How Often Should We Update Plans?

“How often should we update our strategic plan?” sounds like a reasonable question.

I think it’s the wrong one.

The question assumes the strategic plan is a static document that eventually becomes outdated and needs to be refreshed. A better starting point is to assume that parts of the plan will need to change from the moment you begin implementing it.

That doesn’t mean your strategy should be constantly moving. In fact, quite the opposite. Your long-term direction and strategic pillars should probably remain fairly stable. They are your North Star, particularly when the environment around you becomes unpredictable.

What should be much more flexible is how you get there — timelines change, tactics stop working, funding shifts, policy changes, or teams discover barriers nobody could have predicted during the planning process. If every change in circumstances sends you back to the drawing board, you don’t really have a strategy. You have a series of reactions.

The goal isn’t to keep rewriting the plan, it’s to build an organization that knows how to use it.

Your North Star Should Be More Stable Than Your Route

I work with organizations in sectors where things genuinely can change on a dime. Funding decisions, government policy and shifting client needs can alter the operating environment quickly. It’s understandable that leaders question the value of a three - or five-year plan when they can’t predict what will happen six months from now.

But that uncertainty may actually make a clear long-term direction more important, not less.

When something significant changes, your strategic priorities give you a filter for deciding what to do about it. Without that filter, upheaval can quickly turn into panicked decision making.

Most of the time, I would expect the strategic pillars and long-term outcomes to remain intact. A truly significant external change might warrant reconsidering them, but that should be rare.

What should remain open to adjustment are things like:

• timelines;

• tactics and implementation activities;

• the sequence in which work happens;

• KPIs or OKRs when the original measures are no longer telling you what you need to know; and

• the supports, capabilities or resources required to achieve the outcome.

There’s an important distinction here. Changing how you achieve the strategy is not the same as changing the strategy.

In fact, if you have implemented an ambitious strategic plan over several years and have never needed to adjust anything, I’d question whether the plan was ambitious enough, or whether your measurement was actually informing your decisions.

I’ve Changed the Route Midway Through an Engagement

I was working with a team after a merger to develop their team strategy and build greater synergy across previously separate groups. One of our goals was to strengthen vulnerable leadership, with more honest communication, deeper clarity and faster problem solving.

We had planned training and activities designed to build those skills.

Then the behavioural data started telling us something important: the trust across the teams wasn’t there yet.

We could have stayed committed to the original implementation plan. After all, we had designed it for a reason. But pushing ahead would likely have meant asking people to practise vulnerability before the conditions existed for it to land.

So we changed the route.

I worked with the leadership team to identify the skills and experiences the group needed first, and we adjusted the program accordingly. The goal didn’t change — the steps required to reach it did.

Eventually, the team developed a level of collaboration and respect that senior leadership could see and even commented on. We didn’t abandon the strategy when the original approach wasn’t working, we used measurement to make the strategy more achievable.

That’s what a working strategic plan should allow you to do.

So, How Often Should You Actually Review It?

There is still a cadence I recommend, because “the plan is a living document” can easily become code for “we’ll talk about it whenever we remember.”

I recommend reviewing KPIs and OKRs bi-weekly.

That rhythm keeps the strategy visible and reinforces that progress is expected. More importantly, this shouldn’t happen only at the executive level. Teams and individuals throughout the organization need to understand what they are working toward, what progress looks like and how their work connects to the bigger direction.

I’d then hold a more substantive quarterly strategic review with leadership, along with an annual review of the strategy as a whole. Summaries of those conversations should be shared back with teams so people understand what leadership is seeing, what is changing and why.

But those meetings aren’t the only time the strategy should appear. Teams and leaders should be referencing it when they make decisions throughout the year.

Strategy, boiled down to one thing, is choices.

Does this choice move us toward where we said we were going? Does this new initiative support one of our priorities? Are we about to spend money, capacity or leadership attention on something that has very little to do with what we said matters?

That is how you start building a strategic culture instead of simply owning a strategic plan.

Don’t Confuse Adaptability With BSOS

There is another side to this. I call it BSOS: Bright Shiny Object Syndrome, and I’m prone to it myself as a business owner.

Something doesn’t seem to be working quickly enough. A new idea appears. Suddenly the new thing looks much more promising (and shiney) than the thing I’ve been patiently working on.

The problem is that if I keep changing direction before anything has had enough time and intentionality to produce an impact, nothing gets very far.

Organizations do this too, except when a leader does it, the rest of the organization experiences the consequences. Priorities keep changing, people become wary of investing in the latest initiative, and eventually “strategic” starts to mean “whatever leadership is excited about this month.”

Most of the time, staying the course is going to be the wiser decision.

Change should be prompted by evidence, not impatience. I’d start considering an adjustment when you’re seeing repeated data that an approach isn’t working, significant changes to funding or policy, barriers appearing across teams, behavioural data showing that adoption isn’t happening, or unintended consequences emerging.

Even then, I don’t think significant adjustments should be made by a leader sitting alone with their thoughts.

Bring others into the discussion. Get the people closest to the work involved. Understand what the data might not be telling you. Consider what else will be affected by the proposed change.

Thinking is work. Sometimes slow is fast.

A Memo Is Not Implementation

I recently spoke with friend in construction who gave me a pretty spectacular example of what happens when organizations fail to make that distinction.

Leadership had been sending site supervisors memos about changes to equipment and safety protocols. I’m talking significant changes, not housekeeping items.

Then he found out about a foreman driving a forklift down the streets of Toronto to get from one job site to another. The equipment wasn’t insured for street use, and more importantly, it created a very real public safety risk.

When he raised it with the site supervisor, the supervisor seemed completely unaware of the issue. It turned out he hadn’t read the memo. Worse yet, he didn’t even know it had been sent.

Leadership had technically communicated the change. Operationally, nothing had changed.

That’s the danger when strategy, policy or organizational change lives primarily in documents. People can end up doing things that aren’t just misaligned with the plan, but actively work against it. In service organizations, that disconnect can directly affect the quality of service clients receive.

Before You Update the Plan, Get Practical About It

So, if you’re wondering whether it’s time to update your strategic plan, I’d start somewhere else.

Get clear about what achieving the strategy actually requires.

What capabilities need to exist? What resources will people need? Is there budget attached to the priorities you’ve named? Do you currently have those things in place?

Then move one level closer to the work.

What do your middle leaders need to do differently? What does your frontline need to do differently? What behaviours would you expect to see if the strategy were actually taking hold?

Aspirations have their place, but eventually a strategy has to survive contact with Monday morning.

The organizations that execute well aren’t the ones that perfectly predict the next five years. They are the ones that know where they’re going, measure whether they’re getting there, and are willing to adjust the route without losing sight of the destination.