How to Facilitate a Strategic Planning Session for 2023 [Strategic Planning Workshop]

By Ted Skinner

How to Facilitate a Strategic Planning Session for 2023 [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 happen because someone is committed to how to facilitation a strategic planning session THINKING through the purpose and outcome, PLANNING all the details in advance, and DOING the challenging work of running the meeting. This is the role of an excellent virtual planning facilitator that can help you better define your strategy, create a winning annual plan and leave with an action plan to get your annual initiatives done. To facilitate a planning session, there is a lot of hard work needs to be done.  These same techniques should be used for in-person sessions and virtual strategic planning sessions with your management team.  While you can run a strategic planning session on your own, many people 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 and taking your team away from their "day job".   If you don't maximize your collaboration to define an effective business strategy for the entire organization, you are burning payroll.

At Rhythm Systems, our consultants are trained strategic facilitators and play a key role in the strategic planning process. They are planning experts that help you get the most ROI out of 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 key 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 of the stakeholders and fully participate at the same time. And the CEO’s contribution and participation is extremely important to reach the desired outcome. Session facilitation is an extra burden that is better placed on another team member or an expert facilitator. You should learn how to be a good facilitator with tips and tricks or consult with us to see if hiring an expert makes sense for you.

Free Guide: How to Facilitate a Strategic Planning Session

Rhythm Systems Annual Planning Facilitation Guide


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 prior to 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 2023 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 comes with shared goals and expectations for your time together. It will also give you clarity as you move into step 2 and begin planning for the session.  Make sure that this aligns with your mission statement.  This is different than your team meetings and setting expectations up front is critical for your strategic objectives. 

An effective Objective Statement consists of three parts:

1. TO: (What is the action? What are you going to do? Start with a verb.)

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

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

Sample Objective Statement for one company’s Quarterly Planning Session


TO: Conduct an effective strategic planning session


  • 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
  • Allows us to discuss-debate-agree critical topics as a team
  • 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
  • Allows us to identify strengths and weaknesses
  • Answers the key questions facing our company and industry
  • 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 strong start to next year.

strategy planning

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

Anytime you bring your team together for a meeting, whether it’s for a few hours or for a few days, you are making a big investment in time, energy and money. The way to make sure you get the most out of your investment is to make sure you are adequately prepared. The preparation checklist below will help you.

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Strategic Planning 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 in charge of creating the agenda, preparing content material (slides/visuals), arriving early to ensure setup is correct and materials are in place, testing technology, and facilitating the session. If you must choose someone on your team that will be in attendance, remember to occasionally stop during the meeting and ask their opinion if not previously shared. If you choose someone that would not usually be in attendance, make sure 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 – Having a meeting or planning session in your own conference room can be very ineffective. The opportunity to lose focus and be interrupted by operational issues increases exponentially. This is fine for short, weekly, routine meetings, but for 1-2 day planning sessions, we recommend taking your team off-site if you can. 
  • 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 make sure that it is written for your target audience.  
  • Email the meeting agenda and pre-work to the attendees - Communicate with all attendees at least 2 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 make sure all of the meeting details have been addressed: supplies ordered, lunch planned, technology arrangements made, attendance confirmed, etc.

strategy planning

Remember to be realistic about what you can accomplish in the time you have available and set the agenda appropriately. The strategic planning facilitator also must keep the team focused on having the right discussions needed for your organization. Understanding and working with the group dynamics is essential, especially in a large group.  You can read more details about a virtual strategic planning session in this related article.

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Virtual 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 are able to 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 to do their best thinking and practice. To do this, the facilitator encourages full participation, promotes mutual understanding and cultivates shared responsibility. By supporting everyone to do their best thinking, a facilitator enables group members to search for inclusive solutions and build sustainable agreements.”

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

Here are 15 Tips you can use to keep the strategy session moving in a positive direction.

Download Guide: 3 Steps to Ensure Your Virtual Meeting Will Be a Success

15 Expert Tips for Facilitating a Great Zoom Strategy Meeting

1. Set ground rules at the beginning of the meeting. Let the team discuss their expectations for full participation, candor, side bars, interruptions, tangents, and cell phone and computer use. Having this conversation upfront creates an environment of accountability and a high level of 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 and post for reference throughout the meeting.  To start with some energy, I suggest using one of our Zoom icebreakers to get things started.

2. Trust the process. Remember that you have put a great deal of time into steps 1 & 2, so you are going into the day with a good game plan. There may be times when things seem disjointed or the team doesn’t understand where you’re going. Let them know that 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 process and content has been tested and proven to work many times. It may not all come together until 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 the problem solving will occur.

annual planning

3. Give yourself permission to deviate from the time plan if a topic requires more time than you thought it would. As long as the additional time is used for good, healthy debates on important topics, 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 choose to cut or shorten the time allowed for another topic. Involving the team in this discussion and decision increases engagement, energy and commitment (see #11).

4. 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 tough subject. Check-in with each other along the way to make sure you’re all staying engaged. After breaks, consider restating what’s been accomplished and where you are in the agenda.

5. 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 actually serves several purposes. It gives team members a chance to share information with each other, it allows team members an opportunity to get to know each other better, and it starts the meeting off on a positive note. We recommend that you start every meeting with some version of good news.

6. Encourage full and equal participation. A team is made up of many different individuals, each with their own personality and preferred work style. Some are naturally more dominant and expressive, while others may be more thoughtful and reserved. One style is not better than another, and the fact that they’re on your team means that you value their input. It’s the facilitator’s job 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 to have at the beginning of the session as you are setting the ground rules.

Set the expectation of full and equal participation clear and give the team a chance to discuss how they will do this. The facilitator may have to step in throughout the meeting, specifically calling on individuals that have not spoken up. The facilitator may also choose to 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.)

7. 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 that 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 and allow your visuals to distract from the meeting. People have different styles of learning, 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 important visual aids that you have, make sure that you make people feel like they are being heard.

virtual strategy planning facilitator

8. Use different methods for brainstorming. Round robin, freewheeling, group pass and silent reflection are all proven methods you may try. The point of brainstorming is 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.

The general rules for all brainstorming methods are:

  • Focus on quantity first 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 it can be helpful to give a brief overview of brainstorming rules, there's no need to go into an elaborate explanation. "Let’s brainstorm annual priorities that will move us toward our 3-5 year strategic plan. Remember, let’s not judge the ideas but just 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 makes the correction.

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Round Robin

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 continues to chart the answers, going around the room until everyone has had a chance to contribute at least one idea. You can then try to take a second pass around the room if the ideas are flowing freely, or you may open it up to anyone who has another idea not previously mentioned.


Suppose you’re working with a group where equal participation is not an issue. In that case, you may be able to open the brainstorming session up by asking for ideas and allowing people to offer suggestions in any order at all. Be sure to use the participants' words to chart all ideas with short bullet points. This method can go fast, so you may want to 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 then 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 are giving 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 a sheet of paper. If you use sticky notes, you can then ask them to read one idea at a time and place them on the wall, grouping all similar ideas together. If they are written on notebook paper, you can use the Round Robin method to share and chart the ideas.

9. Use a Parking Lot. Stay on track by creating a place to capture ideas that are inappropriate to the discussion at hand but that you don't want to lose. Make it visible to all 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 need to keep the team on task; using a parking lot can help you accomplish that.

planning facilitator

10. 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 in the past or who may 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. Helpful language when talking to the dominant person might include, "Jim, I’m trying to increase participation in this meeting. I really 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 in advance 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 every time the language becomes personal; before you know it, your team will police this behavior themselves. Conflict resolution is a central role for the facilitator.

11. Keep the energy high. Enthusiasm is contagious - 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 that of the facilitator, so it is vital to keep your personal energy high as well. 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 hard!

12. 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 that 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 going forward. Supporting a decision means that you will speak positively about the decision to others, you will do everything in your power to make sure 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 reach a resolution. 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 final conclusion and generating the best ideas and solutions. Structuring a process for team decision-making is a critical facilitation skill.

Here are some tips to help team 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 too full 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. Not everyone gets 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 are often ones that will 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.

annual planning

13. Document and publish the Who-What-Whens. 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 very important 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-Whens and beginning meetings with confirmation on completing the actions assigned.

14. 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 important 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 that you give everyone a chance 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.

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

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. No matter how you choose to receive feedback, 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 make every effort to incorporate all helpful suggestions into your next session. Stay encouraged and stick with it. You will get better every time you facilitate, so 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 to 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 guide, please click here. We hope that you enjoy the facilitation techniques outlined in this article to keep group discussions both positive and productive. We hope this thoroughly answered 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, drop us a line and we'll see if it makes sense for you.

Need help getting your team aligned to achieve your growth goals? Rhythm systems software was ranked the #1 easiest software to use, highest ROI, fastest implementation, and highest adoption rate on G2.  Learn More About Rhythm


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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 CEOs 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 Validated Your 3 Year Strategic Plan?

Strong 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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