5 Questions To Consider When It Comes To Strategic Planning

5 Questions To Consider When It Comes To Strategic Planning

“This is the year that we are going to take planning seriously.”

For some organizations, this might mean booking a two-hour meeting in the board room where senior management are asked to speak to budgets and goals for the coming year. For others, this might seem like an ambitious pipe dream based on resources. 

We all know how important strategic planning is for an organization, but when it comes down to it, this time is far too often viewed as a ‘nice to have’ or reserved only for years with big and bold plans. Instead, strategic planning should be looked at as a way to help open up the lines of communication across your organization, generate new ways of thinking and approaching problems, and as an opportunity to take a big picture approach to the challenges and opportunities facing the organization. 

Having worked with organizations of all sizes from a variety of sectors, here are five of the most asked questions we hear when it comes to strategic planning. 

Can We Afford It? 


For some organizations, a robust strategic planning process is standard. A combination of board meetings, strategic planning sessions and management meetings make up an annual process that just seems to happen year over year. For others, this is a laborious endeavour that seems expensive both in terms of time and dollars. 

Strategic planning doesn’t need to be a strain on resources as it provides a way to ensure resources and priorities are allocated correctly. A single, effectively organized meeting can make all the difference in ensuring team alignment of goals and priorities, enhancing engagement amongst staff members, and improving awareness of the challenges and opportunities facing the organization. Can you afford to ignore these types of results?

Do We Need a Facilitator? 


‘Why would we need to bring in someone else? We know what we are doing.’ Far too often we hear this from organizations as a response to the question of whether to use a third-party to help facilitate strategic planning meetings and team retreats. 

Bringing in a third party requires some added time and cost but the advantages far outweigh the potential negative outcomes that could lead from a lack of direction in meetings, getting bogged down in the weeds of the operations, or even worse, outcomes driven by group think. 

A facilitator helps to do more than ensure a meeting is run on time; they make meetings matter. By having a third-party facilitate decision making, they can help build team alignment in areas of importance, stimulate discussions around challenging topics, deliver actionable outcomes and instil the confidence to make strategic decisions. 

By helping to expand thinking with a fresh perspective, facilitators offer a process that helps drive strategic decision making while seeking the best answer as opposed to just consensus. 

Who Should We Invite? 


Each organization must carefully consider who should be involved in strategic planning. A few individuals that should play a role in a strategic planning process include: 

  • Planning Process Champion – usually the executive director or board chair, this person must be a believer in the value of strategic planning and will help keep the work on track. 
  • Planning Process Facilitator – considering involving a third party to help lead the session and stimulate discussions when needed. Not only will this allow the entire team to focus on the questions at hand but will stimulate and at times, provoke discussions that need to be had. 
  • Staff – staff members have the expertise and information that will contribute to and shape discussions. As they will be the ones directly impacted by the outcome, they should be both informed and involved. 
  • Board of Directors – developing a strategic plan is an excellent opportunity to engage the board of directors by having them take an active role in shaping an organization’s future. While ultimately adopting the plan and using it as a guide for future decisions and actions, the board of directors should be kept informed of its progress throughout. 

Are We Big Enough? 


2, 10 or 100 employees, regardless of size, strategic planning should play an annual role, if only for the opportunity to take time to think strategically. Often smaller organizations do not have the resources for a full planning process but setting time aside to stop and huddle with your team to talk about strategic challenges and opportunities brings tremendous value. 

How Do We Prepare?


Whether it’s a board retreat, strategic planning session or a meeting aimed at tackling a tough question, challenge or opportunity, it pays to be prepared. 

Preparing for the session by creating and distributing a prep package helps to ensure your team is prepared for the topics and discussions outlined in the agenda. The contents of the package will vary depending on the nature of the session itself but should look to ask questions and provide reading that helps to prepare attendees in getting into the right headspace. 

From completing an environmental scan for the organization to reviewing organizational strategic plans to considering questions and key issues for discussion during the meeting; this package will help equip your team with the right mix of pre-reading materials and topics of discussion to help  ensure important discussions can be had. 

About The Author


In his role of Principal, Jesse Meyer works with clients to solve challenging problems and generate revenues, drawing from over 10 years of marketing, branding, strategic planning and stakeholder relations experience in the public, corporate and not-for-profit sectors. He has spearheaded effective organizational change, operational excellence and innovation by working collaboratively with stakeholders to build the foundation, structures and processes for long-term success.

About Incite


Incite is a marketing and strategy consulting firm specializing in growth, brand, and communications. From market expansion and brand development, to supporting post-merger integration and building internal engagement, Incite’s strategic approach helps clients to better understand their market, clearly articulate value, align organizational resources, and connect with key stakeholders to achieve success.

Jesse Meyer
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