How to Facilitate a Strategic Planning Session [2024 Strategic Planning Workshop]

As strategy planning experts, we often get asked how to run a strategic planning meeting, as great strategic meetings don't happen by accident. They occur because someone is committed to THINKING through the purpose and outcome, PLANNING all the details, and DOING the challenging work of running the meeting. This is the role of an excellent strategic planning facilitator who can help you better define your strategy, create a winning annual plan, and leave with an action plan to get your yearly initiatives done. A significant amount of difficult work needs to be done to facilitate a planning session. These same techniques should be used for in-person and virtual strategic planning sessions with your management team. While you can run a strategic planning session independently, many prefer to bring in expert facilitators to get the highest return on investment. If you've never run a strategic planning workshop, it is too valuable of a meeting to try on your own. Think of how much salary you have in the room, taking your team away from their "day job." You are burning payroll if you don't maximize your collaboration to define an effective business strategy for the entire organization.

At Rhythm Systems, our consultants are trained strategic facilitators who are crucial in strategic planning. They are planning experts who help you get the most ROI from your meeting with their expert facilitation skills. We have facilitated hundreds of successful Strategic Planning, Annual Planning, and Quarterly Planning sessions for our clients. In this blog post, we will share expert insights from these sessions so that you can scale up your company. Strategy planning (and expert facilitation) is vital as the longer-term strategic priorities drive the shorter-term goals, projects, and actions with complete organizational alignment.

Note to strategic CEOs: Along with our ability to educate, coach, and facilitate specific content and methodology during on-site sessions, one of the main reasons CEOs choose to bring us in to run their sessions is so that the CEO can fully participate and implement their 5 year plan template. It is impossible for a CEO to effectively facilitate a session with all the stakeholders and fully participate simultaneously. The CEO's contribution and participation are significant in reaching the desired outcome. Session facilitation is an extra burden that is better placed on another team member or an expert facilitator. You should learn to be a good facilitator by using tips and tricks or consulting with us to see if hiring an expert makes sense.

Free Guide: How to Facilitate a Strategic Planning Session

Strategic Planning Facilitation Step 1: THINK Through the Purpose and Outcome of the Meeting

Stephen Covey advises us to "begin with the end in mind." What is the purpose of this meeting? What do we hope to accomplish? Who should attend? What are our strategic objectives for this workshop? What work should the meeting participants get done before the meeting (research and homework)? What are the specific outcomes or outputs we are looking for from this strategic planning session? What is the role of a facilitator in a strategic planning session? Do we need a plan B for a potential 2025 recession?

Creating an Objective Statement that you can share with the rest of the team in advance is a great way to ensure everyone who attends the meeting has shared goals and expectations for your time together. It will also clarify things for you as you move into step 2 and begin planning for the session. Make sure that this aligns with your mission statement. This differs from team meetings; setting expectations upfront is critical for your strategic objectives. 

An Objective Statement consists of three parts:

Part 1: TO: (What is the action? What will you do? Start with a verb.)

Part 2. IN A WAY THAT: (How will you do it? List criteria, scope, involvement, success measures, specific tactics, side benefits, or any other relevant information. Use bullet points.)

Part 3. SO THAT: (Why are you doing this? Why is it essential? What is the main benefit?)

Sample Objective Statement for one company's Quarterly Planning Session

QUARTERLY PLANNING OBJECTIVE STATEMENT

TO: Conduct a practical strategic planning session

IN A WAY THAT:

• Brings the Senior Leadership Team together for two full days to develop an effective strategy
• Highlights the previous quarter's accomplishments
• Updates and advances our Annual Plan and long-term goal attainment
• It allows us to discuss-debate-agree critical topics as a team
• It prepares us to overcome any potential obstacles to hitting our year-end goals
• Identifies 3-5 Company Priorities, complete with owners and clear success criteria
• Identifies clear Individual Priorities for each member of the leadership team
• Prepares us to begin thinking about next year's Annual Plan
• It allows us to identify strengths and weaknesses
• Answers the key questions facing our company and industry
• It helps us clearly define and communicate our business strategy to the entire organization
• Fun ideas for strategic planning are always considered and change up the energy in the room

SO THAT: We finish this year strong and set ourselves up for a solid start to next year.

How to Facilitate a Strategic Planning Session Video

When it comes to facilitating a strategic planning session, having a well-thought-out plan and being prepared is key to success. In this video, we will explore the essential steps and strategies to ensure your session runs smoothly and effectively. From setting the date and selecting the right facilitator to choosing a suitable location and preparing the meeting material, every detail counts. By following these expert tips and guidelines, you can lead your team through a productive and engaging strategic planning session that yields valuable insights and actionable outcomes. Join us in this video as we dive into the ins and outs of facilitating a successful strategic planning session.

Strategic Planning Facilitation Step 2: Plan all the Details in Advance

Anytime you bring your team together for a meeting, whether for a few hours or days, you invest time, energy, and money. To ensure you get the most out of your investment, you must be adequately prepared. The preparation checklist below will help you.

Strategic Planning Process Meeting Preparation Checklist

• Set the date – You will want to determine and set the date as soon as possible so that everyone on your team can attend. The longer you wait, the harder it is to find a time that works. If this is an ongoing, standing meeting, ensure everyone has it on their calendar every time it occurs and actively works to protect the scheduled time with the team.
• Select the Facilitator – It is essential to pick the right person to facilitate your session. The facilitator is responsible for creating the agenda, preparing content material (slides/visuals), arriving early to ensure setup and materials, testing technology, and facilitating the session. If you must choose someone on your team who will be in attendance, remember to occasionally stop during the meeting and ask their opinion if not previously shared. If you choose someone who would not usually be in attendance, ensure they understand that their job is to facilitate, not offer opinions on discussions they would not typically be involved in. Role clarity is essential.

• Select a location—A meeting or planning session in your conference room can be ineffective. The opportunity to lose focus and be interrupted by operational issues increases exponentially. This is fine for short, weekly, routine meetings, but we recommend taking your team off-site for one—to two-day planning sessions. 

• Choose a Meeting Coordinator – This person is in charge of handling all of the logistics for the meeting, making sure participants have made travel arrangements, the conference room (on-site or off-site) is booked and set up for the session, and that all participants are aware of any homework/preparation that is needed for the session. Use someone on your team who is meticulous with details and have them build a strategic planning checklist for future meetings.
• Prepare the meeting material – You and the facilitator should refer to your Objective Statement when creating the agenda. Be careful not to overload your agenda. Be realistic about what you can accomplish in the time you have available. Create a basic time plan to accompany your agenda. This will help you know whether or not you are on track during the meeting. Less is more when it comes to slides. The old rule was no more than 6x6 (six words long by six bullets). In today's Twitter and drive-through world, you're better served to stick to 4x4 or, better yet, 3x3. Consider revealing information one bullet point at a time, especially if you must have more than 6x6 on a slide, and always ensure it is written for your target audience.   Use our AI Goal Coach if you have any questions!
• Email the meeting agenda and pre-work to the attendees - Communicate with all attendees at least two weeks before the session, sharing the objective statement, agenda, and any pre-work you want them to do. Realize that some people - even with proper instruction - may be in the habit of attending meetings unprepared. If you consider the pre-work essential, let the team know that it's mandatory and require them to return it in advance, or instruct them to bring copies to the meeting and build time to share the output into your agenda. This will allow people to think about the strategic goals for themselves and the company ahead of the meeting.
• Last minute details - Work with the meeting coordinator to ensure all the meeting details have been addressed: supplies ordered, lunch planned, technology arrangements made, attendance confirmed, action plans, etc.

Strategic Planning Facilitation Step 3: Do the Hard Work of Running the Strategy Session

Three definitions of the role of the facilitator:

1. "An individual who enables groups and organizations to work more effectively, to collaborate and achieve synergy. He or she is a 'content neutral' party who, by not taking sides or expressing or advocating a point of view during the meeting, can advocate for fair, open, and inclusive procedures to accomplish the group's work."
2. "One who contributes structure and process to interactions so groups can function effectively and make high-quality decisions. A helper and enabler whose goal is to support others as they achieve exceptional performance."
3. "The facilitator's job is to support everyone in doing their best thinking and practicing. To do this, the facilitator encourages full participation, promotes mutual understanding, and cultivates shared responsibility. By supporting everyone in doing their best thinking, a facilitator enables group members to search for inclusive solutions and build sustainable agreements."

The word facilitation means to make it easy. Too bad facilitating a group of people isn't. It takes a tremendous amount of energy, focus, quick thinking, and patience to facilitate a meeting. Following the first two steps in this blog post (Step 1: THINK and Step 2: PLAN), you are set up for a successful session. But there is still much work to do.

Here are 15 Tips to keep the strategy session moving positively.

15 Expert Tips for Facilitating a Great Zoom Strategy Meeting

Set ground rules at the beginning of the meeting. Let the team discuss their expectations for full participation, candor, sidebars, interruptions, tangents, and cell phone and computer use. This conversation upfront creates an environment of accountability and high commitment to the meeting. Ground rules will help reduce the stress of group interaction and make it easier to resolve problems when they arise. Capture your ground rules on a flip chart while discussing them and post them for reference throughout the meeting. To start with some energy, I suggest using one of our Zoom icebreakers to get things started.

Trust the process. Remember that you have put a great deal of time into steps 1 & and 2, so you are going into the day with a good game plan. Sometimes, things seem disjointed, or the team needs to understand where you're going. Tell them there is a method to the madness, and ask them to trust the process with you. When utilizing a slide deck and agenda provided by Rhythm Systems, know that the function and content have been tested and proven to work many times. It may only come together at the very end, but if you are going in with a clear objective and well-thought-out agenda, the results you're looking for will follow, and problem-solving will occur.

Permit yourself to deviate from the time plan if a topic requires more time than you thought. As long as the additional time is used for good, healthy debates on important issues and not the beating of dead horses, it will be a good use of time. If you do deviate from the time plan, involve the team in deciding how you will make it up. You may choose to stay late or start early one day, or you may decide to cut or shorten the time allowed for another topic. Involving the team in this discussion and decision increases engagement, energy, and commitment.

Celebrate your progress as you move through the session. Reflect on lessons learned and breakthroughs. Acknowledge someone when they're brave enough to bring up a tricky subject. Check in with each other to ensure you're all engaged. After breaks, consider restating what's been accomplished and where you are on the agenda.

Use icebreakers with purpose. Ice breakers are quick, interactive exercises designed to get the team's brain working and mouth moving. They are usually used at the beginning of a session, after breaks, and after lunch. They can also be great for raising the energy level late in the afternoon. A quick Google search will provide hundreds of ideas for icebreakers. One of our favorites is a quick round of victories or good news. This serves several purposes. It allows team members to share information, allows them to get to know each other better, and starts the meeting positively. We recommend that you start every session with some version of good news.

Encourage full and equal participation. A team comprises many individuals, each with their personality and preferred work style. Some are naturally more dominant and expressive, while others may be more thoughtful and reserved. One type is not better than another, and the fact that they're on your team means you value their input. The facilitator's job is to recognize these different styles and run the meeting in a way that gives each person a chance to contribute. This is a good discussion at the beginning of the session as you set the ground rules.

Set clear expectations for full and equal participation and give the team a chance to discuss how they will do this. The facilitator may have to step in throughout the meeting, explicitly calling on individuals who have not spoken up. The facilitator may also design the meeting to include specific opportunities to hear from everyone. Examples of this would be small group breakout sessions or employing different brainstorming methods (see #8.)

Use visual aids effectively. Any combination of flip charts, whiteboards, sticky notes, posters, PowerPoint/Keynote, and handouts will do. We've all seen the person who used every animation tool within PowerPoint - wiggly jiggly icons, annoying animations, slides swiping in from 20 directions in 5 different ways. Don't overdo it; allow your visuals to distract from the meeting. People have different learning styles; Some are visual learners, some auditory, some kinesthetic, and some experiential, so mix it up and use all aids in moderation. Keep in mind that your body language is one of the most essential visual aids that you have; make sure that you make people feel like they are being heard.

Use different methods for brainstorming. Round robin, freewheeling, group pass, and silent reflection are all proven methods you may try. Brainstorming aims to produce a comprehensive list of potential ideas, solutions, or plans. When done well, brainstorming should increase participation, reduce inhibition, stimulate ideas, increase creativity, and be a group process.

Strategic Planning Brainstorming Methods:

• Focus on quantity first and capture as many ideas as possible.
• Encourage and welcome all ideas. Ask the team to dig deep and think beyond the obvious. Every idea submitted should be captured.
• Hold off on judgment, criticism, or reality checks - this should be a "safe time." Ideas will be discussed and debated later.
• Use short phrases and bullet points, not paragraphs and lengthy explanations.
• "Piggyback" on others' ideas. Outlandish ideas can be stepping stones to good, workable ideas.
• Although giving a brief overview of brainstorming rules can be helpful, there's no need to go into an elaborate explanation. "Let's brainstorm annual priorities moving us toward our 3-5 year strategic plan. Remember, let's not judge the ideas but capture and understand them first." Then, begin your chosen method of brainstorming. As you move through the process, anticipate that someone will break the rules - that's when the facilitator steps in and corrects.

Round Robin Brainstorming

Ask for a volunteer to start the brainstorming process with one idea. The facilitator captures the idea on a flip chart for all to see. Ask the volunteer to choose whether to go to the right or the left, allowing the person sitting next to them to offer one idea. The facilitator continued to chart the answers, going around the room until everyone could contribute at least one picture. You can then take a second pass around the room if the ideas are flowing freely, or you can open it up to anyone who has another idea not previously mentioned.

Freewheeling

Suppose you're working with a group where equal participation is not an issue. In that case, you can open the brainstorming session up by asking for ideas and allowing people to offer suggestions in any order. Use the participants' words to chart all ideas with short bullet points. This method can go fast, so ask for a volunteer to help chart answers using a second flip chart.

Group Pass

Each person in the group starts with a piece of paper, writes down one idea, and then passes the piece of paper to the next person. The following person builds on the original idea, adding a few thoughts. Continue around the room until the owner returns their original piece of paper. You can then ask each person to take a minute to review their original idea and share it with the team.

Silent Reflection

Some people need a little time to think and formulate their ideas. Instruct the team that you give them a certain amount of time (5-15 minutes, depending on the topic) to think and write down their ideas. You can ask them to write their thoughts on sticky notes, one idea per note, or list them on paper. If you use sticky notes, you can ask them to read one statement at a time and place them on the wall, grouping all similar ideas. If they are written on notebook paper, you can use the round-robin method to share and chart the ideas.

Use a Parking Lot

Stay on track by creating a place to capture ideas inappropriate to the discussion at hand but that you don't want to lose. Make it visible to everyone using a whiteboard, tear sheet, etc. This helps you keep the meeting focused without chasing too many "rabbit trails." It is important to honor all ideas, questions, and concerns during a session, and by placing the item in your parking lot, you send the subtle message that all contributions are essential. Refer to the parking lot items while facilitating when appropriate and review any unresolved items at the end of your session, moving them to an action item list. In a strategy meeting, you must keep the team on task; using a parking lot can help you accomplish that.

Deal with difficult people ahead of time

Before your meeting, think about participants who tend to be outspoken, dominate, or argue in meetings. Think also about participants who may have felt bullied or intimidated or have a history of not participating openly. Have a conversation with these people before the session, explaining your concern and asking for their help in creating a healthy and productive environment. When talking to the dominant person, helpful language might include, "Jim, I'm trying to increase participation in this meeting. I appreciate your outspokenness and value your input. If it's ok with you, I'd like you to go last so I may first hear the rest of the team's thinking before you share yours." Be sure to reevaluate and give that participant a chance to share.

This is also an excellent topic to discuss while setting ground rules at the beginning of the session. Discuss the expectations for politeness and tone during the meeting, and ask the team for permission to point it out if things get off track. If a conflict arises during a meeting, the facilitator must be prepared to step in and take control of the meeting. Anytime the discussion becomes accusatory or personal, the facilitator can ask the participant to reword statements so that they are focused on solutions, facts, and business issues, not people and blame. An excellent technique for redirecting a heated discussion is to ask the team to discuss their learnings rather than their frustrations. Be sure to do this whenever the language becomes personal; before you know it, your team will police this behavior themselves. Conflict resolution is the central role of the facilitator.

Keep the energy high. Enthusiasm is contagious - and so is negativity. Some people need to doodle while they think, some need toys like a Koosh ball or rubber Gumby, others need talk time with other participants, and others need to stand up or walk around the room from time to time. Think through your meeting day and plan ways to keep the energy high for the entire time to keep the group paying attention.

Have participants work in pairs, write something down, work together on puzzles, make mini-presentations on topics assigned before and after breaks, schedule group breakout sessions, etc. Remember that the room's energy is often a notch or two below the facilitator's, so it is vital to keep your energy high. Try to get plenty of sleep the night before, eat well, have plenty of water on hand, and take breaks as needed, as group facilitation is challenging!

Get to a consensus. Many discussion topics require moving the group from several individuals, independent ideas to one agreed-upon group decision. Consensus can be defined professionally as an acceptable resolution everyone on the team can support. It does not mean that everyone on the team has to agree that this is their number one favorite resolution, just that they will support the decision in the future. Supporting a decision means that you will speak positively about the decision to others and do everything in your power to ensure the decision results in a positive outcome. You will not say," They decided."

Explaining the definition of consensus and support to the team at the beginning of the discussion can help resolve the issue. An essential step in reaching a consensus is ensuring that all ideas are evaluated and everyone's perspective is heard. This is important in getting buy-in for the conclusion and generating the best ideas and solutions. Structuring a process for team decision-making is a critical facilitation skill.

Expert Tips for Strategic Planning Decision-Making:

• Use the brainstorming tips above to identify all viable solutions (see #8)
• Combine and link similar ideas
• Use structured methods, like The Six Thinking Hats, to help take the emotion out of the discussion.
• Set a time limit for discussion on each potential solution
• Make sure everyone is participating in the debate and, make sure everyone is actively listening and applying their listening skills
• Work to narrow the options down to as few as possible
• Don't be afraid to call for a vote to see how close the group is to completing the agreement
• If there are just one or two holdouts, seek to understand what and how firm their objections are
• Engage the group in troubleshooting to minimize the potential negative impact identified by any complaints or concerns raised
• Restate the most popular resolution, adding one or two points addressing the concerns raised, and ask the holdouts if they can support that decision
• Sometimes, people will get caught up in the moment and continue the debate just to argue. Ask the holdout if they will lose sleep if the group moves forward with the proposed resolution. Refer to the definition of support and ask if they will support the decision.
• With consensus, there is often compromise. Only some get everything they want out of the final decision. However, because you created an environment where everyone has had an opportunity for input, the conclusions reached will often be very successful and highly supported.
• If you are running a virtual strategic planning session, visit the link to learn some additional tips to help you get the most out of your planning session.

Document and publish the Who-What-When. Who-What-When action items are leading indicators of successful meeting outcomes. How often do teams meet, discuss, and debate critical topics, then set the next meeting date only to discover that no progress has been made at the next meeting? As the facilitator, it is essential that you make sure that every critical discussion ends in a documented action captured in an action list of Who is accountable (one person only), What they will do, and When it will be completed. Create a habit of ending meetings with a review of the Who-What-When and beginning discussions with confirmation on completing the actions assigned.

Finish strong. People won't always remember what you do or say, but they will never forget how you made them feel. And what they will remember most is how they felt at the end of the meeting. Whether you completed every objective you laid out or worked through the agenda, it's essential to recognize the team's accomplishments and celebrate their focus, contribution, time invested, and hard work. Finish the meeting by recapping the decisions, reviewing the actions committed, and confirming the next steps. We also recommend allowing everyone to share how they feel as they leave. You can go around the room and ask each person to share a one-word/one-phrase closing statement or share one takeaway or breakthrough they gained during the meeting.

Ask for feedback. Great facilitators are not born overnight. They develop and improve over years of experience, and the most experienced facilitators know that asking for feedback is the best way to improve. Before they leave, ask the team to write down one bright spot from the meeting and one area to work on or do differently next time. Please feel free to email everyone after the session asking for feedback. Or, you can ask for a quick one-on-one conversation with a few trusted advisors.

You would like to encourage feedback on the agenda, pre-session communication, design of the day, homework, and how you performed and handled difficult situations during the session. If you want to receive feedback, please take it seriously. Don't take it personally or complain to others about it. All feedback, even negative feedback, is a gift. Thank the person who shared with you, and I'd like to make every effort to incorporate all helpful suggestions into your next session. Stay encouraged and stick with it. You will improve every time you facilitate, so please volunteer and look for opportunities to practice. Over time, the tips in this blog post will become second nature. Good luck!

This blog post shares tips and tricks for facilitation from the Facilitator guide written by Chris Cosper and Barry Pruit and adapted to a blog post by Ted Skinner. If you'd like to download the strategic planning manual, please click here. We hope you enjoy the facilitation techniques outlined in this article to keep group discussions positive and productive. We hope this answers your question about how to lead a strategic planning session; if you want to get the best ROI on your investment of time and energy, please feel free to drop us a line, and we'll see if it makes sense for you.

Need help aligning your team to achieve your growth goals? Rhythm Systems software was ranked the #1 easiest software to use, with the highest ROI, fastest implementation, and highest adoption rate on G2.  

Read our other strategic planning and facilitation articles below:

Annual Planning: 9 Tips to Focus & Align Your Team with a Great Plan

Annual Planning Playbook: 5 Steps to Create a Winning Annual Plan

How CEOs Can Avoid High-Cost Mistakes in Annual Planning

Best Practices for Annual Planning

16 Strategic Planning Tips to Keep Your Strategic Plan Alive

The CEO Strategy-Execution Gap...And How To Fix It

Choose Your 3-Year Strategic Growth Initiatives Wisely With This 4-Step Process

5 Steps to Getting Started on 3-Year Strategic Plans with Winning Moves

Have you been able to validate your 3 Year Strategic Plan?

Robust 3 Year Strategic Plans to Grow Revenue and Stay Competitive

16 Strategic Planning Tips to Keep Your Strategic Plan Alive

Don't Confuse Strategic Thinking And Strategy Execution Plans

9 Steps to a New Revenue Growth Strategy [Infographic]

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