Decision Vision Episode 146:  Should I Hold a Corporate Retreat? – An Interview with Jared Kleinert, Offsite

Intro: [00:00:02] Welcome to Decision Vision, a podcast series focusing on critical business decisions. Brought to you by Brady Ware & Company. Brady Ware is a regional full-service accounting and advisory firm that helps businesses and entrepreneurs make visions a reality.

Mike Blake: [00:00:22] Welcome to Decision Vision, a podcast giving you, the listener, clear vision to make great decisions. In each episode, we discuss the process of decision making on a different topic from the business owners’ or executives’ perspective. We aren’t necessarily telling you what to do, but we can put you in a position to make an informed decision on your own and understand when you might need help along the way.

Mike Blake: [00:00:44] My name is Mike Blake, and I’m your host for today’s program. I’m a director at Brady Ware and Company, a full-service accounting firm based in Dayton, Ohio, with offices in Dayton; Columbus, Ohio; Richmond, Indiana; and Alpharetta, Georgia. My practice specializes in providing fact-based strategic and risk management advice to clients that are buying, selling, or growing the value of companies and their intellectual property. Brady Ware is sponsoring this podcast, which is being recorded in Atlanta per social distancing protocols.

Mike Blake: [00:01:13] If you would like to engage with me on social media with my Chart of the Day and other content, I’m on LinkedIn as myself and @unblakeable on Facebook, Twitter, Clubhouse, and Instagram. I also recently launched a new LinkedIn group called A Group That Doesn’t Suck, so please join that as well if you would like to engage. If you like this podcast, please subscribe on your favorite podcast aggregator and please consider leaving a review of the podcast as well.

Mike Blake: [00:01:39] Today’s topic is, Should I hold a corporate retreat? And the timing of this is very interesting because, up until very recently for the last year-and-a-half, almost two years, having a corporate retreat was probably a preposterous question. Or if you did hold a corporate retreat, it would look pretty weird with a bunch of people on Zoom meetings, I’m guessing, or Zoom screens or whatnot. But, of course, now as the Delta variant subsides, and who knows what variant is coming past that in our trans-pandemic period, corporate retreats are back on the menu again.

Mike Blake: [00:02:15] And, boy, do companies have a lot to talk about. Since the last time companies have done their retreats, this thing called digital transformation has happened, we’ve seen a seismic, I think, fundamental shift in how labor and society relate to one another in our country and in our economy. And the very nature of leadership and the very nature of what we even think is productivity is being at least reevaluated, if not outright being called into question.

Mike Blake: [00:02:50] Interestingly, corporate retreats can have a bad rep. For example, there is a story in allbusiness.com that spoke of – and it’s in 2008 – while the Great Recession was underway and after immediately receiving bailout money, AIG executives spent over $400,000 on a corporate retreat hosted at the luxurious St. Regis Resort and Spa in Monarch Beach, California, it was reported that the executives treated themselves to over $150,000 in food alone in only one week. That’s a lot of avocado tacos, man.

Mike Blake: [00:03:27] And I do think that there’s a little bit of branding to overcome and, first of all, talk about. I don’t know that you could be much more tone deaf than that. But, nevertheless, I do think that, to some extent, corporate retreats do bear some of that stigma that they’re not necessarily as productive. They can be more of a boondoggle. And so, it’s important to get that right.

Mike Blake: [00:03:54] Now, in fairness, I’ve been on some corporate retreats which have been fantastic. And it’s something that I need to do for my group, I think, sooner rather than later. So, I plan to learn a lot from this conversation. And as I often do with the Decision Vision podcast, really, is simply disguised mooching to get some free advice under the auspices of giving somebody some publicity.

Mike Blake: [00:04:20] So, I like to welcome back to the podcast Jared Kleinert. He came back on, I think, he’s one of the first 30 or 40 people who came on the podcast, so it’s fun to have him back. And he has a new venture, he is Cofounder and CEO of a company called Offsite, which helps you plan the perfect team retreat. Previously, Jared was one of the first ten employees of 15Five, a leading B2B SaaS company, powering over 40,000 teams to bring out the best in their people.

Mike Blake: [00:04:52] Jared is also a TED speaker, award-winning author, and USA Today’s Most Connected Millennial, who has personally facilitated offsites for Fortune 1000 global executive teams, started companies ranging from a marketing consulting firm to a series of high end summits for entrepreneurs, and more. To learn about Offsite, visit www.joinoffsite.com. They are the easiest way to plan, manage, and follow up after team retreats and other offsite meetings. They help you choose the perfect venue, offer a detailed agenda that will increase employee engagement, and generate measurable return on investment from your offsites all in one place.

Mike Blake: [00:05:30] And their clients include some of the hottest seed and Series A venture backed startups, Inc. 5000 companies, Y Combinator backed teams, venture capital firms. They’re crushing it as we would expect from Jared because he’s a crush it kind of guy. He’s a power hitter. Jared Kleinert, welcome back to the program.

Jared Kleinert: [00:05:51] Thanks for having me back.

Mike Blake: [00:05:53] So, we talked a little bit before we started the program, I mean, you’re doing well, obviously. It seems like every day you’re posting about a new client and a new success story with offsite retreats – I presume offsite retreats. So, congratulations for your success there.

Jared Kleinert: [00:06:13] Thank you.

Mike Blake: [00:06:15] So, let’s start off, you know, and I do think this is important here. It probably seems obvious to a lot of people. But in light of the AIG anecdote that I spoke of at the start of this discussion, I don’t necessarily know that it’s obvious to everybody. So, what is exactly a corporate retreat?

Jared Kleinert: [00:06:34] The way I view it is, the future of work is changing very rapidly. I don’t think anyone would argue that the workforce is decentralizing, just like finance and many other industries, and this has been the trend for the last ten years. When I was at 15Five, I was one of the first ten employees and we were a remote-first company. I was an unpaid intern from South Florida working for this company in Silicon Valley, then I got on payroll. But, you know, team members were zooming in from all over the place and we got to reconnect once a quarter during these offsites.

Jared Kleinert: [00:07:19] And more and more companies have gone remote or hybrid since. The pandemic has pushed us five or ten years into the future, so much so that now Facebook is rebranded to Meta, and Dropbox is creating metaverse stuff now. And so, the future of work is changing very rapidly. And the companies over the last ten years that have built the best remote-first or hybrid company cultures have relied on these things called offsites or team retreats in order to bring their team together, build trust and intimacy, potentially do some strategic planning such as OKRs on a quarterly basis.

Jared Kleinert: [00:08:01] You know, there’s different types of offsites, even internally for your team. And regardless of how you run your offsites, it’s important more now than ever to get everyone together in-person when 330 plus days of the year we’re at home or we’re working from wherever we want, and we might be lonely, we might be disengaged, we might be looking for other job opportunities.

Jared Kleinert: [00:08:27] And so, what used to be something that the most well-funded startups in Silicon Valley are doing is now becoming essential for any remote-first company to do. And not just to do it once a year, but to do it, perhaps, quarterly, I would argue, to have different types of offsites for the entire team once a year and all-hands meeting, executive team meetings, a sales team meeting, perhaps some client facing offsites where you’re treating your most valuable clients to an overnight stay or two nights.

Jared Kleinert: [00:09:00] We haven’t gone into the corporate retreats that you started with as far as stereotyping, like golf outings and doing a lot of enterprise stuff quite yet. We’ve been working with fast growing startups and Inc. 5000, primarily. But there is a huge opportunity to go into corporate as well to take the offsites that are already happening and just make them more transformational, make them higher ROI than, maybe, what the tone deaf story you shared is.

Jared Kleinert: [00:09:31] So, yeah, it’s something that companies have been doing for a while. It’s only increasing in terms of urgency as systems are breaking when companies have been forced to go remote. And it was already hard to run a company now to run a remote-first company and keep people engaged and performing is really hard. So, offsites are one tool in the remote-first company toolkit that a CEO can bring out to re-engage their team.

Mike Blake: [00:10:00] So, I mean, I get the name of your company is Offsite, but companies have held retreats onsite. Let me rephrase the question this way, I mean, clearly you believe that offsite retreats are more effective, at least I think so or you wouldn’t be doing this. If that’s the case, why is it more effective to have retreats offsite versus on? Or am I putting words in your mouth? Maybe I’m saying that’s not true.

Jared Kleinert: [00:10:30] I don’t think it matters where you do your retreat, necessarily. The fact is that more companies are giving up their offices or their sites now more than ever. Or they’re giving up their big headquarters.

Mike Blake: [00:10:42] There’s no site to have it on.

Jared Kleinert: [00:10:44] Yeah. There are smaller regional sites, and so it may very well be that you need to actually bring everyone onsite. But, now, your workforce has left one city and they’ve gone to other cities, other countries. A lot of our clients that were signing on have team members that have been hired in the last two years and haven’t met their colleagues. And so, the place you have your offsite is less important.

Jared Kleinert: [00:11:09] To me, it’s more about having the intention to get everyone together, making the financial investment, but also really the investment of everyone’s time, collective billable hours, creating an agenda that engenders trust and intimacy, and then leveraging that trust and intimacy to accomplish your business goals. And, again, that could be learning and development, that could be simply getting some Facetime with each other if you haven’t seen each other ever, and that could lead to more trust or better cross department collaboration. It could be strategic planning. It could be thanking your clients. Again, there’s a million reasons to have an offsite, but it’s building trust and intimacy and then leveraging that for your business goals.

Jared Kleinert: [00:11:59] And the last time I was on your show, you know, we were talking about Meeting of the Minds, which is my other company. And it’s basically what we’re doing, is, we’re doing a meeting of the minds for other companies now. And so, I’ve been doing this for a while. My cofounder, Keir, owns a bunch of hotels, and so he’s approaching this from a hospitality angle, you know, taking care of the where we’re doing these offsites and making sure hotels can understand the needs of startups and other clients that we’re serving. And we’re just going for it because there’s a need of the market and, you know, we want to solve it.

Mike Blake: [00:12:33] So, sometimes everybody can go on the retreat. Sometimes everybody can’t because it’s just a matter of logistics and finances. In my case, my team is four people, soon to be six, when we have a retreat, we’re all going on. But if you have a company of 30 people, it may not be practical to have a 30 person retreat. It may not be desirable to have a 30 person retreat. But I can also see how that can be a very kind of delicate question to pick who gets on the retreat and who doesn’t, because somebody who’s not picked can read a lot of things into the fact they’re not being picked.

Mike Blake: [00:13:14] That’s a long preamble to the question being, how do you pick who’s going on the retreat? And then, to the extent that you can comment, how do you communicate that to the people that you’re not inviting on that retreat?

Jared Kleinert: [00:13:32] So, the way we think about it, we’re working with the person planning the offsite. And for the size companies and teams that we’re working with, typically, the teams are anywhere from 10 to 500 people right now. And the companies tend to, you know, 1,000 people right now, although we’re quickly exploring working with teams within larger enterprise companies. And the team leader is deciding the objective for the offsite. It could be an all-hands meeting, which means everyone at the company or as many people as possible. And we’re sort of actively planning all-hands meetings for 40 person companies, 100 person companies, and more.

Jared Kleinert: [00:14:23] Then, we’re looking at executive team meetings where it’s typically 8 to 12 people and that’s a C-suite. There is also team meetings for certain departments, so sales teams may want to have their own offsites, engineering teams may want to have their own offsites.

Jared Kleinert: [00:14:42] And so, that’s how we’ve approached it. As we’re evolving our company, we’re starting to talk to higher level people leaders within companies, people that are chief culture officers, chiefs of staff, maybe it’s a co-founder as well. But then, they’re establishing a cadence for offsites where they want to have a regular executive team meeting once a quarter. You know, give the ability for certain departments to have regular offsites and then also have an annual all-hands meeting. So, really the budget that was previously put towards offices, you could argue, being reinvested in these offsites, at least for a lot of VC funded tech companies. And that’s kind of where we’re starting. And so, it’s really up to whoever is planning the offsite.

Jared Kleinert: [00:15:39] One of the first things that we do when we bring on a new client is we give the planner of that offsite a customizable feedback form to actually send to the team. And in that feedback form, we’re getting the basics of travel preferences, blackout dates, if they have personal things like weddings or they’re going on maternity leave and they can’t attend. We ask for dietary preferences, other travel sensitivities. And so, you know, occasionally there are people that can’t make these offsites, but we do encourage the planners of these offsites to think inclusively about who’s attending.

Jared Kleinert: [00:16:19] And then, also, all the details that would make a more inclusive experience from your menu and catering to traveling to locations that are LGBTQ friendly, if you have members of your team that are part of that community. And just thinking holistically about your team, their needs, and what is the best environment for your team. That’s today.

Jared Kleinert: [00:16:43] We’ve also started exploring what hybrid offsites look like, where you have 80 percent of your staff in-person and 20 percent remote, and what are the AV needs that you’re going to need from your meeting space.

Jared Kleinert: [00:16:55] One of our investors is the co-founder and CEO of Convene, which is like a multibillion dollar Wheeler competitor, and they have hybrid solutions that they’re playing around with. I mean, I think in ten years we’ll be doing offsites in the Metaverse as well and doing virtual offsites. We’ll see.

Mike Blake: [00:17:15] So, what about timing? Is it better to hold a retreat during the work week or over a weekend?

Jared Kleinert: [00:17:23] Most of our clients are doing the work week, because to ask people to leave their families during weekends poses all sorts of challenges around child care, around their personal lives, and taking them away from family. And so, I would say 80 percent of our clients are during the week. And then, maybe some client facing offsites, like we have some consulting firms that are hiring us and then looking to do sort of high ticket conferences for a smaller group of clients, they may do a weekend. But some of the programming is inclusive of significant others and spouses and kids, so we can help with that too.

Mike Blake: [00:18:06] Now, do you have a view on whether or not you should hold a retreat in a place that is, I guess for lack of a better term, fun? A lot a lot of conferences, for example, happen in places like Vegas, Orlando, and so forth. Lots of fun things to do, but you can also make the argument there’s a lot of distractions. Versus a place that’s maybe more mundane, which might be a more dedicated conference center or event center that allows you to be more focused. But then, again, it’s not as fun to be in that place. What’s your view in terms of which kind of venue is more suitable for a productive retreat?

Jared Kleinert: [00:18:44] It could be another non-answer, but it really depends on the objectives of the offsite. And so, if you are doing strategic planning where you need everyone’s full undivided attention, perhaps you choose a more secluded environment where you are coming in to work, you get some flex time to workout, call family, take a nap, but otherwise you are there to get things done. Right now, a lot of companies are doing more team building oriented offsites, and so they want to do more “fun”. And then, you may choose cities, environments that lead to more fun.

Jared Kleinert: [00:19:31] There’s also an element of this that is employer marketing. And what I mean by that is, companies are looking to have offsites and capture photography, videography, increased employer net promoter scores from these offsites, and maybe use the offsites to then ask their team to introduce them to more high quality candidates for roles. And so, if you’re going to host an offsite with some of that intent, then you may want to choose a place like Miami, which is, notable, or Vegas, or something like that, or Austin. So, it really depends.

Jared Kleinert: [00:20:13] But we’re also learning, so at the end of the day, we’re building software to automate a lot of the offsite planning process. We are still in the early days, so we’re doing white glove concierge service. But in a matter of months – maybe by the time this comes out – we might have MVP software out there and then over time, we’ll be able to learn what people are really looking for. Are they looking for more secluded environments? Are they looking for more urban environments? And we’ll probably be able to track based on the type of offsite they’re planning, and the team size, what environment is best for them. So, who knows, maybe there’s like an AI component to this as well that we can build out.

Mike Blake: [00:20:55] I’m sure that there is.

Jared Kleinert: [00:20:55] I mean, this is like inning number one in terms of this company, I’m hoping. So, we can have another rendezvous in ten years and see how it turned out.

Mike Blake: [00:21:07] Yeah. Well, I don’t think we’ll need that long. So, in terms of best practices, how much runway do you need to give yourself? And I understand, I guess, it’s going to vary depending on the size of the organization. But assuming that’s not a huge retreat, mega conference kind of thing, how long does it take to plan a retreat? How much advanced planning or how much time lead time do you need to to put on a good retreat?

Jared Kleinert: [00:21:38] If you’re planning for six people, like yourself, you can do that in three weeks. If you’re looking to do more of what our clients are doing, you know, the 10 to 50 person offsites, I would ideally hope that you’re giving yourself 90 days. And part of it is the planning, you know, the farther out you plan, the better rates you’re going to get with hotels and other vendors, the better agenda you’ll be able to create because you’ll have more intention around it. You’ll be able to assign reading materials to your team and pre-work so that they show up to the offsite already thinking about what you want to discuss. And then, you can use the offsite for high level decision making, high level planning things like that, versus actually having to play catch up once you’re there.

Jared Kleinert: [00:22:30] But, also, there’s an element of giving your team or your clients something to look forward to. And just the anticipation of going to an offsite is valuable in it of itself. And so, in a perfect world, you’re giving yourself three to six months of runway. And by doing that, you’re saving money, you’re actually engaging your team, starting to have those back and forth conversations. Ideally, you’re creating a cadence of these offsites so that you’re building anticipation three to six months out. You have this peak transformational experience. And then, it starts to taper down, and right when it’s about to go back to normal, bam, you have another offsite that everyone’s invited to.

Jared Kleinert: [00:23:13] And, again, it goes back to inclusivity as well. You know, people are busy and so the more advanced notice you give people, especially if you’re looking at an executive team or sort of high level VPs, then the more likely you will get full attendance.

Mike Blake: [00:23:27] So, many retreats, not all – but I think many. I don’t know if it’s a majority or not, you can tell me – have an external facilitator for at least part of the retreat. What are the arguments for that? Why do companies hire external people to to kind of run the content portion of their retreats?

Jared Kleinert: [00:23:50] Yeah. So, I mean, we take the approach of not mandating external speakers or facilitators. I do personally think it’s a great idea. The benefits of outside facilitation are, (1) just being able to stay on time, (2) being able to stay on task, (3) there is an opportunity cost of having someone else on the team lead the session.

Jared Kleinert: [00:24:20] So, if it’s not an outside facilitator, then it’s probably the team leader, which could be a CEO, it could be a department head. And that person can certainly facilitate and also offer their opinions, help influence the decisions being made. But it requires a lot of skill to do that. And a lot of CEOs, a lot of department leaders, don’t necessarily have facilitative skills on par with their other decision making skills or team leadership or overall leadership skills. And so, those are some of the positives.

Jared Kleinert: [00:25:01] You know, another one would be that you don’t want any offsites to fall into a category of having negative experiences. And so, you want to have heated debates and conversations that lead to positive outcomes, but you don’t want to risk having those lead to negative outcomes. And so, a skillful facilitator can sense when the conversation is getting heated, sort of step in, reorient the room, refocus everyone. And if you’re looking at the biggest investment in these offsites, there is a financial investment that you’re making.

Jared Kleinert: [00:25:38] But I would argue the biggest investment is everyone’s time. Especially the larger the offsite, the larger the company, you’re looking at anywhere from 20 to 40 billable hours per person, if it’s like two to five days and then you multiply that times ten people or times 25, 50, 100, you’re talking about thousands of billable hours for these high tech startups that are paying premium salaries. You’re talking about hundreds of thousands of dollars of billable hours. And so, it makes sense to pay an outside facilitator a few thousand dollars a day to make sure everyone stays on track.

Jared Kleinert: [00:26:17] So, the negatives of outside facilitation could be the added cost. It could also be that you’re bringing in someone from outside of the team. And so, if you already have a team that hasn’t seen each other in two years and then you’re integrating this other person for your offsite, then that could take the energy that people should be investing in each other. And they may be sort of working with a facilitator a little more than they should with their other team members. And so, I think a skillful facilitator would know when to actually lead sessions and then when to go to their room and let the team have fun at dinner as opposed to going with the team and having dinner and enjoying nice tequila or something like that.

Mike Blake: [00:27:03] How do you choose the right facilitator? I got to imagine facilitators are differentiated. Each has a different skillset, different background, different capability set. How do you choose the right facilitator? What do you consider in making that choice?

Jared Kleinert: [00:27:25] So, many of our clients actually haven’t chosen facilitators yet, but I think it’s because we haven’t placed options in front of them. Part of this software that we’re building is a vetted marketplace of facilitators. And so, I think simply having a vetted group of facilitators and speakers versus the Wild West of the National Speakers Association or Google to go find anyone that says professional speaker or facilitator will be helpful right then and there.

Jared Kleinert: [00:28:03] Additionally, companies have different operating systems for how they run their business. So, there’s a book called Traction, and they have an EOS system that a lot of companies follow and there are facilitators specifically trained in that modality, you could say. And then, there’s other facilitators that are trained in the way that YPO runs their meetings or EO runs their meetings. So, that’s one way of looking at facilitation, is, how do you run your company and who has experience in that.

Jared Kleinert: [00:28:37] Two is a relationship oriented approach. And so, I’ve definitely heard of facilitators sticking with startups over the life cycle, especially with an executive team, where it’s more intimate because there’s already trust that’s there.

Mike Blake: [00:28:59] Right. And they’re going to build institutional knowledge too.

Jared Kleinert: [00:29:02] Correct. Third, could be to look at the specific objectives you have for your offsite and what facilitators match that. So, if you are doing something related to, like if you’re running a board meeting for a nonprofit or a Fortune 1000, are you bringing in someone with experience there?

Jared Kleinert: [00:29:25] For example, I used to work with Keith Frazee back in my teens. And before I worked with him, I got to shadow him for a few days in Los Angeles. And I got to sit in on a state board meeting for the March of Dimes, which is a nonprofit. And Keith was brought in as an outside facilitator. They brought him in because he had been an outside facilitator for a lot of Fortune 500 companies and was a C-suite executive himself previously. So, he had a lot of social proof and a lot of previous experience with similar stage and sized organizations.

Jared Kleinert: [00:30:05] So, it all comes down to a relationship and social proof. It’s the extent offsite can shorten that cycle of vetting someone, I think, we’ll be able to help our clients.

Mike Blake: [00:30:18] So, when you plan a retreat, in your mind, is there an optimal length of a retreat? Is there a minimum size or sort of a sweet spot of duration for a retreat to be effective?

Jared Kleinert: [00:30:33] It can be effective with two days, one night, if you’re mindful of your agenda. I would say the average that we’re working with is a three day, two night. And then, the longest I would recommend is a one week offsite. I’ve heard horror stories of companies bringing, like, an entire engineering team together for two weeks, keeping them away from family. But that’s only doable if you have a really young team that’s more college kids.

Mike Blake: [00:31:07] That’s bizarre.

Jared Kleinert: [00:31:07] There are some companies that have international teams that are only doing one all-hands a year, and they might stretch it to five, six days, and then have optional weekend stays that they’re willing to pay for. So, that is one strategy to have. Maybe five days of work time as your max and then have optional hangouts before or after, which would typically fall on a weekend. So, that would probably be the max I would recommend.

Mike Blake: [00:31:37] What are the most common goals that retreats are trying to accomplish? Or if you want, you could reframe this as one of the most realistic goals that a retreat can accomplish. Take your pick on how you want to answer that.

Jared Kleinert: [00:31:51] Yeah. At least right now, I mean, we’re recording this in late 2021, I imagine this will be true for early 2022 as well, is that, for a lot of the companies that we’re working with, they’re newly remote and/or they’re fast growing and they’ve doubled, tripled their headcount over the last two years during the pandemic. And so, their biggest need, they keep saying, is team building.

Jared Kleinert: [00:32:21] When they say team building, it could be as simple as making friends at work, and that will lead to actually retaining your top talent longer. Because on the days that they feel lonely or isolated, they’ll be able to reach out to a friend, maybe, in another department, or they’ll be able to make jokes and slack, and then that makes for a more fun organization.

Jared Kleinert: [00:32:46] Sometimes you have issues between departments because one group is getting more budget, or hiring more people, or the sales team is promising too much, and the customer success gets mad at them or engineering and gets mad at them, sales has a quota so they need the other teams to understand what they’re doing. So, cross department collaboration is a big hot button issue or a big place companies want to invest.

Jared Kleinert: [00:33:16] It could be that we’re just all in these Zoom screens, and even having two or three days in-person with someone gives you enough of a relationship if properly facilitated, where you can really trust the team leader, the CEO, with your career for the next six months to a year or possibly longer. And so, I would say team building is the word or phrase. But it really goes down to employee engagement, retention, also, innovation. You know, if you’re considering some of the benefits, potentially, of an office environment, it’s the water cooler talk, it’s people bumping into each other, having side conversations, going to lunch. And we lose a lot of that in Zoom. And you know, you could try and recreate it in Slack or in all the other myriads of virtual spaces that have been created.

Jared Kleinert: [00:34:11] But, now, offsites are your chance to really facilitate those environments and those conversations and, possibly, get some of those idea generating sessions or planning sessions where you can then go back home and get to work on the things that you came up with.

Mike Blake: [00:34:30] What about for post M&A integration? One of the most important reasons that, I think, mergers fail is because of the integration phase. Are retreats ever used to try to help mesh new teams from two different companies that suddenly need to work together? And if so, is that an effective way to address it?

Jared Kleinert: [00:34:51] It sounds like a great reason to use an offsite. And that’s why I’m excited about this company is because there are so many use cases for offsites and many that haven’t even been introduced to the market or haven’t been created, like a metaverse offsite. Or if you have a 1,000 person company and 20 people want to go work remotely because you can work from anywhere, and why not go work in Tulum on the beach, we can help you maybe facilitate that.

Jared Kleinert: [00:35:22] Anecdotally, my former employer, 15Five, did acquire a business during the pandemic and had to integrate about 50 employees, from my understanding. And almost all those people stayed at the company after the acquisition and many have been slotted into leadership roles. And so, I know that they’ve been desperately waiting to have an all-hands meeting to better integrate the team. And then, I believe they’ve had executive offsites to address sort of the highest level integrations. But, yeah, I mean that is a great use case for an offsite.

Mike Blake: [00:36:02] So, in your mind, has the pandemic changed or maybe even sharpened the use case for retreats? Are they more important now than maybe they had been previously?

Jared Kleinert: [00:36:14] Yeah. I wouldn’t have started this company or maybe not this soon had it not been for the pandemic. I mean, who knows? All the pieces were there with my 15Five experience, my Meeting of the Minds experience, being a facilitator occasionally for executive offsites, I already had the relationship with my cofounder. But, definitely, as the pandemic went on, I realized this would become more and more of an issue in that our way of working would never really be the same.

Jared Kleinert: [00:36:46] I was actually looking back to when our last recording was, and it was, it looks like, July 2020. And so, we were really only a few months into the pandemic. And, yeah, who knows, in an alternate universe, if we really did contain the pandemic in three to six months, maybe I wouldn’t have started Offsite. Maybe I would have started it in 2022. But because the whole playbook on work has been thrown out the window by force, we’ve all gone remote.

Jared Kleinert: [00:37:20] Now, tools like Notion to run your sort of internal documents, tools like Asana for project management, Slack for asynchronous communication, these have all become necessities, just like office space would be your in-person team necessity. And so, my hope is that Offsite becomes part of that tech stack for running a remote first company. And there’s a couple of competitors that have the same thesis, and we’ll see how we stack up.

Mike Blake: [00:37:52] Why do retreats go bad? You know, I don’t know if you’ve been on bad retreats, but I have. I’m sure you’ve heard horror stories of retreats with the best of intentions that wind up being disasters. Why do bad things happen to good people trying to do retreats?

Jared Kleinert: [00:38:09] Yeah. I think there’s only a few things you can truly control. The first is, who you bring to the offsite. So, in Meeting of the Minds, it would be curating a diverse group of high integrity entrepreneurs and individuals. If it’s a team retreat, then let’s assume you’ve already gotten high integrity individuals to work at your company. Now, it’s about making sure that they have advance notice to come to an offsite, that you’re thinking about all their travel needs. Some people might be anxious to be around others after the pandemic. Some people may have more travel sensitivities than others, or dietary preferences.

Jared Kleinert: [00:38:50] I mean, I show up to the Atlanta Airport an hour before my flight, and it’s like part of my personality to show up with as little extra time as possible.

Mike Blake: [00:38:59] You like to live dangerously, man.

Jared Kleinert: [00:39:00] Yeah. I’m 6’2″ and white, and I don’t feel a sense of danger when I travel. Typically, I travel pretty easily. But that’s not true of everyone. And so, we have to be mindful of that. We have to plan accordingly. And so, if you carry the right people, give them advance notice, and then you set up an agenda that’s intentional, that’s really all you can control. And so, high level agenda planning always start by building trust and intimacy upfront.

Jared Kleinert: [00:39:36] So, you have your travel in day, typically. Leave some flex time for if flights are delayed or there’s border issues right now. Have your first night be something that is welcoming, inviting, people can make friends quickly, get to know everyone. I would even continue building the trust and intimacy on the second day or your first full day with different icebreakers. There’s different activities. Some can be done with an outside facilitator. Some could be self- facilitated. Then, get into the business stuff, you know, day two afternoon, first full day, and that’s where you start doing your high level decision making, strategic planning, training.

Jared Kleinert: [00:40:24] And so, the way you structure your agenda is something you can control. And then, getting the basics right, like having enough breaks. If you need to do AV stuff, make sure ahead of time that your meeting space can accommodate that. Get your catering right. But there is a chance that the hotel can screw that up. There’s a chance caterers can screw that up. Airlines can screw up. COVID can make for all these wonky policies that are ever changing. So, really, you just got to get the people right and you got to get the agenda and facilitation right, in my personal opinion, and that’s all you can control.

Jared Kleinert: [00:41:06] And we’ve had clients, like Canadians coming into the U.S. and have had border issues. And so, they showed up six hours late and then they went to the this beautiful massive Airbnb, and then the power went out, and it took two or three hours to get on. But they still had an incredible time and, like, post on social media that it was the highlight of their year, because they had the right people there and they were able to do the right things with their time together.

Mike Blake: [00:41:33] When you started to answer that question, you started down a path which I thought was really interesting, so I want to push down that path a little bit, which was, you thought it was important that the participants have integrity. And I can see where that has a lot of meaning. There’s integrity in terms of how you interact with people. There’s integrity in terms of the seriousness with which you just take the exercise and you’re not getting drunk and you’re in your minibar and whatnot, and you’re you’re ready to sort of do your thing. And, you know, I think that’s really important.

Mike Blake: [00:42:14] And to that point – and correct me if I’m wrong – if that’s the case, then a lot of the ingredients that are required for a successful retreat are actually in place or not in place long before you ever even think of having one. The matter of culture, the matter even how you hire.

Jared Kleinert: [00:42:38] Correct. Yeah. And maybe we’re choosing clients that have great cultures already and that we’re just elevating those, and I’m sure there’s a case to be made for that. But you’re absolutely right, if you’re building an amazing remote-first company, you should start with how you hire, the diversity of your hiring pools, your ability to compensate those people, and your onboarding practices. And then, maybe part of onboarding is having an offsite, and that could be another use case. Or learning and development or training could also be, you know, added to offsites. But, yes, a lot of ingredients could or should be there already.

Jared Kleinert: [00:43:22] But then, if you’re planning an offsite, you don’t want to take any of these things at service level. You set the intention that we are here to work or we’re here to have fun. If you’re setting the intention to have fun, set some ground rules. Like, no sleeping with colleagues or don’t get crazy drunk, have some drinks, have a good time, but don’t do anything stupid.

Mike Blake: [00:43:47] We’d rather not have to bail you out.

Jared Kleinert: [00:43:49] Yeah. Maybe get some event insurance, and that’s something that we’re looking to help broker in the future through our marketplace, just for the what ifs. And then, you know, at the beginning of each day, remind people why you’re here and thank them for being here. You have an intention of gratitude, end each day on a high note. So that if things got testy during any given session that you remind them that we’re here for a positive reason and that we want to end on a high note. And sort of engineer ending on a high note by having awards or by having your sort of most spectacular, unique shared experience on, like, the last night. And then, everyone flies out the final day.

Jared Kleinert: [00:44:34] So, you’re right that, hopefully, you have a company already where you’ve hired great people and you just let the great people be great. But you can also go above and beyond for the specific purpose of an offsite and remind people to represent the company in the best way. If you’re going to a major city, you could set the ground rules of go see your friends, go see your family if they happen to be here. Or we’re here on company dollars for a specific purpose, so hang out with your colleagues, not with your friends. I would set the rules.

Mike Blake: [00:45:08] That actually segues nicely into my next question, which is, my experience is that most successful retreats have some mix of work and play. And the mixtures and formulas may be different, but it’s not 100 percent one or the other. And so, my question is this, is that, are you aware of any best practices that have evolved or are revolving around ensuring that the retreat doesn’t just become, basically, a boondoggle. And a boondoggle can be immensely damaging, not least of which in that it may be very hard to get budgeting for retreat number two if number one sort of declines into having to bail people out in a wet T-shirt contest, all that stuff. So, what are the best practices to ensure that the retreat stays on mission?

Jared Kleinert: [00:46:02] So, at least for us, we’re just not interested in serving any boondoggles as clients, and so that’s clearly outline on our website and our marketing materials. As we build software, essentially, you will have this onboarding click a few buttons to tell us team size, budget, objectives of your offsite. And then, based on your answers, you’ll be able to launch into a venue selection experience similar to Airbnb, a vetted marketplace of hotels, meeting spaces, places like convene that are equipped for your meetings and hybrid needs and AV needs, et cetera.

Jared Kleinert: [00:46:48] Then, we have an agenda builder we’re building, so you can start with one of our agenda templates. And at the beginning, we’re not going to even give you the opportunity to build your own agenda. Like, you have to choose one of our templates to start with, because we’ve done the hard work of thinking what is the best and optimal way to have different types of offsites. And so, based on how long you’re offsite is, based on your meeting type, maybe based on your facilitation type, if it’s EOS system versus YPO versus the Keith Frazee system – I’m kind of just making this up. But you pick a template and then you start from there, and you can customize like Squarespace or something else.

Jared Kleinert: [00:47:31] But we’re trying to do the hard work for clients that they never have a boondoggle. In the future, maybe some large company decides to have a boondoggle through offsite. But then, hopefully, at least we’re giving them quality vendors. We’re making it clear that here are the rules that your sort of team leader set for this offsite. They’ve also gotten insurance so that it doesn’t fall off the company if anyone does something stupid.

Jared Kleinert: [00:48:04] So, I’m sure if they fully run this company long enough and we become large enough that bad things will happen, just like Airbnb, there are horror stories of people staying in Airbnbs, and that’s probably going to happen if we are successful enough. But it’s definitely our goal to create the best offsites possible, and that will happen through how we create agendas, how we pre-vet and pre-negotiate with vendors through even having diverse vendors on our platform, like diverse speakers, and facilitators, and photographers, videographers. By educating team leaders on how to facilitate if they want to do it themselves. These are all the things that we’re going to be thinking about over the next decade plus so that, hopefully, the average offsite is just better.

Mike Blake: [00:48:57] We are talking with Jared Kleinert and the topic is, Should I host a company retreat? Is there an ideal time of year to have a retreat?

Jared Kleinert: [00:49:08] I would argue once a quarter is. I mean, there’s a lot of companies planning, like, January offsites to kick the year off. Certainly, a few December to celebrate the year. So, I would encourage companies to think about the lifecycle of their business and how they operate. And if you have a quarterly system of planning, then maybe you want to have your offsites mirror that, at least for your executive team or for department leaders. If you’re doing an all-hands, you may want to consider when you can have the most attendance.

Jared Kleinert: [00:49:48] I guess I don’t have a clear answer. And over time, our AI and our analytics will best determine that. I mean, we’re looking at a lot of all-hands meetings in Q2 2022. I guess probably avoiding summer, if kids are out of school is going to make some sense. And then, avoiding major holidays for an all-hands meeting. But it’s also going to come down to, like, where your team lives. And if we’re dealing with truly international teams, different places have different seasons, so if you say you want to go somewhere warm, what does that mean?

Jared Kleinert: [00:50:22] We’re going to come into all these geographical challenges as well, which I’m excited about. It’s really based on how you run your company, and what you want to celebrate, what you want to plan for. If you’re doing an offsite around integrating a new team from an M&A, then you probably want to do it right after the M&A stock. And that may happen in January or June, you know, we don’t know.

Mike Blake: [00:50:48] Should employees or should people who are going to participate in the retreat be involved in planning the retreat itself?

Jared Kleinert: [00:50:58] Yes, with a caveat. I think one route our clients are taking that we encourage is the top down approach, the team leader knows the dates, knows where they want to have the offsite because they have a certain vision for it. They know that everyone’s going to get a private room versus maybe shared accommodations to save on costs. And then, they are integrating their team in the planning process by asking, certainly, for their dietary preferences, sensitivities. And then, maybe select questions, like what would make this a great offsite for you? Or, what’s an idea you have to improve company? Or, can you give us an employer net promoter score rating now, and then after the offsite, we’ll do that again.

Jared Kleinert: [00:51:53] If team leaders don’t have strong opinions about where, when, and even some details, like should it just be team members or should it also be significant others and kids that are invited, then some of those questions we would roll into an intake form and invite the team to sort of vote on that or have a say in it. And so, yes, you should include your team with at least one pre-offsite feedback form. The specific questions you ask can lead to how much, say, they have, which could potentially influence where, when, and sort of how the offsite will happen. Or it could just simply be we’re going to get your travel needs right, we’re going to get your diet right. And then, maybe be inspired by something that someone says.

Mike Blake: [00:52:48] Jared, I know we’ve got a little bit of a hard stop with you, so I want to be respectful of your time. I know we didn’t get to all the questions that I had prepared, and there probably ones that our audience would have wished we would have covered or maybe ones we might have covered in more depth. If somebody wants to contact you to ask for advice or more information on whether or not to host a retreat, can they do so? And if so, what’s the best way to contact you?

Jared Kleinert: [00:53:17] Sure. You can go to joinoffsite.com. And then, jared@joinffsite.com is my email related to this business.

Mike Blake: [00:53:29] Well, that’s going to wrap it up for today’s program. I’d like to thank Jared Kleinert so much for sharing his expertise with us.

Mike Blake: [00:53:36] We’ll be exploring a new topic each week, so please tune in so that when you’re faced with your next business decision, you have clear vision when making it. If you enjoy these podcasts, please consider leaving a review with your favorite podcast aggregator. It helps people find us that we can help them. If you’d like to engage with me on social media with my Chart of the Day and other content, I’m on LinkedIn as myself and @unblakeable on Facebook, Twitter, Clubhouse, and Instagram. Also check out my new LinkedIn Group called A Group That Doesn’t Suck. Once again, this is Mike Blake. And our sponsor is Brady Ware and Company. And this has been the Decision Vision podcast.