How to Facilitate a Strategic Planning Session

Published On: November 27, 20226 min read

As the saying goes, Rome wasn’t built in a day. Similarly, a solid strategic plan doesn’t just happen. It requires data-driven thought processes, synchronization among all those involved, and effective review. The best way to hash it all out is with a strategic planning session.

What is strategic planning?

Your strategic plan defines your goals and how you will achieve them. Strategic plans build resilient teams and create opportunities for innovation, keeping everyone in sync with the company’s desired vision, values, and purpose.

Many companies conduct strategic planning sessions, but not all get them right. We’ll share more about how to facilitate a great strategic planning session. First, it helps to understand the bigger picture.


What goes in a strategic plan?

A strategic plan may vary depending on the organization. Generally, you want start with a high-level overview that focuses on company attributes. It should also reflect forward-thinking information such as your unique vision, mission, and desired future value propositions. You can then use this plan as a guide for breaking down your initiatives into actionable steps.

Generally, your high-level strategic plan will include:

Company Overview—This section includes information about historic milestones and achievements, products and services, market outlooks, core competencies, financials, sales statistics for recent years, and current high-level key performance indicators (KPIs).

Strategic Analysis—This is a detailed analysis of internal and external environments. The intent is to understand the business context of what’s happening within the company and what’s happening in regard to external factors. There are a number of things that are considered:

  • Current vision, values, and company mission
  • Departmental challenges
  • Analysis of external factors using a PESTEL analysis chart (PESTEL is an acronym for political, economic, social, technological, environmental and legal).
  • Competitive analysis
  • 7-S analysis, (This involves an analysis of skills, style, strategy, staff, structure, systems and shared value)
  • Market growth/share matrix

SWOT Analysis—SWOT (strengths, weaknesses, opportunities, and threats)

Strategic Objectives—These are statements about what’s critical for the strategy. The strategic objectives connect to the measures and activities the company will take.

Vision Statement—Describes where the business will be in 5-10 years time.

Mission and Core Values Statements—Describes what the company hopes to achieve in the future.

Future Business Model—This section is about how the company will do business. Think about how the organization creates, delivers, provides value, and engages in business. It considers social, economic and other contexts.

Future Value Proposition—Thinking from the future state a company considers why their customer chooses them, their products and services.

High-Level Goals—Identify high-level goals that link to the strategic objectives, and detail the projects that support reaching the goals.

Action Plan—This section includes manpower, timelines, KPIs, and progress tracking. Once you’ve built your high-level strategic plan, the next step is to break it down into smaller, more specific bites that help define which goals are most important, and which steps need to happen to achieve them. This is where annual and quarterly planning sessions come in.

Preparing for your quarterly planning session

The first thing to know is that the purpose of an annual or quarterly planning session is not to redo your high-level strategic plan. Rather, it’s to use that plan as a guide for your more frequent sessions to help ensure that shorter-term goals and initiatives are reflective of the information in your high-level plan.

Leaders will often enlist help from an external business specialist or coach to help facilitate a structured planning session. Meeting on a regular basis provides more frequent review opportunities and allows teams to pivot as needed. They are the hands-on team working on the day-to-day activities in accordance with the strategic plan.

There are a few things to consider when facilitating the strategic planning session. First, you’ll need to work out the logistics. Consider the following:

Schedule it—Choose the date and book it.

Select the facilitator—The facilitator is the person who creates the agenda, prepares the material (any slides, visuals), arrives early, sets up, and checks to make sure any technology is working. They also open the discussions to keep everyone on schedule and focused on the right topics. If the facilitator is someone on the team, it’s key to pause and remember to get their input as well.

Select a location— It’s common for strategic planning sessions to be held off-site. This limits distractions that may come from daily operations. Being off-site improves focus. It’s important to select a location that has the setup required.

Choose a meeting coordinator— The meeting coordinator will handle the logistics of the meeting. Any location bookings, equipment rentals, and travel requirements will go through the meeting coordinator. This person is very detailed and creates a seamless meeting while working behind the scenes before and during the meeting.

Material Prep— The CEO and facilitator will create the agenda and prepare the materials. The agenda is based on the parts of the strategic plan. It’s important to understand the boundaries of time and be realistic about just how much the group will get done.

Communicate— Meeting details and agenda should be communicated ahead of time. The goal is to get everyone thinking strategically and when they see the outline for the strategic planning session, their creative mind engages ahead of time. Remember, strategic planning sessions involve thinking big, creative ideas.

Clarifying goals & expected deliverables

A strategic planning session creates an atmosphere for open and honest communication. The goal of the session is to get real about where things are at, inspire a future vision, identify the gaps, and develop a plan to get there.

The clearer the facilitator is about the goal and purpose of the meeting, the clearer participants are throughout. Things may get off track but a clear goal and defined purpose are easy to come back to.

Selecting the appropriate team member for each task provides accountability. When individual roles and responsibilities are defined, team members are more productive and it’s easier to stay focused. It also helps eliminate mishaps in miscommunication is every team member knows who is responsible for which target.

Using software to run your strategic planning session

The challenge lies in creating a plan that is realistic and achievable, and then getting your team to buy into it and follow through on the actions. Many businesses turn to software tools to help them with this process. SaaS tools can provide a “virtual boardroom” where stakeholders from all over the company can come together to create or improve the plan. They can also help you connect the long-term goals to the everyday actions of your team.

Goal management software like Align provides a space to store and update your plans. It also provides team meeting tools to help facilitate the session. You can essentially run your planning session right out of Align, having swift access to priorities, targets, KPIs, and all other critical documentation.

Learn how Align can help you create or improve your strategic plan and connect the long-term goals to the everyday actions of your team.

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