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Facilitating Strategic Planning

ByKristi Meredith

My Guide to Strategic Planning Sessions

With the fall here, I’ve been very busy running strategic planning sessions over the past couple of months. The start of the school year is the perfect time to bring everyone back together after summer and get aligned on the goals and projects we need to tackle over the next few months. Since I’ve been deep in these sessions lately, I wanted to share some thoughts on what strategic planning is, why it’s helpful, and who should be in the room.

So, what is Strategic Planning?

Strategic planning is, in a nutshell, about getting people together to map out the organization’s long-term vision and goals, and then figuring out how to get there in a more tactical sense. It’s the process that ties all the daily work teams do to the bigger picture, making sure everyone’s on the same page and working toward the same goal. A good strategic plan should cover these basics:

  1. Long-term vision and goals: Where do we want to be in the next 1-3 years?
  2. Building a plan: Laying out a roadmap of the short-term steps needed to reach those goals.
  3. Setting success metrics: Defining benchmarks to track progress and making sure we’re on track (or adjusting as needed based on real data).

The goal is to make sure everyone knows how their role and daily work fits into the bigger picture, giving clarity and purpose. It’s important to have a mix of people in the room—leadership, end-user representatives, subject matter experts, product owners/project managers, and the key team members who’ll be doing the work day-to-day. I’ve run sessions for 80-person for an entire branch, and I’ve also done smaller ones with a subset of the organization. Both approaches work; it just depends on what’s best for your team. A good facilitator should be able to help you determine what is the best approach for you.

There are lots of ways to approach strategic planning—some do short meetings stretched out over time, build out business cases, or create team charters. Personally, I like bringing everyone together (whether in-person or virtually) for one or two days to really dive in. We dig into what the organization is all about, what they want to achieve, and how they’re going to get there. Here’s why these dedicated sessions are so valuable:

  • Building culture: It’s a great way to reinforce and strengthen the company culture by having everyone together. In-person sessions have been exponentially more valuable given the shift to more remote working since the pandemic.
  • Aligning on priorities: It helps everyone get clear on what’s in and out of scope based on the organization’s priorities
  • Breaking down silos: Getting everyone together in one room (virtually or in-person) helps people understand what other teams and people are up to. It builds transparency and reduces duplicated work through collaboration.

These benefits are especially helpful for bigger organizations with lots of teams or departments, as it brings everyone together under one game plan.

I could talk about strategic planning all day, so I will stop there and keep it short so this doesn’t turn into a novel! Honestly, I love running these sessions—they’re my absolute favourite because you can physically see the team getting aligned, making connections, and having those “aha” moments together. If you’ve got any questions about strategic planning or just want to chat about how it could work for your team, feel free to reach out – I am happy to chat.