How to Lead an Effective Strategic Planning Meeting

Want to hear a not-so-secret secret? A lot of business leaders are geniuses at persisting through challenges to get their businesses off the ground but struggle to pause and look ahead. When money’s tight or the business hits a rough patch, they lean on their hardheadedness and determination to outmaneuver faulty game plans and outearn bad decisions. But especially in the early Stages of Business, their focus tends to be on immediate fires instead of taking time to set clear goals and build systems for the future they desire.

Sound like you?

High fives for hustle and stick-to-itiveness. But determination alone won’t carry you forward forever. To scale your business, you need a strategic plan. That’s what aligns your team around the right goals and turns big dreams into real achievements.

But creating a killer strategic plan requires you to do something that might make you sweat bullets—pause, gather your core leaders, and lead a strategic planning meeting.

To do that effectively takes work. And you probably have all kinds of questions.

• What is a strategic planning meeting?
• How do I prepare for a strategic planning session?
• How do I facilitate a strategic planning meeting?
• How do I lead a strategic planning meeting follow-up process?

No worries. We’ve broken the elements of an effective strategic planning session into three parts—before, during and after—so you see how doable it is to master yours.

First, let’s get on the same page about what a strategic planning meeting is. Then we’ll show you how to run a strategic planning meeting that drives business growth.  

What Is a Strategic Planning Meeting?

A strategic planning meeting is where you and your key leaders come together to set goals and plan the next steps for your business—aka create your strategic plan (or what we call your desired future). You’ll track your progress toward existing goals and refine strategies and objectives as you need to. Think of strategic planning meetings as where you map out the big picture of your business’s impact so you’re not just reacting to what happens day to day but actively shaping your business’s future.

Ultimately, you’ll want to have strategic planning meetings once a quarter. But it’s totally fine to start with annual business planning. During this yearly yearly meeting, you’ll talk about the future you desire and come up with a focused statement that guides your business decisions for the coming year. Quarterly and annual strategic planning meetings fall within the regular communication rhythms you need to keep your team heading in the same direction and to know what winning looks like for your company.

3 Stages of a Productive Strategic Planning Session

Now that you know the purpose of strategic planning meetings, it’s time to get ready for your first strategic meeting of the minds.

Here’s a plan from start to finish to help you get the most out of your strategic planning session.

1. Before: How Do I Prepare for a Strategic Planning Meeting?

Preparing for a strategic planning session starts with your mindset. When you’re planning for your company’s future, the stakes are high.

You’ll need to minimize distractions and maximize momentum, so ask yourself, Am I committed to investing a half to whole day for me and my core leaders to go off site to wrestle through and plan for the company’s future?

We know . . . this is a huge investment in resources. But a simple change of scenery (and calendar commitment) does wonders for unifying your leadership team so they can focus on key challenges, new ideas and a plan for the next 12–18 months in your business.

Once you’re firm on your commitment, ask yourself, What’s the desired future I want my entire leadership team to buy into?

Spitballing ideas the day you gather won’t work, so get clear on your strategic planning session agenda, aka what you want to accomplish during the planning session. (We’ve got specific agenda ideas in the next section.) Now you’re ready to work through the finer details as you prepare:

• Choose a location. Like we said earlier, getting out of the office allows you to stay focused and lets the rest of your team know you’re unavailable unless there’s a true emergency. Rent an Airbnb, use a church basement, or host in your own home—but don’t forget to tell your spouse!
• Get the right people there. You’ll need your core leadership team, which should consist of one member from each of the major areas of your business. Pro tip: Having a facilitator will free you up to participate in the session.
• Set ground rules before the planning session. Send an email invitation to your leadership team with your clear expectations—from being on time to leaning in and speaking into the business.
• Order snacks, food and supplies. The last thing you want is a hangry group of leaders. Plus, sharing meals together is a great way to bond. So note your leadership team’s dietary restrictions and favorite treats, plus any supplies like easel pads, markers and sticky notes to make the day great.

Questions to Ask in the Planning Stage:

• How do you want the session led—by you or by an outside facilitator?
• What outcomes do you want?
• Which of the business drivers do you want to focus on: personal, purpose, people, plan, product or profit?
• Where do you want to do the session?
• Who do you want to be there?

Related articles:
What Is a BHAG (Big, Hairy, Audacious Goal)?
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2. During: How Do I Facilitate a Strategic Planning Session?

You—with the help of the facilitator if you choose that option—set the tone for the meeting. Opening with prayer or silence will help everyone center their minds and remove distractions before you dig into these steps.

• Start with an icebreaker. Ask a fun question to help get everyone relaxed and engaged in the conversation. You can give one of these a try or come up with your own: Would you rather fight one horse-sized duck or 100 duck-sized horses? What’s the funniest thing you believed as a kid? If you were a kitchen appliance, which one would you be and why? You’ll be amazed by the things you learn about your team members.
• Lead a reflection exercise. Before you can build the future of your business, you need to review the last business season and acknowledge what happened—the highs and lows and everything in between.
• Create (or review) your strategic plan and defining objectives. If you haven’t already created your strategic plan (desired future) and defined how you’ll reach it (defining objectives) for the next year, this is where you’ll do that. To work out your defining objectives, come up with three to six benchmarks that answer the question, “What must be true to reach our desired future?”

If you’ve already created your plan and objectives, use this time to review and refine them. You’ll want to dedicate one meeting each year to re-crafting your desired future and defining objectives. Then, at each strategic planning session throughout the rest of the year, use your desired future to guide your updates and pinpoint problems.

• Have a reality check. Do you have at least a 70% chance of reaching your goals? If your desired future statement is way too hard or way too easy to achieve, keep refining. And keep this in mind: Your desired future statement will be your guiding star for every initiative and new idea. If an idea or tactic doesn’t drive toward your desired future, it doesn’t get added to anyone’s workload.  
• Discuss key topics. Address the key topics you need to work through. (Ask your leaders for their list of issues before the meeting and continue adding to the list during your strategic planning meeting.) This is a chance for everyone to discuss challenges in the business.
• Assign action items. Never leave an off-site without laying out next steps and assigning action items to key leaders who will own the defining objectives.

Tips for the Meeting Stage:

• Present one key question at a time to the team.
• If you’ve talked to a team member about the topic before, give them a chance to give an update.  
• Ask specific questions that drill down on the problem you need to solve or idea you want to flesh out.
• Read the room and body language. Are people open and engaged? Tired and checked out? Confused and defensive? Make sure everyone’s with you at every step.
• Pay attention to how long it’s been since someone has spoken. You can keep more dominant personalities from overshadowing those who need to process internally before sharing.
• Take a break every one and a half to two hours.

3. After: How Do I Lead a Strategic Planning Meeting Follow-Up Process?

This is where the rubber meets the road. Schedule follow-up meetings to keep your team moving toward your desired future.

• Emphasize the importance of the first two weeks after your strategic planning session. While the business priorities you just worked through are still fresh, each core leader who was part of the planning should share your desired future statement and defining objectives with their teams. Once everyone is clear, you can lay the groundwork for achieving this goal together.
• Lead a weekly leadership team meeting. Here, you’ll track progress and flag potential business blockers before they get too big. Having a weekly meeting will also help you stick to your plans.
• Plan quarterly off-sites. For more accountability and momentum, get three more off-sites on your calendar for the year to review your desired future and pivot when needed.

Questions to Ask in the Follow-Up Stage:

• Is the status of your progress toward your desired future green, yellow or red? (Green = on pace; yellow = slightly off pace; red = will not meet the goal at the current pace.)
• What blockers do you need help with?
• What additional resources do you need?

Related article: 11 Productivity Tips for Small-Business Owners: Manage Your Day and Your To-Do List

Ready for another not-so-secret secret? This strategic planning meeting process is the same one Dave Ramsey used to scale Ramsey Solutions into a $250 million business and national brand. He and his leadership team use these meeting principles quarter after quarter, year after year to stay focused and aligned for growth.

Strategic planning meetings are just one part of Ramsey’s EntreLeadership System—the business road map that takes the guesswork out of growth. Learn more about strategic planning, healthy communication rhythms, and how the EntreLeadership System will guide you toward the future you desire too.