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5 Best Practices To Run A Successful Strategic Planning Session in 2024

A well-run strategic planning session is a powerful tool for any organization. By bringing together key stakeholders and decision-makers, it provides an opportunity to take a step back and assess where the organization is currently at and where it wants to be in the future.

In fact, according to Harvard Business School, strategic planning is important as it creates one, forward-focused vision and it draws attention from biases and flaws in reasoning. In addition, it also can help to track the progress of your organization based on strategic goals.

In this blog post, we'll outline some tips for facilitating a successful strategic planning session. By following these tips, you can help ensure that your team is able to develop an effective strategy that will help your business grow.

What is strategic planning?

International Encyclopedia of the Social & Behavioral Sciences defines strategic planning as “a deliberative, disciplined approach to producing fundamental decisions and actions that shape and guide what an organization (or other entity) is, what it does, and why it does it.”

In other terms, strategic planning is an organizational management activity that is used to set priorities, analyze opportunities and threats, strengthen operations, ensure financial stability, and establish the long-term direction of an organization.

In for-profit corporations, strategic planning is typically focused on how to grow the business, generate revenue, and increase shareholder value. In nonprofit organizations, strategic planning may be more focused on organizational mission and vision.

Regardless of the organization type, strategic planning is a process that involves setting goals, analyzing current resources and capabilities, formulating action plans, and monitoring progress.

It is important to note that strategic planning is not static; it should be revisited on a regular basis in order to ensure that the organization remains on course. When done effectively, strategic planning can be a powerful tool for organizational success.

strategic planning

Why is it important?

There are a variety of reasons why strategic planning is important. Here are five of the most important ones:

  • It helps organizations set a clear direction. - Strategic planning provides a framework for setting goals and objectives and determining what needs to be done to achieve them. This process can help organizations clarify their mission, vision, and values, and ensure that everyone is working towards the same goals.
  • It helps organizations allocate resources effectively. - Strategic planning can help organizations determine where to allocate their resources in order to achieve their goals. This includes financial resources, but also human resources and other assets.
  • It helps organizations make better decisions. - The strategic planning process can help organizations identify and assess risks, and make informed decisions about how to respond to them. This can prevent costly mistakes and help organizations stay on track.
  • It helps organizations keep track of progress. - Regular strategic planning can help organizations track their progress towards their goals, and make necessary adjustments along the way. This feedback can help organizations course-correct and avoid veering off track.
  • It can help organizations attract and retain talent. - Organizations that engage in strategic planning are often seen as more professional and competent, which can help them attract and retain top talent. This can give organizations a competitive edge in the marketplace.

Who needs to be included?

In order for a strategic meeting to be effective, it is important to include key stakeholders who can provide input and help make decisions.

These stakeholders may include senior leaders, managers, and employees from various departments within the company. It is also important to invite experts from outside the organization who can offer insights and perspectives on the issue at hand.

Finally, it is also helpful to have a facilitator who can keep the meeting on track and help the group reach a consensus.

strategic planning

What is the purpose of a strategic plan meeting?

Generally speaking, a strategic plan meeting is held for two reasons:

  1. Collecting input from key stakeholders to make better decisions
  2. Solve a problem or take advantage of an opportunity

In short, a strategic plan meeting is designed to help an organization move forward in a more effective and efficient way.

Through this process, the stakeholders should gain a shared understanding of the organization's current situation, its desired future state, and the steps needed to get there.

This will help ensure that everyone is on the same page and working towards the same goal.

Best practices for running a successful strategic planning session

When it comes to conducting a successful strategic planning session, there are certain best practices that should be followed in order to ensure that the process is smooth and productive. Here are some tips to keep in mind:

1. Define the purpose of the session upfront

The first step to running a successful strategic planning session is to define the purpose of the session upfront. Without a clear purpose, it will be difficult to keep everyone on track and focused.

Before the session begins, take some time to think about what you hope to accomplish. Do you want to develop a new long-term strategy? Or are you looking for ways to improve your current operation?

Once you have a good understanding of your goals, communicate them to the participants. This will help ensure that everyone is on the same page and working towards a common goal.

In addition to defining the purpose of the session, it is also important to identify who should be involved. The participants should be carefully selected to ensure that they have the knowledge and expertise required to contribute to the discussion.

Ideally, the group should be small enough that everyone can have a chance to voice their opinion. Too many voices can make it difficult to reach a consensus, so it is important to strike the right balance.

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2. Create a realistic agenda

In order to create a successful and productive session, it is important to create a realistic agenda. The agenda should be designed to provide a framework for discussion, while also allowing for flexibility and input from the attendees.

It is also important to make sure that the agenda is followed closely, as deviating from the plan can lead to confusion and frustration.

When creating an agenda:

  • Keep it short. An agenda should be no more than a page long. Be clear about what you want to accomplish.
  • Be realistic. Don't try to accomplish too much in one meeting. Set a time limit. If the agenda is for a weekly staff meeting, limit it to 60-90 minutes.
  • Be flexible. If something comes up that is more important than what is on the agenda, deal with it. Prioritize items on the agenda. Make sure there is time for discussion.
  • Plan for breaks. If the meeting is going to be long, or if people are likely to get antsy, plan for breaks.

3. Build trust in the room

Any experienced business leader would know, trust is essential for any team to function effectively. Without trust, team members will be reluctant to share their ideas, and the resulting dialogue will be stilted and unproductive.

When running a strategic planning session, it is, therefore, essential to create an environment of trust. One way to do this is to start by having each team member share something personal about themselves.

This doesn't have to be something heavy or intimate - simply sharing a favorite hobby or memory can help to create a sense of connection. Once the team feels comfortable with each other, they will be more likely to openly share their ideas and perspectives.

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4. Keep it interactive

The best way to run a successful strategic planning session is to keep it interactive. This means engaging all participants in the process, from start to finish.

It is important to provide opportunities for everyone to share their ideas and perspectives, and to receive feedback from others. The goal is to create a shared understanding of the company's current situation and its goals for the future.

The interactive nature of the session will help to generate creative solutions and new ideas, which can then be used to develop an effective strategic plan.

To keep the session interactive:

  • Make use of online tools. There are a number of online tools that can help you make your strategic planning process more interactive.
  • Use physical tools. If you’re looking for a more hands-on approach, you can use physical tools to make your strategic planning process more interactive. One option is to use sticky notes to brainstorm ideas and create mind maps.
  • Gamify it. Another great way to make your strategic planning process more interactive is to gamify it. Rolljak is a game-based engagement platform that can be used to engage your team in a fun and interactive way.

5. Be open to new ideas

This means that you should not only consider the opinions of those who agree with you but also be willing to listen to the perspectives of those who may have different points of view.

It is also important to encourage everyone in the group to participate in the discussion. This will help ensure that all voices are heard and that the final decision is made with the input of all stakeholders.

Finally, be sure to allow plenty of time for the planning session so that all options can be fully explored.

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Strategic planning with remote teams

A lot has changed in the last decade. The way we work, live and play has been redefined by technology. Today, more than ever before, people are working remotely.

This presents both challenges and opportunities for businesses of all sizes. Strategic planning is key to success when your team is scattered around the globe.

But how can you run a strategic planning session with your remote and hybrid team? Is online strategic planning even possible?

Turns out, it is. According to FacilitatePro, collaboration technologies have made it possible for remote teams to conduct successful strategic planning sessions, no matter where team members are located.

Such collaboration tools are not only changing the way we work but also the way we do business. And that’s a good thing. After all, organizations that embrace change are the ones that succeed.

How to run a remote strategic planning session

Here are some tips on how to run a successful remote strategic planning session:

1. Keep it simple

When you’re planning strategically, less is more. That means avoiding information overload by keeping your presentations short, sweet, and to the point. This also goes for written materials. You want your team to be able to digest the information and come up with ideas, not feel bogged down by it.

2. Make use of collaboration tools

There are a number of great collaboration tools available that can help you run a successful remote strategic planning session. One such tool is Rolljak. Rolljak is a game-based engagement platform that can be used to create interactive activities that allow the participants to assess and evaluate one another’s responses. This is a great way to get your team engaged and evaluate the strategy and plans suggested.

3. Keep everyone involved

When you’re dealing with a remote team, it’s important to keep everyone involved in the conversation. That means no side conversations or multitasking. It can be helpful to appoint a “scribe” who can take notes and keep everyone on track. You might also want to consider using a tool like brainstorming software, which allows everyone to contribute ideas in real-time, no matter where they are located.

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Rolljak as the best strategic planning tool for remote and hybrid teams

When it comes to strategic planning, there is no tool more effective than Rolljak. For remote and hybrid teams, Rolljak provides the perfect platform to gather input, reach consensus, and communicate the plans. With Rolljak, team members can stay connected and engaged in the planning process, even when they’re not in the same physical location.

Rolljak is an online tool that allows users to create and share interactive games and surveys. It’s perfect for strategic planning because it makes it easy to identify areas where the team needs to focus their efforts in real time.

Here are the other reasons why Rolljak is a great strategic planning tool for remote teams:

  • First, it is user-friendly and easy to use. This makes it ideal for those who are not familiar with complex planning tools.
  • Second, Rolljak allows you to create and share your own games. This means that you can customize the tool to fit your specific needs.
  • Third, Rolljak is flexible and can be used for a variety of purposes. For example, you can create polls to help the team make decisions more effectively or use Rolljak’s open-ended activity type to generate a list of ideas and goals, or simply get their opinions about something.
  • Rolljak also allows your team to collaborate. With this, you can build from each other’s ideas to come up with the best one which you can use to implement better systems, processes, and more.
  • Finally, Rolljak is affordable and offers a free trial. But what sets Rolljak apart from other strategic planning platforms is that Rolljak is designed to be more engaging and fun, and you can use it with any size of your team, big or small.

When used correctly, Rolljak can be a powerful tool for remote and hybrid teams. It’s easy to use and helps keep everyone on the same page, which is essential for any successful strategic planning process.


It is evident that a properly conducted strategic planning session can be of great value to any organization. By taking the time to assess the current situation, identify goals, and develop a plan of action, organizations can ensure that they are positioned for success in the future.

While there may be some upfront costs associated with a strategic planning session, the long-term benefits far outweigh the initial investment.