Strategic Planning is certainly a meaty topic and can often seem like an intimidating undertaking. Approaching the process intentionally can save you headaches in the short and long term and will result in a much more cohesive execution.
We’ve distilled our best tips for effective strategic planning into 6 easy-to-swallow pieces to get you started.
It’s no secret that organizations that create and execute better strategies are more likely to succeed than those that do not. Strategic planning helps leadership teams make choices about where to focus, what to invest in and what the organization needs to accomplish. But its value depends largely on how those choices guide decisions and work after the planning session ends.
These six practical tips can help strengthen your strategic planning process, set achievable priorities, and follow through on your commitments.
1. Stay Connected to Your Raison D’être
Although there are certainly differences between “Core Purpose”, “North Star”, “Mission”, “Vision”, or the myriad of other foundational statements organizations create; for the purposes of strategic planning, it matters less about which ones your organization uses, and more that you make them central to your strategic planning process.
For each proposed priority, ask: How does this support our purpose and future direction? What would it mean in practice for our employees, clients or members?
These questions can help identify a disconnect between an attractive opportunity and what your organization is trying to accomplish. They can also reveal where familiar ways of working need to change.
Your current culture should inform your strategy, but it shouldn’t prevent you from pursuing necessary change. If the strategy requires different behaviours, new capabilities or a shift in priorities, make that part of the implementation plan.
Staying connected to your organization’s raison d’être not only reduces the likelihood of your strategy falling flat, but ultimately helps you build a culture of strategic execution.
2. Create Space for Focused Strategic Discussion
It probably won’t surprise anyone to see this one on the list. There are good reasons to hold an off-site strategic planning retreat. Getting away from the office can reduce the number and frequency of outside distractions, allowing participants to be more focused and mindful of the task at hand, while also providing an opportunity for some additional team building.
Having seen, and participated in strategic planning carried out in pretty much every conceivable way, I’m firmly of the belief that having an off-site retreat is worth the effort involved in clearing schedules and arranging logistics.
The potential upside is immense. Every game-changing idea I’ve come across during strategic planning sessions has occurred during an off-site retreat. That isn’t to say you cannot have a good strategic planning process without an off-site retreat because you definitely can. But why settle for good, when great is possible?
Whether you meet offsite, in the office or virtually, protect the time. Agree on how urgent interruptions will be handled and keep routine updates out of the agenda.
The aim is to give leaders enough space to examine assumptions, debate trade-offs and make decisions that are difficult to address between regular meetings.
3. Utilize an Outsider Perspective
No matter how diverse the thinking amongst your senior leadership team, there are inevitably some common experiences and other factors that result in potential for biases and group think to limit the value you generate from your strategic planning process. An outside perspective can help surface questions that have become difficult to see, or uncomfortable to ask.
Why not inject some more diverse thinking by having an outsider participate? Having someone with very limited knowledge of the business, but who can ask great questions, (and isn’t afraid to ask the tough ones) is invaluable.
An external facilitator can bring that perspective while helping the team work through the planning process. Their value goes beyond managing the agenda and capturing discussion points. A good facilitator prepares carefully, learns enough about the organization to ask informed questions and challenges participants to explain their reasoning.
They can also help ensure different views are heard, keep discussion focused and distinguish between an issue that needs more information and a decision the team is ready to make.
An outside perspective should strengthen the leadership team’s judgment. Responsibility for the strategy and its execution remains with the organization’s leaders.
4. Avoid the Long-Term Thinking, Short-Term Focus Problem
Most strategic planning processes use either a three- or five-year planning window (with a heavy emphasis on what needs to be done in the upcoming year). There are certainly good reasons (and supporting evidence) for thinking long-term. But long-term objectives need nearer-term commitments if they are going to influence what happens next.
You may return from your off-site retreat enthusiastic about the direction, only to find a backlog of work, competing priorities, and decisions waiting for approval. Plus, there’s the regular day-to-day tasks and whatever else is happening at work and at home. Sometimes there are process delays (board approval or another internal validation mechanism is postponed). Without clear next steps, strategic initiatives can lose momentum while everyone remains busy.
Before the planning session ends, agree on what you can realistically accomplish over the next three months. Identify which actions need to happen first, where work depends on another decision and what resources will be required.
Be explicit about trade-offs. If the plan adds work to a team that is already at capacity, what will stop, move or receive additional support?
A shorter planning window gives people a practical starting point and creates an opportunity to learn before committing to the next stage.
5. Hold Yourself Accountable
Near the end of your next strategic retreat, after you’ve settled on your main objectives for the up-coming year, spend a little extra time talking through what you want to (realistically) achieve in the next three months.
For each priority, agree on an accountable owner, the outcome you want to achieve, a measure of progress and the next milestone. Check that the team has the time and resources to deliver, including what may need to stop or be deferred.
Then schedule regular strategic check-ins. Quarterly reviews may suit some priorities, while others need monthly attention. Choose a rhythm that reflects the work and the decisions required.
Keep the discussion focused:
- What has progressed since the last review?
- What is blocked or at risk?
- What has changed in our assumptions or circumstances?
- What decisions or support are needed before the next milestone?
Inviting your “outsider perspective” person to the meeting can help challenge assumptions and maintain focus, but accountability belongs to the leadership team
Be aware of meeting creep. If you are meeting more often, shorten the length of your meeting and use written updates for information that doesn’t require discussion. Spend the time you do have together resolving obstacles, making decisions and adjusting the plan where necessary.
With practice and intention you can drastically reduce the duration of strategy check-in meetings while maximizing their ability to drive execution.
6. Long-Term Thinking About Long-Term Thinking
In the end, strategic planning is likely something your organization will do for as long as it is around, so you might as well take a long-term approach.
You don’t need to introduce every possible tool, meeting or measure in one planning cycle. Start with the changes that address your most significant gaps. That might mean better preparation, clearer priorities, stronger ownership or more useful progress reviews.
At the end of each cycle, ask the team what helped and what got in the way. Did the plan guide resource decisions? Were priorities clear enough for people to act on? Did reviews lead to decisions, or simply repeat status updates?
Use those answers to refine the next cycle. Over time, strategic planning should become more closely connected to how your organization makes decisions and gets work done.
Want to strengthen your next planning cycle? Stratford helps leadership teams develop strategic and operational plans, facilitate focused planning sessions and establish practical steps for execution.
Let’s talk about your strategic planning priorities.
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This blog post was originally published in January 2022 under the title, "When it Comes to Strategic Planning, Don't Bite Off More Than You Can Chew." It has been updated with new content.