Ultimate Offsite Insight #1: Finding Your Offsite’s Purpose

The word “offsite” used to evoke very specific imagery for me. Long hours in a company office or co-working space; a manager droning on about roadmapping or annual planning; Awkward icebreakers, minimal breaks, bad catered lunches and having to remember every receipt so you could expense those lonely room service dinners. 

I know this is not everyone’s experience with offsites, but it was mine way too often. (I know I’m not alone.)

It seemed to me that leaders were having offsites just to have an offsite. There was no explicit purpose. They followed the same tired format, just to check the item off their list. What they weren’t realizing was how incredibly damaging a bad offsite was to their teams. Where a pointless meeting only wastes an hour, a purposeless offsite wastes days.

That complete disregard for me and my time, speaks volumes about how your company values its employees. This inevitably breeds resentment, which eventually leads to a complete lack of motivation to be a contributing team member. I know this may seem extreme, but I’ve witnessed it countless times. Purposeless offsites are culture killers. 

Changing this perception of offsites became a mission for me early on in my career. Having sat through and forced to plan so many bad ones, I knew exactly what needed to change to improve them. We needed to stop focusing on the work and start focusing on the humans doing the work. The second you shift the focus to their offsite experience; providing great food, fun activities, showing genuine interest in them as people…you incentivize them. They no longer feel like they’re worker bees just here to do a job. This company went above and beyond for them and they’re gonna return the favor. A team that feels valued will continue to do their best work long after the offsite has ended, because feeling valued is the ultimate motivator. 

Don’t get me wrong, offsites are still about getting work done together. I always allow ample time for working sessions in my agendas. I just believe you get better quality work done when you take this people first-approach. 

Now that you know my offsite philosophy I want to teach you how to achieve it.

What will I learn in this post?

If you’ve ever planned an offsite you know it’s no easy feat. It’s actually not that much different from planning a wedding. An insane checklist of tasks, and each task has its own layers of detail. It’s also similar in that every planner approaches planning  differently. Where one planner thinks it’s important to stick with traditions, others will experiment; designing the experience around the couple rather than copy and pasting from tried and true formats. 

I bet you can guess which planner, I am. 😉

All this to say…it’s freaking complicated to plan an offsite. If I were to try to unpack every detail of offsite planning, this would be the longest post known to man. That’s why I’ve decided 2 things:

  1. This is not going to be a step-by-step offsite how-to. It’s more of a brain dump. I will dive into the key components required to plan an offsite and share my insights into how I design them. Tips, tricks, advice, do’s, don’ts, best practices. I’m just laying it all out there for you to sift through. Plug and play as you see fit. 

  2. We’re doing this in segments: The amount of info I need to share would require me to write a book. None of us got time for that…yet 😉. Each new post in this series will tackle a different element of the planning process, from Selecting a date to Arrival Day, I’ll get into it all. 

For the 1st installment of Ultimate Offsite Insights, let’s start at the very beginning…finding your offsite’s purpose. 

Identifying Your Offsite’s Purpose. 

As I described in my offsite philosophy, having a clear purpose for your offsite is paramount to its success. Asking people to leave their families and personal obligations to travel for work is not a small ask. You better have a good reason and a well-planned event.

Depending on the various reasons for wanting to have an offsite there is always one, central purpose behind them all. Here’s my ways to find it, build for it and communicate it to your teams. 

  • Keep asking “Why”: I have the following conversation all the time: 

    • Leader:  “We haven’t had an offsite in awhile, we should do one.”

    • Me: “Great, why?” 

    • Leader: “Well, like I said it’s been awhile and we could use the focus time.” 

    • Me: “Awesome. Why do you need focus time right now?” 

    • Leader: “Oh uh, to be honest, there’s this deadline coming up that’s put a lot of pressure on the team.” 

The conversation proceeds with me asking “Why” until we finally unearth the real reason this leader wants an offsite. Spoiler: It’s rarely the reason they started out with. I encourage you to keep asking why about your next event. If after digging you find no real purpose behind the event, you probably shouldn’t be having it. (A much due credit to Priya Parker for developing this brilliant process.) 

  • Send a Pre-event survey: Before you get into the details of planning, send out a pre-event survey. Ask your team what they hope to get out of an offsite, or if they think an offsite is even necessary to accomplish this task. If you start the planning with a collaborative spirit, I tend to find deeper investment in the offsite in general. (Check out this sample Pre-Offsite Survey. Maybe it will inspire your own.😉)

  • Clearly communicate the purpose: When starting to plan with the team make sure you are clearly communicating the purpose of this offsite. Giving them a well designed, clear reason for requesting their presence will ensure higher attendance and engagement rates. 

  • Let it inform everything: The purpose should not only be clearly communicated, it should feel engrained in most, if not all, the events you plan. For example, your team is having an offsite to create company values. You don’t feel confident leading the main discussion yourself, also you want to be able to participate in it rather than lead it. Consider hiring a values expert to facilitate a meaningful workshop for your team. Bringing in a professional indicates a genuine interest in your teams perspectives and opinions. This will likely increases their desire to find the answer and lead to a rich, successful discussion. (Psst: It will also be successful because you booked an event that aligned with your purpose. 👍)

  • Preserve the product of your purpose: It happens more often than you think. You have this great offsite, do all this amazing work together, then Monday morning you sit down to action these ideas annnd it’s all a blur. Make sure all the work towards the purpose of your offsite is preserved in some way. Whether that’s a recording or pictures of the whiteboard, take the time to translate this into a post-event retro doc to share with all attendees.

  • Send a Post-event survey: In order to create a thorough retro doc of your experience you need to know that you actually did achieve what you set out to. Always send a post-event survey that mirrors the questions from the Pre-event survey. You want to be able to clearly see what the expectations were of the offsite as compared to the results.


Storytime

Good Research & the Power of Purpose

Recently my dear friend, Raj Bandyopadhyay and I collaborated on a project for a company called, Good Research. They are a tech security start-up, made up of 10 globally-distributed team members. The founder, Nathan Good, is a compassionate, heart-forward leader, who is extremely proud of the strong and quirky culture he and his team have created. Nathan is preparing to start scaling the team and he found himself worried about preserving this close-knit, awesomely weird culture as they add new and different personalities to the team. He decided he wanted to have an offsite to build on team bonds so they will stay aligned as they grow. As he began to build the offsite, he wanted to design working sessions that aligned with that bonding purpose. He contacted Raj to assist with one of his ideas.

Raj is a brilliant photographer and we’ve been friends since he did my branding photoshoot in 2021. (Like, every picture on my website he shot. 💗) Nathan hired Raj to document his teams offsite. He wanted to capture it all, he even wanted Raj to offer the opportunity of professionals headshots for each of the team members. Raj felt they could take it one step further than just pictures. That’s when he contacted me for two things: Create a post-offsite survey to collect team feedback; design a photobook with all the images. Raj felt having something tangible that aligned with the purpose of the offsite was the best gift we could give them. I wholeheartedly agreed.

The offsite came and it was a monster success for the team. They brainstormed, played, bonded, and really got to know the humans they work with. For me, one particular team-building session really stood apart from the rest. They called it Nerd Outs (I think you can see the appeal already 🤓). Each offsite attendee had to prepare a presentation on one of their nerdiest interests. They took turns presenting projects on gardening, computer games, Anime, architecture…it looked like the best time ever! And that’s the thing that got me… I wasn’t even in that room! All I had were the pictures Raj had taken. I was able to feel every emotion they had while participating in that offsite just from putting together their photobook. If I could feel that strongly, I could only imagine what they were feeling. Or how every time they look at this photobook they will be reminded of the unique and special bond they have with their team.

This offsite is now my quintessential example of the power of purpose. The Good Research team quite literally checked off every box in my advice above.

  • Ask “Why”: They didn’t just have an offsite to have an offsite, they dug deep and found the purpose: To enrich and strength the bonds of my team before they begin to scale.

  • Pre-event Survey: Raj sent a pre-event survey to gauge what the team was hoping to achieve with this offsite and how they believed photography would enhance the experience.

  • Clearly Communicate: With the feedback from the pre-event survey, Nathan & his colleague, Cassia Artanegara ensured the team was aligned with the purpose.

  • Purpose Informs Everything: This was achieved in so many ways and was a true collaboration. From encouraging the team to wear outfits that expressed their true personalities, to Nerd outs and thoughtful working sessions; they let the purpose guide every piece of their decision making.

  • Preserve it: The use of photography was spot on for capturing the authenticity and success of this offsite; and the photobook was the perfect swag to preserve the purpose for years to come.

  • Post-event survey: I created a post event survey that mirrored the questions from Raj’s pre-event survey. Without that survey we would have never been able to definitively tell you that the offsite achieved it’s purpose. (Good Research post-event survey for your reference.)

 

Cover of the Offsite Photobook

 

I had an amazing time collabing on this project with Raj and the Good Research team. It confirmed what I already knew to be true…finding the purpose of your event IS paramount to it’s success. I hope this story inspires you to find your purpose as you design your next event.

Until the next post….Happy Planning!


📣Tune in to the next installments of Ultimate Offsite Insights when I take on: 

  • Offsite scheduling: Avoiding the Dreaded Date Dance

  • Agenda & Budget Planning 

  • Travel & Accommodations Booking 

  • Activities & Restaurant Selection 


Previous
Previous

The 5 Tips to Avoid WFH Burnout

Next
Next

LL - A Career Journey