10 Questions for Your Strategic Planning Session

Strategic Planning Session

What Is A Strategic Planning Meeting?

Strategic planning meetings are team discussions to determine if the business’s current practices are aligned with the mission and vision. These meetings decide if the course should be corrected and what steps should be taken to reach the ultimate vision. 

Strategic planning sessions shift the focus back to definitive actions that are most important for business growth and success. They serve as an anchor point to keep team members steady as external factors and daily fire-fighting scream for attention. When decision-makers regularly come together to discuss strategy, organizations are much more likely to accomplish goals and mitigate blind spots.

Why Are Strategic Planning Sessions Important?

The following data points from Funding For Good help to reveal the critical nature of strategic planning:

  • 71% of fast-growing companies have strategic plans, business plans, or similar long-range planning tools in place
  • Companies with written business plans grow 30% faster 
  • 95% of employees don’t understand their company’s strategy
  • Companies that are poorly aligned with strategy report weaker financial results than their peers

 

These statistics bring to light two things: 1) a lack of strategic planning can lead to decreased employee buy-in and business results and 2) high-performing organizations separate themselves by focusing on strategy. Creating a business strategy is important but arguably more important is the process of execution. The list below highlights why the implementation of strategic planning meetings is necessary for the organization’s future.

  1. Maintains Alignment 

The mission and vision are the heart of the organization. Without them deeply ingrained in the company culture, there is a significant danger that unchecked daily decisions can veer off course, leading the business astray from its original intentions. This may result in unmet goals, low performance, or employees who are no longer engaged. Holding strategic planning meetings at a consistent frequency serves as a way to remind leaders of the greater purpose. They also help to unify team members by brainstorming ways to solve problems and improve results.

  1. Corrects the Course

If the meeting unveils misalignment in any aspect, these discussions are positioned to tackle it with the bright minds in the room. Working collaboratively to identify problems, find solutions, and ideate for the future is what strategic planning meetings are about. Even if all indications suggest that the organization is perfectly aligned, it is still crucial to hold these meetings on an annual basis. This ensures that intentional time is dedicated to analyzing the past in order to forecast future success.

  1. Accountability

Encouraging employees to actively participate in these meetings fosters a sense of accountability and commitment to both their individual goals and the team’s objectives. Observing team members taking ownership of their responsibilities cultivates a positive atmosphere of high morale and strong team unity.

  1. Keeps the Business Agile

Scheduling protected time to discuss wins, losses, market impact, and the market at large is a surefire way to prevent the business strategy from going stale. These dialogues keep things nimble and leaders comfortable with assessing the state of the workplace against important external factors, such as competitors, policy updates, or economic changes.

What Should A Strategic Planning Meeting Include?

Every successful meeting starts with a well-defined agenda. However, this doesn’t mean that strategic planning meeting agendas need to be meticulously planned out minute by minute. It is actually recommended to keep these agendas flexible to allow ample time for brainstorming and meaningful discussions. Another recommended best practice is to share the written agenda ahead of time – at least 24 hours before- so all participants can feel prepped and ready to engage. 

The bullets below indicate steps to take before the planning session begins.

  • Set a date– Be sure to choose a day and time when there will be limited interruptions (within reason) and adequate time so beneficial conversations are not cut short. 
  • Choose attendees– If possible, all departments should be represented to ensure every aspect of the business is accounted for. Top leadership and all decision-makers should be included as well. The goal is to avoid as many blind spots as possible by empowering all voices in the organization and, if applicable, hearing from voices outside the organization as well, such as clients or consultants. 

 

The following list highlights what should be included in the strategic meeting agenda. 

  • Share mission and vision- Begin the meeting by revisiting the mission and vision. This will set the tone for the discussion and keep the focal point where it should be.
  • Include discussion questions- Posing challenging questions about business success is the point of the strategic planning session. Written questions keep the conversation on track and remind participants that tangents or unrelated discussions should be tabled for another time or meeting. IIf a couple of questions make participants feel slightly uneasy, it’s usually an indication that the meeting is delving into the depths and uncovering crucial insights that will steer the organization in the right direction.
  • Action items– It is critical that each strategic planning meeting ends with a list of action items. Action plans will include what should be accomplished, when it should be accomplished, and who should accomplish it. Delegation fosters a sense of responsibility among team members and empowers meeting participants to take ownership of the business strategy.

 

A recipe for all strategic planning meetings should include a healthy dose of interactivity, open dialogue, and celebration of recent wins. While these meetings are serious in nature there should always be an effort to make them engaging and enjoyable.

Strategic Planning Meeting Questions

The following 10 questions were created to help get you started with strategic planning meetings. However, the questions should be adapted to your business’s needs as the correct strategic approach will be as unique as your organization. 

  1. What is the one thing your company did best this year? How can we leverage this more?
  2. What is the one thing your company should improve upon?
  3. Which employee(s) prevented you from doing your best this past year?  What should you do about it?
  4. Which department, team or function(s) prevented you from doing your best? What should you do about it?
  5. Which team member was most responsible for your company’s success this year?  How can we maximize this member’s impact on others?
  6. Which department, team or function(s) was most responsible for your company’s success this year? What best practices can we pass on to others?
  7. What is the single Key Performance Indicator you least liked hearing about this year? What strategies and action plans can we implement to improve?
  8. What is the single metric you will measure your company’s success by? What can you do to make sure the goal is achieved?
  9. If you had a clean sheet, what changes would you make to your company?
  10. If a perfect competitor opened up across the street, what would they look like?

 

Agenda for a strategic planning meeting

Plan Your Strategic Planning Session With WorkDove

Partnering with the right software tool will ensure your strategic planning sessions produce real actions and are documented appropriately. The WorkDove Agendas app allows you to easily create a flexible script, invite all participants at once, and delegate action items with just a few clicks. Keep your business strategy fresh and your team members empowered with simple but powerful agendas!