15five company retreat

Best-Self Management Podcast, Episode 2: Life-Changing Company Retreats

By Shane Metcalf

Corporate offsite. Even typing the words makes me cringe. They’ve gained a reputation for being dry, forced, and inauthentic. A company retreat is not about transferring corporate bureaucracy to a different setting for a few days. Retreats are about transformation…

Welcome back to the Best Self Management Podcast blog series! In episode one, we unpacked the journey that brought us to 15Five, and shared how we’ve created a highly engaged organizational culture and leadership team that empowers employees to be their best selves. 

In episode two, we take a deep-dive into the importance of company retreats. 15Five has facilitated deeply connecting and transformational experiences for our workforce since the very start of the company, even when there was only a handful of us. (Four to be exact.)

Now at 135+ employees, we are even more committed to creating annual company retreats, each one more life-changing than the last. These retreats are purpose driven events designed to bring every employee together, re-align them around our company mission, and to allow for vulnerable connection in a beautiful natural setting away from office walls.

In this episode, we also discuss:

• The ROI that comes with a retreat that can’t easily be quantified
• Presenting the retreat to your employees so they understand its real purpose—to accelerate business growth
• The detailed structuring of a company-wide retreat including where to do them and what to focus on day-by-day
• Candid and inspiring reflections that our employees have had about our retreats
• What happens when the retreat doesn’t go as planned
• Retreats as a space for your employees to connect to their own personal dreams and ambitions

Here is a preview into our newest episode where David and I discuss the many benefits we’ve experienced as a result of our company retreats, and how to get your employees enthusiastically bought in.


15Five’s first company retreat

Shane: This is a deeply passionate and personal topic for both of us, and something I think we’ve done extremely well throughout our history as a company. We both can credit the retreats that we’ve created, either company-wide, for the leadership team, or for each department, to building an extraordinary culture.

David: Yes, it’s something we’ve done really from the start. 

Shane: It started when you rented a cabin up in Tahoe for the four employees we had. You said, ‘I’m going to fulfill this dream I’ve had, rent a cabin in Tahoe for a month, work remotely, ski everyday, and launch this company’.

David: I believe it was January of 2013. I invited you, Krystian, and Nazaar up since there were only four of us at the time, and we were announcing a funding round. We just got back from our latest retreat where there were about 70 of us, so we’ve grown a lot since then.

Shane: Looking back at the last six years of retreats that we’ve held, there’s so much that happens when you get together in person. We’re coming at this from the frame of being a distributed team, so we don’t see each other in person everyday. 

So, the dynamic does shift a bit when you’re all working together in the office, but it’s still a huge opportunity to get everyone out of the office and into an a-typical situation where there can be a much greater level of bonding and connecting as a human team. 

David: And it’s worth noting that we are distributed, but we’re a hybrid. We have fairly large offices in both San Francisco and Raleigh, NC. We also have a smaller office in New York City, and an emerging one in Utrecht, right outside of Amsterdam in the Netherlands. And there’s quite a few people also working from home and all over the world. 

Check out Episode 2 of the Best-Self Management Podcast here!

What’s the purpose?

Shane: One of the things we talk about in Best-Self Management is that we’re borrowing a lot from Maslow’s hierarchy of needs, and the process of a human being realizing their full potential. Realizing our full potential as a fully developed adult human being is not an easy task. And it doesn’t just happen by default. 

The way we think about these retreats is that it’s an opportunity to create an emotional renewal for everybody, and peak experiences. Maslow talked a lot about the necessity of peak experiences to achieve a level of self-actualization and self-realization. That’s really how we think about these retreats. It’s almost a happy excuse to create peak experiences for people in that company that reconnect us to our deeper passion. 

At these retreats, we experience growth, high levels of vulnerability, and connection with each other. It’s pretty magical what happens. We’re going to get into how we think about the ROI, because they’re not cheap. It’s definitely a budget item that we take into account, yet the return is so vast on them. 

David: For our business-focused outcomes that we do at these retreats, whether its a company-wide retreat or a leadership retreat, we are setting goals, we’re talking strategy, we are doing those business-oriented things that you would typically do if you took a team meeting, or you take once a quarter to get out of the office.

But we’re taking it to the next level. My belief is that when we get out of the rhythm of our day-to-day experiences, it snaps you into a more heightened state of awareness. We’re more strategic, innovative, and future ways of thinking are possible…


Discovering your full potential doesn’t just divinely happen on its own. At 15Five, we feel strongly that company retreats provide the opportunity to level up your growth and foster healthy connections that people need to become their true best selves. 

A retreat layered with emotional renewal and peak experiences (necessities in achieving self-actualization according to Abraham Maslow) can make incredible impacts in your company’s culture and overall success. 

We see retreats as a way to strengthen a company’s culture and values. Success here involves many factors, such as choosing an inspiring location, creating effective content, facilitating deeper connections on the team, and delivering peak experiences along with time afterwards for integration.

Discover how you can plan and executive your next company retreat by listening to tips from David and myself here

Shane-Metcalf-CCO

Shane Metcalf is Chief Culture Officer at 15Five, continuous performance management software that includes weekly check-ins, objectives (OKR) tracking, peer recognition, 1-on-1s, and 360°reviews. Shane has spent his career studying organizational & human development, which now translates into the high performing 15Five culture.

David-Hassell-CEO

David Hassell is co-founder and CEO of 15Five. David formerly served as President of the San Francisco chapter of the Entrepreneurs’ Organization and was later named “The Most Connected Man You Don’t Know in Silicon Valley” by Forbes Magazine. David has been featured in The Wall Street Journal, Inc., Entrepreneur, and Wired. Follow him on Twitter @dhassell.


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