead the company, it was really scary because I technically couldn’t afford her. I knew that the company had to make more money to sustain her salary, but the only way it could do that was if I focused on things that brought in more money. That meant I needed to get out of operations and swerve into the growth lane ASAP. I taught her how to take over most of the day-to-day while I spent a majority of my time thinking up grand plans to recruit more customers. And what do you know? The business grew. Fast.

But after a year or so, my gut told me there was trouble in paradise.

Here I was, finally able to focus on big-picture projects and bringing my vision to life. But now she was stuck on the hamster wheel, completely overwhelmed by the daily to-dos and too busy to help me on projects that would actually move our company forward. I began to feel disconnected from her, and I think she felt the same way about me. We didn’t have any goals that we were working toward together. We barely had time to talk, and when we did it was always hurried. I was frustrated and I knew she had to be too.

I could see the writing on the wall: If I didn’t do something, she was going to check out (and I wouldn’t have blamed her). I had to give her a reason to check back in . . . and pronto.

I decided we’d go on a trip. It’d be a chance for us to work “on” the business and “on” our relationship. A chance to do meaningful things instead of menial things, to create goals that would align us, and to become reenergized about the incredible opportunity we had to build this company together. I would have loved to fly us to a swanky boutique hotel on an island somewhere, but all I could afford was a two-night stay in a double-queen, non-smoking room at a Marriott two hours away. So we got in the car and that’s where we went.

I kept the agenda simple: I asked her to share what she loved and didn’t love about her job, I did the same, and then we came up with plans to attack the things that drained us most. I spent time describing—in as much detail as possible—the future I saw for Student Maid and asked her to contribute her own ideas to my vision. We spent time setting goals for ourselves and for the company in between eating takeout and relaxing. We brainstormed. We reflected. We got to know each other more. It was awesome.

So much came out of that trip, but the most important thing was this: I realized that it only took getting out of the office for a couple days to completely realign us. Working “on” the business and “on” our relationship as the leaders of the company was definitely where the magic was. In fact, the momentum from that one trip lasted a whole year. And then it was obvious we were due for another one. And after another year, another trip. And so on and so forth.

Annual offsites like these became critical as the company grew. Our leadership team became larger, the work became harder, and the stakes grew higher. We were all on the hamster wheel at times, and we needed the time away to regroup and recalibrate. We took trips all over: a cruise to the Bahamas, an AirBnB in New Orleans, a secluded resort in Sedona, a party hotel in Vegas. Each trip was nicer than the one before it. But by “nicer,” I mean that the hotels and accommodations got better. I can’t say the same for the content.

When times were stressful at Student Maid, the offsites became more about blowing off steam than thinking about goals. We had a lot of fun—perhaps a little too much fun—but we knew it wasn’t great to spend all that money and then come home without accomplishing anything that would move our company forward. So then, the pendulum swung the other way . . . all work and hardly any play. The new mentality became that if we were going away on the company’s dollar, then we better work the whole time. And work we did—strategizing and brainstorming until we couldn’t see straight. The result? We got a great deal accomplished, but we came back exhausted instead of excited. The last thing we wanted to do was go back to work and work some more.

Those offsites weren’t glowing successes, but they weren’t total wastes either. No matter what, we always learned things about each other and came back closer as a team. But they weren’t accomplishing what I had intended them to, and I knew they could be so much better. I just hadn’t figured out the right formula for a larger team facing a whole different set of circumstances and challenges.

It’s taken me 12 years of leading my company to figure it out, but with this trip to Mexico, I feel like we are finally on to something. Will we improve the way we do offsites? Absolutely. Will I write another blog post in a few years making fun of this one and how I was actually clueless? I wouldn’t put it past me. But it’s been two weeks since we got back to the States, and we’re all still riding high from our time together, so that’s got to mean something.

In case you want to give it a try for yourself, here’s our agenda. I hope you steal it and share it with everyone you know.

  • 360 Reviews: If you’ve read my book, you know I strongly believe that feedback builds trust. Not only do 360 reviews provide each person with a holistic view of how they’re doing, but they also lead to extremely meaningful and honest conversations. Here’s how it works: Each person must come to the offsite with two strengths and two weaknesses for themselves, and they should think through the strengths and weaknesses of each person attending the offsite. (If you have a large team, it might make sense to split people into groups based on who they work with most.) As the leader, I always go first to set the example. I start by getting real vulnerable and I share two things I’m doing that are hurting the team and the business—my weaknesses. I talk about why the behavior is happening and where I think it’s coming from, as well as what I plan to do about it. Then I open it up to the team to share their thoughts about my weaknesses. During this part they are able to add additional weaknesses that I did not mention. After this, we move on to strengths. I share two things I’m doing well that are really helping the team and the business, and then the team comments on these too. They can also add additional strengths I have during this part. After everyone has given me their feedback, we move on to the next person and follow the same steps. It takes about an hour per person. (Tips: Dig deep, be specific and have examples to support your feedback, and have the courage to share what is really on your mind and your heart, even if it might hurt someone’s feelings—even if it hurts, you will build trust and have a stronger relationship because of it.)

  • Book Discussion: I’m obsessed with reading, so whenever I find a book I love or that challenges my perspective, I share it with our executive team and ask that they read it. In preparation for this offsite, I asked everyone to read Dying for a Paycheck by Jeffrey Pfeffer. The book is about how modern management harms employee health and wellbeing, and because it’s so important to me that everyone at Student Maid is happy and healthy, I thought it was a timely and important read. Whenever we read a book as a team, I come up with questions for everyone to answer, and these become the basis of our book discussion. Some example questions are: 1) What feelings did this book evoke for you and why? 2) Find a specific passage that resonated with you and/or changed your perspective. Explain why this is the one you chose and the impact it had on your thinking. 3) What can we take from this book and apply to Student Maid? 4) What can we apply to ourselves as leaders?

  • Financial Review: I believe in 100% financial transparency. In this part of the offsite, I go over last year’s numbers and show everyone where we ended up. I also give them the chance to ask questions and give feedback. Do they think we spent our money wisely? Are they proud of where we are financially? How can we do better? After reviewing the previous year, we move to the current year and look at the budget we’ll be operating from. Again, everyone has the chance to give feedback and suggestions that we then take back and incorporate into our budget after our offsite.

  • Future Discussion:  Something I’ve struggled with a lot as a leader is allowing people to move on from the company. I used to take it personally: If people left my company, I thought it meant I was a failure. I’ve since learned that a leader’s success is not solely defined by the people who are still working with you. It’s also defined by the people who feel free to move on and leave even better for having worked with you. It’s taken me awhile to get to this point, but I’m comfortable with the idea of people moving on. So, every year at our offsite I ask people where they are. Do they want to be here? Are they ready for something new? How long do they see themselves here? We go around the room and each person shares. (Want to know what’s so funny? When you make this an open and honest conversation and you don’t hold people hostage, they actually don’t want to leave! At our offsite this year, each person said they see themselves here for life. Ironic, right?)

  • Best Year Yet: This is the best mistake we ever made. Monique, our Chief of Growth, meant to order a book called “Your Best Year Yet” but ended up ordering a different book with the same title. After she realized the mistake, she began flipping through the pages and thought it sounded interesting, so she decided to keep it. The book, called Your Best Year Yet by Jinny Ditzler, offers ten questions that force you to reflect on the previous year and set goals for the upcoming year using what you learned. It’s designed as an individual exercise, so Monique did the exercise personally. When she realized how valuable it was for her, she suggested we do it as a team—so that’s what we did! Holy moly, talk about clarity. This is hands-down the best goal-setting exercise we have EVER done as a team. Do it. I promise you won’t regret it. We will be doing this every year for sure.

  • Yearly Planning: After we’re clear on the goals for the year, we block out the meetings and strategy sessions we need to have in order to achieve them. Instead of waiting for our calendars to be filled with other things and attempting to squeeze in meetings where we can, we put the well-being of our team and our company first. We schedule all the meetings we need to work “on” the business for the entire year. We also choose dates for our company-wide gatherings, our next offsite (sometimes we do two per year), and other significant events.

  • Personal Goals: Each person comes to the offsite with a personal goal they are working on for the year. We go around the table and share our goals, but most importantly we talk about how the team can hold us accountable to them. We also discuss why we chose the personal goals we did and the impact it would have if we achieved them. This is another great chance to build relationships and trust because it requires each person to be vulnerable.

  • Acknowledgements: We so look forward to this part. Each person writes what we call an “acknowledgement”—a letter that explains how much that person means to you—to each person at the offsite. Think of it as recognition on steroids. I like to use these questions to get people thinking: What was your favorite memory of this person last year? How have they grown? What do you admire most about them? We usually write them during our free time at the offsite, and then on the last day everyone gets their letters and reads them. There are always tears and hugs. This year we attempted to do something different and gave acknowledgments verbally over dinner instead of writing them. We decided we don’t love doing it this way—written means so much more. The challenge though is that we want to spend our free time at the offsite hanging out, not writing. We decided we are going to try something different this year and do acknowledgements around Thanksgiving instead of doing them at our offsite. Highly recommend you do them, though, whether at an offsite or some other time!  

  • Rating and Reflection: We always close our retreats with a rating and reflection. During the rating portion, each person gives the offsite a score from 1-10 and explains why they gave the score they did. This helps me learn more about what people love and what they don’t love when thinking about future offsites. During the reflection portion, everyone shares what they got from the retreat, as well as anything else on their minds and hearts. I always do the closing reflection and try to make it the most inspiring sendoff possible, reminding everyone why we do what we do. (This year, a double rainbow came out of the sky as I was giving my reflection. I’m going to take that as a sign that 2019 is going to be a great year!)

And there you have it.

We follow the agenda above, in that exact order, but we space it out over several days. For our Mexico trip, we had 7 days. We took one day off completely to go island hopping on a catamaran, and we ended each day by 6pm so that we could do something fun. Sometimes we went out to dinner and sometimes we cooked at our AirBnB. We never started earlier than 10am because we wanted to give everyone time to ease into their day, and when we felt like taking a break, we did. The perfect balance of work and play.

Your offsite does not need to be in another country. It doesn’t need to be a week long. (Remember, I started with the Marriott two hours away.) But you do have to get out of the office. It’s too hard to do this kind of thinking and reflecting when you are in the space you are used to being in every day.

I’d like to wrap it up by saying this: No matter how hard we try, we all get stuck working “in” it. You get stuck there and so do I. Trivial stuff just has to get done—it’s what keeps the bus moving. And as much as it would be nice to step away and work “on” things every day—things that are bigger and more exciting and more important—it’s not always possible. What I’ve learned is that we have to make time. It’s the only way we’ll grow, and it’s the only way we will remain connected to our team and to the higher purpose of our work.

Big Hugs,