Transcript Episode 15

Transcript Episode 15: 8 Tips to Host a Virtual Team Retreat

Transcript Episode 15

Stephanie Skryzowski:

Welcome to the 100 Degrees of Entrepreneurship Podcast, the show for purpose-driven entrepreneurs who want to get inspired to step outside of your comfort zone, expand it to your purpose, and grow your business in a big way. I’m your host, Stephanie Skryzowski, a globe-trotting CFO whose mission is to empower leaders to better understand their numbers to grow their impact and their income. Let’s dive in.

Hello, my friends. Today, I am Excited to share with you a little bit of behind-the-scenes of our virtual team retreat. You may know that our team has grown pretty significantly. In the last year, I started 2020 with myself, one other full-time employee, and a very, very part-time assistant. At the end of 2020, we ended up with four CFOs that all serve our amazing clients, a marketing director, an operations director, and an assistant that is nearing full-time, almost full-time, so we’ve grown a lot. I really have been wanting to bring everybody together in person so not only could we get to know each other a little bit more on a personal level, but we can also really help shape the direction of the business together. I don’t want this to be The Stephanie Show anymore and I feel like as your business starts to grow, it is really important to bring in your team into planning and helping shape that direction so that they have ownership and they’ve got buy-in, so one of my goals at the beginning of 2020 was to bring everybody together in person.

Of course, being the person that I am, I had an Airbnb list of all these potential beautiful beach homes that we could go to and meet on the east coast of the US from Charleston, South Carolina, to places in Florida. I just wanted us all to be on the ocean. Obviously, for very selfish reasons, I wanted to be on the ocean, too. Then March happened, March 2020 and COVID struck and I knew that we were not going to do an in-person team retreat. Travel was such a big goal and a big priority for my family and for myself in 2020, including being able to bring everyone together. But obviously, nothing happened in 2020 the way that any of us had planned. But honestly, I look back and in some ways, 2020 reality was better than 2020 plans.

I haven’t been on an airplane in a year, maybe probably more than a year, but our family actually discovered our new favorite road trip destination in coastal Maine. Instead of presenting in front of hundreds of people for a couple of conferences that I was going to do, I actually presented at virtual conferences in front of thousands of people, way more people than would have been there in person. Honestly, I wasn’t really anticipating growing my team to the level that we did this year, but we were able to. We grew the team literally beyond my wildest dreams. Instead of all hanging out at a beach house for a few days, we decided to come together for a virtual retreat instead. Maybe you’re in the same position where you have a team that has grown, or maybe not, your team doesn’t have to have grown, but maybe you have a team and you’re not able to bring everyone together in person.

I feel like in this online business world, people are just literally all over the place. I mean, we have people from Maine to Philadelphia area to Atlanta, to Mexico, to Ohio, we’re kind of all over the place. You may be in the same boat. Maybe you’ve never even met some of your team members. I have not. Would you believe that? I have not met most of the women on my team in person. I feel like we know each other through Zoom, but we’ve not met everybody in person, which is just crazy. I decided a virtual retreat was going to happen. I really wanted to get us all on the same page for Q4. I wanted to do some professional development for each of us, and so I said, “Okay, let’s do it. Let’s make it happen.”

I’m going to share today the eight things that we did to really make our virtual team retreat successful. Honestly, I walked away from the retreat and we did a post-retreat survey for our whole team and we all felt that it was very, very successful. We got a lot out of it. At the end of the day, no, it’s not going to be like an in-person event, but there are things that you can do to make it as successful as possible. We really feel like we hit it out of the park and that is not because of me personally by any means. It was because of the team planning that went into it, which I’m super, super proud of. Here it is, the eight things that we did for our virtual team retreat that made it a smashing success that you can also do, too, if you want to plan a team retreat for you and your assistant, or maybe your team of 20 or somewhere in-between. Here’s the eight things to do for your virtual team retreat.

First of all, determine your goals. The very first thing that my operations director and I did was figure out what we actually wanted to get out of our time together. We’re all so busy with packed schedules and lots of different priorities, so I really was sensitive to the fact that our time together had to be worthwhile. We had to get some big stuff out of this retreat. I didn’t just want to sit and stare at each other on Zoom for a few days. My goals, and I incorporated ideas from the team as well, our goals were to build relationships with each other and establish some norms for future collaboration. What I mean by that is that I wanted us to get to know each other a little bit better so that people could work together outside of me. For so long, I’ve been the hub of everything having to do with the business, which is natural. I’m the founder and CEO. I’ve been here since day one and nobody else has, right? But I wanted to show the team ways that they could collaborate with each other without me, because at the end of the day, they’ve got amazing ideas, too, and I do not need to be at the center of that.

Our second goal was to begin putting together a 2021 plan for all facets of the business, both client-facing and internal. We wanted to think about how we were going to serve our clients better in 2021, as well as what could we do internally to make our work more efficient, to improve what we’re doing, so I’ll talk a little bit more about how we actually did that.

Then the third goal was to provide some professional development for the whole team. Now, I surveyed the team and asked them what topics they would be interested in learning about and so they shared that with me and I’ll share a little bit more about that as well. We went into this with three goals: To build relationships and establish norms for future collaboration, to begin putting together our 2021 plan, and to provide professional development for the whole team. Those were our three goals. That’s it. I knew that every single thing that we did in the retreat needed to be in service of one of these three goals.

Okay, so number two, the second thing we did was map out an agenda. Once we had these rough goals in place, we mapped them out on the calendar. Since we were virtual, I obviously didn’t want everyone to be sitting on Zoom for eight hours a day, so we determined that five two-hour sessions would be the entire retreat, so we did a Wednesday morning, Wednesday afternoon, Thursday morning, Thursday afternoon, and Friday morning. Those were our five sessions, two hours each. I wanted to make sure people had adequate breaks in-between, that we weren’t running over into people’s dinnertime, and again, I think so much of the value of an in-person retreat comes outside of the planned sessions and on the margins of your planned day. Unfortunately, we were not able to create that magic virtually, but it was really important to me that people were not on Zoom, but then also on their email, or in QuickBooks, or doing something for a client, or whatever. I wanted everybody’s focus and shorter sessions was the key to doing that.

We built our agenda for those five sessions based on the three goals that I shared above and we had initially come up with a list of all these different things that we wanted to do and sessions we could have, but once we started actually building the agenda, we had to ask ourselves the tough question, “Well, which of these items are in service of these goals? If they’re not in service of these goals specifically, let’s use a future just regular team monthly meeting that we have to do that instead,” so we got our agendas together.

The third thing that we did was hire experts. I was very clear from the beginning that I did not want this to be The Stephanie Show for 10 hours of people listening to me talk and having me lead and me teach. I did not want that because one of our goals was to provide professional development for the whole team. I’m not an expert on everything, right? I’m not a productivity expert. I can share some tips and tricks that have worked for me, but I wanted to bring in paid experts to teach our team.

Here’s what we decided on. One of the things that I have recently done was take the StrengthsFinder assessment. The Clifton StrengthsFinder assessment is amazing and it basically ranks you on, I think it’s 34 different strengths from your top strength, so which of these characteristics is really most strongly reflected in you, all the way down to your bottom strength. I wanted to do this in service of goal number one, which was to build relationships and foster a spirit of collaboration, so I paid for each of our team members to take the full assessment. Then we brought in an expert to analyze everyone’s individual results and compile them as a team and teach us how we can use that information in our work and in our lives, so now I know that I am really strong in X and this person is really strong in Y, so we can come together and collaborate and support each other’s strengths and weaknesses, basically. That was the first expert we brought in.

The second expert was actually our operations director. Productivity was one of the things that our team really expressed a lot of interest in, which totally makes sense. A lot of us are moms. We’re balancing home life and in 2020, several people were balancing remote schooling and we are balancing our families and many clients. All of our CFOs work on a number of different clients, there’s a lot going on, and so we really are all interested in becoming more productive. Our operations director did an awesome presentation with several dozen productivity hacks, from software tricks, to ideas on setting boundaries. The team loved the session. This is the one that they still talk about today. That was the second expert that we brought in.

The third one was Sarah Jane Case. She is a mindset coach and an Enneagram expert to talk to us about self-care. Again, we are all busy women, many moms, and self-care is not often at the top of our priority list, but it needs to be. I think we all know that we can’t pour from an empty cup, and so taking care of ourselves in a number of different ways, that it looks different for all of us, but that was really important as well. Again, I could share my own personal tips and tricks on this, but I loved to bring in an expert instead. That was really in service of the professional development for our team. I knew I wanted it to not be just me for the entire week, so experts it was, and they were amazing.

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The fourth thing we did to make our virtual team retreat really successful was to get the team involved. Our team’s input before and during the retreat was absolutely crucial. Like I said, 100 Degrees Consulting is no longer The Stephanie Show, so it was really important to me to make sure that all voices were heard. We sent everybody a pre-retreat questionnaire. We asked questions about their wins, about their challenges, their personal and professional goals, and how we can grow better and better support our clients. Our operations director compiled the results and this really kicked off our first discussion. Instead of just coming in totally cold with a blank slate, we had something to get us started with and ask clarifying questions and move in the right direction from day one. I love the fact that we asked the team their input upfront because it just helped us really kick things off smoothly. Ask the team. That’s number four, get the team involved.

Number five: Make it special. We all have a lot of Zoom meetings, a lot of Zoom meetings. I recently counted how many Zoom meetings I was on because I saw somebody else on Instagram had done that as well, so I counted and it was some horrendous number, 60, 90, a hundred, I don’t know, in a not-that-long amount of time. I’m getting very Zoom burned out. I don’t know about any of you. I wanted this to be special. I wanted this to be more than just, “Ugh, another Zoom meeting on my calendar.” My team knows that I am completely obsessed with curating and sending gifts and the retreat was really the perfect opportunity to send each woman on our team a little care package, so our time together felt special and out of the ordinary, so I put together gift boxes with cozy little socks and a little mug and a coaster from Nepal and a notebook and a note and a Starbucks gift card. This was in the fall of 2020. I really wanted everybody to feel special and cozy. That was really fun to see everybody posting their pictures with their new cozy things as we are settling in to do our retreat.

The sixth thing that we did to host our virtual team retreat was I removed myself. As the CEO of the organization, I really wanted to give authority and ownership to the team and step out of the way, empowering them to brainstorm and to come up with ideas without me. I think we all know that when the CEO is always in the room, people consciously and unconsciously lean in their direction and agree with their ideas. I really wanted to hear from everybody else without my own opinions and thoughts in there, so what we did in order to make this happen was to have a breakout session one of the afternoons where our CFOs serve our clients. They all got together in a separate Zoom room and then our marketing and ops team got together in a different Zoom room and they all brainstormed and began to build some 2021 plans and come up with some major strategies that we’re going to be working on in each of their respective departments.

I did not go to either of those meetings, so I was not present at all. They were able to really dig into some opportunities for us, some challenges. They were able to dig into ideas in a different way than they would have if I was in the room. Then the next day, they actually then presented their ideas to the whole team, which was really fun. I can just envision how this would have worked in person: Each little group of three or four people went off into a separate room and with the big giant Post-it Notes and came back and presented and shared to the group and it would have just been so awesome in person, but it was pretty awesome via Zoom, too. I just loved what they came up with and the different challenges that they brought to light that might not have surfaced otherwise, so remove yourself.

Number seven is: Make it actionable. I don’t know about you, but one of my major pet peeves is walking away from a conference totally overwhelmed with information and a notebook full of notes, but no clear action steps, no idea what to actually do after I get home. If we didn’t actually implement anything we learned, then what was the point of spending all of that time and money and energy being together and brainstorming if we’re not going to actually do anything about it? We spent the last session going around and sharing one thing that we planned to incorporate into our daily lives and work and then one goal that we have for 2021.

What’s one thing that we could take away and do immediately? A lot of people listed some of the productivity hacks, some of the self-care things that we talked about, and then one goal that people have for 2021. A lot of times, these were a little bit bigger, bigger goals, professional development, and client service, and things like that. We are actually following up on these in our team meetings to make sure that we’re all holding each other accountable and that we’re supporting each other and helping each other actually take action and make it stick, which is so fun because we’re continuing that retreat spirit throughout our team meetings going forward.

Number eight, the last thing that we did and our virtual team retreat was have fun. I know this is a little bit cheesy. This was honestly probably the hardest thing for me because I’m not really a dance party on Zoom kind of person. I have been to other Zoom meetings where the host puts on music and people are literally dancing with their cameras on and it’s so fun and energetic, but that’s just not me. I just can’t do it. I can’t do a Zoom dance party by myself in my office on camera. Awkward. However, we didn’t do any Zoom dance parties, but we did keep it light. We chatted before each session and we really made sure we showed up to contribute and support. I think that by doing those shorter sessions, that really helped us to do that with a fresh mind and fresh energy each time.

I’m really hoping that an in-person experience and a beautiful oceanfront home with dinners out and champagne toasts is in our future, but for now, a virtual team retreat was really successful in pulling us together in Q4 of 2020. In terms of our business, I would definitely do it again. I really would. If we are still unable to travel for the duration of 2021, oh, my goodness, fingers crossed, please don’t let that be the case, I will definitely do a virtual retreat again and I will survey the team and see what they really feel like they need and I’ll bring in experts to make sure that they can help fulfill those needs. I think it will be awesome. I think the key is, like I said, to prepare, to make sure you’re using your time wisely, and to make sure that everybody has actionable things that they can do after the retreats to, again, make that time worthwhile.

I would love to know, have you ever had a virtual team retreat before? What was it like? Was it fun? Were you on Zoom all day long, or did you break it up into different chunks? I definitely think this may be the way of the future. I think it’s going to be a while before everyone feels comfortable traveling again. With our online businesses, so much of our teams are remote that this is probably going to be our new reality, at least in some parts, or you could also use this virtual team retreat as a mid-year check-in, so if you end up doing an in-person retreat, maybe this is a way that you can do a mini-retreat maybe halfway through the year. I know that I’m going to do this again. I loved the experience. It was so much fun and I think we all really got a lot out of it. Would love to hear from you. Definitely screenshot the episode and tag me over on Instagram at @stephanie.skry. I would love to know, have you done a virtual team retreat before? Tell me all about it. I’ll talk to you soon, friends.

Thanks for listening to the 100 Degrees of Entrepreneurship Podcast. To access our show notes and bonus content, visit Make sure to snap a screenshot on your phone of this episode and tag me on Instagram at @stephanie.skry and I’ll be sure to share. Thanks for being here, friends, and I’ll see you next time.

Transcript Episode 15

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