Meeting in Person with Jared Kleinert

Jared Kleinert is the CEO and Co-Founder of Offsite. He is also the founder of Meeting of the Minds, as well as a TED speaker, 3x award-winning author, and USA Today’s “Most Connected Millennial”.

With the pandemic, we could consider that companies that wanted to reduce travel and expenses received absolute proof that everything could be done remotely. But will the new world of work really spare the commute time and costly office? And if it happens, will we ever need to meet in person?

Jared Kleinert is the CEO and Co-Founder of Offsite. He is also the founder of Meeting of the Minds, as well as a TED speaker, 3x award-winning author, and USA Today’s “Most Connected Millennial”.

In the episode, you will learn:

  • the importance of meeting in-person in the future of work,
  • what needs to happen before, during and after an offsite,
  • the criticality of facilitation,
  • how to build and deepen relationships,
  • hiring advices from a serial entrepreuneur!

Listen to the episode here:

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Here is the transcript of the episode

Alexis

Hey Jared! What is your role and how would you describe it to someone you just met?

Jared

My role I’m the co-founder and CEO of Offsite. Offsite provides end-to-end retreat planning services and software for remote and hybrid companies. As the CEO, I wear many hats. So some days I’m selling some days I’m fundraising other days I’m managing the team. At a high-growth company that means recruiting, it means keeping everyone engaged and happy, it means getting everyone aligned on the company’s direction. It’s an all-encompassing job and every day is pretty unique.

Alexis

Excellent, What was the pivotal moment that led you to start Offsite.

Jared

I’ve been a remote worker my entire career. I’m 26 at the time of recording. I was fortunate to start my entrepreneurial journey at a young age at 15 and not that anything that I started in my teens really got anywhere but I was able to work for a VC-backed startup in Silicon Valley from 16 to 18. That company was called 15Five. Today they’re over 300 employees. They are an employee engagement and culture management software product that powers 40000 different teams around the world with employee engagement and retention and I got to be there when they were less than 10 people working directly under the 2 cofounders and so. That was a really exciting experience because I was working remotely from South Florida in the United States where I grew up and I was working for this Silicon Valley startup the only way I got to meet the co-founders and the rest of the team was by going to these team retreats or off-sites and so just the experience of being at a high-growth company in its early days being able to attend these offsites as an employee and understand the impact that had on the rest of my day-to-day work when I wasn’t seeing my colleagues, participating in zoom meetings weekly when we weren’t meeting quarterly for these offsites. Yeah, that was just overall a very formative experience.

Jared

So after I left 15five I took like a 7-year speaker author consultant turn where I was started a few small businesses: a marketing consulting business, an event business where I was hosting entrepreneurs once a quarter for these similar types of offsites but they were more of a mastermind with entrepreneurs getting together and helping each other grow their businesses. I wrote a couple of books. I was a TEDx speaker and did some corporate speaking so all these ideas sort of came together. What is seemingly like a very disparate and chaotic like career path has all sort of come together for building a company like Offsite.

Alexis

It’s really interesting that you already speaking about the kind of chaotic career path and you are only 26. It’s a little bit funny that you already have more than 10 years of experience. It’s quite impressive. I have a question about that new world of work. We heard a lot of time that with the pandemic companies that wanted to reduce travel and expenses received absolute proof that everything could be done remotely. I wonder if the new world of work would already spare the commute and costly offices and if it happens will we ever need to already meet in person.

Jared

And yeah I mean I think the future of work is different for everybody and so I would guess or bet that the vast majority of people want to work remotely or in some sort of hybrid setting where they don’t have to commute. They can spend more time with family they can travel and bring their laptop and work wherever they want when they’re traveling be able to go to doctor’s appointments or work out in the middle of the day if they want to, really optimize their schedules. But there will be some people that enjoy an office environment and don’t get me wrong I love meeting my team members in person here and there I’m more than willing to get on a plane and meet potential investors or clients I love going to conferences and events. And so I think how we work will be different for everyone but at a company level, I don’t think we will have a lot of companies that choose to have an only in-person company experience if they can avoid it there are a lot of benefits to having a remote-first or hybrid company and so that’s sort of where we’re going.

Jared

At the same time as you mentioned there is a huge benefit to getting people together in person but doing so very intentionally. Again I’m biased. But that’s where the idea of an offsite comes into play and having a cadence of these in-person experiences where you’re able to bring people together. Maybe once per quarter or as in the entire company together once or twice a year have. Two or three days of programming where you are deepening relationships with your team. Maybe you’re doing some skill-building. Maybe you’re doing strategic planning for the quarter ahead or the year ahead. But you’re also having fun and you’re having just a unique shared experience. Unique shared experiences that build relationships and so I think that’s the wave of the future. It’s something that if you look to the past the top remote or hybrid companies have been doing for a decade like 15Five or the company that owns WordPress which is called Automattic or Buffer, Zapier, Basecamp, or Gitlab. They’ve all been doing this for the last decade.

Jared

What we’re trying to do is just create software to make the offsite planning process easier because there has never been software to solve this really painful and expensive problem for whoever’s planning the offsite which is typically a chief of staff such as yourself. It’s someone who’s a people leader at a company a department leader. Maybe even a CEO of smaller company. They shouldn’t be spending their time planning an off-site but at the same time, It’s very important to plan offsites regularly if you’re remote or hybrid. So I think that’s part of the future of remote work and it may change. It may be in 20 years we’re all taking meetings in the metaverse. I have no idea but I do think it will be unique for everyone.

Alexis

I hope not to be honest! You mentioned the gathering and the idea of scheduling them in advance and add think a cadence of them I Really like that. What needs to happen before the gathering to really ensure success and what are the successful patterns and maybe the common mistakes people are making.

Jared

Yeah, so planning a successful offsite happens in advance as you were saying and so considering your team size if you’re planning an executive team meeting of 10 people, you could probably start planning that two or three months out of time. If you’re planning for 10 to 100 people just to simplify the conversation, you might want 3 to six months. If you’re planning anything over 100 people like an all-hands meeting, you may want six to nine months to plan that ahead of time or you might even take an entire year to plan that. In the planning process, you want to facilitate a couple of pre-off-site feedback forms that will include getting the basics from employees of travel information, dietary preferences, any blackout dates, maybe someone has an important life event that they can’t get out of or if there’s a certain executive that you need to have at your meeting, you have to make sure that they’re available before you’re starting to book an offsite these are some of the basics you need to get. Before you start planning but you also can use the opportunity to start having a conversation with your team about what would make this an amazing offsite for them or what are they hoping to cover on the agenda at the offsite. You might ask a question like an employer net promoter score or an E-NPS Score to be able to track the engagement of someone at your company both before and then maybe even after your offsite and see if that grows over time. Hopefully, it’s trending in the upward direction. And these are the conversations you want to have well before the off-site occurs from a logistics standpoint you also want to think about where you’re having the off-site and ideally book your venue well in advance if you plan ahead of time then you can have a lot of negotiating power with a hotel or a meeting space, be able to choose the best option for you logistically, but also negotiate your room block and negotiate discounts or concessions on meeting space on food and beverage make sure that there are no hidden fees, that the taxes are clear. So these are all the things that you want to start thinking about well ahead of schedule you want to put it on people’s calendars so that they can plan to travel you want to encourage them to book their flights ahead of time to save money or possibly even book those flights for them.

Jared

And then you free yourself up to focus on the agenda and make sure that you’re scheduling an offsite that really maximizes your time together and so if you’re planning ahead of time then you can develop an agenda with your team’s input that really accomplishes your business objectives for having the offsite while also allowing plenty of flex time for breaks and for team building for fun activities. You could even then share parts of that agenda with your team to encourage them to do pre-work or sort of preparation ahead of the offsite so that when you’re having certain debates or making certain decisions or doing certain training at the offsite, people have already thought in advance about what you’re discussing and they’re not just hearing about it for the first time when you’re together. So  I could go on for another 30 minutes but these are all the things you can consider if you’re planning ahead of time.

Jared

The challenge is that a lot of people aren’t used to planning offsites. They may not have the expertise to plan an amazing offsite you might be an amazing department leader like a sales leader or you might be an amazing executive assistant but you might not be a world-class offsite planner. It’s a totally different animal and so you may not have the expertise to plan this. You may not know how to best negotiate with hotels and other vendors. You may not know all the nuanced details that you need to consider like the number of outlets in your meeting space or the wi-fi speed. At your meeting space or dietary considerations from your team any travel sensitivities from maybe minority groups and making sure you’re going somewhere that everyone is going to feel included in safe there’s a lot of details that go into planning these offsites and so. The earlier you plan the more time you afford yourself to work through some of these challenges the better prepared you can make your team and likely you’ll save money as well compared to planning at the last minute not having as many of your team members showing up and then not. Using the time together most effectively.

Alexis

Yeah, that’s true that covers a lot of different skills. It’s not only the event Planning. It’s the content of it and getting the input from the team and building something that will make the time together already Meaningful. So There are a lot of different aspects. When I think of facilitating successful collaborations I already picture the facilitation that happens during the gathering as a really important aspect. Do you feel the facilitator or the facilitation of the event is something important?

Jared

Absolutely, I’ve been hired to facilitate executive offsites at the fortune 1000 level before I started Offsite. That’s another experience that leads me to want to start a company like this and grow it. It depends on what type of offsite you have and the team dynamics. But for most teams and for most companies bringing in an outside facilitator who is skilled in that ability will allow you to stay on schedule will allow you to have important conversations. With empathy and with a healthy debate encouraged with participation courage from everyone present and so yeah, we definitely believe in the power facilitation part of what we’re building at offsite is a marketplace of hotel partners that we have and part of the marketplace is not just hotel partners that you can have your offsite app but also various facilitators that you can hire that we’ve already screened for you that we’ve prenegotiated rates with so that you can trust who you’re hiring know what their fees are going to be ahead of time and then simply book them and invite them to your offsite and so we’re definitely encouraging more teams to consider facilitators.

Jared

We also have an agenda builder feature that we’re creating. In that agenda builder feature, you can think of it as sort of a template series of templates for your meetings, and once you start with one of our templates, there will be notes for whoever’s planning the offsite on how to facilitate those sessions themselves. So even if you don’t hire a facilitator you already have the programming notes and the shorthand notes on how to actually facilitate a session by yourself because to your point, facilitation is very important and so if you’re not going to allocate a budget for hiring a facilitator. We want to make sure you still have a great experience and that is a wholly unique skill set and so with a little bit of coaching and notes where we’re making sure that companies are having better offsites than they would have without us.

Alexis

And I imagine that in the agenda builder if you hire an external facilitator, the external facilitator will have also the opportunity to enter the agenda builder and to help you use the default Modules in the best way. We covered before the offsite, during the offsite and there’s after the offsite, after the gathering. Could you tell us what needs to happen after.

Jared

After the offsite I think is a missed opportunity that a lot of companies have is not doing a post offsite feedback form. You want to make sure within the week of your offsite you’re sending feedback form to your team asking them for feedback on certain sessions to share ideas that they gathered from the offsite that could have a positive impact on their role, their team, their company. You certainly want to ask them how they are feeling about their colleagues, and whatever questions you prompted them with beforehand such as an Employee Promoter Score or a one out of 10 about how connected they feel to their colleagues. You want to ask that same question after the offsite and see if the gathering made a difference or not. And then you want to ask them when they want to do it again and where they where they want to have their next offsite and so I think establishing a cadence of these offsites is important so that you constantly have something to look forward to as an employee working at home or working at a coffee shop. Maybe you’re lonely one day and instead of starting to look for other jobs or sort of losing productivity having another offsite to look forward to makes a big difference on the day-to-day front.

Jared

Another thing that companies sort of drop the ball on is actually leveraging any of the ideas or next steps that can come from an offsite and so if you’re doing strategic planning during your offsite. How are you translating the ideas that come from your offsite to your project management tool like Asana or to your Notion, wiki, or whatever you’re using to run your company. How are you taking the ideas and the decisions that you make during the offsite and translating that into your day-to-day work and so you want to think about. How you’re going to leverage the offsite and continue benefiting from it afterward and you want to continue the conversation by doing a post offsite feedback form asking for how the offsite went how it could be better next time and then starting to plan your next offsite immediately afterward.

Alexis

You have been named by USA today, the most connected millennial, and of course, I’ve watched your TED talk. That’s really impressive. Can you tell us why you believe it is important to build relationships?

Jared

I think the quality of your life is a direct result of the people you meet and how much you learn from them and so that all translates to networking and relationship building being mindful about who you spend time with how you go about. Strengthening those relationships, staying in touch with people, and until we are all in the metaverse and until we’re all sort of part cyborgs I think the human connection we have with each other is is one of if not the most important things that determines our life.

Jared

I believe there are even scientific studies that talk about longevity and one of the sorts of top predictors of longevity is the amount of friendships you have. It’s not necessarily whether or not you smoke or how much you drink or how much you exercise, but it’s about the quality of your relationships and, so it has an overall impact on your health, your wealth, your career trajectory and so I’ve just spent a lot of time thinking about how to build relationships, how to how to deepen those relationships and how to ultimately, do meaningful things with that access whether it’s writing books that inspire others or get the opportunity to do keynote speeches or Ted talks that others will view or create companies or communities. I’ve just sort of leaned into the whole networking relationship-building thing. Ah, it’s probably the only thing I’m good at. I am not good at anything else. I’m not a technical founder of a startup. I’m decent at marketing. But I wouldn’t say I’m a world-class marketer but I am world-class at ah, yeah, building relationships and bringing diverse perspectives together to hopefully accomplish bigger things for society.

Alexis

So we will benefit from your world-class skills there. What would be the critical advice to someone who wants to develop their network to build those relationships?

Jared

I actually have a book that is about to come out called Networking. I break the book into 3 parts. The first part is connecting with yourself. The second part is connecting with others and the third part is connecting with others at scale. The best place to start is connecting with yourself and that means a few things first it means understanding where you want to go in your career, in life and so there are various exercises in the book like a vivid vision exercise where you write down like in journaling where you want to be in 3 years and in all aspects of your life, romantically with money with your career where you live etc and start to chart an intentional path for your life 3 years out you also want to think about a relationship action plan. What types of people do you want to meet in order to accomplish some of your goals on that vivid vision exercise and then you want to think about what you can do to provide value to those types of people. So what actions can you take to deepen relationships whether it’s sending a birthday card or calling someone on their birthday or sending someone a congratulatory text message after you see a career update or making a valuable introduction for someone to a new client or investor or employer. These are all specific actions. You could take to deepen the relationships. You also want to think about, just what’s going to make you stand out whether it’s credentials whether it’s, unique personality traits or experiences or views of the world, different communities. You can introduce other people. Thinking about where you want to go, who you want to meet, and ultimately how you’re going to build and deepen relationships with them. That’s all the work that needs to be done before you go and connect with others. So that’s the connecting with yourself category.

Jared

Connecting with others. That part of the book talks about how to send cold emails effectively how to ask for and receive warm introductions and just all the different tactics you can use to go about building your network. If you don’t do the connecting with yourself work. It’s going to be much harder to build relationships when you start going out into the world and connecting with people and you’re going to have a challenging time, actually keeping those relationships going. Yeah because there’s there’s no sort of goal in mind for deepening those relationships or no purpose

Jared

So then it’s connecting with others at scale and we’re talking about yeah things like podcasting where you can offer value to your network in a one-to-many fashion or having an-mail Newsletter. We’re starting a community whether it’s in-person or online. There’s all these sorts of more advanced tactics where now that you have a really big network. How do you continue staying top of mind? How do you continue providing value? How do you leverage that network whenever you need support. There’s a  lot to it and I’ll probably keep updating the book once or twice a year because I’m sure some of the tactics around networking will change especially with new social media channels or new ways of working. But at the end of the day. It’s sort of connecting with yourself and then going out and connecting with others in a very intentional way where you’re looking to provide value upfront and then sort of leverage the relationships respectfully and intentionally as you develop though.

Alexis

Yeah, and it’s very interesting because of the way you frame it. Some people think of networking or building a relationship as a way to get from others and the way you are framing it is thinking about what you can give. And I Really like that because then when you are clear about where you want to go and what you can offer to the world then you can connect with people. So that’s a fair summary of what you said?

Jared

Yeah, great job.

Alexis

Do you believe that it has to happen in person?

Jared

No. I definitely think the in-person connections allow you to deepen a relationship maybe more quickly than doing it online but I have plenty of yeah, online friends or virtual friends that I’ve never met in person. Or I’ve been able to, build relationships with over, 8 years and maybe finally just met them in person a few weeks ago for the very first time. But yeah, this can all happen online I do recommend trying to use Zoom or use some sort of video platform as much as possible because the sort of best type of connection is going to be in person in my opinion then it’s going to be a video chat then it’s going to be audio like a phone call. And then it’s going to be your email or sort of social media exchanges and text messages are probably last yeah text is not great. But it’s really about the quality of interaction and being willing to just  explore deeper facets of that conversation with someone. This is we’re like we’re not talking about the weather here or we’re not talking about sports we’re talking about things that we’re passionate about and we’re going to resonate with each other because of that and yeah, that’s going to carry our relationship for yeah months even if we didn’t speak again for another three months for some reason we’ll look back at this conversation say wow that was a really interesting conversation and I learned a lot. Those are the type of interactions that I try to have with people where I’m not wasting time with them. But rather we’re having these deep and meaningful interactions and that allows us to develop a very rich relationship over time.

Alexis

Really important. You worked with a lot of leaders and among those you admire? What’s the 1 treat that stands out to you?

Jared

And well the one trait that stands out of yeah I guess an entrepreneurial passion or like a mindset of entrepreneurship. There’s a lot of problems in the world. And many of those problems are growing exponentially and I think the only way we solve a lot of those problems is to get more people to act on their passions in life and be entrepreneurial and then unite in solving those big pressing problems and so I wrote a couple of books where I was profiling top-performing millennials from business owners, to olympians, to actors, to nonprofit founders. I’ve been fortunate to consult New York Times bestselling authors and small business owners that have built successful companies. And whether they’re business owners or they’re they work in corporate or they’re athletes like they all have a sense of entrepreneurship about their careers and lives or even in solving problems. Like a nonprofit founder where they’re not sitting back and asking if someone else is going to solve a problem but they’re actively taking steps to better their own lives, better their careers, solve problems that they’re passionate about and so I think that’s really important and it probably extends even to my hiring practices like I overwhelmingly have tried to hire entrepreneurs at my company or people that have a side hustle or some sort of entrepreneurial spirit about them because I don’t want them to sit around and wait for directions on how to solve a problem. I want them to just go and solve the problem. And I think we need more of that because there is no rulebook anymore. The world is so chaotic that there are no safe institutions anymore we have to figure out how to solve these problems or we’re doomed. I would use another word but I don’t know if we’re allowed to use it.

Alexis

Yeah, let’s keep that for the imagination of people. Jared, you are the CEO and Co-Founder of Offsite. He is also the founder of Meeting of the Minds, as well as a TED speaker, you are an award-winning author, and as I mentioned before the “Most Connected Millennial” according to USA Today. 

Thank you for having joined me today.

Jared

Yeah, thanks for having me appreciate it.

Photo by Quang Nguyen Vinh from Pexels

Author

  • Alexis Monville worked in multicultural and distributed environments for years, coming back from the US and now based in the southwest of France. When asked if he misses the work in the office, he usually answers that he spent half of his 30 years of management experience in diverse sectors outside of the office and a lot of that working from home. Alexis is Chief of Staff to the CTO at Red Hat, a long-time hybrid open-source software company with more than 100 office locations in 40 countries, where half of the 20,000 people work remotely. Alexis is a firm believer that change starts with the self. He is the author of two books: Changing Your Team From The Inside and I am a Software Engineer and I am in Charge. Alexis facilitates successful playful collaborations. He designs and builds sustainable and high-impact teams and organizations.

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