Off-site Planning Retreat

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Sei-Wook and I arrived in Livingston Manor, NY earlier today for our off-site planning retreat. The house, which we found on AirBnB, is in the Catskills region. It’s in a remote area on a lake. The lake is frozen pretty solid.

This is the second time that Sei-Wook and I are taking a couple of days away from the office to pow wow about various topics. Here are a few topics that we plan to cover on this trip:

  • Financial planning for 2015: setting goals, examining expenses, and forecasting revenues
  • Better systematizing employee compensation
  • Brainstorming ways to more effectively centralize training and knowledge for our different departments
  • Exploring ways to better manage our client information through a customer relationship management (CRM) software like Salesforce

Our first off-site, which took place at an AirBnB home in Hudson Valley, was very fruitful. We had time to talk deeply about the direction of the company and also share our perspectives on various strategic initiatives. The most valuable piece was that by the end of the two days, we felt a sense of alignment in knowing the priorities of the business.

Not too long after we resumed our hectic day-to-day schedules, we found ourselves wanting to talk about new topics that had popped up as well as revisiting some of the decisions we had made on the prior trip. With the holidays coming up, we decided to schedule one more retreat.

Rather than having fried eggs and bacon, I made a proper soup this time around.

Rather than having fried eggs and bacon, I made a proper soup this time around.

Doing something a second time means we can improve on our initial experience. Here are some adjustments we made:

  • Rather than having long 3-hour sessions to tackle big topics (e.g. “what is our mission”), we opted to for 1-2 hour sessions with the hope that we would approach each with greater intensity and focus.
  • We planned our meals in advance and did a much better job buying groceries. Last time, we subsisted mostly on fried eggs and bacon; this time, we have enough ingredients to make a few tasty meals. This afternoon, I made a rustic kale and sausage soup.
  • We’re going to avoid reading emails and checking in on the team in-between sessions so we can keep clearer heads and think about our long-term needs.
A big sturdy table is a must for us to do our work.

A big sturdy table is a must for us to do our work.

Part of the fun with these off-sites has been staying at very cool AirBnB homes. We’ve stuck to a set of criteria when looking for options:

  • Good Internet connection
  • A nice kitchen
  • 2 bedrooms, preferably 2 bathrooms
  • A big sturdy table to do work on
  • 2-3 hours outside of the city
  • In a quiet area surrounded by nature
A spacious, well-stocked kitchen makes all the difference.

A spacious, well-stocked kitchen encourages cooking on these trips.

This Catskills home is pretty sweet. It’s cozy and has a really beautiful view of the lake. I saw that there was even a New York Times article written about the home, which was cool to find out after we booked it.

I’ve worked with Sei-Wook for over 8 years, and while we’ve occupied the same office space for most of that time, it’s surprising how little of that time was actually used to engage in meaningful, thought-provoking conversation. Over the past year, we’ve adopted a few new routines to help facilitate more dialogue and collaborative planning. This includes a weekly breakfast meeting every single Monday at 8:30AM and also a couple of “War Room” sessions during the week, one to review business development and the other to talk operations. And while these have been incredibly helpful, there’s still so much more to cover. I think these off-site trips are a welcome addition to the mix, and I hope it’s something we can keep up in 2015.

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