Reinventing Company Gatherings: Casey Boyles on Creating Impactful Team Events

[00:00:00] Debbie Goodman: Welcome to On Work and Revolution, where we talk about what’s shaking up in the world of work. I’m your host, Debbie Goodman. I’m CEO of Jack Hammer Global, a global group of executive search and leadership coaching companies. We help find great leaders and we help develop them into even better ones. My main mission with all of my work is to help companies and leaders to create amazing workplaces where people and ideas flourish. And on the topic of thriving remote workplaces, one of the perpetual questions that is still being asked is whether it’s possible to create great work culture remotely. And if so, how the heck you do that? And fortunately for us, I am chatting today to Casey Boyles to tackle one of the pieces of the puzzle on remote work culture.

So listen up. Okay, so Casey is Chief of Staff at Guild Education, where she bridges strategy and operations to drive effectiveness for, I mean, well, for everybody. Guild is an edtech company of about a thousand people, most of whom work remotely. And Casey for better or worse found herself being tasked with managing all of the company and team wide on site gatherings of which they have been more than 20 in the last six months.

It turns out that a key part of successful remote work is periodically bringing people together in person. And today we’re going to chat to Casey about her learnings on how to manage team gatherings well. Welcome Casey.

[00:01:39] Casey Boyles: Thank you for having me. I’m very excited to have this conversation.

[00:01:43] Debbie Goodman: Yeah, me too. Okay. So team building or company onsites or offsites. I mean, that’s not really a new thing. I mean, team building has been happening in companies all over the globe for as long as I can recall with pretty mixed responses from people in the teams who are required to attend these events.

I’ve spoken to hundreds of people over the years who like roll their eyes at the thought of some cheesy team building activity. and I think that’s Others would do anything not to attend. And then from time to time, they’re those who actually just like love their company get togethers. So historically at Guild, how did most people in the company feel about these in person events?

[00:02:24] Casey Boyles: Well, I think speaking from my personal point of view, they’re not something that I love doing. Um, they take up a lot of time. I have to travel, be away from my family, and the content is there. It’s always kind of boring. You get talked at on stage for days, you’re in the basement of the Sheraton, there’s no natural light, you, you get bad food and there’s not enough of it, they give you too much alcohol, and it’s just so very stale, and, and I’m an extrovert, and I get a lot of energy from people and I just dread to think about the introverts, neurodiverse people, it’s just not tailored for the modern world.

[00:03:05] Debbie Goodman: right. Okay. So that’s the base level of what, we find as most table stakes in get togethers, definitely the one that is a killer for me is the no natural light. I think for every single team gathering I’ve organized in the last 20 years, that has been like the main requirement. I don’t care if we’ve got shitty this or that, but give me natural light, otherwise I’m going to die.

Anyway, share some context into then, if that was kind of the way things have been, what was the challenge for you in taking on the responsibility as part of your job, which is a bit of a catch all job, right?

[00:03:43] Casey Boyles: Yeah. So, I think I’d done a few events before. Um, didn’t make success. I think they were fine. They weren’t very groundbreaking, but I felt a lot of pressure with this. Because we’re spending a lot of money on these events. They’re a big financial investment. Also with the teams I work with, it’s a big time investment.

A lot of people, we have a call centre model. So people are on live channels on the phone. And so when we take people off of the channels to come to a live event in person, it means we’re not serving our members. We’re not doing our job. So there’s just another big trade off. And also I felt a lot of pressure to not make it a boring event.

Like how do I surprise and delight people? How do I leave people walking away being like, Oh, that was a good use of my time. So it was a lot of pressure and money to feel like it make this a good use of people’s time.

[00:04:36] Debbie Goodman: Okay. That sounds like a ton of pressure because it’s not just about producing something that people go away going, Oh, that was cool. But also the impact on revenue and service to the company by having people not doing their day jobs, which I guess is what most companies have to contend with in any event, you take people out of their day to day work.

It’s going to come at a cost, but, aside from that, let’s take a step back. Why was it so important to get this right? What would getting it right, really right, mean then for the company?

[00:05:11] Casey Boyles: Yeah, we got a lot of, feedback in our employee engagement surveys that people wanted more time together. As you mentioned, most of the company is remote. We have headquarters in Denver, but people are based all over. I’m remote myself. And there was just people wanted to see their friends. A lot of people haven’t even met their team members, because they joined a company during a pandemic, they may have like missed the last onsite, so people actually hadn’t met and there is, the thing I actually love about events is that when you get to build that relationship with someone in person, it feels so much easier to go back online and do the work. and there was, I think a lot of times it’s sort of like an underlying tension between people. Stuff gets lost in communication online, messages can be misconstrued, but if you already have that foundation and you know someone beforehand, it just makes it easier to get the work done, especially when things get hard.

We’d also just had a large reduction in force. We’d laid off 25 percent of the team. And one of the directors was like, we need to get people together to show them that we care and that we’re invested in them, and so this was the primary driver of sort of the first big event back in June to help people recover and get people together quickly to show them that we have a plan for the path going forward and to make them feel confident in that.

[00:06:36] Debbie Goodman: Okay, so it sounds like, there was a fair amount of fresh thinking that you needed to apply to this relatively new landscape with, particularly the RIF, which I think many companies they’ve just done this cost cutting initiative and the thought of laying out some more money in order to bring people together feels like, uh, should we be doing this?

Should we be sensitive to how much money we now spend? Nevertheless, the benefits of bringing people together a from a communication point of view, from a healing point of view, from, uh, once you’ve met and know each other, everything else happens so much more smoothly and quickly, and all the niggles that get lost in translation can be ironed out.

So we know what the benefits are, but then the question around, should we invest in this becomes a big question. And I actually want to just stop on that point because, I imagine what’s going through a lot of people’s mind is, yeah, they just laid off my friend or colleague, or now I’m stuck with more work because the, you know, because I’ve got, I’m doing two people’s jobs and yet they are putting so much money into this, lavish team gathering.

How did you get the balance with that right?

[00:07:50] Casey Boyles: It was, it was really hard. And I like felt it myself because we also had a directive to do company swag. And I was like, we’re not having any swag. That is not necessary. We don’t want to do that. And so I thought about how we should spend our money wisely and what we should do to show people we care about them.

I worked with the hotel and I was like, this, this can’t look really expensive. We’ve done events before that looked really expensive, had a big stage, makeup artists, all that stuff. So it was just sort of like very bare bones and simple, but it was like, It was nice. And I actually, um, threw in a question into, we had like a panel discussion where, because people wanted answers about like, why did this happen?

And stuff like that. So I actually threw a question into the panel, uh, like a plant. And I was like, Can we just say this wasn’t that much expensive because it was so last minute I organised it and managed to get a lot of deals and I was like, it’s not that expensive and so I had to reassure people because I just didn’t want people to feel like we weren’t investing money in the right things.

[00:08:52] Debbie Goodman: Right. Okay. So that’s definitely, we’re going to talk about the learnings in a little while, but that’s certainly something to take into consideration on the one hand, you want to do something that isn’t cheap ass, but on the other, um, not too over the top, because people will start asking questions about why you prepared to spend money on this versus something else that we consider to be important.

Okay. But let’s go back to the fresh thinking. What else did you need to bring to the table with wanting to revitalize or do things differently?

[00:09:23] Casey Boyles: Yeah, I had to rip up our playbook for events. We’d always do the same thing. We’d have an executive panel. We would have, some activity where you put things on post it notes and then you come up with some great ideas and you never see those post it notes again. Um, love those ones. Um, and then there’ll be some, um presentation from product or finance and you’d just be talked at.

So we had to shift away from the like, sage on the stage model to a more interactive and get more people involved. I was trying to find things that would really surprise and delight people. I think the first thing I was thinking about was like, a venue, that natural light. What’s a place we can go that feels different?

We had a big team and we couldn’t fit in the office, so I was like, where can we go off site that feels like a little vacation, a break away from the norm? And so yeah, the venue, the content, make sure the food was good, like all of the little things we had to do completely differently.

[00:10:26] Debbie Goodman: Oh, yeah. In terms of those key elements, because now we’re getting into some of the nitty gritty, what do you think are like the key pillars to make something that can be simple, but really impactful.

[00:10:41] Casey Boyles: A clear purpose. You really have to start with why you’re meeting, and if you can’t answer that yourself, everyone’s going to be asking, wait, why are we here? What are we doing? And so you have to set really clear goals and make sure that the work you’re doing is aligned to those there.

[00:11:00] Debbie Goodman: Can you give an example when you’re talking about have clear goals? Because on the one hand it’s like, yeah, we have to bring people together because that’s how we roll and it’s important. Full stop. What, what else beyond that?

[00:11:11] Casey Boyles: Well, really pointy. So, one of the goals that we had was to make sure people understood what their job was, and like, what their role was going forward, and how it was part of the company. So we spent a long time helping people understand what the team did and their specific role in it. We did have like as well, some belonging goals.

So we want to make people feel more connected to their teammates and feel part of the team and get to know them. But they have to be more specific than like, we just want to hang out. And as a few times I’m like, do we actually really need to meet? Like, the things you do in person should be things that are really valuable in person.

If you’re just going to talk at people, you can send them a pre read, make a recording, do it virtual. So really understanding the goal and does this warrant this time investment to have a big production.

[00:12:03] Debbie Goodman: You know, it’s interesting that, the investment to bring people together feels like one then needs to be filling up all the time with stuff. And in fact, a lot of that stuff is much more easily distributed, shared and communicated online, actually. And the reason often to bring people together is so that they can just, just, and I’m using the air inverted commas, if you can’t, if you can’t see my hands, but the just.

To just be together, to just hang out, to just feel each other’s energy, to just have a laugh, to do things that are unplanned and unstructured and happen in the moment, the things that we used to do when we were all in person and that we just can’t do these days. And so it feels in some ways that that’s a waste of time to let people just hang out when in fact that is often the main gig.

That’s the main thing for many organ, for many of these get togethers. Is to leave enough time for that to happen.

[00:13:02] Casey Boyles: And it’s very counterintuitive because you’re like packing the agenda but you’re just going to make people exhausted because it’s back-to-back there’s no time to decompress and so I’ve been very disciplined lately not because things always go over time. People get excited things over time but you cannot run over and skip the breaks.

I did that a lot in the beginning. Like you need to keep those breaks and because people need time it’s hard to be fully engaged and present all day. People need just time to decompress, to maybe do some work, emails, you just got to give them that time so when they’re with you they can be fully present and engaged.

[00:13:40] Debbie Goodman: Question. Do you, did you have any sort of like rules, like no, cellular communication while we’re in session? Cause I mean, I know I have attended certainly a lot of conferences, where people are there in person, their bodies are there, but their brains are, and their emotional state is somewhere else completely because they’re on their phones.

So did you have any rules around that?

[00:14:02] Casey Boyles: Yeah, sometimes we do set rules because we do want people to be present. Sometimes it’s a little bit hard because we do have, a business to run and, if there is an escalation or an emergency, people need to do that. So we normally say, we trust you, that if you’re, using your phone it is because there is an emergency we ask you to step out of the room to do that but when you’re in here we should be present but take the breaks that you need but when you’re here you are here.

 and we also set other guidelines around I like a few ones like be real like be authentic because we do a lot of like sharing. Sometimes I get a bit touchy feely on my onsites, especially on leadership ones. And so we all encourage people to be authentic. I think the biggest, way to get people to do stuff is to model the behaviour. So I always encourage my leaders to be like, Hey, I don’t want you on your phone. I need you to like volunteer, put your hand in. I need you to be mingling, like don’t be off in the corner at the happy hour. I need you to walk around. And so I always just have my leaders model the behaviour that we want everyone else to do.

[00:15:09] Debbie Goodman: Okay. That’s a really, really good point. How can you expect the team to, or the, you know, everybody else in the organization to be the perfect example of engagement when, leaders are kind of doing their own thing? There is a lot more innovative technology these days, to drive engagement.

I mean, it sounds also, once again, a little counterintuitive using technology to drive engagement, but there are a couple of things that, that I recall you’d mentioned, some little tips, tools, apps, things. You want to care to mention a couple of those because they sound pretty cool.

[00:15:42] Casey Boyles: Yeah, so we always used to have like an executive panel, where we’d get two people on stage and they’d talk, and it was fine, it was very interesting to hear from them, but we decided to sort of flip it on its head. We had the executives up on the stage, and then every so often we’d put a QR code

up there where people could sign in to answer a question for themselves. So one of the questions was about, innovative workplaces and we asked people what’s a trait of an innovative workplace that you have been part of? And we had them answer, and it started to populate a word cloud on the stage.

And it was fun because there was like 200 people in the audience and all of these things were bubbling up. And the themes were coming up. And the executives were able to take those and use those for their answers and that made the audience feel more connected to it because they were contributing to the discussion in a less I’m going to raise my hand in front of 200 people and say something.

It just allowed people to, engage without having to give too much.

[00:16:46] Debbie Goodman: right. Oh, that’s pretty cool. Yeah. I think some people, you’ve always got your one or two people in an audience who ask all the questions and, need to have their voice heard, but there’s so many more who would be interested to participate, but aren’t prepared to stand up or put their hand up and certainly introverts will never do that.

So that’s a cool way to involve more people. What are your thoughts on hybrid sessions where you’ve got most people in person, but then there’s the odd person, you know, the, you know, people who have to dial in, I mean, I did that today with my team. That’s my South Africa based team. They had their year end get together.

 and I’m in LA and so I literally, I dialled in at 4:30 AM to give a year ends Speech that was kind of weird and awkward and half the people couldn’t hear and the technology was terrible. And I was, you know, it just was, it felt poor because I, mostly because technology let us down a little bit. So what are your thoughts on not just people presenting, but participants dialling in, when most people are in person?

[00:17:54] Casey Boyles: It’s hard. I always dread it. Because you have to run three events. You have an in person event, a virtual and a hybrid, like how they work together. And it’s a lot more work. And so for a while I was like, I’m just not going to do them. But it’s just not very inclusive. There are so many reasons why people can’t and won’t travel.

And we just have to figure this out. So I’ve been experimenting some more. Technology is the key. You need to have good technology that works and have to invest in it. And even then, that will let you down. I find it’s also really helpful if you have a few people online, is to have a virtual person who’s in the room with you, but is online interacting with the folks.

So they can field questions, they can make sure the tech works, they can get feedback for sound.

[00:18:41] Debbie Goodman: Right. Okay. So there’s a virtual liaison, so to speak.

[00:18:45] Casey Boyles: A virtual liaison. Yeah, I find that really helpful. Um, the other day we had an onsite and there was a person, there was probably about 25 leaders in the room and there was one person who hadn’t made it in, who was coming in later.

But they were really crucial. And I didn’t want them to miss out. And so we made it work. We got them like they were on a laptop and we just, because we had lots of like breakout activities where there were two people working together. So we just had them on a laptop and we, we treated them like they were a human.

And so some person would come out and they’d be having a conversation online and we were switching them back and forth between seeing the big screen and not. It was a lot of work. I don’t think I could have done it for more than like one person. but it worked, but it’s a goal to get better at this because it’s only going to get harder.

Yeah.

[00:19:34] Debbie Goodman: Technically and theoretically with VR and AR and holograms, we should be able to do this, um, eventually quite affordably where people can be very much in person without being physically in the room. But let’s see how that evolves. I haven’t seen, I haven’t heard of any companies who are really doing that effectively yet using that type of technology.

So. I’d be keen to know, where those hybrid, get togethers have evolved to. okay. So you’ve done 20 of these things in the last several months, which is a lot. What have been like big picture? What are some of the key learnings that we can share with people who listening

Cause I know from 2025 onwards, so many strategy meetings and team get togethers, people who once again are approaching it with a sense of dread, either as a participant or as an organizer. What are some of the key learnings and what do you want to share with people who have to take this task on for 2025?

I mentioned a little bit about the flexible agenda. I think that’s probably my biggest learning because there are going to be some times when you need to stay longer on something and other times you need to move on and it, you’re not productive. So just having that space to be able to shift and be like, right, we’re not going to do this session at all.

[00:20:53] Casey Boyles: This is what we need to do now. And just being okay with it and having a really strong facilitator. I think I didn’t understand what, like the power of a good facilitator. And I’ve spent some time over the last six months learning, watching people who are fantastic at it, taking all the notes, doing lots of reading, and the power of the facilitator to guide the conversation, to synthesize, to make sure people are pushing in the right direction and get to

To right conclusions, to put the crowd at ease, to listen to them. It’s such a powerful skill and I would say if you’re going to be doing these events, just invest in learning to do that better. I think it’s a skill that will last you for a long time.

[00:21:39] Debbie Goodman: so just on that, do you think it works better to have somebody internal part of the leadership team or part of the organization who’s got those skills? Or do you sometimes hire an external facilitator who’s really great at it and this is what they do for a living?

[00:21:53] Casey Boyles: I, we’ve done both, um, and we have some fantastic external ones. We have this woman that comes in and like sits in with the leadership team. She’s one of their coaches and helps guide the conversation for the exec team meetings. I think it’s better to train up your people in house. I think like everybody should be a good facilitator.

And so if you start to build those muscles, I would invest in making your team good facilitators.

[00:22:17] Debbie Goodman: Okay. Well, that’s an interesting insight and learning. I’ve also tried both and depending once again, depends on the facilitator, because both can be either equally excellent, external, internal, or equally awful. Um, so, yeah,

[00:22:33] Casey Boyles: seen them both.

[00:22:34] Debbie Goodman: right. what other recommendations for, let’s say somebody is the event coordinator or the leader who’s going, we’re going to DIY this.

And what are the key things that I should be thinking about and what should I do based on somebody else has done this 20 times in the last six months in this, you know, in this type of scenario, what are the three things that are critical?

[00:22:57] Casey Boyles: so start with clear goals in mind and audit your agenda. So if you’ve already put together your agenda, Take a step back and like, what are you trying to do? I actually like to color code my goals. Two or three goals. And so I’ll write them at the top of my planning document. And this eventually gets, a version gets shared out with all the attendees.

And it will be like, red for our goal around Understanding like product knowledge or blue for team things and then each item in the agenda. I also colour code So people can see exactly what we’re trying to do And it’s very helpful because if there’s no colour on something I’m like, why are we doing this?

And it allows me to like change up the content. And also you can make sure you have a good distribution. Like, are you spending, if it’s me, I probably spend too much time on the belonging stuff. I’m like, I’m going to get a little bit of meat in there. And so it allows you to push things back. And also it’s a good way to really, show that this is a meaningful expenditure.

[00:23:54] Debbie Goodman: Hmm.

[00:23:55] Casey Boyles: Like, this is why we’re doing this. This is the purpose. These are the outcomes. Don’t do it all yourself. That’s my next piece of advice. Like, get help, for all of the things. I am a little bit of a martyr and I, you know, I like to do it all and struggle. But the last event, last sort of big event I did for 200 people, it was a team I didn’t really know very well.

And in the registration survey, I asked if anyone would like to run a session or do anything and 60 people raised their hand and said, I’d like to do something. I was like, well, that’s a lot more than I expected. And so I actually held some focus groups and it was great because it gave, I took my goals to them.

I said, I think this is what we’re going to try and do. Does this feel like a good use of our time? Does this feel meaningful? And I got really good feedback. I adjusted the goals, I changed them and people commented, they felt really like included and inclusion was one of our goals and so people had their voice was heard, we changed things and it made a big difference.

[00:24:56] Debbie Goodman: right. Oh, I think that’s a, that’s a great one. I think about the number of times where I’ve, put agendas together that are mostly my agenda, then wondered, did this land, whereas I could have ahead of time just polled some interest from, um, from my team. So that’s a really great, uh, great point there.

Okay. So anything different that you are going to be doing in 2025? Based on your experience and learnings.

[00:25:24] Casey Boyles: Well, I am like laser focused now on tying these events to business outcomes. I really need to show that, these events are meaningful. I’ve got a big budget for next year and I don’t want to waste it. I want to have it the year after. and so I’m finding different ways to show that the work we’re doing here is actually advancing our agenda in other areas.

It’s not just hanging out and we’re all bonding and everyone gets along. Um, one example is that we do a lot of pre and post surveys for the event. So we ask people the questions before, based on what the goals are. So if we’re trying to help people know product knowledge, we will say, how comfortable do you feel with all of our products between, I don’t know, one to ten, and we ask them the same question after.

What I want to do is tie this into our already existing company surveys. We use a tool called CultureRamp to measure employee engagement and I want to start making sure the questions match our CultureRamp surveys and then using the same software so I can get trend data and see where like my events peak those things.

[00:26:35] Debbie Goodman: Okay. Right, very good use of CultureRamp as well, is for these team events. Great.

[00:26:43] Casey Boyles: Yeah, we’re paying for it. We have it already. We have trend data. because sometimes if you have a big team, you don’t know where the hotspots are coming from on the surveys. And I don’t want to ask people who they are. I want to give them like freedom to say their true feelings without offending me.

Your event was terrible. Like I want them to feel they’re able to speak up. And so that will really help me like pinpoint. Are we targeting the right stuff? Yeah.

[00:27:08] Debbie Goodman: Okay. Well, that sounds very exciting. and I’d love to hear your In a year’s time, how things have evolved. Casey, it’s been such a pleasure to talk to you. Thank you for sharing all of your experience, your insights, your learnings. This is such an integral part of every single organization, regardless of whether you’re remote, hybrid, or in person. Team gatherings, we all need to learn how to do them better.

[00:27:33] Casey Boyles: And, um, hopefully 2025, everybody will be very much more excited about attending these, certainly anybody who’s listened to this podcast. So thank you so much.Thank you, Debbie.