Episode Transcript
If you’re approaching quarterly planning, you’re probably going into it with one of two perspectives. You might be going into it with a lot of hope, thinking this is the quarter we’re finally going to get it right. We’ll get aligned, set motivating but realistic goals, get our dependencies mapped out, and end up with a plan we can stick to—and more importantly, a plan that delivers the results we’re hoping for.
Or you might be going into planning full of skepticism. Here we go again. Our leadership team is going to come in with a bunch of unrealistic targets. We’re going to make up some estimates and map our dependencies. Those won’t be able to hit those leadership stretch goals, so we’ll make up a new plan that somehow magically delivers on their wishes. Once the planning is over, we’ll go back to our day jobs, knowing that the actual work will involve unexpected customer needs and stakeholder requests, discoveries we didn’t anticipate, delays from other teams, and shifting priorities. All of the signals that indicate we’re working in a complex system, despite our quarterly planning being built on the assumption that things are predictable.
For almost all of the clients we’ve worked with, quarterly planning is designed for a world that no longer exists—or maybe never really did. It tries to impose certainty on work that doesn’t behave that way. And when your goals depend on multiple teams or departments, the problem gets worse. Coordination gets messy or overly detailed. Dependencies make commitments risky. And no individual or team can see enough of the system to plan the best path forward.
But there is a way to do this well, given what we know about complex systems. When done in a complexity-aware way, quarterly planning can become one of the most energizing activities in an organization. Quarters are long enough to see meaningful learning and value, while being short enough to stay connected to reality. They match the rhythm of budgets without falling for the fiction of annual predictions.
When it’s done well, quarterly planning helps us reconnect with purpose, choose meaningful goals, make reasonable commitments, design smart experiments, and establish a cadence for learning and delivery that the system can actually support.
Over the years, we’ve noticed that quarterly planning consistently works well when three essentials are present. When any one of these is missing, the quarter gets harder for everyone involved.
The first essential is shared understanding across teams. Quarterly planning is almost never a single-team activity. Big initiatives often cross team and department boundaries. Teams depend on one another. Nobody has the full picture. And without a shared picture, even well-intentioned goals collapse under misalignment.
When we talk about shared understanding, we’re not talking about everyone agreeing on every detail. It means the group can see the system clearly enough to make coordinated decisions. That doesn’t require task-level precision. It does require shared understanding of why we’re doing the work, the current reality and context, and the desired outcomes. Underlying all of that is an awareness of the domains from the Cynefin model.
That domain point is critical. A lot of quarterly planning problems come from treating everything like predictable work. Some initiatives are Clear. Some are Complicated. And some are genuinely Complex. More accurately, most initiatives contain some mix of all three. If teams can’t see which is which, they either over-plan or under-plan the wrong things.
One of the biggest failure modes we see is teams jumping straight into task breakdowns and dependencies before they’ve aligned on purpose or constraints. They skip the sense-making step. Then halfway through the quarter, surprises pop up and the whole plan has to be renegotiated.
This is where CAPED gives us a useful lens. Before making quarterly commitments, teams need to know which initiatives are ready for Analytical Planning, where detailed commitments are reasonable, and which need Active Planning first. If you assume everything is predictable, you get brittle commitments.
Shared understanding is about starting the quarter grounded in reality—what we know, what we don’t know, where coordination is required, and which pieces of work require exploration before they’re committable. When teams skip this, the quarter becomes a series of escalations and adjustments.
When shared understanding is present, the rest of quarterly planning gets easier. Goals are clearer. Commitments are more realistic. Teams coordinate without over-specifying the entire quarter. It creates the foundation the other two essentials depend on.
Once teams have a shared understanding of the system, the next step is setting meaningful quarterly goals and commitments. This is where a lot of planning efforts fall apart. Teams either set goals that are too vague to guide real decisions, or they commit to outcomes they can’t influence in a predictable way.
Quarterly planning often assumes all work should be planned the same way. Everything becomes a measurable target or a feature list. But different kinds of work require different goal structures. If we force them all into one format, we end up with goals that look clean on paper but don’t help teams make choices during the quarter.
Going back to the Cynefin and CAPED lenses, work in the Clear and Complicated domains can support commitments. You can define success, estimate it reasonably, and expect relatively stable cause and effect. But Complex work doesn’t behave that way. You can’t commit to a specific outcome when you don’t yet understand the problem, the solution, or the path between them.
Instead of pretending everything is predictable, we match the goal type to the domain. For Clear work, we might use health metrics—operational or reliability targets the team maintains. For Complicated work, outcome goals or OKRs can make sense. And for Complex work, we define hypotheses and clarify the next actions to test those.
Here’s the practical version. Don’t commit to output for work that’s still in discovery. Don’t write exploratory goals as if they’re guaranteed outcomes. And don’t leave predictable work so vague that no one knows what success looks like.
We also encourage teams to limit the number of quarterly goals. A handful of consequential goals gives teams focus. When a group sets eight or ten goals because everything is important, we know those goals won’t steer decisions. They’ll just sit in a slide deck until the next planning cycle.
A meaningful quarterly goal does three things. It points to a real outcome that matters. It fits the Cynefin domain of the work. And it’s small enough that a team or group of teams can actually influence it in a quarter. You want goals that drive choices, not goals that create guilt.
There are two big benefits to this approach. First, teams can prioritize and sequence work with confidence. Second, they can adjust during the quarter without feeling like they’re failing. The goals give direction, not pressure.
Once teams have set meaningful goals and reasonable commitments, the question becomes how they stay aligned during the quarter. Many organizations experience quarterly planning as a week of clarity followed by eleven weeks of drift. The goals sit in a slide deck. Teams go back to their day-to-day work. And by the time anyone checks in again, the quarter is almost over.
Most planning systems assume the world will hold still long enough for the plan to remain accurate. But things change. New work shows up. Risks become real. Dependencies shift. And teams encounter complexity that only becomes visible once they begin doing the work.
Instead of expecting perfect predictability, teams need a rhythm that keeps learning visible and makes progress on delivery transparent. The idea of Scrum Sprints is based on this same need. Teams plan a short slice of work toward quarterly goals, then check in with the people impacted by that work.
Whether you’re using Scrum or just holding regular reviews, it helps to match the content of the review to the type of goals you’ve set. For Clear work, health metrics can often be reviewed asynchronously. For Complicated work, reviewing progress against key results and actions makes sense. For Complex work, the focus should be on what hypotheses are being tested, what actions were taken, and what was learned.
There’s a psychological benefit to this kind of cadence. People stay motivated when they see real progress on meaningful goals. Research on the Progress Principle shows that even small wins create momentum. But if progress isn’t visible, the emotional system treats the work as stagnating, even when it isn’t.
A simple quarterly rhythm might include a weekly or biweekly check connecting work to goals, a monthly sense-making session to adjust direction based on learning, and an end-of-quarter review to capture what worked and what didn’t. None of this needs to be heavy. It just needs to be deliberate.
That monthly sense-making step is important. Weekly reviews work well for teams and close stakeholders, but for a broader audience they’re often too frequent. A monthly cadence allows adjustments to be viewed as learning instead of failure. In a complex system, adjusting is the responsible thing to do.
A sustainable quarterly rhythm isn’t about forcing the plan to hold. It’s about keeping the plan honest. The goal is to surface learning early, so teams can change course while it still matters.
When teams do this well, surprises become manageable instead of disruptive. Leaders get clearer signals about what’s working. And teams feel more agency because they’re steering the work based on real data, not trying to live up to predictions made weeks earlier.
And that closes the loop. Meaningful goals lead to meaningful progress. Progress leads to better sense-making. And better sense-making shapes better goals next quarter. It’s a cycle that gets stronger over time when teams practice it intentionally.
