min read

Facilitating a Successful Strategy Meeting

Article by 
Tefi Alonso
  —  Published 
November 3, 2022
June 7, 2023

What is a strategy meeting? 

A strategy meeting is an assembly of relevant stakeholders to focus solely on executing and improving upon the current strategy. However, typically these meetings are more concerned with the minutiae of budgets or project plan detail while ignoring overarching strategy.

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The bedrock of strategy execution is effective strategic meetings. After leadership creates an execution-ready strategy, it’s easy and common to neglect follow-through: setting up the systems and meetings to ensure consistent communication, progress, and adjustments to the strategy.

In fact, 67% of well-formulated strategies fail due to poor execution [due to no or little follow-through].

Before diving straight into the meeting itself, there are a few organizational ingredients we need to deliver a successful strategy meeting agenda:

  1. Execution ready plan
  2. Top-level buy-in/prioritization from Senior Leadership
  3. Governance around communication and interaction with the Strategy

3 Step strategy meeting agenda

1. Execution ready plan

An execution-ready strategic plan is one that has been structured and formulated in such a way as to give it the highest possible chance of gaining traction in the organization, thereby increasing its chances of success.

This includes creating a list of agreed upon objectives, assigning ownership for key projects, determining deadlines, and determining targets for key performance indicators. If you're not sure if your plan is execution-ready, I’d recommend working though our toolkit: How to know if your Strategic Plan is Execution-Ready.

A strategic plan that is non-execution-ready will make strategic meetings difficult because there wasn't an actionable strategy to begin with, leaving room for ambiguity, confusion, and interpretation. 

2. Top-level buy-in/prioritization from Senior Leadership

Drawing on our experience working with over 10,000 strategic plans, leadership engagement in strategy is essential. By nature, strategy spans across the entire organization, affecting each department and the lives of each manager, employee, and customer. This level of decision requires some change management and a great deal of buy-in. Leaders not only need to endorse the strategy, they need to be involved with the success of the strategy. This means ensuring that there are owners for each project, not letting deadlines slip, passing your knowledge and passion for strategy down to the rest of the organization, and attending meetings!

3. Governance around communication & interaction with the strategy

Some key questions that need to be answered when asking about governance are the following: 

  • How often will you meet to discuss the strategy?
  • What format will those discussions take, and supported by what reports?
  • Who will be involved in those discussions?
  • What information do you need to capture as part of managing the goals in your plan to make the governance process effective?

To the detriment of most strategic plans, these questions often go unanswered… Good thing you’re reading this blog article! We’ll cover the basics of setting up a strategic structure as well as the best practice method for conducting a strategy meeting.

For more on strategic governance, please read this article: The Strategic Management Process.

How to facilitate a strategic planning session

The first step in establishing a successful strategic meeting is to map out the current executive meetings. From there, you can determine which pre-existing meeting could be used to discuss progress on the strategic plan. Speaking from experience, it is easier to incorporate strategic meetings into business-as-usual meetings rather than creating new meetings. A sample table below shows an example of this:

how to facilitate a strategic planning session

If your organization is new to discussing strategy on a recurring basis, try to incorporate strategic conversations into only one of the meetings included within your table. It is much easier to drive change by focusing your efforts on one meeting as opposed to many at a time. Once you’ve shown success in one of the strategic meetings, strategy will be easier to roll out as people begin to adapt more of their conversations to include strategy.

Come Prepared

Before the strategic meeting takes place, it’s critical that people come to the meeting prepared. Coming prepared obviously means something different based on the type of meeting being held. With that said, coming prepared typically means the following

  • Reviewing your top level objectives
  • Assigning a status (on track, behind, complete, etc.) to your projects
  • Knowing how your KPIs are performing
  • Understanding some of the underlying problems that stand in the way of success, and thinking through next steps.

In certain meetings (e.g. Board Meetings) it may be helpful to send out a report which summarizes the progress made so that people can come prepared to problem-solve. You could track each of your Objectives and KPIs with a combination of Word, PowerPoint spreadsheet, and BI tools, or you could track this information with Cascade.

Meeting Agenda

Once the meeting begins, you’ll need to come prepared with an agenda outlining the structure and topics to be covered in the meeting.

As I’m sure you understand, meetings can easily become mired in pointless rambling and constant derailing if there isn’t an agenda in place and a facilitator to keep it on track. The type of meeting will determine what is reviewed and what needs to be discussed, and some meetings require specific nuanced agendas, but overall each meeting should follow these three phases:

  1. What’s happening now?
  2. Problem-solving
  3. Next Steps

What’s happening now?

During this phase, we need to review the success or failure of our prior commitments (more on this later). We also need to identify areas of the strategy (objectives, barriers, KPIs, etc.) that need collective problem-solving.

This includes areas that are lagging behind, unexpected results (good or bad), or upcoming barriers such as budget or resources constraints. The difficult thing with this phase is not jumping straight into problem-solving mode.

People who find themselves in leadership roles typically have a knack for problem-solving, otherwise, they probably wouldn’t be in their position! Because of this, you need to encourage everyone to hold their solutions back until each and every critical area is addressed.

The purpose of this phase is to get a lay of the land. Once the leaders in the room have a broad understanding of what is currently happening, we can move into the next phase.


This phase should take up the majority of the meeting time. Once a list of areas which need collective problem-solving is created (see 'What’s happening now?'), begin this phase by working through the highest priority items first and move down the list to the lower priority items after.

The problem solving phase should include these 3 steps:

  1. Identify the problem 
  2. Understand the cause of that problem
  3. Steps to resolve the problem

1. Identify the problem: Simply recap the problem addressed in “What’s happening now”

2. Understand the underlying cause of the problem: The owner of the objective, project, or KPI needs to describe their interpretation of the underlying cause of the problem and ask the group if they agree or disagree. 

Of note, when holding these meetings, the way you ask questions and hold options matter. Try practicing assertive inquiry: explicitly expressing your own thinking while sincerely exploring the thinking of others. In other words, “I have a view worth hearing, but I may be missing something.”.

This can have a dramatic impact on the group dynamic especially when human nature default is to protect your ideas and thoughts. The best way to solve problems and explore alternatives is not to understand what others see, but what they do not.

Statements like “I may be missing something, but I believe that we’re not gaining traction in this market due to x” elicits much better conversation than “No question about it, we are not gaining traction in this market due to x.”.

Assertive inquiry can be especially helpful in the “Understand the underlying cause of the problem” and “Steps to resolve the problem” stages.

After doing some digging and finding the root cause of the underlying problem, you can move to the next stage: steps to resolve the problem.

3. Steps to resolve the problem: Finally! We can use the collective problem-solving power in the room to solve the problem. After running through these phases we should be confident that we have identified the correct underlying issues for our highest priority items.

This is the most effective way to use our problem-solving! Once the next steps are established, ensure there is a specific owner who is responsible for the completion of this task by a specific deadline. Write these details down move on to the next problem and repeat steps 1-3 for the next topic of discussion.

Next steps: Typically, this section takes the least amount of time because it is essentially a recap of the next steps addressed in the "Problem-solving" step. However, it is important to ensure the "next steps" are recorded and understood by all parties. This reinforces accountability which is the secret sauce of execution.

There you have it! The basics of a great strategic conversation. Please put these ideas to practice and let me know how it goes.

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