DIY: Facilitating a Strategic Planning Session

I used to moonlight as a professional facilitator. A few months before I was trained and certified, I never knew such a job even existed, but I stumbled upon the opportunity to do it professionally and I found it incredibly rewarding. It was right in line with my natural tendency to generate alignment and consensus in my leadership roles and guiding others through the same process was new and fun. I mostly facilitated strategic planning sessions but also had several engagements that involved organizational assessment and design and team building.  I worked with people in industries I didn’t know anything about, ranging from party equipment rental to non-profit organizations and everything in between, and in doing so I learned that the basic principles that guide the process are nigh universal. I also found it to be very exciting work because the team dynamics and the behaviors and even the occasional dysfunctions were always unique to each team. Perhaps the most interesting story I have in that regard is that I once had to pause a strategic planning session for a family business, because I had to conduct an impromptu private marriage counseling session for a couple who held key positions with the company before we could get back on track.

In the process of learning to navigate the unique dynamics of each session, I ended up developing a robust process, several variations of which I have used for many years with much success in my own organizations, as well as for others who have brought me in as a facilitator. I recently realized that what I take for granted as second nature and common-sense when it comes to strategic planning may not necessarily be very commonly understood by those who have not have had that much experience with it. So, I thought I’d share my process in this post, along with a few suggestions to make it work for you. Before we get into the process, let me say that a great deal of the success of this process depends on the facilitator’s ability to relate to the participants and conduct a session that not only achieves the objectives, but creates a sense of alignment and commitment to the outcomes. If you or your internal resources are not naturally inclined to be effective facilitators, I’d encourage you to engage a professional who is. Good facilitators are usually not cheap, but the fees they charge are miniscule compared to the returns they produce.

Now back to the DIY strategic planning process. This process can be used for a new or existing team that is looking to create or renew their mission, vision, and action plans and/or priorities. It also contains suggestions for steps you can take should you choose to add in more team-building exercises. Generally, this exercise works well for teams of 8-12 people. Larger teams may need to modify the approach in some of the steps to best suit their group dynamics.

The main steps are shown in bold with bullet points under each detailing a few suggestions on how to have each step most effectively serve its purpose:

1.   Alignment (prior to the session)

·      The meeting owner and facilitator get aligned on the objectives and desired outcomes of the meeting.

·      Identify the dynamics of the team to ensure that the facilitator has the ability to identify potential problems that may arise and address them effectively.

2.   Welcome and introductions

3.   Review/Generate objectives

·      First, review the stated objectives of the session with the team. These could include items like mission, vision, action plans, etc.

·      Next, ask the participants to come up with their objectives and state them out loud while you capture them on a flip chart. This gives everyone a chance to express their desired outcome and feel some ownership in the process. If any of the objectives are clearly outside the scope of the meeting, go ahead and call it out and ask if you could place it on a “parking lot” list that will be reviewed at the end of the session when the team will decide in what forum and what timing the item gets addressed. Post the objectives on the wall in front of the room.

4.   Establish the ground rules

·      Rather than making a list of the standard items like, “Respect each other,” and, “Don’t use your cell phone,” ask the participants to shout out characteristics of great meetings they have been to and bad ones they have attended. Capture those on a flip chart in two columns and, when you’re done, ask the participants if they are willing to hold themselves and each other to the standards of the great meetings. Also, ask them if there are 1-2 additional items they want to add to the list. Post the list on the wall in front of the room.

5.   Break the ice

·      An ice-breaker is always good to get people to loosen up and bit and be ready to participate. The activity could be purely a fun exercise or it could involve more sharing to get to know each other better. This depends on whether you would like to add in a team-building element or not.

6.   Celebrate accomplishments

·      Before jumping into planning for the future, it is always good to pause and celebrate what has already been accomplished.

·      One way I like to do this is to divide the group into two smaller groups and ask them to write down as many accomplishments as they can think of on post-it notes, and then have the two teams alternate and, one at a time, have each member put a single post-it note up on a flip chart in front of the room while reading it out loud and having everyone cheer them on.

·      The team that has more ideas leftover when the other team has posted all of their ideas on the board is the one that “wins,” but everybody gets present to just how much the team has accomplished.

7.   Best case/worst case

·      Put two flip charts in front of the room. One titled “Best Case” and the other “Worst Case,” and ask the team to think about what the best and worst case would look like 3-5 years from now.

·      Divide the team into two groups, and have each group work on one chart for 5 minutes and then switch so both groups have the opportunity to input to both list and become familiar with them.

·      Give the team a chance to reflect on these lists and why it is important to avoid the worst case and make the best case happen.

8.   Mission Statement

·      The mission is different than the vision. The mission is the purpose of the organization and why it exists. It is not a point-in-time image of the results or the culture, but a statement that describes the unique purpose that the team aspires to serve.

·      Break the team up in groups of 2-3 and have each team generate ideas and put them on post-it notes and stick them up on the wall. One idea per post-it note, written in sharpies so they can be read from a few feet away.

·      Have the team sort the ideas into categories that go together. This may be a messy exercise with everyone at the wall moving post-it notes but it works well.

·      When the sorting is done, assign each category to a small group of 2-3 and have them write a short bullet point on that part of the statement.

·      Have each team present their statement and generate some discussion but leave the wordsmithing of the details to be done as follow-up after the session.

9.   Vision Statement

·      The vision describes the state of affairs at a certain point in time, usually 3 years out. It is stated in present tense and it involves qualitative and quantitative measures.

·      In preparation for the visioning exercise, you could highlight the difference between change and transformation or do an exercise on lateral thinking vs. linear thinking so that the participants get into the mode of envisioning the desired future rather than focusing solely on solving the existing problems.

·      Similar to the mission exercise, have the team brainstorm various elements of the vision and post them on the wall and categorize them.

·      An optional exercise to guide the visioning process is to list all the stakeholders and divide the team into small groups that begin to work on what would be important to each of the stakeholders at the beginning of the exercise.

10. Current state

·      Have the team describe the various aspects of the current state and capture it on a flip chart. This helps highlight the gap between the current and desired state, per the vision, that will guide the action planning process.

11. SWOT Analysis

·      Before getting into identifying strategies and action planning, it is important for the team to get in touch with the internal strengths and weaknesses, and external opportunities and threats.

·      Post four flip charts around the room, one for each of the SWOT elements. Divide the team into four small groups and have them rotate between the sheets and develop a list for each. Then, have the team come together and go over each of the sheets briefly and discuss them for understanding and alignment.

12. Action Planning

·      This step can either begin with identifying key strategies necessary to close the gap between the current and desired state, or by brainstorming all the actions that must be taken to create the desired future and categorizing them under strategies that each group of activities represents. The approach can be selected based on the specific situation and preference of the team.

·      Either way, have the team brainstorm all the actions they think should be taken, irrespective of the sequence or timing of those actions.

·      Have the team check the vision statement, the mission statement, and the SWOT analysis to make sure they have captured all the right actions.

·      Then have the team move the post-it notes around and organize them according to the desired sequence and timing. Sometimes it helps to have the team do this for a few minutes without talking and debating. This gets the 80% of the actions into the right sequence and timing before the team starts debating and discussing the other 20%.

·      Assign names to the actions in the session or as a follow-up to the session.

13. Closing

·      Go over the objectives and identify the ones that were met.

·      Review the list of open issues that need to be addressed and assign names and dates.

·      Identify and agree on the next steps for the team to continue to move forward with the process and establish specifics of the action plans and review processes to keep the work on track, etc.

·      Ask the team to critique the session and identify what went well and what didn’t.

This framework should give you enough to go on and have a successful session. There are plenty of specific techniques and approaches that can be incorporated in this framework. Depending on the response I receive on this post and the questions I get, I am happy to share more details and possibly an FAQ to your facilitation questions. Please comment below or wherever you read this post and let me know if you would like more information on any aspect of designing or facilitating this process for your team.


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Have a great week! May you Boldly Declare, Courageously Pursue, and Abundantly Achieve the Extraordinary! I would love to hear about your victories and/or challenges. Please leave your comments below or send me an email at amir@theghannadgroup.com.

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