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The Right Amount of Planning

August 4, 2022

Planning is a skill. Without it, we can't make funding decisions, we can't map our path towards delivery, and we can't make commitments to our leaders, and therefore, progress towards our objectives becomes random. Time and effort are wasted, and opportunities are likely missed. But the wrong kind of planning can stifle delivery and innovation.

The questions beg: In the context of Agile, how much planning is the right amount? Is an Agile mindset even compatible with short- and long-term planning? How can you use planning to manage dependencies and optimize workflows while maintaining all-important flexibility?

Two Types of Problems

Your planning approach should depend on the type of problem you are trying to solve.

First, we have ordered problems. Ordered problems are predictive, meaning you can predict what will happen along the problem-solving journey. In this context, traditional deterministic planning makes sense. Even further, it’s often the cheapest way to get the job done. You can evaluate possible paths forward and plot the most efficient route. Then, it’s just a matter of following the plan step-by-step.

And second, we have unordered problems. Unordered problems are probabilistic, meaning they are subject to uncertain and changing variables. In this context, a deterministic plan would leave you unprepared for inevitable deviations. Instead, you can keep an overarching goal in mind but plan in small, shorter-term steps. As you uncover new information, you can re-plan your next move in terms of making progress towards your overarching goal.

Where Does Agile Planning Fit In?

Agile planning is an iterative approach to project management best suited to unordered problems. It’s less about sticking to a prescribed roadmap and more about creating options and making decisions when you have just enough, but definitely not all, information.  

Agile ensures you don’t become trapped in a plan that is no longer sufficient or relevant. It provides a backbone from which you can adjust and adapt as you secure feedback and learn on your journey towards an end goal.  

The Agile approach is particularly effective in complex and rapidly changing environments. A set plan is more likely to become derailed as dependencies, interactions, and moving parts increase. You can’t see the future, and in an increasingly uncertain world, what happened yesterday has little bearing on what will happen tomorrow.

How Much Planning Is the Right Amount?

The Agile Manifesto does not say don’t plan. Instead, it reimagines our approach to planning. So, it's less about how much planning and more about your approach to planning. And this comes down to situational context.

As a general rule, the lower the predictability of what will happen, the less deterministic planning you do. The higher the predictability, the more deterministic planning you do. The correlation is direct:

  • In uncertain (unordered) contexts, a plan cannot account for unknown unknowns. It is inherently unpredictable. Therefore, you may have to abandon your plan or, if you stick to it, you may not achieve your objective.
  • In certain (ordered) contexts, your plan can account for most influencing factors. It is predictable. Therefore, you are unlikely to come up against unknown unknowns and can safely adhere to your plan.

Here's a sports metaphor to illustrate. Curling is an ordered context. The team on a curling rink can plan their next move in detail. In contrast, ice hockey is an unordered context. Everything is constantly changing, so planning a specific move for a specific time during the game is pointless. This doesn’t mean ice hockey teams and their coaches forgo planning altogether. They do plan. They have clear objectives, they practice moves, and they develop strategies to achieve their goal. Planning is essential, but the nature of their plan is different to that of the curling team.

Here's another analogy. Let’s say you just moved to a new home and purchased all-new furniture from IKEA. It doesn’t matter how organized your plan is — if you open 25 flatpacks of IKEA furniture at once, chaos will ensue. Instead, if you open one box at a time, build the piece, and learn from your mistakes, you can rethink your approach as you move to the next piece. You stay in control, can adjust your approach as your needs change, and get better at doing the work by learning as you go.

The Fundamentals of Agile Planning in Practice

Agile refers to several related methodologies, including Scrum, the most used, and Kanban. We’ll use Scrum as the basis of our discussion, which starts with the fundamentals, the core tenets that define Agile planning.

Big-Picture Goals

Big-picture organizational goals are the overarching objectives you hope to achieve. These goals typically have a longer time horizon. For example, you might want to expand into a new market or capture a new audience.

How you achieve these goals is not set in stone, just like how the hockey team will make it to the finals of the Stanley Cup is yet to be determined. Unpredictable variables will, without a doubt, reroute your trajectory, but your big-picture goal will remain the same.

Increments, Sprints, and User Stories

Agile uses its own vocabulary to describe the planning process and related activities. First, let’s look at increments, sprints, and user stories and how they connect to one another.

  • Increments are releasable wholes. They might be enhancements or modifications to a product, or an entirely new product.
  • Increments are broken down into iterations called sprints. Sprints have a fixed duration, typically around two weeks.
  • The team has a list of items to work through during each sprint — these items are called user stories.

So, to summarize the relationship between the three: An increment (creation of a new product or update of an existing product) is broken down into sprints (iterations) in which team members work through user stories (items).

As the name suggests, user stories are items that meet a user need. This is an important distinction, as user needs are the focus of an Agile team’s documentation. During the sprint, the team aims to cater to that need as best they can with the information they have.


Agile planning is iterative. Each sprint is of equal length and results in visible, working features that can be rolled out to real end-users. These users can provide feedback, which is then addressed in subsequent sprints.

Let’s go back to the IKEA furniture analogy. The ‘real, working feature’ is a piece of furniture, built and ready to use. It reduces risk by facilitating learnings.

In addition to feedback, Agile’s iterative approach allows teams to discover the following:

  • How many user stories on average they can accomplish within the timeframe of a sprint
  • Roadblocks and problems that stifle or impede progress
  • Successful ways to overcome these roadblocks

Bringing It All Together

Let’s use the terminology we’ve defined to piece together the Agile planning puzzle.

  • At the highest level, we have the organization’s big-picture, longer-term goals broken down into major releases.
  • Move down one level, and we have releases broken down into increments. Increments contribute to the organization’s progress towards the big-picture goals. For example, by enabling expansion into new market segments with a new product release or positioning the company as a market leader with product improvements.
  • Down again, and we have sprints. Through a series of sprints, increments are delivered iteratively.

Now, we can tie these three levels back to our main question: What is the right amount of planning? Successful planning is appropriate to the type of problem you are solving, and perhaps counterintuitively, the more complex the problem, the more uncertainties, and the less deterministic planning required.

For example, when planning a release, teams don’t know what they will learn throughout their first, second, and third sprints. Assumptions made during the planning phase of the release may prove false in the first week of execution, rendering the rest of the plan redundant. Sprints, in contrast, benefit from more structure — in the world of Agile, it’s integral that all team members are working towards a shared goal.

Agile Planning, Financial Forecasts, and Leadership Buy-In

Agile planning doesn’t involve detailed scoping and analysis. Instead, it acknowledges the unknown and leaves space for teams to explore and peruse new ideas, innovations, and lines of enquiry. Agile planning is based on understanding increments of delivery, and not defining every single user story. This is a significant leap for organizations accustomed to forecasting a project’s cost down to the cent. It can be difficult to move forward if the finance department isn’t aligned with IT (or whoever is implementing Agile).

The same applies to business leaders. They want to know what a project will cost and what the benefits will be before they commit to it so that they can calculate the likely return on investment. "I’ll know what it costs when it’s done" may not be a strong enough defence to secure buy-in. Now what?

Agile transformations are not about forgoing planning or making unbreakable commitments to budget, scope, or deadlines. It’s about a shift in mindset, one that won’t happen overnight. If you need a plan to plead your case, create one. Explore the requirements, do some initial design work, and provide time and cost estimates.

Think of the manager of a sports franchise. They can’t say with certainty that their team will win or how. But they can create a game plan, something that gains buy-in and builds confidence. The plan is something the team can execute against, but it isn’t fixed. The same applies to Agile.

This kind of planning does not mean you’ve failed to implement Agile. It is a part of the process that bridges the old and the new. Ultimately, an organization-wide change in mindset will allow you to answer questions — What will be delivered? When? How much will it cost? — with a different approach and level of certainty.

Is Agile Planning Always the Right Approach?

Agile projects are almost 1.5 times more successful than those managed with competing methodologies. According to McKinsey's research into Agile implementation, transformation delivered “around 30 percent gains in efficiency, customer satisfaction, employee engagement, and operational performance; made the organization five to ten times faster; and turbocharged innovation.”

Shifting from slow-moving project management to fast decision-making and iterative development models is inevitable. However, is Agile planning always the best strategy? Or is there still a place for linear project management approaches like Waterfall?

It comes down to the level of certainty. If you are planning a road trip across the US, for example, your problem is predictive. The factors at play are certain and stable — the roads aren’t going to get up and move, and you’re not going to change your starting point or destination. So you can plan your route step-by-step, linearly, with some certainty about how you might manage risk.

Now imagine planning an off-road trip of the same distance through the Sahara Desert or Australian outback. There is more risk and more uncertainty. Planning for every risk makes little sense. Your approach to planning has to be more adaptive and less prescriptive.

Most problems in the modern-day business arena are not as simple as the US road trip — nowhere near it. The number of complex problems an enterprise faces is increasing. So, too, is the level of complexity. In this environment, Agile dominates.

So, if your path to a desired outcome is uncertain and rife with interdependencies and risk, Agile may be the best approach. Just don’t throw the baby out with the bathwater. Project management is still valuable within ordered contexts. But avoid using this as a brake on change. Recognize that more and more problems are unordered. And ordered problems will continue to become less and less common, while unordered problems will dominate.

Striking a Balance that Meets Your Organization’s Needs

Agile is adaptive — not just to external influences like changing consumer expectations but also to internal factors. It's not one-size-fits-all, either. It can be tailored to meet your organization’s needs and the type of problem you are solving. It’s about balance, stopping the pendulum somewhere between too much planning and not enough.

If you are ready to explore what Agile can do for your business, IncrementOne can help. We are experts at Agile planning and Agile delivery. We evaluate your organizational structure and, through cross-functional coordination, incrementally guide you through your transition. Your goals are our goals, and we give you the tools needed to align your delivery capability with strategic demands, empowering your people to create higher-quality products within shorter timeframes.

Schedule an appointment today, and let’s talk Agile. By transforming your company culture and mindset towards Agile on your own terms, you can build a resilient, future-proof operation that thrives in uncertainty.

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