Relationship-Building in a Remote-First World with Jared Kleinert

Jared Kleinert is a serial entrepreneur who's made a living by helping people build work relationships.

USA Today named him the "Most Connected Millennial," He wrote award-winning relationship-building books like How To Build A World-Class Network In Record Time.

He's also a TED speaker, facilitator for Fortune 1000 executive offsites, and formerly one of the first ten employees at 15Five, both a performance management software and a successful remote startup. That's where Jared learned first-hand how transformational relationship-building retreats could be for remote teams, lending him some inspiration behind his new company: Offsite.

So, Jared, what is the vision behind Offsite?

With the pandemic, the future of work has been advanced by at least five years in terms of remote work acceptance. My co-founder, Keir Weimer, and I started Offsite last year to help companies that already plan regular All-Hands retreats and department-specific offsites, as well as teams now considering their very first team retreats. We offer end-to-end retreat planning to keep all the stress out of planning an offsite because we know how important it is to build great company culture.

At Offsite, we customize experiences based on where a company wants to travel, how many people they're traveling with, and the goals for the retreat. Some companies are focused on team-building, others are focused on OKRs or strategic planning for the upcoming quarter, and occasionally we help companies plan client-facing events. Ultimately, we're focused on assisting co-founders to and CEOs connect their teams more intentionally during the few days of the year when they can get together in person as a remote-first company.

Tell us more about the trends you've observed when leading with intent and relationship-building.

A lot of the companies we serve are seed-stage and Series A companies. They've doubled their headcount in the last two years, and many of their employees haven't met each other, so they are working with Offsite to support their team-building efforts.

"Building camaraderie in these cases allows for better collaboration and communication between departments."

— Jared Kleinert

Strategic planning is another bucket several Chiefs of Staff, and Heads of People are considering. Many companies set a cadence where they have an annual All-Hands meeting, then quarterly departmental offsites. They're often focused on their OKRs, a specific project like a design sprint, or workshopping a particular product. 

Some companies might also be trying to reduce employee churn. People are entering and leaving your company, so you might want to have a tremendous offsite experience to build the team and give them a reason not to go.

Why is relationship-building so important right now?

We see shared experiences as being a catalyst for better day-to-day communication. If you're a remote or hybrid company, there's a good chance you haven't met a few of your colleagues. We have Zoom and Slack, but building deep and meaningful relationships without in-person interactions is challenging.

There's also the fact that with COVID-19, we're all more at risk now of being lonely at home and disengaged at work. You'll become more engaged with your team, job, and company by having something to look forward to, like an offsite.

These retreats end up being peak experiences that you can look back at for months until your next expertise comes up, and then you have something else to look forward to and remember together. For an employer, it allows you to keep people at your company for longer, connect with your employees, and ensure everyone is aligned with your mission.

What are the mistakes you see many remote-first leaders make?

Team leaders planning an offsite aren't necessarily aware of why they're planning an offsite. They think they have an idea of what they want to accomplish, but then they get so wrapped up in the details of the hotel, the travel logistics, the food, and where they're going to eat — they forget the agenda. They fail to prepare their team ahead of time to generate the greatest ROI and maximize the special time they'll spend together as a team.

Craft your agenda with intention — if you add up the time everyone spends together, you understand the financial investment of planning a retreat. For instance, if you have a team of 25 people and take 20 hours per person, that'd be two and a half days of meeting time. Even excluding travel time, that's 500 billable employee hours that you're investing in!

But leaving the agenda creation to the last minute is something many companies do, unfortunately. At Offsite, our value proposition is bringing the event planning process down from 50 hours to 5 hours or less for the Chief of Staff, Co-Founder, Executive Assistant, Head of People, or whoever is tasked with the event planning. Additionally, we uplevel a company by building a detailed and customizable agenda with them based on their objectives for having a team retreat in the first place.

Why is leading with intent hard when it comes to planning team retreats?

It's a unique skill. When you're the co-founder of a tech startup, you bring certain product knowledge, technical expertise, or marketing experience to the table. Still, you don't typically have experience running a team retreat. Most startup CEOs struggle with running a team meeting every week on Zoom, let alone being masterful with an offsite!

This is the human side of work. It's a different skill set — a mixture of curation and facilitation. First, you're curating who should be at the meeting and why. Then, facilitation is about engaging all of these people, which must be done a certain way. You have to consider different needs for travel, breaks, comfortable environments, icebreakers, and warm-up activities. Even something as simple as ordering healthy food so people can maintain their energy levels typically goes overlooked.

There's so much that goes into that. Personally, what would you say is your philosophy behind relationship-building?

I've previously constructed a lot of thought leadership about relationship-building — I've been named USA Today's "Most Connected Millennial," and I'm about to publish a book on networking and relationship-building. A lot of that thinking is incorporated into how we organize Offsite and help clients build stronger internal connections.

Personally, the first part of relationship-building is establishing trust and intimacy as soon as possible. You would typically call that team-building, but even groups that have worked together continuously need to re-establish trust and deepen that intimacy. At Offsite, we facilitate that with our clients in many different ways. One of the quickest ways to do it is through unique shared experiences, which goes for any of the activities you might select during a retreat.

Unique shared experiences don't have to be expensive. They could be free, but they should center around giving your team something to do that is different from their day-to-day lives or a shared experience they can look back to when they're trying to solve a problem three months from now or when they're debating over an issue and trying to work through that.

Later, when thinking about leaving the company, they might even think of how fond they are of their colleagues and environment and try to communicate with their employer instead. Unique shared experiences are crucial to establishing the trust and intimacy every company needs.