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, team members don’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 members 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 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 successmeans 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 something. This last off-site might also be called a kickoff meeting . You generally know what you want to do and when you want to do it, but you 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 is why we’re headed there).

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 it later, because from the moment they walk in the door, there are meetings, phone calls, e-mails, 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 it’s 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 think, “These are the people who will 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, then 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-and-fast 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 needs 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, but they do need a sense of elsewhere. They need to be far from the tactical distractions of the office because people 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 have been solved via the day-to-day, it would have 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 seventh-floor boardroom.”

Yes, we could, Fred, but within two hours here’s how it would 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 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 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 2,000 is absurd.

I believe that 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.

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 learning process 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 . . .

Avoid trustfalls. Another traditional off-site move is using 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. As with personality tests, my preference is that the learning we need to do be 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 . . .

Avoid 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. However, 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’re 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 long. You need one evening where everyone gets away from what is hopefully a high-bandwidth conversation regarding whatever it is that ails the company, and gets 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 whiteboard 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 have to 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.