Lindsey Caplan on How to Craft Memorable Offsites

Jeremy · 0:00

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Lindsey · 0:46

Hi, I'm Lindsey Caplan. Today's leadership quote comes from Jerry Seinfeld, who says, The place I like to work in my head to try to reach someone else's.

Speaker 3 · 1:01

The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, game-changing leader assistants.

Jeremy · 1:18

Hey friends, my best-selling book, The Leader Assistant, has a companion study and discussion guide to go along with it. It's called The Leader Assistant Workbook. Now, you can buy the Kindle ebook version of The Leader Assistant Workbook on Amazon, or you can go to leaderassistantbook.com and get a printable PDF version of the workbook. This version has all the space and margin in between the questions that you can write your own answers and take notes with. So it's a great way to print it out and keep track of your discussion and study guide notes. Again, go to leaderassistantbook.com and click on Workbook to check out The Leader Assistant Workbook. Hey, friends, welcome to The Leader Assistant Podcast. It's episode 320, and you can check out the show notes for this conversation at leaderassistant.com/320. That's leaderassistant.com/320. And today, I'm very excited to be speaking with Lindsey Caplan. Lindsey is a screenwriter turned organizational psychologist who helps HR and business leaders design gatherings and change programs for the effect they want. Lindsey, thank you so much for coming on the show, and we're excited to chat. Why don't you tell everybody where you're from and where you currently live, and then maybe what your favorite thing to do outside of work is.

Lindsey · 2:49

Awesome. Well, thanks for having me, Jeremy. It's great to be here. And my name is Lindsey Caplan. I'm actually based in the San Francisco Bay Area. This is where I'm from originally, although I've tried on a few other cities for size. And one of my favorite things to do outside of work, I'm a huge baseball fan, huge, huge baseball fan. So I love going to Giants games and watching baseball and hoping one day my team gets back to the World Series, but I think it's going to be a while.

Jeremy · 3:19

Nice. Well, I actually got to take my boys to San Francisco last year. And we went to a Giants game and set up in the upper deck and got to look at the Bay and everything. And then one of my assistant friends is a, I don't remember the name of the club, but there's some club that the Giants have. And she's a member of it. And she got to take us back behind the scoreboard in right field. And we got to kind of see all the, how they manually change the scores and keep track of the games. And so anyway, it was a beautiful ballpark. And I'm a big baseball guy too. So that's great to hear that you like to spend some time at the ballpark as well.

Lindsey · 4:00

That is so cool. Lucky you. I've never been able to do that, but now I want to. I want to see behind the scenes. But yeah, it is a nice ballpark. So we'll take that.

Jeremy · 4:09

Awesome. Well, tell us a little bit about your career. As I mentioned from your bio, you're a screenwriter turned organizational psychologist. So that's a little bit of a change, I would say. So tell us a little bit about how you got into the screenwriting world and why you transitioned over to organizational psychologist.

Lindsey · 4:32

Yeah. What the heck is that, right? That's kind of, you don't hear that transition every day. Sure. I'll start. I'll go back in time a little bit. A long time ago in college, I studied screenwriting. I wanted to be a TV writer and moved to Hollywood to try to do that. I quickly discovered there was something missing from that dream. Long, long story short, I found my way into learning and development and realized it was more meaningful to develop people in real life than maybe just characters on a page. I was learning how to gather to entertain people and then how to educate them in learning and development. Then I went and got my master's in organizational psychology, where amongst other things, I learned how to gather people for transformation. Over the course of my career, which now spans about 20 years, the gathering theme has been consistent. How do we put people in our room and give them a piece of content and I hope that it poof changes them? Over the years, I've learned how to design gatherings for different effects, which brought me to my current role, which is as the founder and lead consultant of the gathering effect, where I use all of those different pieces of my background, whether it's communication, learning and development, or organizational psychology to design or redesign off-sites, all-hands, town halls, onboarding programs, leadership development programs, etc. to achieve the effect that companies want. So brief story of the past 20 years, but a very rewarding one for myself.

Jeremy · 6:06

Nice. Do you have any claims to fame in your screenwriting career shows that people might recognize?

Speaker 3 · 6:14

Yes.

Lindsey · 6:14

I briefly worked on Kirby or Enthusiasm. I don't know if you've seen that show. It was so long ago. The only thing I remember, and I hope I'm allowed to say this, and I don't think I've actually ever said this on the podcast, is just we weren't allowed to touch Larry David's food drawer. He had a very specific diet and there was a section of the fridge and kitchen that was only for him, and we weren't allowed to touch that part of the fridge. So that's my most distinct memory. Anyway, but yeah, it was a good time.

Jeremy · 6:47

Awesome. Thanks for sharing. Well, we're going to talk a lot about the idea of crafting worthwhile offsites and gatherings for teams. As an executive assistant, we find ourselves scheduling these offsites or coordinating these offsites, and that can come down to the venue and the hotel and the food and all that. But that's just the logistical, practical things of a gathering. And oftentimes, we're also sitting in the room with our leadership team or our CEO or our C-suite executive trying to figure out, okay, how can we make this offsite worthwhile? How can we keep our team engaged? How can we really inspire change that lasts from, you know, when we go to the offsite and we have this meeting, we're all together. And then when we come back to our day-to-day grind, what did we do in that gathering to cause lasting change? And so, this is, at least from my understanding, this is what you are a specialist in. And I know that assistants maybe don't always or maybe they don't have the, you know, high, like, the buck doesn't stop with us necessarily, but we do have a lot of influence, and we do coordinate a lot of that with our executives. And so, how can we help our CEOs and our principals and our executives create these gatherings for transformation or craft these worthwhile offsites?

Lindsey · 8:32

Exactly, I think you said it very well. And two things, one, I think that the question of the podcast or maybe the question I ask a lot of folks is, would you pay hundreds of thousands of dollars for an offsite that employees said they liked the next day but forgot about a week later? And believe it or not, that's pretty common. And so, my hope is in this podcast, I wouldn't be a good learning development person if I didn't say, I hope you leave with three takeaways. So I'm going to share three tips or three takeaways. I hope you leave with one. But I'd love to give some concrete tips on how to avoid what I just described because it is possible. And secondarily, I think you're right, an EA, an assistant may not always be the ultimate decider here and be responsible for this kind of success only on their shoulders. However, I hope I'm speaking to the strategist, the gatekeeper, the leader in all of us in this role, who can have influence and really support and guide in this way. So, you're the quality control person and we can play a big role in helping to educate folks.

Jeremy · 9:43

Yeah, that sounds great. So, I think we should dive right in and, you know, those three takeaways, I know assistants like myself, we love practical takeaways. Sounds like a good plan.

Lindsey · 9:57

That's my goal. Sure, let me just give a little bit of setup as to the problem space, if I can and why this is important and then I'll dive into some of these tips. So, I've been designing off-sites or leading off-sites and gatherings for a long time. And I think especially post-COVID, I see kind of two trends here. I see off-sites that are designed to sort of solve for the kitchen sink. Like we want this to solve for everything. We don't get people together in person very often and so we wanted to do everything, alignment and trust and cohesion and goal setting. And that's what I call the kitchen sink. The other side of the spectrum is casual, where let's bring people to Mexico and have a party. I'm speaking today about the kitchen sink off-site, right? The ones that are meant to solve, you know, I don't want to say just business problems, because I think hopefully both are meant to solve business problems. But more where the challenge is just we have so much that we want to do. How do we avoid this off-site being a panacea? Because if it solves for everything, it's really going to solve for nothing. So that's something I want to describe. And then also, why is this important? Well, offsites are expensive. We talked about that. And also, I think more and more what I'm seeing is these offsites are our culture, our organizational culture on display, more than they were probably before the pandemic or maybe before some companies went remote or hybrid. Because you don't have as many chances to share what you care about to sort of see how other leaders are acting, to sort of walk the talk. And so, again, I think the message here is if you're going to your principal, sort of helping to educate them on why this is important, I hope I'm also arming you with some information about why we should pay attention. So I'll start there.

Jeremy · 11:45

That's great. Makes a lot of sense.

Lindsey · 11:48

I'm sure you can relate or I'm hoping you can relate to this. And I'd love to hear more if you want to share too about what you've experienced, but should I dive into some of the tips?

Jeremy · 12:00

Yeah, that sounds great.

Lindsey · 12:02

Awesome. So I think the first tip is to focus on the desired effect that you want to create, not just the content. Yes, my company is called The Gathering Effect. That's not the only reason why I suggest we focus on this. I think what I tend to see, companies come to me and they hand me a four-page long agenda or ideas of activities or 12 things they want to solve for. The kitchen sink, I should say. I often remind folks that what we're going for is effectiveness, not just efficiency. Instead of starting with activities or content or guest speakers or topics, to really help your principle get clear on the desired effect. What do I mean by that? I mean the so what, the pain points, what we're solving for, what success looks like. A few ways to do this or a few ways to help them get clearer or to ask questions like, fast forward a week or 30 days or three months after the offsite, how will we know that we're successful? Can you give me an example? Can you tell me a story of the before and after? We want to use stories to illustrate what we're going after versus descriptive words or adjectives like cohesion or alignment, because those don't really tell us too much. If I were to look through a camera lens, how would I know if the offsite is successful? There's a couple of questions. Another way to do this is to ask for or source critical incidences that this executive or your principal is experiencing or the company is experiencing. To really gut-check with other people and other stakeholders, is this an issue? Is this what we're solving for? Or again, to get crystal clear on how this shows up for people. The more real and concrete the quote-unquote pain, the more motivated people will be to be a part of the solution. I think what we want to do is create offsites that pull people in and not just push content at them. I'll stop there, but that's really, I think, a very important tip that often gets ignored.

Jeremy · 14:17

Yeah, so like, instead of, hey, we're going to overwhelm you with a firehose of awesome content and speakers and resources, you're starting with, hey, we're going to walk away from this gathering with ABC, or we're going to, here's the problem that we're going to solve with this offsite. Is that what you're saying?

Lindsey · 14:46

Absolutely, and I think it probably sounds obvious. However, I often see this part skipped because it's hard to get clear on this. I think offsite is a very common tool that we use to solve a myriad of problems, but we don't always know what we're looking for it to do.

Jeremy · 15:09

That's just what you're supposed to do, right? You're supposed to get everybody together and have an offsite.

Lindsey · 15:14

Let's have an expensive field trip. Yes, I had talked about what's at stake, but there's more. There's employee trust, there's morale, there's motivation. Asking people to fly across the country and leave their families for a few days. This is something to take very seriously, and the core challenge, I think, of this work is to take what's important to the principal or the executive and help it become important to everybody else. Getting clear on what we want to solve for and getting people bought into the solution is a really important way to do that, and it happens by spending a little bit more time clarifying the desired outcome. So in our role as strategist, I think, and gatekeeper, I think this is something that we can really help people do.

Jeremy · 15:53

Yeah, well said.

Lindsey · 15:57

So that's one tip. And last thing I'll say here is, yes, my background very, very long time ago was as a screenwriter. It's kind of similar to how you start writing movies. You often want to know what happens at the very end, and what happens at the end of the movie, and then you work backwards. So who does his character have to meet? What kind of experiences do they have to have? What are they motivated by? You start with the end in mind versus put people in a room and let's see what happens. So same muscles and principles apply.

Jeremy · 16:30

Yeah.

Lindsey · 16:31

So that's one tip. And by the way, I'm trying to practice what I preach here, meaning we could talk about a lot of tips, right? But in terms of effectiveness, I want to just leave us just with three. So the second tip has to do with agendas, which I feel like is probably the thing that many of us look to as like our safety net. Like, let's just get an agenda. Okay, I can help with the agenda. Let's put an agenda together. And I'm going to offer a very controversial opinion, which is an agenda is really the last thing or one of the last things that we should be doing. I liken it to the bag that you wrap a sandwich in. First, we need all the ingredients of the sandwich. We need the meat and the bread and the lettuce and tomato or whatever it is that you put on a sandwich. It's not the first thing that we do. So a few sort of agenda tips. Once you have your desired outcomes, it's much easier to build an agenda because what you're trying to do is create or suggest or hire for one discussion or activity or experience per outcome and or effect. And I think you're really going for depending on how much time you have, two, maybe three at the most outcomes, not 12. So once you have those, then your agenda flows from there, right? But you have to make sure that every single thing on your agenda ties obsessively back to one of those outcomes. So in your role as the gatekeeper, my guess is, and Jeremy, I'd love for you to validate this, that this is true for you. Everyone's going to come to you with, oh, can I get a few minutes to talk? Or how about we add this session? And when you have clarity on your outcomes and your effect, it makes agenda crafting less personal and more purposeful. So you know who to say no to and why, and who to say yes to. And this goes not just to off sites, but town halls and all hands. And it helps you have a really clear litmus test. Maybe I'll pause there, and I can offer more on agendas, but see if this is landing. I'm curious.

Jeremy · 18:42

No, I think that's super helpful. I like the idea of one activity or experience per outcome. And that kind of gives you guardrails for not overdoing it and saying, oh, we're going to have these seven activities, and they're all going to have different goals or different outcomes. So yeah, I think that's super helpful and to the point, love it. The Ping Pong back and forth game of manually scheduling meetings is unnecessary and inefficient in today's automated world. It's time to embrace calendar automation for increased productivity and capacity. You Can Book Me by Capacity is my favorite automated booking solution. It's a game changer for me and my executive. You can manage scheduling for your entire executive team, send automated reminders, add buffer time between appointments, and much more. You Can Book Me integrates with your existing Microsoft and Google calendars, so you can add automation without disrupting your current workflow. Go to leaderassistant.com/calendar to learn more and sign up for a free trial of this powerful scheduling automation tool. That's leaderassistant.com/calendar.

Lindsey · 20:12

It's possible we may not solve the desired effect in one activity or one experience or one discussion. We likely can't. But it's a start, right? A couple of other things to think about with agendas, because I know it's probably the thing we think about when we think about off-sites, besides all the planning and logistics that go into it, is maybe think about your agenda as a central question that you're solving. Like, I keep sort of using my screenwriting background here, but I love shows like Severance or White Lotus, I don't know if you've watched these shows. But they have a central question that the whole series is answering. So with White Lotus, it's usually a question of who murdered who? There's always a murder at the beginning of White Lotus. Or Severance, which is a great show. I think one of the central questions is, what the heck is happening at Lubin Industries? The reason I'm talking about central questions is, it's something that sort of guides or wraps the entire series. It peaks curiosity, keeps people involved to find out the answer to the very end. And I think if we can design our agenda or offset around a central question, it could be really motivating and help guide the conversation of what we want to include. So maybe consider either creating one central question for your agenda or delineating it by the questions that each section will answer. So, you know, what is our Q4 plan? Or how do we increase trust amongst this team? And again, sort of framing things as questions versus issues gets other people interested and involved in wanting to support and be involved in the solution. So, yeah, that's some agenda stuff to consider. Nice.

Jeremy · 22:04

Awesome. Yeah, that's super helpful. I like the question forming things in questions. You know, I mentioned in my book and in several of my coaching talks and whatnot, the idea that like, it's like, okay, what are some of the best conversations and most impactful conversations that you've had with people? And there's a recurring theme throughout those. And it's good questions like people, you know, or some of the best interviews that you've watched or listened to. It's like, they all, the best therapy sessions you've been in. It's like, there's always that theme of, okay, someone or both, one or both party are asking interesting questions to show that you, to guide things, but also to show that you, you really want to know what the other person has to say.

Lindsey · 22:59

Yeah. And I think it's a lot. Well, I hear this from CEOs a lot or executives a lot, which is a version of why don't people care or why aren't they listening to me. And in employees, when I talk to them, they say, well, why doesn't my voice matter? How come my voice doesn't matter? And I think, you know, one, as an assistant, one thing to help your principal do is using more questions and statements or turning your agenda from issues into questions, does help people feel like their voice matters. And it might be less about being listened to and more about, you know, inspire influencing in a slightly different way. So a good, good communication technique there. And then the third tip, if sounds good to you, is what I call landing the plane. And I like to use a lot of metaphors and analogies here, but, you know, we go on airplane trips and there's always a routine that we follow when we take off and when we land. Put your seatbelts on and put your tray table up and all of that stuff. And what it does is it helps bring the plane safely home. And we have to do the same thing for our offsites. What I tend to see is rushed and hurried endings or offsites where we pump them full of content and there's no time for questions or debriefing or anything at the end. And, you know, my background in learning and development is about helping people absorb and retain and remember and be motivated by content and experiences. And so this tip is really about helping remind your principle or guide your principle to land the plane. What does that mean? That means, let's say you have a one-day offsite, I would spend the last hour of that day having deliberate time to focus on more integration than just more information sharing. So we've spent the past seven hours talking about a bunch of things, doing activities, whatever it might be. Let's do some reflecting and some applying. So it's just guiding them through a series of questions, more questions. What stood out by what we talked about today? What might get in the way of this being successful? What's the one thing you're motivated to try? Just questions that get people, A, putting the experience in their own words, thinking about how it applies to them, thinking more about us and how we work together based on what we did versus just it, the content. And all of what this does is it helps avoid this experience being a one-off, like a one and done. It also increases the shelf life of the experience. And the reason I'm saying this is important as an EA and assistant is, you know, this is helpful to remind folks of, and ultimately, if our goal is to save folks time, we don't want to have to then do another off-site the next month because nobody remembered what we talked about. So small things like this can be really beneficial and useful to guide folks with.

Jeremy · 26:05

Love it. What would be, okay, so you land the plane, everybody gets on the literal plane and goes home. Is there like a good cadence of, hey, you know, a week after the off-site, you know, you should check in or follow up, or is there anything like post-off-site to help things continue to stick?

Lindsey · 26:25

Yes, I think I've experienced this too, the dreaded like, we will commit to doing this next week and then no one does it. It's so common. So, I suggest people do what I call after shows. I don't know if you ever watch Bravo, or like watch What Happens Live. Have you heard of this show on TV? Basically, what it means is, it comes from folks who watch television show, they'd have an after show to sort of carry the conversation forward and discuss it in more detail. And what do we think about what this character did? And I can't believe they did that. And what I often suggest to companies is plan the after show, meaning like the more personalized discussions may be amongst departments or smaller groups that can carry it forward. So either already have it on the calendar or assign it to different leaders in your team, which just allows sort of more of the trickle down of information, the change management of whatever you're trying to introduce and gives people an additional space to sort of process and talk about what just happened. So schedule it, sort of make it, I guess, a ritual inside the organization. And I find that calling things something light, like an after show adds a little bit of levity, but maybe also sort of reminds us that we don't have to take things seriously, perhaps. So that's what I might try.

Jeremy · 27:52

Nice. Well, that's super helpful, Lindsey. I think thank you so much for sharing those tips. I think that's very, very good as far as when we assistants are involved to whatever extent in planning these offsides or these gatherings or these company all-hands meetings that we can help guide our executives to, yeah, make sure they're memorable offsides and they're effective and, you know, lasting. And so thanks so much for sharing those tips. How can, I know you've got a book as well.

Lindsey · 28:35

On the way, a book on the way.

Jeremy · 28:37

Okay, awesome, awesome. So what's the best way for people to reach out if they want to connect and learn more about what you're up to?

Lindsey · 28:44

Yeah, thanks for asking. Folks can find me at my website, which is gatheringeffect.com, or they can find me on LinkedIn. Happy to connect and chat. Awesome.

Jeremy · 28:55

I will put those links in the show notes, of course. And for those listening, if you want to reach out to Lindsey, connect with her on LinkedIn and find out more. You can find those links in the show notes at leaderassistant.com/threetwozero, leaderassistant.com/threetwozero. Lindsey, thanks again so much for being on the show. Is there any last words or final thoughts for the assistance of the world that you'd like to share?

Lindsey · 29:24

I'll just circle back to the leadership quote I shared at the beginning, which is that Jerry Seinfeld one. The reason I love that so much is, he says, the place I like to work is in my head to try to reach someone else's and as assistants, and that's what we can help our principals and executives do, is help them reach others by what's in their head. Offsites are one way to do that, but ultimately, it probably has to do with a lot of the gatherings that we have in our day-to-day work. Yeah, but thanks so much, Jeremy. Thanks for having me on.

Jeremy · 29:57

Yeah, I love it, and I love Seinfeld, one of my favorite shows ever, and I appreciate you sharing, and yeah, take care and best of luck to you.

Lindsey · 30:07

Thank you so much, you too. Please review on Apple Podcasts. gobullos.com.

Jeremy · 30:33

Hey friends, my best selling book, The Leader Assistant has a companion study and discussion guide to go along with it. It's called The Leader Assistant Workbook. Now you can buy the Kindle ebook version of The Leader Assistant Workbook on Amazon, or you can go to leaderassistantbook.com and get a printable PDF version of the workbook. This version has all the space and margin in between the questions that you can write your own answers and take notes with, so it's a great way to print it out and keep track of your discussion and study guide notes. Again, go to leaderassistantbook.com and click on Workbook to check out The Leader Assistant Workbook.