How to Fix Failed Deadlines—Plan by Milestones

Businesses move forward project by project, yet so many projects fail to meet expectations.  Why is this?  The framework of a project seems to be so straight-forward.  But, we seem to miss the mark time and again, even after having incorporated “learnings” from our previous projects.

Project planning is a process of identifying likely scenarios and managing the risks associated with them.  We predict a path and then set expectations based on that prediction.  There are variables we cannot control, but can anticipate.  A construction project is always at the mercy of weather.  But, even the weather can be accounted for over the course of a building project.

But what about projects that involve more unknowns—exploratory and analytical projects with the purpose of revealing something new with the hope that the business could take some action.  New product ideation, business or customer analysis, and even process improvement projects are all examples of projects that often fail to meet expectations set in the initial planning phase.  Often at the start of a project plan the first action is to begin tying project work to a detailed timeline, in overly optimistic detail.

What is truly needed at the outset of any project is a clear goal, scope, and to set expectations based on the milestones to be achieved.  The details of specific tasks and intra-project timelines will come into view and be useful as they’re needed.

Milestone – An action or event marking a significant change or stage in development.

To be an effective project planner a project management framework that includes the use of milestone planning is needed.  Milestones are events over the course of a project’s lifecycle that merit special attention—they represent instants in the critical path progression of a project that highlight key project events such as major accomplishments, progress gates, decision points, and even the health or status of a project.

For most projects, significant events—not dates—should determine milestones.  Date-driven project planning is inherently problematic, requiring numerous rewrites over the life of the project, as new details come into view, and deliver timelines shift.  There is also a natural tendency for the work to adjust itself to the deadline leaving some question as to the reliability of some work-back plans.  Especially in analytics it is important to realize that much of the initial work of a new project is designed to give body to the scope and goals of the project.  Milestone planning puts attention and focus on accomplishments and decision-making—two critical areas of focus for overall project success.

This is a major advantage over deadline-driven project planning and takes into account the exploratory nature of the start of many analytical projects.  Milestone planning allows for the “visible horizon” effect of project planning; where the details at the offing are more difficult to discern.  In other words, many important events in the progression of a project are known at the outset of project and can more effectively guide project planning than assembling a detailed task-level plan that is time-bound at the outset.  In analytical and exploratory project planning it is often not possible (and at times even counter-productive) to plan each task to a timeline.  Only when the project work is closer at hand and better defined following some initial stages of the project does task-level planning come into its own effectiveness.

As an example, consider a typical exploratory project designed to dive a bit deeper into an analytical question or business idea.  The first order of business is to understand what amount of work the analytical question or idea would really require in order to pursue it to a point of recognizing value.  In the simplest of terms, the first phase of the project is to more fully define what the second phase of the project would entail.  This is designed to provide a natural decision point to decide whether or not to move forward with the project once the results from initial phase are understood.  That decision point is a milestone and will be known at the outset of the project plan, even if the specific date is difficult to state initially.

There are three major types of milestones that tie conceptually to the four-stage progression of project management (1. Plan the path, 2. Survey the path, 3. Course correct, 4. Deliver) which are Decision milestones, Execution/Check-In milestones, and Delivery milestones.

  • Decision Milestones typically are inflection points in a project that incorporate some input needed to make a judgment or important decision, either for the progression of the project itself or as an output of the project.
  • Execution/Check-In Milestones typically are set up as “gates” or check points in the progression of a project to ensure progress aligns with goals, scope, and expectations.
  • Delivery Milestones typically signal the completion of key deliverables, major accomplishments, or the completion of the project itself.

Milestone planning enables project managers to more accurately determine whether or not a project is on schedule, as well as derive constraints, dependencies, and risks to the project.  Driving to milestone helps to clarify the project’s critical path (sequential work) and creates a framework on which a timeline can be included as specific dates can be set out with confidence.

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