Meeting in Person with Jared Kleinert

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. 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, keeping everyone engaged and happy, 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. Not that anything 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're an employee engagement and culture management software product that powers 40,000 different teams around the world. I got to be there when they were less than 10 people working directly under the two co-founders. 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 offsites. The experience of being at a high-growth company in its early days, attending these offsites as an employee and understanding 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 — that was overall a very formative experience.

After I left 15Five I took like a seven-year speaker/author/consultant turn. I started a few small businesses: a marketing consulting business, an event business where I was hosting entrepreneurs once a quarter for similar types of offsites — but more of a mastermind where entrepreneurs got together and helped 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 a very disparate and chaotic career path has all sort of come together for building a company like Offsite.

Alexis:

It's really interesting that you're 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. Quite impressive. I have a question about that new world of work. We heard a lot of times 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 will spare the commute and costly offices — and if it happens, will we ever need to meet in person?

Jared:

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, 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. So 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.

At the same time, as you mentioned, there is a huge benefit to getting people together in person — but doing so very intentionally. 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 the entire company together once or twice a year, with 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 just having a unique shared experience. Unique shared experiences that build relationships. That's the wave of the future. If you look to the past, the top remote or hybrid companies have been doing this for a decade — like 15Five, or the company that owns WordPress which is called Automattic, or Buffer, Zapier, Basecamp, or GitLab.

What we're trying to do is 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 — typically a chief of staff, a people leader, a department leader, maybe even a CEO of a smaller company. They shouldn't be spending their time planning an offsite, 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. 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 a cadence. What needs to happen before the gathering to really ensure success, and what are the successful patterns and the common mistakes people make?

Jared:

Planning a successful offsite happens in advance, considering your team size. If you're planning an executive team meeting of 10 people, you could probably start planning two or three months out. If you're planning for 10 to 100 people, just to simplify, you might want three to six months. If you're planning anything over 100 people like an all-hands meeting, you may want six to nine months — or even take an entire year to plan that.

In the planning process, you want to facilitate a couple of pre-offsite feedback forms. Get the basics from employees: travel information, dietary preferences, any blackout dates — maybe someone has an important life event they can't get out of, or there's a certain executive you need to have at your meeting and you have to make sure they're available before you start booking. You can also use the opportunity to start having a conversation with your team about what would make this an amazing offsite, or what they're hoping to cover on the agenda. You might ask an employer Net Promoter Score (eNPS) to track engagement both before and after your offsite to see if it grows over time.

From a logistics standpoint, you also want to think about where you're having the offsite, and ideally book your venue well in advance. If you plan ahead of time you have a lot of negotiating power with a hotel or meeting space — choose the best option logistically, negotiate your room block and discounts on meeting space, food and beverage, make sure there are no hidden fees, that the taxes are clear. Put it on people's calendars so they can plan to travel, encourage them to book flights ahead of time to save money, or possibly book those flights for them.

Then you free yourself up to focus on the agenda and make sure you're scheduling an offsite that maximizes your time together. Develop an agenda with your team's input that accomplishes your business objectives while allowing plenty of flex time for breaks, team building, and fun. You can share parts of the agenda with your team to encourage pre-work, so when you're having certain debates or making certain decisions, people have already thought in advance about what you're discussing.

The challenge is that a lot of people aren't used to planning offsites. You might be an amazing department leader or executive assistant, but you might not be a world-class offsite planner. It's a totally different animal. You may not know how to negotiate with hotels and other vendors. You may not know nuanced details like the number of outlets in your meeting space, the Wi-Fi speed, dietary considerations, travel sensitivities from minority groups, making sure you're going somewhere everyone is going to feel included and safe. There's a lot of details, and the earlier you plan, the more time you afford yourself to work through these challenges, and likely you'll save money compared to planning at the last minute.

Alexis:

That's true — it covers a lot of different skills. It's not only the event planning, it's the content of it and getting input from the team and building something that will make the time together meaningful. When I think of facilitating successful collaborations, I picture facilitation that happens during the gathering as a really important aspect. Do you feel facilitation is 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 led me to want to start a company like this. It depends on the type of offsite and the team dynamics, but for most teams and most companies, bringing in an outside facilitator who is skilled in that ability will allow you to stay on schedule, have important conversations with empathy and healthy debate, and encourage participation from everyone present. We definitely believe in the power of facilitation. Part of what we're building at Offsite is a marketplace of hotel partners — and not just hotels but various facilitators that we've already screened for you, with pre-negotiated rates so you can trust who you're hiring, know what their fees are going to be ahead of time, and simply book them and invite them to your offsite.

We also have an agenda builder feature. You can think of it as a 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. Even if you don't hire a facilitator, you have programming notes and shorthand notes on how to facilitate a session by yourself — because facilitation is very important. If you're not going to allocate a budget for hiring a facilitator, we want to make sure you still have a great experience.

Alexis:

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

Jared:

After the offsite is a missed opportunity that a lot of companies have — not doing a post-offsite feedback form. You want to make sure within the week of your offsite you're sending a feedback form to your team, asking them for feedback on certain sessions, to share ideas they gathered from the offsite that could have a positive impact on their role, their team, their company. You certainly want to ask how they're feeling about their colleagues, and whatever questions you prompted them with beforehand — such as eNPS or a 1 to 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. Then you want to ask when they want to do it again and where they want to have their next offsite. 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 at a coffee shop. Maybe you're lonely one day, and instead of starting to look for other jobs or losing productivity, having another offsite to look forward to makes a big difference day-to-day.

Another thing that companies drop the ball on is actually leveraging any of the ideas or next steps that come from an offsite. If you're doing strategic planning during your offsite, how are you translating the ideas into your project management tool like Asana, or Notion, or whatever wiki you're using to run your company? How are you taking the ideas and decisions you make during the offsite and translating that into your day-to-day work? You want to think about how you're going to leverage the offsite and continue benefiting from it afterward — and continue the conversation by doing a post-offsite feedback form, asking how it went and how it could be better next time, and then start planning 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. 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. 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 one of, if not the most important thing that determines our life.

There are even scientific studies that talk about longevity, and one of the 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 — it's about the quality of your relationships. So it has an overall impact on your health, your wealth, your career trajectory. I've spent a lot of time thinking about how to build relationships, how to deepen them, and how to ultimately do meaningful things with that access — whether it's writing books that inspire others, getting the opportunity to do keynote speeches or TED talks, or creating companies or communities. I've leaned into the whole networking/relationship-building thing. It's probably the only thing I'm good at. 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 building relationships and bringing diverse perspectives together to hopefully accomplish bigger things for society.

Alexis:

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 three parts. The first part is connecting with yourself. The second is connecting with others. The third is connecting with others at scale.

The best place to start is connecting with yourself, and that means a few things. First, understanding where you want to go in your career and in life. 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 three years across all aspects of your life: romantically, with money, with your career, where you live, etc. Start to chart an intentional path for your life three 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? Then think about what you can do to provide value to those types of people. What actions can you take to deepen relationships — whether it's sending a birthday card, calling someone on their birthday, sending someone a congratulatory text after a career update, or making a valuable introduction to a new client, investor, or employer. Also think about what's going to make you stand out — credentials, unique personality traits or experiences, views of the world, communities you can introduce others to.

Connecting with others — that part of the book talks about how to send cold emails effectively, how to ask for and receive warm introductions, all the different tactics to build your network. If you don't do the connecting-with-yourself work, it's going to be much harder to build relationships when you go out into the world.

Then connecting with others at scale — things like podcasting, where you can offer value to your network in a one-to-many fashion, having an email newsletter, starting a community whether in-person or online. There's a lot to it, and I'll probably keep updating the book once or twice a year because some tactics will change with new social media channels or new ways of working. But at the end of the day, it's about 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 leverage the relationships respectfully and intentionally as you develop them.

Alexis:

It's very interesting because of the way you frame it. Some people think of networking or building relationships as a way to get from others, and the way you are framing it is thinking about what you can give. I really like that, because then when you are clear about where you want to go and what you can offer to the world, you can connect with people. Is that 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 in-person connections allow you to deepen a relationship maybe more quickly than doing it online, but I have plenty of online or virtual friends that I've never met in person — or I've been able to build relationships with over eight years and maybe finally just met them in person a few weeks ago for the very first time. This can all happen online. I do recommend trying to use Zoom or some sort of video platform as much as possible. The best type of connection is going to be in person, in my opinion, then video chat, then audio like a phone call, then email or social media exchanges, and text messages are probably last. Text is not great. But it's really about the quality of interaction and being willing to explore deeper facets of the conversation. We're not talking about the weather here, we're not talking about sports — we're talking about things we're passionate about and we're going to resonate with each other because of that. That's going to carry our relationship for months. Even if we didn't speak again for another three months for some reason, we'll look back at this conversation and say, wow, that was a really interesting conversation and I learned a lot. Those are the type of interactions I try to have with people, where I'm not wasting time but rather we're having 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 one trait that stands out to you?

Jared:

The one trait that stands out is an entrepreneurial passion or a mindset of entrepreneurship. There are a lot of problems in the world, and many of those problems are growing exponentially. 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 unite in solving those big pressing problems. 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. Whether they're business owners or work in corporate or are athletes, 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 — they're actively taking steps to better their own lives, their careers, and solve problems they're passionate about. It probably extends even to my hiring practices. I overwhelmingly try to hire entrepreneurs at my company, or people that have a side hustle or some sort of entrepreneurial spirit, 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. 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.

Alexis:

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, 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.