Agile Planning 101:
A Guide to Roadmaps,
Releases, and More

Agile teams pride themselves on adapting quickly and changing plans as needed.

This might make you think that Agile planning is an oxymoron. When really, it’s more all-encompassing than traditional project management approaches because it happens throughout a project instead of just at the beginning.

Let’s take a closer look at what this means.

Agile planning is a collaborative, iterative process that helps teams consistently align on objectives and progress. Unlike traditional project management methods such as Waterfall, Agile planning happens at every phase instead of only before any work can begin. In this way, Agile teams can get started sooner, adapt to changes faster, and make sure the objective and strategy still hold true as progress is made.

Another difference between Agile and traditional project planning is that you don’t spend all your time planning upfront for more extended time frames. With Agile methodology, for example, you wouldn’t take the first two months to plan out the rest of the year.

The idea is that Agile planning leads to better outcomes and fewer roadblocks that derail projects.

User Stories

User stories are short descriptions of features from the user's perspective, guiding development by focusing on user needs and benefits.

Sprints

Sprints are time-boxed development iterations, usually one to four weeks, where teams deliver incremental software updates.

Stand-up Meetings

A Stand-up is a brief daily meeting for team members to discuss progress, goals, and obstacles, promoting collaboration and alignment.

Agile Board

Agile boards are a visual tool to track work progress during a sprint, using columns and cards to represent tasks moving through stages.

Backlog

Prioritized list of tasks, requirements, or user stories representing planned work, continuously refined based on feedback and priorities.

The Agile planning process, visualized as the Agile planning onion, outlines the key phases of any project.

At every layer, being critical, providing feedback, and keeping the user at the center of your project is crucial for success.

The six phases of Agile planning are:

• Vision (which includes two steps: Strategy and Portfolio)

• Roadmap

• Release planning

• Iteration planning

• Daily planning

Most people think about Agile planning as Release, Iteration, and Daily Planning. But there’s a lot more to it, which we’ll get into in the next section.

Agile planning balances a flexible approach with well-defined milestones and releases.

Develop and adjust your plan as needed, but also ensure your team knows the priorities and how they align with the main objective. The Agile planning process includes the following steps.

1. Document project vision (Strategy and portfolio)

When using Agile methodology, start with a user story. Most commonly used in software development, a user story is the who, what, and why of your project. A development team will describe their user, what they need, and why it will help them.

In the simplest terms, you’ll write something like this:

As a [describe your user], I want to [describe product or software] so that I can [benefit statement, or the why of your project].

With a solid user story, the next steps become a lot easier.

• Define the objective and strategy that will help you fulfill that story.

• Set project KPIs so your team knows how success will be measured.

• Then, outline the biggest, most important solutions. This could be one product or many. If your user story requires multiple solutions, you’ll create your portfolio and prioritize what to work on first.

By the end of this phase, you’ll have:

• A user story

• Strategy and objectives

• Portfolio of products or one product defined

2. Create a product roadmap

Here, you’ll outline the specific requirements for completing the project. You’ll take each product from your portfolio and create your product roadmap.

This is the high-level strategic overview of your product. Your roadmap needs to outline the features necessary to meet the project requirements.

Your roadmap might look like a grid with the following line items for each release:

• Objective

• Main features

• Metrics or milestone

3. Define and plan releases

Even though Agile planning is, of course, Agile, you still need some major releases planned so that you know you’re staying on track.

Once you have the strategy locked in, you know the steps to get there, and your project must-haves, you’ll plan releases and have your project team agree to them.

This might look like having a minimum viable product (MVP) ready by a certain date, noting all the requirements it must meet.

This step and the roadmap might be developed in tandem, but you’ll clarify details regarding releases here.

When you’re in this phase, you’ll define releases by scope and requirements more than by strict deadlines. Teams often use quarters to set releases so that it can happen sometime within those three months.

4. Plan the iteration

In this step, you’ll create tasks, assign team members, and plan deliverables for each release.

If you use the Scrum framework for your Agile projects, this step will be considered Sprint Planning.

Sprints are typically 1-3 week durations where team members decide on priorities and only focus on those tasks. Sprints consist of current, future, and backlog lists.

Items should not get added or removed from the current Sprint once it’s started. If necessary, the entire team should agree and adjust plans.

If you’re not using Sprints, you’ll still plan out what happens during a specific period so that your whole team focuses on the right priorities.

5. Plan Daily stand-ups

Again, if you’re using Scrum, this will be your daily Stand-up or daily Scrum meeting.

Led by the Scrum Master, you’ll meet for 15 minutes to discuss what’s happening that day and any roadblocks you have.

If you’re using an Agile project management tool to automate your daily Stand-ups, your team will answer three questions and submit their Stand-up:

• What did you work on today?

• What will you work on tomorrow?

• Any roadblocks standing in your way?

Learning Agile methodologies can feel daunting. But don’t worry, we’ve gathered up several best practices that can enhance project planning for an Agile team. 

• Collaborate: Involve the entire team, including developers, testers, product owners, and stakeholders, in the planning process. Collective input ensures shared understanding and commitment to project goals.

• Create an Agile manifesto: An Agile Manifesto is a guiding document for Agile workflows, emphasizing collaboration, flexibility, and customer satisfaction. It prioritizes individuals and interactions over processes and tools, working software over comprehensive documentation, customer collaboration over contract negotiation, and responding to change over following a plan.

• Prioritization: Prioritize user stories or tasks based on their value to the customer or business. Use techniques like MoSCoW (Must-Have, Should-Have, Could-Have, Won't-Have) to distinguish between essential and optional features.

• Continuously improve: Regularly review and refine the backlog based on feedback, changing requirements, and evolving priorities. Keep the backlog up-to-date to ensure that it reflects the current state of the project.

• Be adaptable: Embrace change and remain flexible in response to new information or shifting priorities. Agile planning accommodates evolving requirements and allows for adjustments throughout the project lifecycle.

• Risk management: Identify potential risks and uncertainties early in the planning process. Develop strategies to mitigate risks and incorporate contingency plans into the project plan.

By following these best practices, Agile project managers can create effective project plans that promote collaboration, flexibility, and continuous improvement throughout the project lifecycle.

The nice thing about Agile project management is that you can do all your planning using the Google Suite, such as Docs and Sheets.

However, there are Agile project management tools that make this whole process more streamlined and get your team involved with the process. 

If you’re ready to ditch traditional project management approaches, Hubstaff with the Tasks add-on is one example that provides Agile features in a simple, visual format. You can use Sprints, Stand-ups, Epics, and Kanban-style project boards in one app. We use Tasks for our own Agile software development and project execution, and we can vouch that it will greatly improve your project management.

You can comment on tasks and assign a team member, add release dates to each task, plan backlog and future Sprints, and much more. Whether you’re handling software development projects, marketing initiatives, or project managing a logistics team, Tasks can help you take your projects to the next level.