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  • Iwona Wilson

How to Prepare for Strategic Planning - Advice For SMEs and Nonprofits

Do you ever find yourself struggling to navigate the uncertain future of your organization? Are you looking for a way to steer your small or medium-sized enterprise (SME) or nonprofit towards long-term success?

Three people sitting around the table talking business
Business Meeting

Strategic planning workshop might just be the missing piece of the puzzle.

But here's the catch: many leaders and board members often fear the strategic planning process (and the workshop part), hesitating to embark on this transformative journey. In this article, we will explore the importance of having a strategic planning framework and why executives and board members should embrace it, pose thought-provoking questions you need to consider, and shed light on the role of a facilitator.

So, are you ready to unlock the potential of strategic planning?

What’s the difference between a strategic planning process and strategic planning workshop?

Strategic planning and a strategic planning workshop are related concepts but have distinct differences in their scope and purpose.

I shared my definition of the strategic planning:

Strategic planning is an ongoing process of defining organizational direction, long-term goals, creating specific plans, implementing those plans, and evaluating results.

It involves a series of steps such as (1) environmental analysis, (2) visioning, goal setting, (3) strategy formulation, (4) implementation, and (5) evaluation.

A strategic planning workshop, on the other hand, is a focused and time-bound event within the strategic planning process. It is a facilitated session or series of sessions designed to turbocharge the strategic planning process so that the key elements of the process can take days as opposed to months.

Strategic planning workshop is about bringing the key stakeholders together to actively involve in the planning and decision making process.

The workshop provides a structured environment where participants engage in collaborative discussions, brainstorming, and problem-solving to develop or refine the organization's strategic plan.

a team discussing and exploring issues in a workshop
Strategic Planning Workshop

The workshop is the heart of the strategic planning process and it can cover anything from environmental analysis, visioning, goals settings, strategy formulation and implementation plan. The workshop is also a great way to shorten the time for strategy development from months to even days!

When its well facilitated, it provides not only a well defined strategic plan but also stimulates creativity, align perspectives, and foster consensus among participants and helps to bridge gaps between various stakeholders by exchanging ideas, evaluating options, fostering inclusive solutions, generating understanding and high energy.

Strategic planning workshop should energize you and the stakeholders involved.

Why leaders or board members often fear strategic planning?

Here are 4 reasons Why Leaders and Board Members Often Fear Strategic Planning:

1. Previous experiences: Starboard Leadership says in this article:

"Too often the last planning process took too long, involved way too many meetings, and resulted in a plan that has been sitting on the shelf ever since. So, strategic planning gets postponed: “We’ve got a lot on our plates right now. Let’s talk about that after the new year.”

Moreover, some organizations managed to build the plan but then everything changed because they assumptions were no longer valid hence they became disillusioned about the power of strategic planning.

2. Fear of the unknown: the strategic planning can be daunting, especially for those who have never been through it before. Uncertainty about the outcomes and the potential disruption to the status quo can create resistance.

3. Time and resource constraints: executives and board members often have busy schedules and limited resources. They may perceive strategic planning as an additional burden that takes them away from their day-to-day responsibilities.

4. Resistance to change: strategic planning often involves making tough decisions, challenging existing practices, and embracing change. Some leaders and board members may resist these changes due to fear of failure or resistance from stakeholders.

In spite of any reasons for putting strategic planning off, the responsibility still lies with you to implement a planning process that provides the organization with a plan they will want to use and embrace to fulfill their mission, achieve their vision by delivering a clear value proposition to their shareholders, customers and employees.

Who can wildly benefit from the strategic planning?

Here are some key stakeholders who can benefit from participating in a strategic planning:

  1. Senior Leadership Team: The senior leadership team plays a vital role in the strategic direction of the organization. By participating in a strategic planning workshop, they gain insights into the current state of the organization, identify future opportunities and challenges, and collaborate on defining the strategic goals and priorities. The workshop enables them to align their vision, set strategic objectives, and develop a shared understanding of the organization's direction.The process can build resilient teams and connections, breaking down departmental “silos” and prompting the leadership tea, or the board and staff to work together to look beyond immediate needs and develop strategies to succeed in an uncertain future.

  2. Managers: Departmental managers are responsible for translating the organization's strategic objectives into actionable plans within their respective departments. A strategic planning workshop provides them with a clear understanding of the organization's overall strategy, enabling them to align their departmental goals and initiatives accordingly. They can contribute their expertise and insights during the workshop to ensure their department's objectives are in line with the broader organizational strategy.

  3. Cross-Functional Teams: Involving cross-functional teams in a strategic planning workshop ensures diverse perspectives and expertise are represented. These teams can contribute their unique insights and knowledge, helping to identify potential challenges and opportunities from different areas of the organization. By participating in the workshop, cross-functional teams can collaborate on developing strategies and action plans that promote coordination and synergy across departments.

  4. Frontline Employees: Frontline employees are the ones responsible for executing the organization's strategy on a day-to-day basis. Involving them in a strategic planning workshop empowers them to contribute their insights and ideas, fostering a sense of ownership and engagement. By understanding the strategic goals and the rationale behind them, frontline employees can align their work with the organization's strategic objectives and contribute to their successful implementation.

  5. Board Members and Stakeholders: Board members and external stakeholders, such as investors, partners, and customers, can benefit from participating in strategic planning workshops. Their involvement ensures their perspectives are considered, and they have a say in shaping the organization's future direction. By actively participating in the workshop, they can provide valuable input, contribute to decision-making, and gain a deeper understanding of the strategic priorities and actions being undertaken. For the Board members, agreeing on vision and priorities will lead to a more vibrant and satisfying board life, with clearer roles and responsibilities, more productive meetings, stronger recruitment and increased engagement.

three levels of the organization
All levels of the organization can benefit from the strategic planning process.

You might even resolve those “elephants in the room” issues.

Overall, a strategic planning workshop is designed to engage a wide range of stakeholders, fostering collaboration, alignment, and shared ownership of the organization's strategic goals. It creates a platform for diverse perspectives to come together, enabling participants to contribute their expertise, drive innovation, and ultimately enhance the organization's strategic outcomes.

When is the right time to engage in a strategic planning process?

Planning can be delayed for many reasons:

  • “It's too busy right now”,”It will be helpful if we add a few more members to the team or board before we begin planning”, “Our new team members or board members or executives need time to get up to speed”, “Political reasons: what can we expect from the Governor, the legislature, the budget negotiations, etc.” - as shared by the Starboard Leadership.

However, It is your responsibility as a leader to develop and implement strategies and methods of working that will help to realize the company's vision for shareholders, customers, and employees.

So, waiting for the perfect moment is impractical as distractions and external factors will persist, but postponing planning leaves your organization susceptible to these forces instead of proactively shaping your own future.

What are the most common reasons to hold a strategic planning workshop?

Why do you want strategic planning? It takes a lot of energy to create a strategic plan, hence a facilitator like myself needs to know the real reason to amplify the benefits.

Internal needs:

  • We have accomplished our plan and need a new one

  • The company has grown and we have a lot of new staff

  • The company has shrunk and the whole group needs to refocus

  • The budget is reduced or expanded

  • There is a new board member or CEO

  • The organization has a new mandate and we have to get everyone operating in the same way

  • We need a new way of operation

External reasons:

  • New funding rules or government mandates

  • Changing demographics or the region

  • A new political situation that impacts the existence of the organization

What is the desired outcomes?

What will we need to have, or have achieved, for you to say that this was a success?

What is the ultimate result you are trying to achieve? What are the expectations of all stakeholders, since they may differ. How much trust exists between the various levels in the organization?

Answers to these questions above will impact how much participation is required and who should be involved?

  • Is this for the board and the leadership group to set up the strategic directions, shall we involve key stakeholders, on what basis, etc? Or is it a tier two scenario where the manager wants to create for their function a set of clear 1 year goals and an operational plan for their function?

  • How will this impact the scope and the level of details required

  • Is the leadership team already anticipating some initiatives or structural changes? Are we supposed to review the mission and values or don't we need to do it?

What issues or questions do you want to make sure we address along the way?

In order to get answers to these questions, we always interview not just the sponsor but also everyone else or most people who attend the workshop. We even run short surveys.

How much stakeholder involvement would you like to have?

I often advise who can be involved but it is the leadership team or my sponsor whom I am working with to put this together who makes these types of decisions.

However, remember that involving as many potential stakeholders as possible increases the value of your plan. This can also lead to greater implementation help from your partners, clients, and other stakeholders.

Will this be led internally? If so, who? Or externally

Here's the truth: If your organization has assigned you (or your department, a colleague) with creating a strategic plan and reporting back to the leadership team upon completion - stop right now!

(!) A successful strategic plan must prioritize organizational buy-in, which means early involvement from the leadership and cross pollination of ideas between different departments.

For this reasons, it needs to be led by someone who is neutral and has no vested interest in the outcome of conversations; this major player who is crucial to its success is the facilitator.

A facilitator's role is to ensure that the right processes are used with the right approach so that the organization can execute on its strategy.

I have worked both, as an internal facilitator for a large energy company and an external one and there are benefits and challenges to both roles. Surely, if you just need an action plan for the next 12 months, perhaps having an internal resource might be a fit for purpose approach where you could save some time and money.

However, there are a few key advantages to hiring an external facilitator to develop a strategic plan over relying solely on internal resources.

  1. Fresh Perspective: An external facilitator brings a fresh and objective viewpoint to the strategic planning process. They are not influenced by internal biases, office politics, or preconceived notions, allowing them to offer unbiased insights and challenge existing assumptions. They are neutral which means they have no vested interest in the outcome of the conversations.

  2. Specialized Expertise: External facilitators often have extensive experience and expertise in strategic planning methodologies and frameworks. They bring a wealth of knowledge and best practices from working with various organizations across different industries, enabling them to provide valuable guidance and ensure the plan is well-structured and effective.

  3. Time and Focus: Developing a strategic plan requires dedicated time and effort. Internal resources may already be occupied with their regular responsibilities, which can lead to limited focus on strategic planning. Hiring an external facilitator allows your internal team to fully engage in the planning process without being burdened by other day-to-day obligations.

  4. Facilitation Skills: Facilitating a strategic planning session requires strong facilitation skills to manage discussions, encourage participation, and navigate potential conflicts. External facilitators are trained in these skills and can ensure that the planning sessions are productive, inclusive, and result-oriented.

  5. Objectivity and Impartiality: Internal team members may have personal interests, biases, or attachments to certain ideas or outcomes. An external facilitator, being impartial, can foster an environment where all ideas are considered objectively, ensuring that the strategic plan is based on the best interests of the organization rather than individual preferences.

  6. Confidentiality: External facilitators are bound by confidentiality agreements, providing a safe and secure environment for sensitive discussions. This enables participants to openly share their thoughts, concerns, and challenges without fear of internal repercussions.

By leveraging the expertise and objectivity of an external facilitator, organizations can enhance the quality of their strategic planning process and outcomes, leading to a more comprehensive and effective strategic plan.

Here is what one of our clients say about the strategic planning workshop using our method.

Additional questions leaders should consider before calling for a strategic planning workshop:

  • What are the current organizational challenges and opportunities?

  • Are the team members and employees aligned with the current vision and mission? how do you know?

  • What's going on in the market? have the industry trends changed? Which ones will stay the same?

  • How do we currently satisfy our customers?

  • How can you involve the key stakeholders in the planning process?

  • How will you foster a diverse, inclusive and creative environment during the workshop?

  • How will you ensure accountability and follow through after the workshop?

  • What is your business model? What problems do you solve, how and whom for? What needs to change?

Book a call now
Book a call with us now

Are you ready to unlock the true potential of your organization and achieve greater success?

I invite you to book a complimentary 30-minute clarity call with us to explore your unique situation and determine if our strategic planning workshop is the perfect fit for you.

During this call, we will delve into the challenges you're currently facing, the goals you aspire to achieve, and the potential roadblocks hindering your progress. We will actively listen, ask insightful questions, and provide an initial assessment of how our workshop can address your specific needs.

Here's what you can expect from the clarity call:

  1. Personalized Attention: We believe in understanding the nuances of each organization we work with. Our undivided attention will allow you to share your aspirations, concerns, and aspirations.

  2. Expert Guidance: With years of experience in strategic planning, we bring a wealth of knowledge and expertise to the table. We'll offer valuable insights and strategic recommendations tailored to your unique situation, helping you navigate challenges and identify growth opportunities.

  3. Honest Evaluation: Our aim is to ensure a mutually beneficial partnership. During the call, we'll honestly assess whether our strategic planning workshop aligns with your organization's needs and goals. If we determine that our workshop isn't the right fit, we'll provide alternative suggestions or resources that may better suit your requirements.

  4. No Obligation: Our clarity call is completely free of charge and without any obligations. It's an opportunity for you to gain clarity and make an informed decision about your strategic planning journey. We prioritize building meaningful partnerships, and if you decide our workshop isn't the right fit, we respect your choice.

To schedule your call, simply click on the link here and choose a convenient time slot from our calendar or email me at

If you have any questions or require further information, please feel free to reach out to us. We're here to assist you every step of the way.

Let's embark on this transformative journey together and pave the way for a strategic plan that drives your organization's success!

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