Unexpected Capabilities. Unmatched Service.
strategic planning session

What Should a Great Strategic Planning Session Look Like?

Is your small business lacking direction? Are your employees working toward the same goals you are? Are your resources being allocated in an optimal way?

If not — or if you’re otherwise unhappy about the progress of your business — you should strongly consider a strategic planning session.

Strategic planning is, loosely put, the process of determining where your business is and where it’s going. More specifically, though, it’s a determination of a company’s goals, and an evaluation of what the business’s structure, resources and procedures need to look like to achieve success based on those goals.

Organizing and executing a great strategic planning session can feel daunting. After all, it’s difficult to plan for the future when there are so many day-to-day responsibilities to juggle. And it’s hard to be critical of the decisions you’ve already made that educate how the company currently operates.

But it’s worth the time and effort. A great plan can more clearly define success, properly focus your workforce’s energy and better allocate resources to achieve your goals.

How to Run a Great Strategic Planning Session

Generally speaking, most businesses are typically looking to determine these things:

  • Mission: What is your core business? What does it do?
  • Values: What are the most important principles your business is built on? How must your employees conduct themselves to stay faithful to what the business is?
  • Goals: This is effectively how you determine success. What accomplishments are you hoping to achieve, and how long should it take to achieve them?
  • Strategy: What actions will you take to reach your goals?

No strategic planning process is going to work the same — how an under-resourced small business with five employees approaches it will be different than a resource-rich small business with 95 employees who have much more specific roles. But regardless of whether you have to squeeze your planning into a single-day session or can dedicate months’ worth of meetings to determine your company’s direction, here’s what every session should have.

Big-Picture Thinking

It’s often much easier to think about small operational tweaks than it is to evaluate the broader vision of a whole company. But you and your employees alike should feel comfortable spending at least a few hours simply brainstorming about the highest levels of the business. “Who are we?” “What do we stand for?” “Who do we serve?” “What makes us different than our competitors?” The answers to these questions are ultimately going to educate many of the decisions to come, so don’t ignore them, and take them seriously.


It doesn’t matter whether your meeting has two people or 20. Chances are that at least one attendee (if not many more) will be on a different rung of the corporate ladder than someone else. While the meeting itself should have a very clear leader to keep it organized and moving, everyone should feel free to speak without repercussion, and everyone should be encouraged to treat all ideas on their face, regardless of who’s delivering them. Every attendee should feel empowered to question others’ ideas and challenge the company’s status quo.

Clear Discussion Structure

Try to enforce rough time limits when any person speaks. For instance, in a brainstorming session, give every member five minutes to express their ideas, without interruption – other people may respond, but don’t let a response go over one minute. Other portions of the meeting likely will be dedicated toward discussing and fleshing out ideas, so there’s no reason to take up additional time during initial idea presentations.

Thorough Note Taking

Ideally, strategic planning sessions will be conducted by a facilitator who will also keep copious notes throughout. But chances are, most small businesses don’t have the resources. In that case, make sure someone is in charge of note-taking throughout the process so ideas can be ushered from section to section throughout the meeting, and so that no one’s thoughts are just lost in the ether.


You spend a day or two determining your company’s vision, cementing goals and laying out various plans for how to achieve success. That’s great, but if you don’t immediately set up mechanisms to make sure those plans are followed, as well as review sessions to determine whether your new strategy has worked, then you’ve wasted all that time. A strategic planning session is only as valuable as the efforts made to see it through.

Worse: Letting great ideas die can demoralize employees who joined in the planning.

If you’re looking to define (or redefine) your business, you don’t have to go it alone. McManamon & Co.’s consulting services include assistance with strategic planning activities, such as strategy sessions with key management, developing and implementing strategic plans, and follow-up meetings to monitor progress. All you need to do is bring the ideas, the employees and a determined attitude.

Don’t let your small business aimlessly wander through the next few years. Sharpen your focus and hone your strategy. Call us at 440.892.8900 or contact us online today.

Tags:  , , , | Posted in Consulting, McManamon & Co., small business