When was the last time all of your startup’s management team came together to take a step back from day-to-day minutiae and think big picture?  I think it’s actually incredibly valuable for startups to occasionally, and regularly, have offsite planning sessions.  Unlike at “big companies,” a startup offsite isn’t about a boondoggle, it’s not about fancy hotel rooms, nor is it about silly team-building exercises so dilberts in accounting can interact with dilberts in marketing.  Instead, a startup’s offsite provides the leaders of a startup with the opportunity – and excused absence from one day’s operational details – to review where the company has been and point it in the right direction for the future given that context.

The benefits of an offsite for a startup include:

1. Challenging assumptions.  In a startup it’s always about executing.  Part of the elegance of the startups machine is that there are explicit and implicit assumptions which under which people are empowered to make the right choices and judgment calls on everyday decisions.  It’s helpful to challenge them sometimes, not to waiver in strategy, but ensure that they’re on right track and course-correct if need be.
2. Shifting thinking & responsibility out of silos into where it’s more appropriate.  It’s natural for people become heads down and worry about only what they’re supposed to do, even in small nimble organizations.  That’s their job.  But in a startup, things are fluid.  Product is marketing is technology is operations is sales; they’re really not wholly separate functions.  Bringing everyone together to talk about direction of the company places all these functions under a collective brain-trust.
3. Helping identify what’s missing.  As an individual in an organization, it’s harder to see what isn’t being done than it is to see what is being done (sometimes incorrectly).  Again, collective minds together can overcome what one person (often even the CEO) can’t perceive.
4. Empowering leaders to set real stretch but achievable goals.  When everyone is on the same page about what constitutes success for the overall company, it’s easier to set lofty but achievable functional goals because there is context to them.
5. Re-energizing excitement.  Even in a startup, daily activity can cloud what everyone together is building towards.  An offsite reminds people of bigger picture and helps with intrinsic motivation.  And yes, it can build a team atmosphere even without water-baloon toss.

The challenge with startup offsites is all of the demands of a company of this nature don’t stop that day.  I think especially because of that fact, it’s important to physically get out of the office, even if it’s to the conference room of an investor or that of another friendly local startup.  It is called an offsite for a reason, after all.  (While we’re atypical ourselves at NextView Ventures as a “startup VC,” we think offsites are essential and conduct them consistently quarterly – always somewhere outsite the office.)

Also, I believe that it’s necessary to having someone planning and drive an agenda to lead sessions, otherwise there’s real risk of wasting productive time.  Leadership buy-in into an offsite is key, and not just from founders/CEO, but everyone evolved investing in the day’s process.  (As an investor and board member, I’ve participated in startup offsites for portfolio companies, which can be helpful in adding an additional partially-outside perspective, but nowhere near essential and sometimes perhaps distracting.)  I’ve seen many portfolio companies hold offsites of various sizes and shapes (in terms of people involved & structure), all tailored to the unique situation of their company.  In the end, what is put into a startup offsite directly corresponds into what comes out of it, which if done effectively, is quite a bit.