Project Milestone Planning for Remote Teams

Milestone planning takes the center stage while getting ready for project execution. It is all the more crucial when you are driving projects with remote teams. Defining milestones and sharing with your remote project management teams is just the tip of the iceberg.

There are a lot of factors that need to be accounted to ensure remote team alignment with the project goals and guarantee project success.

What are Project Milestones?

The common understanding of milestones revolves around the fact that it is achieving a specific key objective in the overall project vision.

Milestone completion is also a quick way to gauge how the project is progressing, is it on track and if it is in-line with meeting the specified strategic goal.

Milestone goals usually include

• Accomplishing an agreed completion stage
• Completing defined sections of a new service or product
• Roll out of a specific portion or feature of the service or product to a small or wide user community
• Spreading awareness, communicating and impart training to specific business departments
• Obtaining sign-offs on agreed deliverables
• Assess and make the Go – No-go decisions etc.

Milestone completion attracts a lot of executive attention (PMO, Business Sponsor, CXOs, Customer & stakeholders)

Running through a milestone also involves multiple project management processes right from

• • Contract management
  • Vendor management
  • Procurement management
  • Schedule management

• Scope management
• Quality management
• Communications management
• Risk management
• Resource management
• Change management
• Cost management
• Stakeholder expectation management

I listed some of these processes above to indicate the significance of milestone planning, execution and completion before me get into the details on how to execute them successfully.

As a program manager or project manager you have tremendous responsibility in terms of managing multiple moving items

• Customers
• Vendors
• Project teams
• Scope
• Delivery
• Timelines, cost & quality

Hence, ensuring you are well supported by your remote teams is your top priority. The remote team also includes your PMO and key decision makers.

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How to Plan Your Milestones?

Milestone planning must be done at 2 levels

• Strategic
• Tactical

Strategic Planning is all about identifying crucial points along the project journey that further the agreed project goal and vision.

In simpler terms, each milestone must deliver outcomes of business value that takes the organization closer to achieving the strategic business goal they have set or expect to achieve from this project.

We all know that plans are at the end just plans unless executed successfully. But before that, planning is purely an empirical exercise.

Project or milestone planning is dependent on the best estimate, expert judgement or average of past successful project performances.

Agreed that, we are backed by artificial intelligence & big data led approach to project management but we are still far from realizing their true potential at the moment.

So, the general practice is to account for a majority of best case scenarios, some assumptions and risks as well as key business specific challenges in defining the project milestones.

Well, when we say plan we usually tend to think in terms of time, resources and cost.

But at the strategic level it is about “where to be” and “being there” than how to be there.

Hence, the key lies in careful assessment of the stages that one has to go through to achieve the goal.

Use a simple e.g. of building a house. What milestones would you set for it?

This will give you a good idea of what to look for in your project roadmap and how to break it into key milestones and reach the goal!

Tactical Planning is somewhat scientific in nature and deals with the ground realities. It is purely at an execution level. You answer also the “How’s, When’s and who’s” at the milestone execution level.

This is where you take a hard look at your project schedule, resource management, capacity planning, available funds and overall communication plan to ensure well-oiled execution.

Project Managers will need to maintain a steady communication channel with their remote team to drive the message home & ensure successful project management.

Let us take a granular look at how you enable your remote teams for successful project management.

Milestone Planning with Your Remote Teams

Remote teams or not explaining the project vision and roadmap with absolute clarity must be the first step towards a robust execution strategy.

Bring the teams on a common understanding w.r.t the

• key deliverables
• agreed timelines and quality
• impact of the deliverables on the project goal
• duration of the milestone
• execution approach to complete the milestone
• communication plan, frequency and medium

These aspects are to give the remote teams a solid understanding of what is expected of them.

Invite questions and concerns and address them proactively.

Unless the team buys into the approach and delivery expectations, obtaining desired outcomes would be a challenge.

Key Actions to Set the Milestone Execution in Motion

• Develop a solid task breakdown structure with the help of an enterprise project management software.
• Take the agile approach where applicable.
• Establish clear task dependencies.
• Allocate resources based on skill and expertise level to the relevant tasks.
• Provide clarity with proper task categorization – use of custom task types, custom labels or tags and custom status come in handy.
• Define estimated hours Be aggressive yet realistic so as not to prove counter-productive.
• Stick to the task due dates and do not accommodate changes unless absolutely unavoidable
• Build and share the RACI matrix with the team.
• Provide a common remote team collaboration platform to brainstorm and resolve issues in real time or use the in-app chat capabilities.
• Make progress visible to all, use Kanban boards to track task progress at a granular level.
• Hold quick status review meetings with the teams. Preferably twice a day -15mins each to catch-up on issues identified if any and progress made.
• Enable desktop and email notifications to stay on top of progress as and when it happens.
• Define mini-goals within the milestones to drive healthy competition among the team.
• Celebrate key small wins regularly on a shared platform – e.g. resolution of a critical or long standing issue.
• Use custom task reminders to prevent task delays.
• Ensure key project information, progress updates, issue & risk updates are easily accessible for the team. Like a central document management system baked inside the enterprise project management tool.
• Protect critical project info from unauthorized access with custom user role permissions.
• Track resource allocation, availability and utilization regularly to prevent resource burnout and assignment conflicts.
• Maintain momentum by sharing feedback and comments as and when received from the PMO, Stakeholders and customers as applicable.
• Do make it a point to share accolades and appreciations
• Lastly, make sure the team know you have their back and that they can fall back on you when needed!

Wrapping Words!

Maintaining remote team engagement is at the top of the project management challenges list.

Being paranoid about the team’s availability, work hours etc. going to serve you in an economy driven by digital transformation and equally digital knowledge worker.

The key is to be transparent, empathic and maintaining constant connect via preferred task management and collaboration platforms in real time.

As long as the expectations, quality guidelines and delivery schedules are well established and understood remote teams will perform optimally.

Understanding how to tap the right energy within your remote teams will go a long way in achieving business goals with certainty.

As they say, uncertain times call for certain moves!

How successful was your last milestone delivery? Which all key actions did you tick from the above list?

And lastly what’ your preferred enterprise project management tool?

Don’t have one? Choose the right tool today!