Offsites Are the New Office: How to Drive Connection and Alignment in a Distributed World

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Jared Kleinert: If you are remote, hybrid, distributed, if you want to keep talented people working at your company, you must plan team retreats. It is unavoidable for 99% of companies.

David Rice: Welcome to the People Managing People podcast. We’re on a mission to build a better world at work and help you create happy, healthy, and productive workplaces. I’m your host, David Rice.

My guest today is Jared Kleinert. He is the founder and CEO of Offsite. We’re gonna be talking about some of the benefits and challenges of planning and developing offsites for your company or team and what you can do to ensure your people take the most of what they can from the experience.

Jared, welcome!

Jared Kleinert: Thanks for having me.

David Rice: So I wanna start by asking, how have things evolved over the last two years with offsites because, I know obviously with a rise in distributed teams, you’re probably seeing more interest in these than ever, I imagine. But even with companies returning to office like offsites still have a function they always did.

So maybe the goals of it are a little bit different. I guess take us through how you’re seeing things change and develop with things like return to office orders and all that.

Jared Kleinert: Sure. I started Offsite during the pandemic, was vetting that a lot of companies were going remote or hybrid in part ’cause of the pandemic, and I saw that trend happen over the 10 years leading into the pandemic where we went from very few companies being remote or hybrid to maybe 10 to 20% of knowledge working teams were remote or hybrid pre pandemic.

So I was betting on that trend. I thought it would accelerate. I thought a second order of that would be that a lot of companies would plan team retreats, VCN, and GitLab automatic and buffer save beer. They plan lots of team retreats as an inescapable part of building company culture when you’re remote first or distributed or hybrid, and they knew from planning Offsite and conferences and whatnot that the planning process sucks.

And so if you can make it suck less, then you could probably have a cool company. While we did start during the pandemic, we started taking our first clients on probably when Omicron was coming in and out in that wave. And then, companies were very excited to have offsites, so there was an initial burst in the right direction.

And then tech got hit really hard with a tech recession two, three years before a possible macroeconomic recession that we’re possibly experiencing now or may experience sometime in the next six to 12 months or 24 months. And at least in our customer base, there was a retraction of offsite, but then people were determining if offsites were a nice to have for their company or a must have.

And slowly it turned into this must have where if you are remote, hybrid distributed, if you want to keep talented people working at your company, you must plan team retreats. It is unavoidable for 99% of companies. So then I would say there’s been much more offsites and then it turned into more traditional companies adopting offsites as well.

Certainly there’s been slight pullbacks with return to office, but I find that’s mostly Fortune five hundreds and larger companies, and it is. Scary headlines that may or may not reflect like the trend at the end of the day. And so like I still see tailwinds that are saying that there’s gonna be more remote, hybrid distributed work in the next 2, 5, 10 years, but there’s certainly gonna be drawbacks here and there.

This is also like in an employer’s market. Like what happens when it switches back to being an employee’s market or a talent market and the economy opens up again at some, or like loosens up again, which could be two years from now, five years from now, who knows? But it will get better at some point. And then what happens when large companies get out of their expensive leases?

Are they going to keep those leases? Are they gonna shrink their office space? And is that gonna make for more distributed work and remote and hybrid i’m just betting on the remote work trend personally, I don’t know about you.

David Rice: Yeah, I know. I think it’s just the way the, it’s the way the world’s gonna go and it’s not because like, truthfully, I don’t even think it’s gonna be because it’s what talent wants. I think it’s just gonna be the thing that makes the most sense if we’re, if we’re honest. Especially like you said, if you’re not a Fortune five company and you can’t have a skyscraper. You know what I mean?

Like it’s one thing when you’re a massive company with 50,000 employees and you can afford to have an entire building in a downtown somewhere. It’s another thing when you’re like 80 people. And you’re wanting to have a team that’s located in a completely different city. It just makes more sense.

It’s and especially for startups in this space, like I don’t think there is like a office centric culture for the, of the future for that type of a company, really.

Jared Kleinert: Yeah, I agree. I think there’s generational shifts that’ll benefit that I think. The data is showing that companies are more profitable, more effective, et cetera.

When you’re remote first or distributed or hybrid, people are happier and they get to work out and spend more time with family and be healthier and sleep more and all that, and like just makes sense all around.

David Rice: Yeah. No, I agree.

I’m curious ’cause like my, the company that I work for, we’ve done offsites as well. I’m curious from your perspective, like what are some of the most common mistakes companies make when planning their offsites, particularly when it comes to aligning the event with like their broader organizational objectives?

Jared Kleinert: Lack of intention is probably the biggest one. So not knowing what those business objectives are, not realizing how they can align their agenda.

To meet those objectives, even the venue and the vendors that you’re investing in. An offsite should be to accomplish something for your business, whether that is strategic planning for the upcoming quarter or year, whether it’s a sales kickoff or go to market kickoff, get your year started off in an energetic way, whether it’s a customer conference that is for marketing and is development.

There should be a reason for gathering people for 2, 3, 5 days in person investing all that money and really investing everyone’s time. That’s the biggest thing. You’re investing. You’re also putting your reputation as an employer on the line. Hopefully you are increasing employee engagement, retention and alignment as a result of doing a good offsite, but there’s always the risk that it goes poorly and that leaves a bad taste in people’s mouth.

And I would say you should have a really good reason for planning an offsite and the good news. There’s a lot of good reasons, but you should make sure that whatever the reason is for your team for that time of year, that it’s well thought out and it is reflected in where you go, what you do. Are you doing things in person that can only be done in person, it can’t be done on Zoom, those sort of things.

David Rice: Absolutely. When I think about ’cause these things can be pretty expensive at times, right? So if you’re a leader in say, HR or people operations, you’re kinda looking at ROI on offsites and how are you gonna communicate that out to other senior leaders? What advice do you have for gaining buy-in around it and communicating the sort of strategic value of the event?

Jared Kleinert: So with our clients, we to have them do a pre offsite feedback form where they can ask the basic logistic questions, dietary preferences, travel sensitivities, things like that. But then also ask for an employer net promoter score.

How likely they’re you to, recommend your place of work to a friend or a connectedness to colleague score or a belief in the company’s future score. Whatever your sort of employee engagement metrics are, you can ask that before offsites and then afterwards and hopefully see that you are having a positive impact with your team retreats.

You can ask more open-ended questions like, what do you wanna accomplish as a result of attending this offsite? And then ask what do you think we accomplished, from the offsite? And so that’s one of the best tools that. We find an HR leader or a people ops leader can develop when planning an offsite and it makes future years a lot easier to justify.

You can also look at retention rates and are you able to get talented team members to stay at your company for an extra six months, a year, two years, or more as a result of having regular team retreats or as part of the formula for success there? Because replacing talent can be very expensive.

Downtime with less people can be expensive. There’s a lot of intangibles, which are harder to track, but you can definitely feel, and that would be seeing increased trust as a result of team retreats and making friends at work. Basically, you could see, so the activity levels pick up in slack. I know Slack has like sentiment analysis tools that they feed into other systems.

So maybe if you use like 15 five or Lattice or Culture Amp, they might have sort of sentiment analysis stuff that you could pick up on. But yeah, you can definitely just feel that before and after an offsite and hopefully it’s better for weeks and months afterwards they can reflect back on a great offsite and that could be a relic of company culture and success.

Then other tangibles could be, are there great initiatives that come out of an offsite, like a good marketing idea or business development idea, or was there a product or engineering idea that came out of a team retreat? We had our last all hands meeting at the first week of February that I led a workshop on basically how to think about.

Operationalizing and automating your day-to-day workflow. And since I shared that with the team, I could see every single person at the company trying different AI tools and writing better SOPs about their work and finding ways to optimize their workflows. Use tech tools offshore more to VAs, and that’s having a material impact on our company.

And so you could also find like different takeaways from your retreats for things like that. And then I guess the last thing that a lot of people don’t think about is the employer branding aspect of this. And so make sure you have a photographer or videographer and you take photos of the team having a great time, take some video of that and use that for recruiting efforts.

And I think that is just low hanging fruit. And CEOs do that anytime they have a funny announcement, they’ll share like the last happy go-lucky team photo. Be like, I love my team. But if you’re on the HR team, you should think about some of the employer branding aspects of this.

David Rice: Yeah, absolutely. That’s what it is. Just a natural and as you’ve got everybody on a hi, right? So it’s like there’s a lot of good feeling in the rooms, a great moment to capture.

A lot of teams pandemic became distributed. You started hiring people across different borders. It became very multicultural in a lot of organizations. And there’s diverse age groups represented. I’m curious, what strategies do you employ to ensure the Offsite is like inclusive and meaningful for everybody?

Jared Kleinert: For us, again, that pre Allstate feedback form allows us to get a sense of what people are into and not into. What needs they have don’t have so we can take care of the food that we’re serving.

Someone on our team is like scared of heights, and so we’ve learned that and made sure they always have access to a ground floor room whenever we go to offsites. You also have to think about our people leaving their families and do they have access to childcare and pet care and making plans for that in advance.

We do all hands meetings twice a year at offsite. Then one out of those two times we bring significant others with us or allow for people to bring their significant other. That’s been a really cool addition to what we do. So you can see like a different side of someone if you want to create that culture of your company, which we do and we enjoy.

And so that’s added a new wrinkle and allow people to bring their families if needed. And then you can ask questions related to the activities you might plan. Like how. Open, are you to something that’s active versus something that’s more relaxed? If you have a wide range of answers to that, you can have optional activities during, a half day where group one can do this, group two can do that.

Group three can do the third thing. And just giving people permission to participate at varying levels, but also encouraging them to lean into whatever you’re doing. And so a lot of sessions that. We’ll run our personal in nature and desiring to. Create more deep, meaningful connections with everyone in the room.

And that sometimes includes like journaling prompts or opportunities to be vulnerable and share more about your life and what you’re going through and or what you’ve gone through in the past. And so as a leader, I will typically lead those sessions and be super honest and transparent and that can set the tone.

But there’s also permission to only go on the shallow end of the pool if you’re not comfortable. But then also invite people to go deeper if they want. And so I. I mean at the larger and larger, the offset gets like the less and less you can personalize it, but I think being mindful of as many logistics as possible.

Catering your activities to your unique company culture. Those are some good ideas and you could even save money when you’re doing that. We’ve had a couple clients do like talent shows as part of their like evening plans and allow people to showcase what they do for fun. There’s some great musicians or people with cool hobbies on your team and they can enroll everyone else in, in getting to know them better that way.

David Rice: Yeah, that’s awesome.

Before you had mentioned, you do a survey before and a survey after, and you can see if you’re moving in the right direction. I think that’s obviously very impactful and telling of the, the success of your event. But I’m curious, are there some long-term indicators that you’ve identified with clients like that suggest the offsites that you’re doing are really like having a broader, maybe like transformative effect?

Jared Kleinert: Yeah I think it would go back to seeing those results compound over time. And seeing the different ideas compound over time as well. You also are just building relationships with other humans at a increasingly deeper, increasingly more meaningful level, and a lot of that comes from unique shared experiences.

And so as you’re traveling to different places, potentially as you’re having different cuisine, as you’re trying different activities, as you’re talking about different challenges throughout the year in this very intentional way that is going to foster stronger relationships with your colleagues.

And that alone is worth it if the extent you can build company mission, vision, values in one offsite, and then the next offsite sort build upon that. And the third offsite talk about how you’re gonna accomplish your OKRs, leveraging your mission, vision, values, or, and even celebrate people for living out the company values over the course of a year.

You could see how this can start to build on top of one another. You can also refine your budgets. You can refine your activities. From those surveys and just keep asking people what they like, what they didn’t like, and then hopefully calibrate more and more to something that’s increasingly well received, increasingly valuable for your specific company.

David Rice: Planning any event, it’s one of those things like everything else now, right? People are using AI to inform what they’re doing, to make travel plans, doing all kinds of things with it. That’s interesting. But I think a lot of things with AI can lead to some either homogenization of approach or can, make some assumptions that aren’t exactly line with reality.

But can you share a specific Offsite design that you’re particularly proud of and what made it unique and what were the unexpected outcomes that you got from it?

Jared Kleinert: Yeah, the best offsites are a mix of the client’s, like unique culture. Then some of the best practices that we see across hundreds of retreats.

10 days ago, there was a YouTube video that went out from the founder of Stan, which is a, I think it’s a Series B backed startup. At this point. They’ve raised 30 million or more, and we did their offsite in Park City, Utah in January for about 50 people. And the founder has a YouTube following. He had this like vlog style review of their offsite, as it was happening.

We didn’t know about it. We didn’t ask them to do this. And he did a really great job of explaining from his perspective why it was so valuable for them. And I think for them specifically, it came down to celebrating their progress. It came down to building strong relationships and continuing momentum ’cause they had doubled their headcount in the last few months and a lot of people didn’t know each other, so they got a chance to connect. They are a company that helps content creators monetize their followings and build their platforms. So they were recording lots of content as they were skiing and tubing and having lots of fun.

And then they were able to do sessions around their company values. They were able to look at financials and project out the next year as they want to become a, a hundred million dollar a year revenue company and a unicorn startup. And, they were also, they had department leaders leading different sessions after the CEO gave his State of the union, if you will, had lots of dinners and then fun.

And, he was just explaining that one idea from any of these sessions could not only make the offsite itself valuable, but it could be a hundred x idea that makes the company a billion dollar company. And so to the extent that he can foster that is incredibly valuable. And he was also explaining how as a leader as a CEO at his stage, there’s only so much he can do as an individual contributor.

Like he could be on sales calls all day long and is probably not gonna move the needle, for how much revenue they need to create. So what he has to think about instead is how can he create a culture where people have autonomy to make decisions, are making the right decisions, are following out on the company strategy.

And so offsites are one of the best ways, if not the best way, to really get everyone on the same page culturally and strategically. And that can be worth millions, billions of dollars potentially. And so I just thought he was. Really articulate about that, and I’m happy to give you the YouTube video so you can put in the show notes and if you want.

David Rice: No, I love that because I think what you’re, getting at there is like, when you’re doing an offsite, you’re trying to create a feeling. You’re trying to create like a sense of like we said, connectedness and all these other things. It’s all, but it comes back to a feeling and it’s gotta be driven by human insight into how people are feeling, right?

Like you can do the data and you can look at all these things, but at the end of the day, like you know your people and you know what you want and it’s gotta be driven. I think I kinda asked that question with the AI and the uniqueness because I was looking for that right there, right? Like you’re creating this sense of connectedness and human driven insight. I think that’s really cool.

I gotta ask though this question. So offsites are one of those things like it’s great to do, but obviously we can’t do it all the time, right? It obviously depends on budget, but if you’re doing it effectively, you’re doing it efficiently, let’s say it’s an ideal world. From your perspective, I’m curious, so what is the right amount of time to spend at offsites?

Jared Kleinert: Different companies have different cadences for offsites. It does depend on stage size, how well the company is doing or not, but we’re 20 ish people, 2025, depending on, how you count, head count. But we do a quarterly executive team retreat, and then we do two all sites a year with everyone.

And so that is pretty significant. One’s you get to a hundred people. We’ve seen companies do some sort of sales kickoff or sales marketing go to market kickoff, and then. I do think the quarterly executive team or like senior leadership team offsite is very high ROI, like every company should do that regardless of size, but then each department may have one to three offsites in addition to some all hands meeting at least once a year. So you might find yourself as an employee of a remote first or hybrid company going to two to four offsites a year of varying shapes and sizes. Like you might be on the sales team, you’re going to a sales kickoff.

Hopefully you’re on the, you get President’s club and you go on a trip for that. And then maybe there’s one other sales offsite and then you’re all hands, so you might go to three or four in the year. Product and engineering, maybe you guys prefer just having lots of deep work time and so perhaps you only have the all hands meeting or maybe you do one other offsite throughout the year to align sort of midyear.

And so that trend is something that scales up is having everyone at the company be prepared to attend two to four offsites a year. That’s something that Airbnb came out with like during the pandemic and said, we’re gonna be a fully remote company, and if you work here, you can expect to go to an offsite quarterly.

Dropbox has this sort of 90 10 rule where they say about 10% of your working time, you can expect to be in person, 90% remote. And so that translates to 25 days or so. Being at Offsites. So that’s maybe four times a year at three to five days, and maybe it’s like a different type of offsite where it’s more getting together and doing lots of deep work, but just being around colleagues and going out to dinners and stuff.

But again, every organization’s gonna have different things, especially if the more distributed you are, it might be harder to get everyone together, still worth it at least once a year for your all hands. And then hopefully another one to three times per person.

David Rice: Interesting. Before we go, I wanna give you a chance to, tell people where they can find you. I always like to give our guests a chance to, deal with people where they can connect with you, sorry, find out more about what you’re doing.

Jared Kleinert: You can go to offsite.com, make a free account. It works like Airbnb, where you can search through thousands of curated offsite venues or vendors for like photographers, videographers, swag providers, travel providers, so on and so forth.

Spoke directly with them and save lots of money and lots of time. We also do end-to-end offsite planning as a service, and we’ve done that for hundreds of companies all over the world. You can email me, jared@offsite.com anytime, and happy to give you a discount if you mention the show. And yeah, reach out with any questions. Happy to help.

David Rice: The second thing is, we have a tradition here on the podcast. I always like to give my guest a chance to ask me a question, so I’ll turn it over to you. Ask me anything you want.

Jared Kleinert: Aliens, do you think they’re real or not real?

David Rice: Oh, I love it. Everybody always asks the question, like tied to the thing. I love this. It’s a really great question.

Yes, I do, but I think it’s probably not like what we think, like what do we define as an alien? I’ll bet you there’s like a bacteria on another planet that’s like communal or something,

Jared Kleinert: you think there’s another like humanesque creature?

David Rice: I don’t know about that. Maybe, I don’t know. I don’t think so. I feel like, maybe in a completely different galaxy, ’cause who knows what’s out there. But in this one, no. I just think, I think it was probably not gonna look like us or behave like us, or at least I hope. No, I’m just kidding.

But no, it’s a, that’s a good question. I definitely think there’s some other sentient form of life out there. I’m sure.

Jared Kleinert: Nice. All right.

David Rice: Thanks for coming on the show today. I really appreciate you giving us a little bit of your time.

Jared Kleinert: Yeah, thanks for your time. Appreciate it.

David Rice: Alright listeners, if you haven’t done so already, make sure that you go on over to peoplemanagingpeople.com/subscribe. Get signed up for the newsletter, you get all this stuff straight to your inbox.

And until next time, start planning that offsite. Don’t invite the aliens.