What are they good for? Absolutely nothing! Or quite a lot? No one knows!
I’ve found the best offsite meetings to be the ones where field engineers and factory engineers get to spend lots of time with each other. Tanium’s TAM Weeks were an excellent example of this. I find that small startups can sometimes produce the effect because there’s only one location and everyone meets there. It’s the cross-pollination that RTO policies hope (and usually fail) to engender. However, it’s entirely possible for a startup to isolate the field folks to a separate space and a packed agenda that might as well have been in another city: communication failures are not isolated to big organizations.
Factory
Get all the factory people together… well, that’s doing what you were doing anyway. Whether your software production team sits in open plan office space together or communicates in virtual space, they’re working together, on the same wavelength, in scientific harmony. The offsite may simply be moving the activity to a new venue, or else you’ve got a major problem to fix in what you were doing. One thing to note though; no matter how introverted your fully remote factory team is, humans are still social creatures. We can do a strictly mercenary exchange of hours for dollars, but we only devote our time to a team because we like those people. It’s not strictly necessary to have in-real-life meatspace face time to build a team, any more than it’s necessary to do escape rooms or trust falls or wine tastings. But that real, unplanned face time does help to build connections that increase meaningful connections and reduce the attractiveness of competitive offers.
Of course, renting a venue and traveling to it for a factory offsite is a special use of budget, and managers very rarely use this to just execute another sprint. Instead, this is usually innovation time: Hack Week, Just Do It Week. There’s almost certainly self-organizing teams, presentations of work done, maybe a friendly competition. New ideas, progress on deprioritized old ideas, infrastructure tooling, experiments with non-boring tech.
Field
Get all the field people together… they do that all the time anyway, QBRs and the like. There’s always lots of time to refine “how do we efficiently sell this thing”, and field engineers are a critical part of that conversation. They’ll go insane if they’re trapped in the room for account manager performance grilling and territory projections though, so they always get little breakouts to go do the same Hack Week stuff the factory engineers do. And again, the meatspace value of team building applies: different humans learning to identify and like each other.
Factory and Field Together
So, if the field and factory engineers are both doing hack week development projects, and the company recognizes that they’re related types on a spectrum with each other instead of different species that shall not mix… then the organization stands to benefit by merging these events. At some of the organizations I’ve worked in, this outcome was a matter of frugality; quarterly business review was at headquarters, there just wasn’t room to isolate the field engineers, and factory wasn’t going to be productive with that interruption, so company does a hackathon. At other organizations, it was intentional: an offsite where field and factory are together on equal footing and encouraged to work together on new projects. Building human connections between people that don’t regularly work together is a broad and nebulous utility; giving them time to ideate and work on potentially useful projects is a sort of internal venture. I can name half a dozen successful products that started in this way. (To be clear, I think that’s only possible in a platform company.) Hackathons can drive useful work on the second tier of critical projects as well. So, one nebulous value proposition and two direct value propositions; pretty good outcome potential for the five to six figure outlay of a week long offsite.
Team Building Activities
There’s some potentially pernicious issues to watch for in the offsite. Work is work, but an offsite puts humans together and keeps them together for their non-work time. Sadly, sometimes jobs end at offsites: people can get drunk, they can make mistakes, and they can get fired. Harassment can happen. Lawsuits can happen. Getting to know each other better doesn’t always end well. Working or personal relationships can be damaged instead of built up.
In order to avoid these bad outcomes, wise event organizers follow some rules. (Note that I am discussing observation as a frequent attendee, not training or experience as an offsite organizer myself.)
- Give people privacy. Thankfully, I have never worked at an organization that has even suggested sharing rooms, but it is absolutely a thing that is done. Say that you have a small startup team in Northern California and you want to have an offsite in Sonoma or Tahoe; you might be too small to get a block from Marriott or Hyatt, but can rent a nice house from AirBNB or VRBO, and it just doesn’t have enough rooms… Personally, I draw the line at working somewhere this small. I know people who have happily and successfully done this thing. I also know people who skydive. I do not want to sleep in the same room as my colleagues.
- Give people downtime, but not too much. The hallway track is a very productive place for me in conferences, and some of those successful hackathon projects I mentioned were started at a bar instead of in structured session. This week at my office, a remote engineer, a founder, a product manager, and a solution architect happened to meet in the office kitchen at the end of the day and have a very productive conversation. Unstructured downtime is generally net positive: it’s when emergencies get handled, it’s when dreams get aired, it’s when questions get answered. Too much of it can lead to boredom and team dissolution; people start asking why they’re here instead of home.
- Keep people busy, but not too much. Planning maximal use of every hour prevents serendipity and recovery. Some people can concentrate non-stop for hours on end, but others need to change channels frequently. Everyone can use a recovery break. In my experience, if downtime breaks aren’t planned for, they get taken anyway and some of the planned sessions turn into ghost towns. That’s not fair to the presenters who get overridden by socio-psychological needs.
- Clear expectations for travel days. A very common pattern is to plan content for three days. Monday is a travel day, Friday is a travel day, Tuesday through Thursday are work days. There are organizations where this plan means that a quarter of the team rolls in late Tuesday morning, and half the team is gone before lunch on Thursday. That’s not fair to the presenters, and turns your Hack Week into a Hack Day. You don’t have to ask people to travel on the weekend, but you do have to be clear and firm on expectations. A wrap-up presentation with the CEO as the last item on the agenda is wonderfully clarifying.
- Activities. Like many introverted technologists, I dislike structured activities. They can be particularly dicey when the physical reality of humans is considered. Once upon a time I was at a company retreat where the incoming leader was really into physical activity, and really wanted to have a team hike up a nearby hill. This was nothing too strenuous, maybe four miles total round trip. Unbeknownst to this incoming leader, one of his new directs had a non-obvious spinal injury, but felt compelled to try anyway. That day ended in agony, and they left the company the next week. You might think that you don’t need to worry about this because your team is small and you know everyone’s medical conditions, current as well as past… but power dynamics and desire for privacy can produce unexpected surprises. It’s not enough to make activities optional. People will feel compelled to use time with the boss or avoid the risk of being left out. The best activities I’ve attended were time at museums, which generally have great accommodations for the mobility limited and allow for mixed levels of social time. While I personally might enjoy a ropes course in the redwoods, that always leaves a handful of engineers on the ground feeling left out.
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