Standards for Company Offsites and Retreats

It's offsite season for growth-stage companies.

From September to January, leadership teams (and sometimes, their entire workforce) come together to do annual planning and goal-setting, team retreats, company reviews, vision/mission/values revisits. This season, I further believe that after nearly three years, some will also re-boot their longer-term strategic planning.

I've led many such events, and over the years, created a playbook for myself to make them as high-impact, efficient, and custom as possible. Upon reviewing this playbook recently, I realized there was a long list of standards that I've set to make an offsite successful.

What follows is a list of 12 planning and logistics categories, each of which I discuss briefly and then summarize with my personal standards. Also, it's worth mentioning that these standards are for offsites in the physical world. I have too little experience with remote ones to share enough thoughts.

LOCATION

There's a reason planning retreats are often called "offsites" - they're held in a city or neighborhood away from the company's offices (today, many remote-only and hybrid workplaces are holding "onsites" that bring their team together). By doing this, offsites have a stronger chance to be successful for a few reasons.

1. The further we are from our daily routine, both literally and figuratively, the more able we are to change our mindset and think differently, which is what an offsite requires.
2. If a company is still in-person or hybrid, a true offsite helps minimize distractions, both those caused by other people and those we succumb to ourselves because we're close to the office.
3. A unique location helps create energy and excitement for the participants through fresh scenery, different weather/climate, food and entertainment options, etc.

My standard: At least 2-3 hours away for most participants, often requiring overnight lodging.

VENUE & MEETING ROOMS

To me, this is the most critical logistics item because it's where most of the time is being spent.

I like having enough space and/or rooms for people to move around for poster brainstorming, activities, breakout conversations, individual reflecting, as well as sitting on different furniture or even the floor. This is, obviously, in addition to the space that the conference table takes up in the room. And, depending on climate and arrangements, having access to outdoor space is ideal, especially for agenda items and conversations.

The outdoor space is even more critical if the main meeting room lacks windows. But when I have decision-making influence, I will often advocate for rooms with windows and natural light because they simply make the offsite sessions more productive and enjoyable.

On a side note, I've found that retreat centers and co-working spaces typically offer better options, greater flexibility, and more energy than hotels, which are not only more expensive but can also be far less inspiring and less modern. However, logistics are easier with hotels since the rooms and food service are built-in.

My standards: Plenty of space to move around and as much natural light as possible.

NUMBER OF DAYS

This depends on how many people are participating. For smaller leadership teams of 2-3, I believe an offsite can be done in one long day (with a working lunch) although two is preferable. My experience is that most offsites for growing companies have 4-8 attendees, therefore, I like to have at least two full days, preferably three.

A multi-day event creates time and space for everyone to contribute, social outings, adequate meal time, camaraderie and team-building, personal time, and other opportunities for human activities. Having this time and space can not only optimize the offsite itself but help accelerate the execution of the work when everyones returns home, serving a similar purpose as vacations sometimes do: a chance to re-boot, refresh, and become re-inspired.

If budget and a company's operation allow for it, I believe a full work week is the ideal length of time. It creates plenty of space for the above items plus actual working sessions.

My standard: A minimum of two days, preferably three.

LENGTH OF DAYS

Good offsites are intense. They require a completely different way of thinking and working than most leaders are accustomed to. There tends to be ideation and brainstorming, analysis and brain gymnastics, disagreement and conflict, in-depth conversation and quiet contemplation.

I've heard from many offsite participants that such events are the hardest they've ever had to work, mostly because they're doing things they normally don't do. That said, I believe there needs to be enough "white space" for breaks and meals, solitude, mindfulness activities, and the outdoors.

My standards: If a company's culture allows, start at 8:00 or 8:30am and end at 4:30 or 5:00pm, followed by social time/cocktail hour and dinner. On Fridays, an end time of 2-3pm, and on Saturdays, a start time of 9-10am and an end time of 12-3pm.

AGENDA

Perhaps the most important part of the planning process, a detailed agenda requires more work than people might think. I typically spend 2-6 hours crafting the agenda, mostly because my standard is having two versions:

1. An agenda for me, usually 2-3 pages for each day. This is my "operating manual" for the offsite. It has questions to ask, things to say, people to call on for certain reasons, how I want to arrange the room, where I can put poster sheets, etc. I look at this during every break, meal, or activity so I know what's coming next and to ensure I execute the plan. And I don't share it with anyone.
2. The agenda for participants, usually one page for each day and completed after I'm done with my own. It includes start and end times for every working session, activity, meal, break, and each day's conclusion (which often includes appreciations, takeaways and/or reflections). I refer to the agenda constantly during the offsite to show everyone that it's a serious working document, and often create a poster-sized version that stays in the front of the room.

And while another standard is to obviously follow the agenda, once in a while a critical topic demands more time which means another standard is being empathic, open-minded, and adaptable by having some buffer time built-in.

My standard: Two versions of the agenda, ensuring that it's followed as closely as possible.

PRE-WORK

In my experience, this is the best way to optimize an offsite's effectiveness. A standard for pre-work helps engagement, builds energy and excitement, shows seriousness, and provide a host of other benefits. Most critically, the pre-work should help get through specific agenda items with less time and greater efficiency because the "thinking" is already done.

In most cases, I send the pre-work one week in advance, estimating that it will take attendees 1-2 hours to complete. Depending on the company, attendees, and the agenda, the pre-work typically contains a blend of the following:

• Looking back: anything related to the past, such as personal or company highs and lows for the past year; company performance; feedback and reflections; how well the company has been living its vision/mission/values.
• Looking forward: anything related to the future, such as goals or desired outcomes; what they want to accomplish in their role or department; how they see those roles evolving; what they're concerned about for the future.

This pre-work is above and beyond anything that individual participants need to prepare for themselves. For example, if a discussion of financial results or the company's new branding is on the agenda, the CFO or CMO is likely responsible for completing that pre-work.

My standards: Sending pre-work one week before, and using it at the start of the event to build immediate engagement and set the foundation for the balance.

MATERIALS & SUPPLIES

This largely depends on a company's culture but I've found the more analog, visual, and tactile an offsite is, the more engaging and productive it becomes. Therefore, I believe that whiteboards, poster sheets, markers, and handwritten notes are better than slide decks, tablets, and other digital tools.

There's one other supply that I love to include, and that's toys. Yes, toys.

I typically get a variety of options: Play-Doh, fidget spinners, squishy balls, puzzles, twisty things, etc. At every offsite I've ever had toys, not only have they been used but at least one person commented on how much they appreciated them, especially those with attention span issues.

My standards: Sticky poster sheets, markers, flipchart easel, whiteboards, notebooks, and toys.

FACILITATION

Admittedly, this one is harder for me to address because I've done far more offsites for other companies than I've done for my own.

That said, I believe it's critical to have an outside facilitator if budget allows so that each participant can be fully engaged. The only exception might be if one of the leaders is a highly seasoned facilitator who knows how to walk the fine line between leading such an event and contributing to it (in my own experience, it was far harder than I thought it would be).

My standard: An external facilitator, if possible, otherwise an internal leader whose primary role is to facilitate and secondary role is to contribute.

ENGAGEMENT

For me, there are three drivers of participant engagement at an offsite:

1. Preparation. This includes many of the items above, like the location, venue, and pre-work but the most important one is the agenda. In planning the agenda, I believe there must be thought given to how the participants will be engaged. In my opinion, an offsite shouldn't be about presentations but conversations.
2. Facilitation. A good facilitator knows when to speak, why, and for how long. They know how to ask questions, read the room, and clarify or summarize what's been said. They know that at times, they're the most important person in the room and, at most times, they're the least important one. They must be able to engage quiet and reserved participants, and disengage talkative participants and big personalities when necessary.
3. Participation standards. This is a declaration of specific guidelines that the offsite planning team can develop in advance. Sometimes, these may reflect the company's participation standards for regular meetings; other times, they may be unique to the offsite itself.

My standards: Prepare for how people will be engaged, have a facilitator who knows how to engage the group, and articulate participation guidelines at the start of the event.

NOTES & DOCUMENTATION

This is an often-overlooked standard based on what I've heard from companies over the years. Even at their "best" offsites, some have mentioned that while the meetings themselves were productive, they did a poor job at documenting the sessions and the work that needed to be done after the offsite.

There are a few options for this standard:

1. Assigned note-taker. Ideally, it's someone who is not a participant but whose sole job is to document the conversations, brainstorms, conclusions, action items, etc. They can do this either on a laptop or a whiteboard/flipchart (note: when using a whiteboard, it's critical to take photos before erasing it!). And it can be another employee from the company or a freelancer.
2. The facilitator. I know from experience how hard it is to try taking notes while being a present facilitator for each session. Doing this makes the offsite less time-efficient because it's hard to keep a conversation going while taking notes on a flipchart or whiteboard (especially if one's handwriting is poor ;-)
3. Collective responsibility. This is where everyone contributes to the note-taking and documentation process. Perhaps it's rotating responsibility for each session. Or one person documents key ideas/brainstorms while someone else maintains action items and next steps. Or someone takes all the poster sheets home, and then transfers the notes to the project management or collaboration software.

My standard: Ensure this is addressed during the offsite planning.

POST-WORK

Once the offsite is done, the real work begins.

I believe it's essential for the same team that participated in the offsite to come together soon afterwards for a debriefing and planning meeting. Ideally, this is scheduled either before or during the offsite so it's gets on everyone's calendars before returning to business-as-usual.

The goal of this session is not to look back and re-hash or debate what was discussed/decided at the offsite. Instead, it's to look forward and discuss how to prioritize decisions/projects, assign responsibilities, distribute workloads, set action items, share outcomes with the entire workforce, schedule review sessions, etc.

If note-taking was done well, this meeting is easier because the information is documented. If the meeting is held within 1-2 days of the offsite, it's easier because people's memory recall is stronger. And if the participants treat the importance of this meeting with the same seriousness as they did the offsite, it's easier because they're more engaged.

My standard: Before or during the offsite, schedule a meeting for 1-2 days after it ends for debriefing, action planning, and setting review sessions.

HAVING FUN

Finally, it's critical that there are laughs at every offsite. They help build an emotional connection to the work and build deeper bonds among the people.

Laughing and having fun happens naturally at social outings, during meals, and with toys. But I believe they can also be planned (for everyone) within the offsite sessions as well.

There are a variety of ways this can be done but my favorites are:

1. For smaller offsites of 3-6 people, having each individual draw and present their ideas for a brainstorming session. Inevitably, some people generate laughs and awe with their artistic abilities (I've seen some go beyond drawing) while others use the opportunity to show their humility and laugh at themselves.
2. For larger offsites, having teams prepare and deliver a skit for brainstorming or planning sessions. Most times, these take the form of game shows, TV/movie offshoots, cable news pundit panels, etc., drawing a ton of laughs from everyone.

My standards: Poster drawings and/or skits, ideally related to the work being produced at the offsite.

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There you have it - a collection of 12 standards I've set for company offsites and retreats, and by no means an exhaustive list.

So I ask and encourage you to share other standards that you can think of or wonder about. Perhaps they're standards you, or a facilitator you've seen, have used at such an offsite. Or maybe they're simply questions you have about other aspects of an offsite.

Ask and share away!