Management has a set of power words that it’s appropriated as a means of giving it a sense of identity. This list is endless and entertaining. When these words are spoken, they are said in such a way that you are meant to wonder in awe, “What does that mean?” but you don’t ask for fear of looking like an idiot.

Today’s word: off-site. An off-site is a… meeting. There are some specific characteristics to an off-site, but all it is a meeting with a group of people that likely lives up to its name in that it’s elsewhere, it’s off-site.

Now that you understand what it is, let’s understand why you might hate it.

Why I Get in Fred’s Face

The reason an off-site exists is simple: you, the leader of the people, need certain essential work to occur that cannot easily occur now under normal conditions within the building. It’s a little sad. When it was only 20 of you, each of three different off-sites I’m about to describe would just happen… organically. Fred would stand up in the middle of the office and say, “Ok, we need a new UI framework. I’m going to do it, and anyone who wants to get in my face needs to do it now.”

So you got in Fred’s face. You argued. You debated. Fez and Phil jumped in and in 17 very important minutes, you fundamentally changed the UI architecture of the product.

At an organizational size that varies for every team, natural cross-pollination and communication activities that used to happen organically, that allowed for cultural and strategic work to get done, and allowed for big decisions to be made, can no longer occur. The team can no longer look around the room and get a sense for how everyone is doing because there are too many everyones.

Zeitgeist has become diluted. Random hallway error correction doesn’t happen because the right folks aren’t bumping into each other. It’s sad especially for the folks who vividly remember standing up and getting in Fred’s face. You need to recreate the space and place where a team can bond, a strategy can be devised, or you can begin an epic journey.

You need a well designed off-site.

Who We Are, What We Need, and Our Epic Journey

The reason you invoke the off-site is going to vary from group to group. The following are three specific scenarios where I believe you need to employ the off-site, but there are more.

We need to understand who we are. If you’re familiar with my writing, you’ll know I don’t think you really know what the hell is going on in a team for 90 days. You have moments of comforting clarity during the first three months, but you don’t really know all the moving parts until a chunk of time has passed. Now, multiply that early confusion by every single person who has been hired in the last nine months.

During times of rapid growth, a team doesn’t necessarily take the time to stop and get to know each other because they arrive and the first thing they notice is, “Whoa. Everyone is in a big fucking hurry, so I must hurry as well.” Their normal instincts regarding getting to know those around them are buried in their goal of being recognized as a person who is also in a hurry.

You need an off-site not to solve a strategic product problem, but to give the team time away from their hurry to get to know each other. Socialization will happen via each of the off-sites I’m about to describe, but the need for a team to understand itself is a cause worthy of an off-site all by itself.

We need a new direction and/or we need fewer disasters. Something significant is broken. Either disasters are occurring and the normal processes of detection and correction aren’t working, or everything appears to be working but we’re not achieving success — for whatever success means at that stage of the company. In either case, the status quo represents a legitimate threat to the company.

The purpose of this off-site is deep brainstorming. The group is tasked with discovering and refining ideas, proposing experiments to test these ideas, and finally stepping up to run with these ideas back at the ranch.

We are embarking on an epic journey. Nothing’s broken, it’s just time to start. This last off-site might also be called a kick-off meeting. You generally know what you want to do and when you want to do it, but need all the leaders responsible for making it happen to be in agreement about where you’re headed and why.

This off-site is an alignment meeting. Strategy can be discovered as part of this meeting, but that isn’t the primary goal. You are collectively pointing folks in the correct direction (this is where we’re headed) and defining the urgency (and this why we’re headed there).

A Meeting with Certain Characteristics

While an off-site is just a long meeting, it is a meeting with certain characteristics that differ from your average daily meeting. I’ll explain each and I’m going to bring Fred along because Fred has no problem telling us exactly what he hates.

By definition, you can’t invite everyone. Remember, the reason you need an off-site in the first place is that the team has grown to a size where they are consumed by hopefully essential tactics. They don’t have time to step back and think about later because from the moment they walk in the door, there are meetings, phone calls, emails, and interviews that simply must happen. Everyone is consumed in the work. Yes, the individual has a free hour here and there to take a deep breath, but collectively the team doesn’t have time to figure out what it is thinking or why they are working so hard.

Depending on the goal of your off-site, you need to pick the people who are both capable and willing to solve the hard problem sitting in front of you. If you’re trying to understand who you are, you invite every person that you want to know. If you want fewer disasters, you invite both the folks creating them and those with the ability to fix them. You need to be able to look around the room and confidentially think, These are people to solve the problem.

Fred hates it. He says, “Man, why are we being exclusive? I want everyone to weigh in on the important decisions that affect the company. We’re all shareholders and we should all get a vote.”

There’s a name for a meeting where everyone is invited, Fred. It’s called an all-hands and if the all-hands isn’t part of your regular company meeting regimen, I can see why you’re pissed. However, your all-hands is 120 people and my question is: when is the last time you saw 120 people efficiently propose, debate, and then make a decision? An off-site is not an opportunity to ignore opinion; an off-site is a chance to select a group of folks who are going to best represent the company on whatever huge problem we’re solving. Yes, the selection process is hard.

Everyone presents, or at least speaks. Once you’ve got an initial list of folks, ask yourself this: “What appropriate presentation would I ask each invitee to do?” My rule of thumb is that each person at the off-site has a deliverable, and that usually means that they need to step up and present. This exercise teaches me two things. First, if I can’t think of something I’d want this presenter to talk about given the problem at hand, why are they invited? Second, I start to see duplication. Well, Sarah and Frank are both great about talking about our lack of design process. Do I really need them both?

This isn’t a hard rule. There are many times you need to invite folks simply because you know they’ll speak up randomly and brilliantly. However, as you’re building your off-site, this step illuminates both your agenda and your audience.

Fred doesn’t really hate this because he likes the democratic and flat feel it gives to the affair. Thanks Fred.

It’s not in your usual building. The other word frequently associated with off-sites is “boondoggle”. When you learn that the senior leadership team is spending the weekend in Vail, I can assure you, yes, that is a boondoggle. I’m certain there is a clear business justification that explains why the company needed to fly seven executives to Vail in the middle of fall, but I’m also certain they could do the same work at a lower altitude.

Off-sites don’t need to be swank, they need a sense of elsewhere. They need to be far from the tactical distractions of the office because they need a new view. One of your goals for an off-site is to create grounds where people feel comfortable speaking heresy. If whatever problem sitting in front of you could be solved via the day-to-day, it would’ve been solved. Drastic measures call for creative thinking, and now that you’ve gathered these bright people together, you want them to feel comfortable saying whatever compelling ideas cross their minds. Speaking heresy is easier when you aren’t surrounded by visual reminders of obvious constraints.

Fred hates it. “Do you know how much this is costing us? We could do exactly the same thing in the 7th floor board room.”

Yes, we could, Fred, but within two hours here’s how it’ll play out: someone is going to figure out we’re hiding out in the boardroom and they’re going to find something that appears to be earth-shatteringly important that will pull one of us out of the room. Folks will return slowly from breaks and sometimes won’t return at all. You are paying a premium to make sure everyone in the room can focus, but if you have an off-site worthy topic, it’s a small price to pay for this group’s attention.

There’s someone responsible for flow as well as action. With the correct group in the room, getting a healthy conversation started on the problem isn’t hard. In fact, once the group gets started, the issue will be figuring out how to get them to stop. To manage this, there are two roles you need to designate before the festivities begin: a Master of Ceremonies and a Taker of Notes, and they are usually not the same person.

The Master of Ceremonies is the person responsible for not just moving the day along, but also knowing when to stop and pivot. Again, getting this particular group into a healthy conversation shouldn’t be hard, but don’t confuse a healthy conversation with progress. A deeply engrossing conversation is a great thing and a target rich environment for finding the core of a great idea, but there are many conversations to be had and this is just one. A good Master of Ceremonies knows when an idea has been explored as best it can and it’s time to move on.

The Taker of Notes reads like an administrative job, but it’s the most important gig in the room. Once an off-site really gets going, once the team really engages, it’s all going to sound like great ideas. The Taker of Notes is tasked with not only capturing the bright ideas, but the right ideas. After years of off-sites, my observation is that you only find three new ideas that you act upon. These can be huge company-changing ideas, but there are only going to be three and it’s the immense burden of the Taker of Notes to not only find them, but assign them to the people who can and will drive them forward.

Fred hates it. “They’re messing with the flow… man. Why can’t we just have a conversation? A debate? Why are we on the clock?”

Fred, I understand that you hate process. You equate the appearance of process with a decrease in free will. You believe that process is going to slowly going to sap this company of the creative ninja spirit that got us from 12 to 120 people and you’re right. Blindly landing process without considering the culture it needs to support it is a recipe for disaster. However, believing that the loosey-goosey make-it-up-as-we-go rebel spirit that got us to 120 is going to take us to 2000 is absurd.

I believe each time your company doubles in size, it needs to reinvent how it communicates, and each subsequent transformation is increasingly radical and foreign. Fred, if we’re going to grow we need to constantly reinvent ourselves.

No personality tests, no trust falls, and no outsiders. There are a couple of traditional moves that well intentioned folks who have attended off-sites elsewhere are going to suggest, but that I want you to avoid:

• Personality tests. If you’re working the team bonding off-site, personality tests are going to be tempting. The idea of starting the off-site with perspective-altering personality tests feels… right. I want them to better understand each other, so have them answer a bunch of questions and we’ll explain ourselves to each other and — WHAM — understanding. Personality tests in their endless variety do exactly that. They tell you which well-defined bucket you comfortably belong in and explain to others your bucket’s intricacies. These buckets become social tent poles of the off-site and suddenly everyone erroneously believes they’ve figured each other out. And while, yes, they now have convenient labels for each other, they haven’t really figured each other out: they’ve cheated. You’ve bypassed the process of learning via a set of clever labels.If you want to understand someone, my advice is to sit next to them and solve a very hard problem together. You will learn who they are by watching how they think. Similarly…
• No trust falls. Another traditional off-site move is staged games or activities to get folks socially and mentally limber. These are endless and not entirely useless. Just as being in a different place gives the team a sense of elsewhere, your initial content needs to get them thinking in unfamiliar ways. Like personality tests, my preference is that the learning we need to do is done in support of working on the problem. If you can find a goofball trust fall-like exercise that is going to get us closer to figuring out how to have fewer disasters, I’m a fan. If you’re putting the team through an uncomfortable and irrelevant social or strategic exercise because you’re attempting to build trust, why not make it relevant? It builds trust faster and you get actual work done. Lastly…
• No outsiders. The last traditional move to avoid is the importation of outsiders. Facilitators, mediators — whatever. The justification for these external parties from the folks building the off-site will be, “I want to participate,” or, more deviously, “Someone has to manage the flow and the action”. An external facilitator gives a professional air, and they will move things along at a comfortable pace, but while they would never admit this, they couldn’t give a shit whether you solve your problem or not. It’s not that they’re callous people, it’s that they are Other. They don’t know the culture, the problem at hand, the politics, or the personalities. They’re simply not qualified to participate beyond holding a stopwatch. You need someone running the show who has skin in the game.

Fred, not surprisingly, is actually cool with all of this, too. Thanks again, Fred.

They need to sleep on it. There’s a moment I like each person to have as part of an off-site and I call it the bright and shiny inflection point. At some point after a compelling talk or brainstorming session, they start to believe. They finally let go of all the tactical things they need to do and allow their brains to jump into the creative soup that the organizers have been vigorously stirring. They see beyond the week and begin to see the next year. They have epiphanies and they start to see the beginnings of solutions to complex problems that have been nagging them for months.

How do you get them there? You’ve go to get them soaking in it and that takes time. An off-site must be at least two days. You need one evening where they get away from what is hopefully a high bandwidth conversation regarding whatever it is that ails the company, and get a chance to process this conversation in the back of their heads. When they walk into the unfamiliar location the next morning, whether they’ve mentally made progress or not, the big huge problem is still sitting there on the white board waiting to be attacked.

Fred hates it. “Since when do we need to spend two days solving this one problem? This company was founded by two guys high on Diet Coke at the Creamery. We had a prototype in a week and that prototype was live the week after.”

Fred, the curse of success is that we move slower and it’s a confusing curse. See, we’ve been successful and the result of that success is that we’re able to hire more people to do the seemingly impossible amount of work our success has created. But each person we add to do more work strategically slows us down. Each additional person levies a communication tax and unless we figure out how to constantly improve our communication, we’re just going to get slower. That’s why we’re here; even if perfect solutions came to us during caffeinated highs, we’d still need to vet them with the many bright people we’ve hired to help us grow.

What Fred Really Hates

The morning that Fred arrives at the off-site, which is at some nearby location, and after a delightful breakfast, Fred and the rest of the off-site team gather in a room where someone important stands up at the front of the room and starts talking. As the morning’s coffee kicks in, Fred’s initial knee-jerk reaction to this talking is, “You know folks, I have essential stuff to do and this yap-yap-yapping isn’t helping me get this stuff done.” Fred folds his arms, clenches his jaw, and resigns himself to simply waiting until it’s over so he can get back to important work.

At some point during the first day, Fred silently has his bright and shiny inflection moment. He turns off his phone and furiously start scribbling down ideas. That night at the off-site dinner, the conversation is about work, but it isn’t about the shit he’s been slogging through daily, it’s about the strategic work he could do to make that shit go away — forever.

And then it’s over. Fred returns to the office and he’s pumped and ready to start changing the world, but the moment he walks in the door, everything he hasn’t done is staring him in the face. As he starts rebuilding his daily work context, he realizes, “Not only do I have a lot to do, but now I’m behind.” The bright and shininess of the off-site he’s retained fades quickly.

A week passes and now he’s angry. He’s angry because now that he’s caught up, he’s never going to get ahead because no one is making any time for him to apply all of his bright and shiny epiphanies. In fact, after a week, nothing from the two day off-site has survived except Fred’s lasting opinion: “Well, that was a waste of our time.”

The successful off-site is one that maps the discoveries of the off-site to the reality of the work. Bright and shiny inflection points are full of energy, but unless that energy is carefully channeled back into the building and immediately acted upon, all an off-site represents is an frustrating opportunity to dream, but not to act.