Let’s all hop into a bus and head to the Santa Cruz mountains or the beach in Monterey! Let’s have an off-site this week.

Not so fast! Organizing an off-site is not that easy. It takes careful preparation. Depending of the group, topics and overall company backdrop, it is a tricky social experiment each time around. Here are few tips and tricks I learned by attending and organizing both great, motivating and successful off-sites, as well as the kinds you do not want to remember at all.

Organizing an offsite takes preparation, and so does participating

Who should attend?

Let’s start with the attendee list. Most importantly an offsite should build trust among the team. So you must define who is really necessary to be there. No lurkers allowed. Do not invite a list of interested parties or stakeholders. This is not a kick-off meeting, or briefing meeting. Keep to the core team.

Participation is mandatory. Make it clear that all invited are expected to prepare for the offsite and participate. Consider this also when creating the agenda. Topics should appeal to the collective: “What’s in it for me?”. If some important topics only appeal to a few, consider sub-teams meeting prior to the off-site and have them present the summary at a team meeting or at the end of the off-site.

The CEO, Vice President of the organization or other boss-like figure is always a tricky attendee. Make sure they understand they are are invited as a full participant, equal among the team. If the boss wants to observe or audit the offsite, explain you will send an offsite report and that their presence may be overwhelming and counter productive.

What shall we discuss?

Define an agenda several weeks in advance. Solicit topics in a group setting (e.g., during the weekly team meeting). Keep the agenda and topics as a public document where people can add new topics, or add comments to established topics. This gets early buy-in to the meeting, and most importantly it avoids people from showing up with their own and new agenda topics to the offsite. People pushing their own agenda surely will ruin an offsite.

Equally dangerous are topics with a foregone conclusion. Do not try to lead the team to a conclusion. You are far better of describing the problem and spelling out a conclusion for discussion, while also being open to alternatives. Foregone conclusions are a waist of time, and people feel manipulated. You are sowing the seeds for trouble later.

For each topic, define what success means. For example, while discussing roles and responsibilities, success could mean a documented responsibility map. Having a discussion on the success criteria gives you an idea about how complex or easy a topic will be. It also helps the team understand what we are trying to achieve. Managing the offsite to results within a prescribed time will be very challenging.

Next, figure out how much time each topic should take. Error on the high end of needed time, as most often discussions will take longer than anticipated. This will allow you to create a real agenda. Try to stick with the proposed allotted time, (or decide to pick it up later). Not doing this will assure you will get only to one or two topics on your offsite agenda. Make sure you also reserve some time for new topics which come up during the meeting and which have been deferred to the parking lot.

Before finalizing the agenda, consider the flow of topics. Do not start with a soft topic, or a contrived team building exercise. Several articles advise you to the contrary. My experience shows the opposite. It is better to have a Kumbaya moment the night before the offsite, or have some casual chit-chat before the meeting starts. On the day of the offsite, take the bull by the horns from the gecko. Great teams become great when they produce great results. I’ve seen too much time wasted in the first half of an offsite on soft topics. Starting soft sets the tone for too much debate and not enough results.

One last item: down-time. Make sure you preserve some time at the end of the off-site to relax, have a beer, and chit chat. Do not (DO NOT!) allow folks to run home or catch a plane early. Building trust happens most often outside of the typical work setting.

Now that you have an agenda, with a proposed amount of time and success criteria for each topic, discuss which topic require specific preparation in small teams. You may need to need to do some data analysis or run a few reports in advance. It is much better to start from a few pre-defined mission statements, than trying to make it up on the spot. It is important that any pre-off-site meeting do not short-circuit the off-site all together. This will erode trust within the team. Do not present decisions or results. The preparation should be the starting point to allow effective debate.

At this point, the team should have a good idea about, who will attend, what will be discussed, and what prep work they need to do in small team, as well as personally.

Put it all together: the logistics

If you think the agenda was the hard part, you are seriously underestimating the logistical details of putting an offsite together. Think busy calendars, strong opinions about the location, or the food.

Where

• No hotels! Seriously! Forget the windowless hotel ballrooms or “boardrooms”. You are much better off meeting in the attic of a goat farm. The place should make folks at ease, and the same time not distract.
• Find a place which allows for focus and debate. Make sure you have some sort of whiteboard or flipboard. Even if it is in the woods, bring a flipboard. I do not advise to meet up in somebody’s living room. Only on rare occasions does this work.
• I always wanted to organize but never been to an offsite in the woods, or mountains while camping. You would need the entire team to be adventurous and a frequent camper to make this work. It would be a great venue to discuss the future of a company around a campfire. There is also the complication of no internet, no phones and no power. The latter being probably the most problematic one for a technology company.
• Travel time: balance the travel time with the time you will spend together. For example, the travel time should be no more than 2hrs/day of off-site.

Set-up

• Everybody attending should be in person! Avoid video conferencing, or dial ins. First of all there are always issues setting up the video conference, plus it almost never works for good debate. And unless the world is falling apart, do not allow late minute cancellations. it is a good idea to have the attendees arrive the day before, and allow for travel delays.
• Feng Shui — pay attention to the way the room is set up. Set it up for optimal interaction. Do not sit all in front of a projection screen or TV. Also everybody should be sitting in the first row. No double row! If you really need a second row, you likely have too many people attending your off-site.
• Avoid projectors — I used to project the live notes. I changed my mind on that, as it kept the focus away from the discussion. A projector should be used as little as possible. It may be a good idea to review the notes at the end of a session.

When

• Avoid Friday’s. People will leave early to fly or drive home.

How

The moderator — Running an offsite is a very tricky thing. It is often the lead or manager who is tasked with moderating the offsite. Don’t do it! To avoid it being a one-man show, the lead or manager should take the role of overall manager of the offsite, making sure everybody is participating, watching the clock, and delegate the role of moderator to several. You can have a moderator per session. Note that the moderator is not the one presenting the main ideas. It is important not to set it up as “let me present my ideas, and have you all poke holes into it”. The result is often a few folks engaged in the tiny details of an idea and the majority of the folks tuning out.

Ideally the moderator has a stake in the topic, and is not the one who cares the most about a specific idea. It should be a more neutral party involved, who has a vested interest in the outcome of the discussion.

Think very hard about the roles and moderators. Do not let people self select (some will chose the easy pickings).

Taking notes — Detailed notes of what happens during the off-site are not important. Focus on summary notes after each topic: “What did we accomplish? What did we decide?”. You may need to share these summaries with others in the company. Decide before the meeting, who and how notes will be taken. To not distract from the discussions, I advise to open up a single laptop for summary not taking at the end of the topic. Any other notes should be on a piece of paper.

Day to day interruptions and parking lot items — unless the company’s survival depends on it, do not interrupt the offsite for day to day work. “Can we take a second to address this email which just arrived?” “No!” Similarly, side topics will pop up. Keep track of parking lot items and discuss when or how they will be discussed.

Breaks

Make sure you have drinks, coffee and snacks. And naturally a few bio-breaks. However, avoid email breaks at all costs!! AT ALL COST! The business can wait for a day.

Bright eyed and bushy tailed!

Starting the meeting on time and with the right attitude is very important. When folks are there the night before, avoid debauchery the night before the off-site. Do it later ;) Everybody should be bright eyed and full of energy. An opening hike would be great. Having an early opening hike also deals with people showing up late. If you know some folks are always late, talk to them before. Be on time!

Closing time, open all the doors and let you out into the world

Don’t end the offsite on the sad and raspy tunes of Closing Time by Tom Waits or Leonard Cohen. Instead, finish with the up-beat Closing Time of The Semisonic. Have some fun at the end of the day. Remember that you reserved some time on the agenda to relax. Have some time to hang out at a bar, or around a camp fire with a few brewskis. Keep it in moderation as you want people to remember the good part of the off-site, not just Jimmy running naked in the woods. You want folks to remember how you discussed important topics, spoke frankly and honestly, and came together as a team.