Even when we think we’ve moved work into the ordered domain, things change. Planning is essential, but so is staying adaptive—because the real world doesn’t freeze while we execute.
Many organizations struggle to balance predictability with adaptability in large initiatives. Too much planning creates rigidity, while too little leads to chaos. In this episode of the Humanizing Work Show, we dive into Phases 3 & 4 of CAPED—our Complexity-Aware Planning, Estimation, and Delivery approach—where we create a structured execution plan while keeping room for change.
Phase 3 (Analytical Planning) ensures that teams build a realistic, risk-aware plan by defining What we’re building, How we’ll ensure quality, and When it will be delivered.
Phase 4 (Iterative Execution) brings that plan to life with incremental delivery, adaptive prioritization, and continuous planning cycles that keep projects aligned and valuable.
By the end of this episode, you’ll understand how to move from uncertainty to structured execution, without falling into the trap of rigid planning.
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Episode transcription
Peter Green
Welcome back to the Humanizing Work Show! In recent episodes of the show, we introduced our CAPED approach—Which stands for Complexity-Aware Planning, Estimation, and Delivery—and we walked through Phase 1: Strategic Planning and Phase 2: Active Planning. If you haven’t checked those episodes out yet, you should do that before continuing with this episode, where we’re going to walk through the final two phases of CAPED–Phases 3 and 4.
Every organization that works on large initiatives faces a tough challenge: how do you create a predictable execution plan without losing some adaptability? If you’ve followed CAPED Phases 1 and 2, you’ve already pulled forward complexity, you’ve resolved the biggest uncertainties, and you’ve earned green for your initiative. In Phase 3, we add the remaining details to the plan and in Phase 4, teams execute and deliver the initiative on time and within budget.
But just because we seem to have moved most of the complexity into an ordered state doesn’t mean things won’t change going into phase 3 and 4. Internal factors like shifting priorities, leadership turnover, and budget constraints can reintroduce complexity. External factors like customer demand, competitive shifts, or economic changes can shake up what we thought was predictable. That’s why the final two phases of CAPED build in regular feedback loops to handle emergence even during execution.
Before we get into the details of how that all works, a quick reminder that this episode is a free resource sponsored by the Humanizing Work company, where we help organizations get better at leadership, product management, and collaboration. Visit the contact page on our website, humanizingwork.com, and schedule a conversation with us if your organization wants to see stronger results in those areas.
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OK, let’s get into phase 3, analytical planning, where we create a detailed plan that allows for predictable delivery while staying adaptable. At this stage, we’re at the same point in time as Pixar would be when they’ve used the Braintrust meetings we talked about in the last episode to resolve the big unknowns in story development, and now they’re scheduling the voiceover recordings with those A-list actors and preparing to animate the movie at full resolution. Or, in the world of architecture, this is where Frank Gehry has finished his experimental models, he’s verified everything is going to work the way he imagined, and now it’s time to create the final designs to deliver to engineers and to the construction team. In short, moving into Phase 3 is moving from exploration to detailed description.
Phase 3 consists of three tracks: the What, the How, and the When. Let’s start with What. In this track we are adding enough detail to ensure alignment and predictability. We start this track by using Jeff Patton’s User Story Mapping approach to visualize the full user experience. We also create our own variation on the User Story Map, what we call a Minimum Marketable Features, or MMF Story Map, which gives us an additional perspective on how we might tackle the remainder of the initiative.
Then, we go through Backlog Refinement, breaking down the big components from the User Story Maps into User Stories that teams can execute. We split these user stories small enough so that six to ten items can be completed in any given iteration. This gives a sense of progress while avoiding an overly detailed task level breakdown. These items are placed in one or more ordered backlogs, depending on the number of teams involved with building the initiative in Phase 4.
With the What clarified, we focus on the second track, How, which is about aligning on quality criteria and our technical approach. In some organizations, we need to map the User Stories from the Backlogs back to the detailed requirement documents like MRDs, PRDs, or BRDs to ensure alignment with cross-functional stakeholders. And that would be part of this track. It’s optional, but it can help keep different parts of the organization informed and aligned. Then, we create a Target Quality document, which sets expectations for quality, testing, and completeness, and a Target Architecture document, which describes the planned system architecture. This kind of document allows us to develop incrementally without creating technical debt or backing teams into a corner.
With the What and the How detailed, we can move on to the third track–When. The first question leadership always asks is, “When is this going to be done?” To answer that, we use Reference Class Estimation, which takes the concept of Reference Class Forecasting, that we learned about in Phases 1 and 2 and applies it at the more detailed level of backlog items. Then, we apply Risk Adjusted Forecasting, which accounts for uncertainty by evaluating key risk factors that could impact delivery–factors like team stability, backlog volatility, external dependencies, and overall complexity, which all play a role in determining how confident we can be in our estimates. By incorporating these factors, we generate a range of forecasts, offering confidence levels that typically span from 50% confidence to 90% confidence. This approach ensures we communicate realistic expectations while maintaining the flexibility to adapt as new information emerges.
With the What, the How, and the When all mapped out, we hold a Plan Review and Coordination session, where we get all the participants and stakeholders into a big room, physical or virtual, and review the overall plan, including who’s building what, in what order, and where dependencies exist. This helps prevent surprises during execution.
At this point, we have a well-defined, realistic plan that balances structure and flexibility. Now it’s time to move into Phase 4, Iterative Execution.
In this phase, teams work on prioritized backlogs delivering value incrementally. If you’re familiar with Agile execution methods, this phase will look pretty familiar. But you may be wondering why we use an iterative approach if the work is all sitting in the ordered domain at this point, which is a fair question.
Even though the work we did in Phase 2 moved us into what we believe to be the ordered domain, the things we work on aren’t static. Internal priorities can shift. Leaders and teams can turnover. Budget constraints can change, all of which can reintroduce complexity. “Outside of the building,” customer demand, competitive shifts, changes in regulations, or economic headwinds can shake up what we thought was predictable. And, after all, we’re still building things with humans, and humans always introduce a bit of complexity to the work. So in Phase 4, we use regular feedback loops to check in frequently with stakeholders, validate assumptions, and adjust as needed. We practice adaptive prioritization, during this phase, which means that as internal and external factors shift, we remain open to reprioritizing work mid-execution.
An important note about Phases 3 and 4 is that not every organization treats them as strictly sequential. Many companies alternate back and forth, revisiting planning at regular intervals to adjust to new information. This reduces risk and ensures that work stays relevant, aligned, and valuable all the way through delivery.
So that’s CAPED Phases 3 and 4. Phase 3, Analytical Planning, gives us a structured, reliable execution plan by defining the What, the How, and the When. Phase 4, Iterative Execution, ensures we stay adaptable to changes while maintaining predictable, visible progress.
If your organization struggles with finding the right balance between predictability and adaptability, CAPED provides a proven approach. Visit humanizingwork.com/caped to learn more.
And if you found this valuable, let us know in the comments! Subscribe if you’re watching on YouTube, and if you’re listening on the podcast, a five-star review helps others find the show. Thanks for joining us, and we’ll see you next time on the Humanizing Work Show!
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