How To Use Project Milestones To Keep Your Projects On Track

Published in

The Digital Project Manager

12 min readJan 20, 2021

Project milestones are not for senior managers. They’re not for project managers either. When you’re making milestones, think instead that the dev team is the customer for them.

If you’re a digital project manager, the first thing to know is that milestone planning is not for you: it’s for the team.

Milestone planning and milestone management are for the contributors. That’s the people who are doing the coding, the marketing, the localization, and the other tasks necessary to drive a successful digital product to market.

One common misconception is that milestones are about reporting the status of a project.

In fact, project milestones indicate the timing of the major decisions you and your team need to make for your project.

Anyone looking over the project timeline and the key milestones should see the decision points where the team needs to keep to the plan or make mid-course corrections. Project milestones are the signposts along the way of a long journey. They tell the dev team and the project manager when to turn, and how far they need to go.

Also, when you define your milestones think about mitigating risk and managing the key dependencies between team members, between functions, or between dev partners and other suppliers. Build your milestones and project timeline around these key dependencies. Place milestones at the inflection points, where these project dependencies come together.

In this article

Project Milestones: An Innovative Approach

In this article, we will describe an innovative framework for project milestones. We will discuss the real purpose and function of project milestones; how to plan and track them; and how to define major and minor milestones. We will also show that most teams are overcomplicating their projects with milestone software that doesn’t add much value.

We will correct misconceptions about milestones, for example: that they are tools for management oversight and for reporting status.

If you want to plan your milestones for the right reasons, using an innovative approach that isn’t the same as your competitors, and that goes beyond Project Management 101, then read on.

What Is A Project Milestone?

Project milestones divide a project into a set of smaller, manageable goals. They represent the inflection points in a project.

You can’t climb Mount Everest and come back down in a day. You need a base camp, and then a series of smaller camps that serve as way-stations, subsidiary goals you achieve along the way, that lead you to the summit. Milestones are like these camps that lead you, section by section, to the top of the mountain.

Since milestones are the subsidiary goals you want to achieve during a project, each has a date. A goal without a date is not a goal. It’s a wish.

However, milestones should not be inflexible. The reason projects have milestones is to make teams execute more effectively and to manage the expectations of senior leaders. If you need to modify the deliverables and milestones along that way, and there’s a consensus around it, then go ahead and modify them. Your work is not for the sake of the plan; the plan is there to help the team to do the work.

Milestones are not meant to occur at regularly scheduled points in the project management timeline. For example, they’re not meant to occur on a monthly cadence. Nor do they need to be attached to a presentation to senior managers that require the team to continue to justify the project. Design your project milestones to get the people with the right kind of skills, to work together on the right problem, at the right time, in order to propel the project forward.

A Guide To Project Milestone Management

Milestone management has two aspects:

Milestone planning
Milestone tracking and reporting

The most important success factor in both activities is to have an experienced digital project manager. Experience in project planning and tracking is key. For a successful project, first define carefully the project’s goals. Understand the project’s business objectives and how they fit with overall company strategy. Scope the project. Create a rough estimate of its length and size.

Then consider the two most important factors in planning milestones: risk reduction and dependencies. I’ll cover those in depth below.

Milestone Planning To Reduce Risk

Digital product development is the reduction of risk over time. When you plan your project timeline and milestones first ask: What are the riskiest decisions you will need to make to execute this project?

Is the risk in the market?
Is the risk in the technology, e.g. because it’s either new to your company or new to the world?
Is the risk in the relationships involved, for example in the management of development partners?
Is the risk in the fact that the project has such complex dependencies that the critical path is long and torturous?

There can be other risks as well, including operational or support risks. Define the risks as much as possible and use risk reduction over time as the operating principle to guide you in building a project timeline and planning the key project management milestones.

Milestone Planning Example: Game Developer Creates B2B App

Suppose your company is a game developer and your marketing team has discovered a new opportunity to use your gaming platform to create a new app that corporate HR departments can use to test new applicants.

The technology is similar to what you’ve designed before, but this new product means entry into a brand new market. It’s a B2B app and not a consumer product. And the new app’s purpose is not entertainment; it’s in the business apps and services space.

The technology risk is low, but the market risk is high.

What you need is access to customers for your HR app and an iterative approach where you can roll-out prototypes to potential customers. Think through the steps required to develop these prototypes and get them in the hands of customers. Where will you find the best candidates for testing? Who do you need to be involved on your side? When in the project timeline should this happen?

Remember, the purpose of this exercise is to reduce the market risk, the earlier the better. When you think you will have reduced risk to acceptable levels, that’s where to place a milestone, at this crucial inflection point in the project’s progress.

Milestone Planning To Manage Dependencies

In addition to risk reduction, also consider the key dependencies. You may use the Critical Path Method to define the key tasks and how they — and the people who will do them — will interact over time.

The goal is to find the longest path to the next milestone and then try to shorten it. Note the inflection points where key individuals or groups come together to accomplish a goal that propels your project forward. That’s where to place a milestone.

In our HR app example, think about who needs to be on the team to test (iteratively) the new app’s product-market fit. Consider when they need to be there, and what are their other constraints. Think about the key deliverables that these groups will need to create along the way.

Map these key dependencies. When they come together to satisfy the need to reduce market risk, accomplishing a key goal along your path to the summit, that’s where you want your milestone.

A milestone planning pitfall to avoid:

Don’t start with a completion date that comes from senior management, and then reason backward from the due date of the end of the project to create the timeline and key milestones. Planning your timeline and milestones should not be top down, but bottom up.

Agree on a timeframe and launch date by consensus between the team and senior management. The people who are doing the work should make the plan.

Project Milestone Tracking And Reporting

After you’ve mapped the Critical Path and planned your project milestones, you need to track them. They should be visible to all stakeholders, including senior management. Management needs some confirmation that the project is moving forward as planned, especially if the team requires minor course corrections along the way.

Teams should publish their list of project milestones which includes the goals, decisions, or accomplishments associated with each of them. You could input this information into your Gantt chart, project plan, or project schedule. It can be as simple as a table with three columns that include the date; the milestone name; and the deliverables, goals, or accomplishments associated with each. Send this table to the cloud. Do not email it, but keep it as a shared, public document.

Management by Exception

The team should only report to senior management where there are exceptions, i.e. when it perceives that it is not going to hit a milestone by the scheduled date, or when it is not going to achieve the deliverables or goals for a certain phase of a project.

This management by exception approach means that 1) your milestones are stated clearly and visible to all stakeholders; 2) there are no status meetings (if you’re working to plan, why waste time making and delivering a slide presentation to that effect?); and 3) only report to senior management when the plan begins to go off course.

Project Milestone Examples

We advise that a typical digital development project should have three major milestones, with perhaps between four and six minor milestones leading up to each of the three major ones. The three major milestones define the following:

1. Concept Fit

The team demonstrates that time-to-revenue is foreseeable and that the revenue potential is sufficiently large. The team shows that the proposed project fits with the overall company strategy. This milestone is achieved when the project has a defined and fully-funded team.

2. Product/Market Fit

By this milestone, the dev team has shown that the product under development is the best solution for the market. They have identified use cases, and have tested prototypes with users to confirm fit with the intended market. The team has calculated accurately the project costs and defined the product’s profit potential. The team has achieved this milestone when there is a workable prototype, at least for internal purposes.

3. Development and Market Launch

To achieve this milestone, the team needs to develop an MVP that is prepared to encounter actual users, that justifies its investment, and that is worth the potential risk to the company’s reputation. The team achieves this milestone when it creates a series of iterations of its product prototype in collaboration with customers. The team will also have achieved this project milestone when it assesses the digital product’s UI, quality, feature set, and support capability.

A three-step product development process. Think of each phase as a product release. The development team ties exit criteria to a sprint. This Minimum Viable Process is a hybrid approach that combines the best elements of phases and gates processes with Agile methods.

Examples of Project Milestone Inflection Points

The first of the major milestones above answers the question “Why this product?” The second answers the question “What is the product and how will we achieve our goals?” The third milestone answers the question “When will we be ready to release it to the world?”

Within each of these milestones, arrange four to six minor milestones that are inflection points that will lead you to each of the three major milestones. For example, leading up to each of the three major milestones we’ve defined above, create minor milestones for each of these activities:

Concept Fit

Project has an experienced, entrepreneurial leader
Product idea fits with the corporate vision
The technology is feasible
Project has the right staff and resources
Product has sufficient commercial potential

Product Market Fit

The technology has been fully vetted
Use cases have been defined
The project has an estimated cost of development
The commercial potential has been quantified and confirmed
User feedback has been collected and understood

Development and Market Launch

Minimum Viable Product developed
Business plan written and confirmed
Market research complete
Customer support infrastructure built
Salesforce trained

Other examples of minor milestones for digital projects:

Product definition complete
Proof of technology feasibility
Prototype complete
UI accepted
Management signed-off on UI
Testing
User feedback (iterative)
Readiness to scale (e.g. localization)

Tips For Using Milestone Software

Too many companies get bogged down in questions about milestone software. Which tool is best? Should we use Brightpod, Basecamp or Microsoft Project? How should we use it? When or how often should we update the data?

Start With A Simple Project Milestone Tool

The best tool, especially at the beginning of a project, is a manual technique. Divide the project into tasks and write them on sticky notes. Then move them around a whiteboard to reveal the Critical Path.

Project management software vendors won’t like to hear it, but most of the tools are too onerous, too complex, and add little value. Most projects don’t require resource planning tools. In most cases, you don’t need a tracking tool that requires the team to spend time feeding it data. With the exception of very large and complex projects, your team generally does not need a tool with more than one screen of information per project.

Digital project managers are fond of digital technology, but sometimes low tech is enough. You don’t need more than a whiteboard and some Post-it Notes® to map the critical path and sketch in the project timeline. Create a slide that shows the core team and the extended team.

Map Your Milestones Visually With A Diagramming Software

You can use a diagramming tool to draw and capture the Critical Path. Then translate the resulting milestones into a table in Google Sheets as described above, with the date, the milestone name, and the deliverables and goals.

When learning any skill from hitting a tennis ball, to doing Tai Chi, to playing the guitar, beginners have a tendency to use too much energy. Masters at these skills use only an appropriate amount of muscle, never too much. When they ply their skill, their demeanor is relaxed.

The same is true in project management. Since so many tools are available, too many teams try to use every bell and whistle, it’s like hitting a tennis ball with too much blind force, or gripping the neck of the guitar like you’re holding on for dear life.

The best tech companies have learned the lesson of lean: if it’s not oriented around adding value that a customer would notice, it’s wasted effort.

Key Takeaways For Project Milestone Planning And Management

Here’s a summary of the main takeaways from this article:

1. The planning of a timeline and a set of milestones is for the team to do their jobs better.

Management needs to be able to rely on the team, and the team needs accountability, but the milestones aren’t for project managers or senior managers.

2. Milestones are not reporting events, they are signposts to ensure that the team reaches the right goals at the right time.

Also, milestones are not a good substitute for good project management. They are the result of managing projects with foresight, with an eye on reducing risks and managing key dependencies so the project team can work smoothly without bottlenecks.

3. For digital product development, have three major milestones that correlate with major business goals.

Use milestones to define the concept, confirm the fit between the product and the market, and then develop and launch. Have about four to six minor milestones leading up to each of these three.

4. Lean is best.

Use the least appropriate amount of technology. Tech companies sometimes think there’s a tech solution to every problem. Keep it simple.

5. Senior Management need visibility on the quality of their investments but shouldn’t meddle unless there’s a problem brewing.

The best project management operates by exception: only interfere when the project moves away from its plan.

6. Above all, have only as many milestones as you need to propel the project forward.

Many companies have too much process. Milestones involve major events and important dates, so don’t get bogged down with trying to keep track of too many smaller milestones. You need just enough process to achieve your goals. Think Goldilocks: not too much, not too little.

What are your main takeaways or lessons learned from your own experience with project milestones? Please share in the comments below or join the discussion in the DPM Members forum.

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Originally published at https://thedigitalprojectmanager.com on November 02, 2020.