Let me set the stage.  You started your company 12-18 months ago with incredible energy, formed a great team, raised some money, and got to work.  You talked with customers, implemented scrum, drank a lot of coffee, shipped some product, held some launch parties, and attended a ton of entrepreneur-focused events.  All was great, for a while.

Then you started noticing some signs that things weren’t all rosy on the home front, and fear started creeping in:

• you felt like your team wasn’t working long enough hours during the week, and God forbid put in a weekend effort, even though sprints ended with undone tasks
• other startups seem to have much better cultures, and overall get more done
• you wonder why team members don’t stretch themselves more to take on additional tasks, or try new things
• kitchen-cleanup never seems to be done by certain people
• certain team members log 5x the bugs of anyone else on the team
• the team is talking less with one another, and snapping at each other more often
• folks aren’t as enthusiastic to attend happy hours together

If any of these are familiar, I’d recommend that you consider holding a team offsite, and make offsites part of your regular routine.  You may feel like they are a bit Dilbertesque, but I’ve personally found them to be very helpful, and I’ve also given this advice to other CEOs at rapidly-growing ($10s of millions in revenue) startups, and they came back with very positive feedback as well.

Why hold offsites?
They are a great way to reset the team – think of them as another CEO tool to engineer for peak efficiency.  You get a chance, out of the office, to (a) share high-level successes and failures, (b) set expectations, (c) get feedback from the team, and really, to remind everyone that they’re important parts of your unique culture and thus have both a right and obligation to actively participate (this is one of the reasons they’re working for you and making less money than they would at a big company, right?!?)  And, hopefully you’ll have some fun as well.

When should you hold offsites?
See above 🙂  It’s possible to just do them ‘as needed’; but you’ll likely find a normal flow to needing them.  My experience has been that they make sense every 4-6 months, as a certain amount of scarring builds up from the stresses of sprints, bugs, and realized inefficiencies.

How do you organize your offsite?
Obviously, you’ll come up with your own flavor over time.  But, if it’s your first one, and your team is 3-10 people, this is what I recommend as a rough template.

First, I’d recommend requesting/requiring ‘writing assignments’ from all team members.  They don’t need to be long (a paragraph or two can answer each, and grammar isn’t important).  Send these out a few days ahead of time, and ask them to email their replies to you the afternoon before the offsite.  Examples of questions we used:

• Why did you join this startup?  What do you want to accomplish?  What’s success for YOU?
• What do you expect from your co-workers?  And what should they expect from you?
• Rank our core values in order of importance/relevance.
• Are there any we should remove, or add?
• What future features/product changes do you feel strongly that we should consider? (they don’t need to be on our current roadmap

I promise that you will be inspired by the answers you receive.  This simple exercise will remind everyone why they joined your company, and let them say in their own words what their goals are, rather than listening to you set the agenda.  And, they’ll help you course correct, as a team, if there are competing agendas.

Rough time/agenda:

• 30-60 minutes (probably a few slides prepared by you to make it easy to follow) – review goals, accomplishments, failures (not finger pointing – they are what they are)
• 2ish hours – have people read their answers to the writing assignments.  Do one question, with answers from everyone, before moving on to the next question.  There will definitely be some overlap in answers, but I promise you that the team will be inspired to hear the goals and expectations, coming from the individual team members themselves.  You should take notes, listening for themes that should be addressed, or issues that you can quickly resolve (do this later in the offsite, rather than real time, so that you allow everyone’s voice to be heard — this also allows you to stay out of tactical shifts in real-time).
• Team lunch/BBQ – make it together (usually this is easy if you hold the offsite at someone’s house, or at a place where you can cook outside).  Invariably you’ll have a few team members who are more adept in the kitchen, and can drive this.
• 30 minutes – review what you heard from everyone in the morning.  Are there themes that arose that can or should be addressed?  Any surprises from people?

These last sections could have some prepared slides to review with everyone:

• 30 minutes – Review how you think your business model works (with actual metrics).  Get reaction to this — is it reality?
• 30 minutes – Review current Product Backlog / Quick-Hit Backlog (top 20-40 of each).  How do these mesh with earlier discussions?  Any changes needed?
• 30 minutes – Discuss ‘how’ you get work done.  Review your processes (scrum, release cycles, etc). Are changes needed?   Longer/shorter?  Work hours/effort needed/expected?  (you may be surprised that others want to see bigger efforts as well!)  Make some changes based on what the team’s telling you, if you all think it will help you achieve your goals.
• 2-3 hours – true/fun activity.  Don’t force it.  Figure out something that fits with your culture, and includes everyone.  For TeachStreet, this may have been us taking a class together (and then going for beers).  But the connection to our culture/values was important, even here.

What do you do after the offsite?
I think it’s important that on the day after the offsite, you summarize what you heard (get feedback if anyone thinks you missed anything important), and share/implement changes or next steps immediately. Don’t lose the momentum from the day!  This can be a powerful way to reset expectations, and make it clear that everyone shared in them.

These are some examples of changes I’ve seen, or been part of.  You’ll come up with your own:

• developed our list of core values
• implemented new sprint cycle length because our initial one was too short (we were spending too much time planning, and too little time building)
• started new process to share work product regularly, on Friday afternoons
• added a new comped snack policy (people asked if we could have snacks — we quickly said “sure – $100-$150/week in snacks – only requirement is that we all shared the responsibility to place the order each week”)
• new work-hour expectations (this is a never-ending challenge!)

Hopefully you’ll come out of the day with more collective energy, and renewed team focus.  And in a few months, you’ll likely need to do it all over again, for many of the same reasons.  Your organization is an evolving organism, so you need to constantly shed the bad behaviors, and try new ones that feel right for your team.  Good luck!

p.s. Please share any offsite tips in the comments.