How To Create Better Strategic Plans by Getting Away From The Office

Spring and early summer are often ideal times for teams to engage in an offsite retreat: the days are longer, and people tend to feel optimistic around better weather and the end of winter’s fog (relative to where you live, of course).

As with anything in business, though, planning an offsite that actually moves the business forward and sparks renewal in your organization is going to require addressing a couple of key questions. In this case, it’s the standard questions of any process: Why, Where, What, How, and Who – with a slight twist.

Let’s tackle these one-by-one.

How To Create Better Strategic Plans By Getting Offsite

Why you need to get away to get results

Offsite meetings cost money to coordinate and execute, and some leaders and decision-makers don’t see the value in spending that money because they aren’t convinced of the eventual results.

If you’re equivocating on the idea of an offsite, here are some things to consider.

You know, if you want to get better at anything – be it yoga, or golf, or even your relationship with a loved one – creating space away from your day-to-day distractions to focus on your goals is by far the most effective way to get results.

During the workday, we all tend to operate pretty independently. Even though many organizations talk about teamwork and collaboration, the reality is that when dealing with deadlines, projects, customers, and short-term goals – we’re mostly working solo.

An offsite is a great way to build up that collective spirit and connection between the disparate parts of your organization. Establishing those bonds and connectivity will help drive your business forward in the long run.

Choosing the perfect location for your offsite strategic planning retreat

Determining the best place to hold your offsite meeting will obviously vary based on where your organization is located — someone in Kansas may not be able to coordinate an offsite to Tahiti, for example — but my two general rules are always:

  • Leave the Building (get away from the home base, even if just 45 minutes)
  • Make it a treat (add lots of break time and social activities)

So many planning teams miss the second rule entirely. They plan a retreat at a beautiful resort with world-class scenery and activities and then they create an agenda that forces everyone to stay indoors and work like dogs.

Inevitably, the team returns home and when their non-work friends ask about the trip and say “Oh, that’s such a great resort!” the employee has to respond, “I didn’t see much of it…all we did was work.” This kind of experience can engender disappointment and resentment, which is the opposite of what we are looking for here. The goal of the offsite is connectivity and bonding. Make it a treat!

We often use the ‘Goldilocks Zone’ rules when selecting the location for an offsite retreat:

  • Not too far, not too close. Just right.
  • Not too pricey, not too cheap. Just right.
  • Not too casual, not too formal. Just right.

If you can hit these three ‘just right’ targets, you’ve probably chosen a great location for your retreat.

What to include in the agenda for your retreat

We could write an entire post on the “what” of an offsite retreat. This really is where the rubber meets the road. Today, we’ll focus on understanding the two basic tiers of activities; the work stuff and the fun stuff.

The Work Stuff
One of the most important missions of an offsite retreat is of course, to get actual work done. To discuss and plan what your organization needs to do to achieve its goals over the coming months and years. When thinking about the “work stuff” you need to incorporate into your retreat agenda, make sure that you’ve included these three must-have strategic elements:

  • WHY – Your Purpose and value activities
  • WHAT – Strategy alignment & Goal-setting
  • HOW – Action plan (how you’ll know you’re moving towards the goals)

The role of the facilitator or leader of the offsite is to model the ideal behavior — what is expected of everyone — and he/she must listen, and listen well. If an offsite seems like an exercise in leadership dominance, others will tune out and the entire endeavor will be ineffective. Organizational leaders are often powerful, dominant individuals who occasionally are not prone to listening.

If you’re not confident that the leaders of your organization can provide powerful leadership while creating an open environment for sharing and collaboration, consider hiring a third-party facilitator who can artfully lead you through these activities.


Need help developing your Strategic Plan? Check out our Ultimate Strategic Plan Template. 


The Fun Stuff
This is where you get to be creative! When consider the fun stuff you can work into your agenda, remember that you’re crafting playtime for adults. Look to make time for non-threatening indoor and outdoor activities, and give people options.

You’ll want to allow quiet, reflective time, while also planning opportunities for shared meals and drinks. Remember, this is about getting away from tasks and deliverables and ‘breaking bread’ together: exploring ideas, stories, and getting to know co-workers better.

The Spiritual Stuff
I’m tucking this third piece in here because I think it’s vitally important and something that most organizations aren’t addressing. The spiritual stuff refers to providing alone time for self-reflection, but it also refers to guiding discussions around bigger questions like “Why does our organization exist?”

Creating space where your people have the chance to connect at a deeper level with themselves and their co-workers can be hard to do when you’re only focused on drawing up action plans. Don’t overlook the power these deeper conversations can have in bringing your team together and inspiring them to develop innovative new ideas and strategies for your business.

The perfect length of time for the ultimate strategic planning retreat

The ideal length of your offsite retreat will vary by how much you can spend, but I consider two full days and one full evening to be the absolute bare minimum. Ideally you should aim for 2 days and 2 evenings and if you have the resources consider spending up to a week. It’s a longer time to be away from family and friends, yes, but it creates a greater chance of everything getting done and experiencing real transformation as a group.

You want to come back from an offsite with a strategy and action plan (good for operational side of the business), but also with more connected team members (good for the functional side of getting things done and not grousing or skating on projects). That’s a tall order when you only have two days together.

Who should attend your offsite retreat?

The people you invite to attend your retreat can make or break its success. While its important to have key decision makers and senior leadership representation, its also important to consider the mix of personalities, styles and strong-suits of the individuals involved. Having a synergy of big picture creative thinkers, and practical analytical thinkers will help you develop great ideas and realistic action plans.

Here are the various groups we like to include when planning a retreat:

  • Senior leadership team
  • Up-and-comers or “high potentials”
  • Anyone with ownership of a key business initiative or service/product line
  • Your trusted strategic facilitator

If you haven’t used an outside facilitator in the past, let me just say this; it can be difficult to have an offsite coordinated or lead by someone internal to the organization. By definition, that person is baked into the politics and relationships already in place — and their actions as the leader might reflect that. An outside or third-party facilitator is neutral. Even though they are getting compensated, he/she isn’t tied to the politics, pre-existing relationships, or power core of the organization. His/her only goal is effective facilitation towards business and personal growth. That’s a powerful advocate to have.

If you’re committed to creating a strategic plan that isn’t just a repeat of what you’ve always done, then it’s time to pack up and hit the road! Plan an offsite strategic retreat for your leadership teams that allows them to; break out of their everyday routines, develop deeper levels of trust and collaboration, all while having a little fun. The results might just amaze you.


Need help developing your Strategic Plan? Check out our Ultimate Strategic Plan Template. 


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