Making the Most of an External Facilitator in Strategic Planning Workshops

Strategic planning is a critical process for organisations to chart their future direction and achieve their goals. Strategic planning workshops brings together leaders and representatives from across the organisation to collaborate, share knowledge, and develop a roadmap for success over the next few years.

These facilitated sessions are designed to help establish a clear vision, define measurable objectives, explore potential threats, and create a practical plan for execution while fostering resilience and internal cohesion. Engaging an independent, experienced facilitator can provide objectivity, expertise, efficient processes, fresh perspectives, and enhanced participation, ultimately leading to more robust strategic planning and strategy implementation.

Selecting the Right Facilitator

When selecting an external facilitator for your strategic planning workshop, it’s crucial to ensure their approach aligns with your team’s needs and dynamics. A skilled facilitator should be able to describe their process, facilitation style, strategic planning method, roles and responsibilities, timelines, costs, scope of work, space requirements, and the final deliverable in detail. Evaluating their proposal carefully can help ensure the facilitator has the necessary experience and approach to support your organisation effectively.

Understanding Your Needs

Before beginning the selection process, take the time to understand your organisation’s specific needs and goals for the strategic planning session. Consider factors such as the size of your team, the complexity of the issues you’ll be addressing, and any unique challenges or dynamics within your organization. This understanding will help you identify the right facilitator who can tailor their approach to meet your specific requirements.

Evaluating Expertise and Experience

Look for a facilitator with extensive experience in strategic planning and a proven track record of success. They should be well-versed in various strategic planning methodologies and able to adapt their approach to suit your organization’s needs. Additionally, consider their industry experience and familiarity with the challenges and opportunities specific to your sector.

Preparing for the Workshop

Setting Clear Objectives

Before initiating a strategic planning facilitation project, it is crucial to define clear objectives with all stakeholders, including sponsors, clients, participants, and beneficiaries. These objectives should be specific, measurable, achievable, relevant, and time-bound (SMART). Well-defined objectives provide a sense of direction and purpose, aligning efforts towards a common goal and facilitating collaboration across partnerships and levels within the organisation.

Defining Success Criteria 

Success criteria are measurable indicators that determine whether the facilitation project has achieved its objectives and met expectations. These criteria should be established beforehand in consultation with stakeholders. For a facilitation project, success criteria could include quantifiable elements like the number and diversity of actively engaged participants, as well as qualitative aspects such as the relevance and quality of information generated, the level of consensus reached, documented action plans or follow-up steps, and feedback on the facilitation process.

Clarifying Roles and Responsibilities

Within a multi-project environment, individual roles and responsibilities can change frequently. Therefore, it is essential to clarify roles and responsibilities before the workshop starts. Essentially, we must reach clarity on the following:

  1. Each team member understands their role, responsibilities, and expectations.
  2. Everyone is aware of the roles and responsibilities of other team members.
  3. Team members know the expectations others have of them in their respective roles.

Resource Allocation 

Proper resource allocation is crucial for a successful strategic workshop. This includes determining the number of participants, identifying any special needs or equipment requirements (such as computers, internet access, flipcharts, remote participation tools, and wall space), and ensuring the availability of necessary resources.

Preparing Materials and Resources

Developing a clear workshop agenda that outlines individual topics, time allocations, and expected outcomes is essential. The facilitator should select appropriate tools, activities, questions, and exercises for each agenda item. Additionally, visualising and rehearsing the meeting, anticipating potential problems, and preparing contingency plans are recommended.

Preparing the Team

Engaging the team in advance is vital for a successful strategic planning session. The agenda, objectives, and any pre-work should be shared with participants well in advance, allowing them to review, prepare inputs, and understand their roles. Your facilitator will likely suggest technology, such as AI and whiteboarding platforms, to streamline the process and pre-populate baseline ideas.

Together, ensure that the topics covered are relevant and aligned with the organization’s vision and mission. Team members can contribute ideas and provide input during the planning stage, fostering a collaborative and inclusive environment.

Building a Collaborative Environment

Effective meetings thrive on active participation and collaboration from all attendees. To foster an environment conducive to open dialogue and diverse perspectives, it is crucial to identify key participants, set up pre-meeting discussions, create a safe space, and encourage diverse viewpoints.

Identifying Key Participants

Assembling the right team is paramount for successful strategic planning meetings. The team should comprise individuals who understand the organisation, can speak authoritatively, and obtain necessary approvals. Continuity in attendance is also critical. This team typically includes the CEO, direct reports, project managers, data analysts, and department heads relevant to the agenda items. Additionally, involving staff-level participants with subject matter expertise can provide valuable context and insights, as they are often directly involved in executing the work.

Creating a Safe Space

Establishing a tone of trust and collaboration is essential for effective strategic planning meetings. Your facilitator will set clear ground rules or norms that emphasize mutual respect, openness, empathy, and accountability, grounded in diversity, equity, and inclusion (DEI) principles. They will encourage candid dialogue and critique by actively listening without interruption, withholding judgment, and acknowledging the validity of others’ experiences.

Incorporating icebreakers and thoughtful questions promotes inclusive learning and dialogue, as they encourage participants to bring out their authentic selves without fear. Regularly evaluate and adjust facilitation methods to continually improve inclusivity and representation.

Encouraging Diverse Perspectives

Diversity enriches the strategic planning experience, fostering productivity and depth of learning. Your facilitator should actively encourage contributions from all participants, regardless of their background or previous contributions, reinforcing the principle that everyone’s ideas are valued equally.

Using numbered groupings to form diverse sub-groups will help participants interact with a range of perspectives and contribute effectively to tasks. Asking open-ended questions, using prompts or scenarios, and inviting  feedback will create a supportive environment where participants feel comfortable expressing their opinions, experiences, and ideas.

Your facilitator should be comfortable managing conflicts or tensions constructively, and avoid bias, judgment, or favoritism. They should be able to use and encourage others to use respectful language, communicate calmly, show appreciation for all contributions, practice empathy, and express gratitude to cultivate a positive and productive environment.

Managing Time Effectively

Effective time management is essential to ensure that the facilitation process remains focused and productive. It involves being mindful of the allotted time, prioritizing key points, and avoiding unnecessary digressions. You facilitator would aim to keep the agenda on track and use techniques such as carparking to avoid too much sidetracking.

Post-Workshop Actions

Gathering Feedback

After the strategic planning facilitation, your facilitator should gather feedback from participants to evaluate the outcomes and process. This feedback can provide valuable insights into what worked well, areas for improvement, and any unresolved issues or concerns. Facilitators should encourage open and honest communication, ensuring that participants feel comfortable sharing their perspectives.

Implementing Action Plans

Given the time and effort invested in a strategic planning workshop, getting started with implementation should be a priority. Yet many companies stumble at this point. Ideally, a strategic plan should be continuous, with room for adaptation and changing priorities. Leaders are recommended to start implementing changes after planning and then schedule review sessions at specific future intervals. If your external facilitator is also a consultant, you can work with them to help keep progress on track.

Within a week after the strategic planning meeting, send a timeline that contains the next steps and deadlines for completing the plan. Also, include any notes that captured decisions from the session. Communicate this timeline to everyone involved so team members know what’s happening with the process. Do not, under any circumstance, cancel the next meeting in the planning or implementation process, as this signifies that the strategic plan is not important. Send the strategic plan on the deadline set, regardless of whether it’s complete, to reinforce the importance of the plan. Your facilitator should be able to etiher provide this material or support you in creating it.

Follow-Up Sessions

After the workshop outputs have been shared, the facilitator can also organise review sessions at set intervals to help your team learn from implementation feedback and improve outcomes.


Strategic planning facilitation is a complex process that requires careful preparation, collaboration, and follow-through. By selecting the right facilitator, fostering an inclusive environment, and actively engaging participants, organizations can maximise the value of their strategic planning efforts.

The facilitation process itself should elevate the experience in all ways. Get in touch with us to discuss how our expert facilitators can make your next strategic workshop the best yet.

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