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To ensure a successful strategic planning meeting, you need a well-defined agenda, actively engaged participants, and expert facilitation. These key elements will help you achieve the desired outcomes, propelling your organization forward with purpose and precision.

• Difficulty:  Moderate

• Time to Complete:  2 Weeks (Planning to Execution)
• Workshop Duration:  Refresh (quarterly): 0.5 - 1 Day; Alignment & Definition (annual): 2 Day Options
• Target Audience: Your leadership team
• Facilitator: Recommended to have some one not part of the core leadership team.  This enables your team to all participate while someone else is taking care of the details and directing everyone. An expert facilitator will be able to move the team along as well as draw out thoughts and ideas from all participants.
• Team Geography: In-Person is most effective but this agenda can be run as a virtual strategic planning meeting

What is a Strategic Plan?

A common term many use to mean several things so lets align on the basic elements. A strategic plan should include your long-term vision, your mid-term goals, and the tactics to achieve those goals.  

• Vision = Why we are here
• Strategic goals = What we are going to do to achieve those goals
• Tactics = How we get there

Your long-term vision is where you want to be in 10 years.  It should be inspiring, aspirational, and even a bit scary.  The vision is what you want everyone to rally around and to move toward.  Your vision is something that shouldn’t change often and is the common thread you beat towards year-after-year. 

Your mid-term goals are the objectives that march you toward that vision.  They ideally are a little ambition and are set to be achieved in the 2-5 year time horizon. You should evaluate these goals at minimum on an annual basis to ensure you have the right strategy in place to meet your vision. A good goal should include the objective of where you want to be and the results you expect.  

Finally, a strategic plan is nothing without a plan to achieve them. It should include tactics or an implementation plan for how get there.  Your implementation plan should include all various departments (such as accounting and finance, marketing, and human resources) within a company to accomplish its goals. The plan should also be evaluating your capacity and the return on each program.  Prioritize against the return, effort, and capacity so you plan is both achievable and gets you the highest return.

When to run a strategy planning workshop

Indications you may need to define, reevaluate, or refresh your strategy:  

• You have not articulated a vision

• Your team cannot state your strategic priorities
• Your employees don’t know why they are doing certain projects
• No one on your team has the 30 second elevator pitch down of why you exist
• People are unsure how their job is fitting into the direction of your company

Cadence for running a strategic planning meeting

Annually: The broader, deeper strategic planning process should be done annually.  This challenges if you have the right goals allowing for you to evaluate changes in: macro-economic conditions, customer expectations, competitive landscape, technology. It also introduces you opportunity to learn from what you have done: what went well, what did we not do well, what should we stop doing.

Quarterly: To keep alignment and ensure you are executing, do smaller planning sessions on a quarterly basis. This incorporates accountability into your regular rhythm of the business.  It also allows for your organization to be more agile.  The market and technology are changing at such a rapid pace, you need to stop and reflect often if you are working on the right things.  Setting these up on a regular basis provide space and permission to adjust your plan to respond accordingly.

Strategic Planning Meeting Agenda

Creating a good organizational strategy, is a bit like planning your once-in-a-lifetime trip. This isn't a solo journey, therefore each agenda item requires participation from everyone.  Facilitate the meeting so you ensure that everyone is aligned before moving onto to the next part.

• Part 1: Set your Compass: Define the North Star 
• Part 2: Define your destination: setting the 3-year strategic goals
• Part 3: Find your starting point: Align on the current situation
• Part 4: Mind the Gap: Identify what you need to get there
• Part 5: Map the Course: Layout the roadmap

The Step-by-step guide

0. Pre-work: Preparing for the Planning Workshop

To make facilitating a strategic planning session the most effective, you need to do some preparation ahead of the meeting.  Engage a small team to do research. Walking into the workshop, have a summary of your internal and external environment.  An understanding of you market, trends, competitive position, opportunities and threats that may exist, and your operational strengths and weaknesses. This will take a couple weeks.  But don’t spend too long, it’s better to have the workshop then spend forever in analysis.  If you time box it, then you walk in with the best available information to make informed decisions. Make sure your team has a summary packet a day or two before the workshop.  

Recommended summary package: financial performance history, Product/Service Line Scorecard, technology and industry trends, all up company SWOT (Strengths, weaknesses, opportunities, and threats) analysis.  Bonus would include customer experience evaluation based on customer interviews and surveys, operational scorecard based on a third party review, and an employee experience evaluation based on employee interviews and surveys.

1. Set the compass: defining the North Star and creating a shared vision

Start out with setting ground rules. An effective strategic planning meeting has engagement and focused participants.  Ground rules might include items such as no phones or laptops while you are in the meeting and agreeing everyone is welcome and expected to contribute their ideas. Once these best practices have been set and agreed to, it's time to start the first section on the agenda.  

The most successful strategic planning meetings start with some inspiration.  People can often get mired down on what is not working.  They will also likely be walking into the room with their tunnel vision of what they and their team has been working on.  So starting with an exercise that gets them thinking bigger than the immediate will provide the energy and atmosphere to get everyone excited about the plan you will ultimately walk away with. 

Activity: Icebreaker - Your Awards Ceremony

You can either jump into the first activity or start with an icebreaker.  An icebreaker that helps to start your stakeholders thinking in innovative ways, is one that has them thinking about the future. Try asking each person to think about themselves ten years from now.  If they were attending an awards ceremony for their greatest achievement, what would they be getting?

Activity: Design your Magazine Cover

For this activity, have your team break into groups of 4-5 people.  Each group will brainstorm your organization's magazine cover of the future.

Ten years from now a respected magazine is featuring your organization for its accomplishments.

• What is the headline? What do we want to be known for?
• What do you want customers to say it is like to work with you?
• What do we want our competitors to say about us? 

After each team has shared with the group their cover's, the facilitator should guide you in identifying common themes.  You likely won't come up with the finalized vision and mission, but you should be aligned on the general direction and attributes of what the vision looks like.

2. Define your destination: setting the 3-year strategic goals

Keeping in mind the 10-year magazine cover, let's look at what we need to accomplish to move towards that vision.  This next activity is a brainstorming session that can be done in the larger group or you can breakout into teams again.

Activity: Postcard from the Future

3 Years from Now:

• What we are happy we accomplished is...
• What led us to success was...
• The challenges we overcame were...

Instructions: For each section, team members should add sticky notes to contribute their thoughts.  If you are a remote or hybrid team, use a virtual whiteboard tool.  The facilitator will review the section as a group and align the team on the top goals and objectives. 

3. Find your starting point: Align on the current situation

Where is 0,0 on your map?  Now that we have a direction, it’s time to understand your starting point.  Now is the time to review the summary of the preparation work you should have done. Do a quick review of highlights from this.  Allocate about an hour for this read out. Time box it so you don’t spend forever.  It is helpful to follow the readout with a retrospective exercise such as a Rose, Bud, Thorn or Sailboat retrospective.

4. Mind the Gap: Identify what you need to get there

Based on the Vision (part 1) and the direction (part 2), along with the understanding of what your current strengths and weaknesses are, start designing the work you need to do. Breakout by areas decided by group. Each team looks at current state and decisions that led us to today. Identifies what needs to be done to achieve the 3-year success.

• Customer: What has hindered us? How do we need to engage with the customer differently? How will potential customers know us?  How do we ensure we have lifetime customers?
• Go-to-Market: What is getting in our way? What marketing support do we need?  How is this different  from today?  What sales support do we need? What does that mean for our current direction?  What investments do we need to stop or start?
• Process & Tools: What processes are getting in our way? What processes do we need to establish? What hidden process should we formalize?
• People & Organization: How is the current organization supporting or detracting from this? What mindset do we need in our teams? Leadership?  Where do we have people gaps? What skills do we need to develop?

5. Map the Course: Layout the Plan

In the last activity, you outlined the general work that needs to done.  Now you will start to prioritize that work and develop action items to move forward. 

Activity: Roadmap what you hope to accomplish

The facilitator should provide you with a template of a timeline.  On this timeline, start laying out the work.   

• Timeline: Present - Year 1 - Year 2 - Beyond Year 2
• Year 1: The first year, you can layout out specific objectives and outcomes you need to accomplish. Think about what is most impactful for moving you toward your strategic objectives.   Balance this with effort.  Prioritize those with highest reward, lowest effort first. 
• After you have laid out you ideas on the timeline, think about what you need to accomplish this work.  Allocate resources to each activity. Review the resources you allocate against what is realistic. 

Once each team is finished laying out their plan, share with the group.  Identify dependencies between groups.  Align as a team what you objectives will be for the next quarter.  In your next strategic planning workshop, use this as your starting point.

Resources

• HBR's 10 Must Reads on Strategy (including featured article "What Is Strategy?" 

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