Your Template for An Effective Planning Retreat

Sep 21, 2017, Written by Sue Miley

Planning Retreat

When asked about doing an annual planning retreat with their team, one client responded, “No way, I am not doing that again. I would throw out a topic and eight pair of eyes would stare back at me. ‘Whatever you think’ was the most I got.”

Another client said his was like a giant all-day complaint session. Everyone could readily say what was wrong, but no one had any idea of what the company should do about any of it.

Without structure, a planning meeting can be frustrating, and feel like a waste of time. However, effective meetings can be the catalyst to significant results.  Ten years into our business, we have had many, many successful planning sessions with these and other clients. The goal is to have a well planned  kick-off meeting for the full end-of-year planning process we wrote about here.

Here is our tried and true format for an official planning retreat:

An Offsite Planning Meeting

I always recommend that the first meeting is offsite. An offsite meeting minimizes interruptions and enhances creativity. There is something about a new setting that helps us think outside of the box. Creating a casual comfortable environment also inspires openness and new ideas.

Team-Building Exercise or Icebreaker

Whether your team has been together for a month or 10 years, I still always recommend some kind of ice breaker or team-building exercise to loosen everyone up, set the stage for collaboration, and start the meeting off with some fun. The time you have allotted for the planning meeting would determine the time and depth of this section. If you have at least a day, and definitely if you have a two-day meeting planned, I would do a more in-depth educational team building segment. Three of my favorites are:

I like having assessments because the team learns a lot about themselves and each other. It is informative and fun. And each of the assessments also help individuals to learn how to work with each other better.

SWOT Analysis

SWOT stands for Strengths, Weaknesses, Opportunities, and Threats.

Strengths and weaknesses are internal. What strengths does your company possess that will help you achieve your vision and plans? What weaknesses may impact your ability to achieve your vision and plans?

Opportunities and threats are external. What is happening in the market or industry that may provide an opportunity for your company? What market or industry threats may negatively impact your business?

The process should be done with your entire group. We have a SWOT template that you can hand out in advance to get your team thinking along with some tips for an effective SWOT Analysis:

  1. Handle it like a brainstorming session. Allow everyone to participate. Don’t debate the validity of any idea provided. You will be able to go back and prioritize later. You can ask for clarification, but you don’t want to have the time turn into a debate over one area of weakness for example.
  2. The more the better, even with weaknesses. I have seen teams get stressed if they start to see too many weaknesses. However, the good news about weakness is that it is within your control to fix or enhance. Threats feel a little more out of our control.

We’ve provided a SWOT Analysis for you below! 

Key Initiatives:  SWOT Analysis Review and Prioritization

Now you should have a long list of strengths, weaknesses, opportunities and threats. I would imagine the list is too long to focus on leveraging all of your strengths, enhancing all of your weaknesses, and maximizing all of the opportunities in the market place. The goal in this section is to prioritize the most important things to focus your company resources and your teams attention.

The size of your team will usually dictate the number of key initiatives you can take on in any one year. The company as a whole should be moving towards 3, maybe 4, key initiatives. If you have a strong management team, each of the managers may also have a smaller initiative that their team could be working on.

One way to get consensus on the team’s priorities for key initiatives is to have them all choose their top 5. I literally have them walk up to the flip chart pages and mark their top 5. Usually there are 2-3 that everyone picks. This process results in finding the very top key initiatives for the company and builds buy-in from the management team.

Organization and Capital Expenditures

There isn’t time to build an entire budget during this planning retreat, however, while everyone is together, it is important to discuss key resources needed to execute and support the plans.  Usually this is people or capital expenditures.

This is another segment of the plan that helps bring unity to the team. Everyone on the planning team hears the needs expressed and discusses the justification. The requests are still just requests. Until the budget is complete we won’t know if we can afford the resources or how much of an investment will be required.

The items still may not make it into the budget, but we know what is most important to the team in order to achieve the objectives and execute the plan well.

Next Steps

Before we leave the planning meeting we set the calendar for the other steps in the annual planning process. You can find the full annual planning process in last week’s blog here.

Next steps need to include:

  1. Who is responsible for leading one of the chosen key initiatives and will coordinate developing the budget for this initiative and the action plans for implementation.  We need a leadership owner!
  2. Dates for follow-up meetings and/or due dates for assumptions and budget input.
  3. A target date to complete each step of the process.

When we leave we will basically have milestones set for the remainder of the year.

Whew!! Just writing out the plan for the meeting is a lot… But I assure you, the business results when you make a plan and work your plan are always better than when you have no plan. Just having goals and key initiatives laid out help you to move toward their achievement.

Take it one step at a time, provide a clear vision of the company’s future as discussed in our blog two weeks ago, make it inclusive of all key members of your team, and… try to have fun!

Outsource:  Facilitation for Your Meeting

Unfortunately it isn’t wise to actually outsource all of your planning.  Your team will be executing so you want them to be a part of the planning.  Plus, your team knows your business best. However, sometimes it is helpful to outsource the facilitation of your planning meeting. The benefits are:

  • You the owner get to participate as a 100% participant. You don’t have to facilitate.
  • You can hire someone with expertise that can share knowledge in your team-building section and in the planning process itself.
  • You have someone who can listen with an objective (not emotional) ear and can point out inconsistency, help resolve disagreements or conflict, and can make sure that everyone’s ideas get heard.
  • You have someone who can manage the time so you get everything accomplished during the meeting that you want to get done.
  • You don’t have to be the one keep everyone focused and stopping the rabbit trails.

If you would like help facilitating your annual planning meeting/retreat, call us. We have worked with many, many small business owners and teams and would be glad to share how we can help with your planning process.





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Sue Miley

Sue Miley MBA, MA, LPC helps small business owners build successful businesses on a foundation of Christian values. After 20 years in business, and 10 years as a Christian counselor, Sue uses a combination of faith, business and psychology to help clients in business and in life.

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