Project Management: Planning: Guiding questions and tips

Planning is a significant part of ensuring a project’s success. While planning your project, you and other members of the team will determine the processes and workflows needed to meet your goals and put together ideas about how to make the project a success.

These guiding questions and tips, compiled by dozens of project managers, can help you determine what goes into a project plan, who to talk to, and how to approach and organize conversations.

Get to know your team

Start by getting to know anyone on your immediate team with a short introduction or coffee chat. 

These guiding questions can help you start to develop relationships with your team:

• Have you ever worked on a project like this before? If so, what did you do? Do you expect to do that here?

• Are you expecting to do any tasks on this project or just give input or review information? Do you expect to delegate tasks to others or do them yourself? 

• What are you hoping to gain from working on this project? Do you have particular strengths that you want to demonstrate? New skills you want to gain? How will it contribute to your desired career path?

• How can I, as the project manager, best support you on this project? 

Also, feel free to ask a few personal questions. It helps to get to know others as people, including what they care about. Strong personal relationships are an asset to any project.

Identify milestones and tasks

When setting milestones, review your project charter, business case, and the description of the project. Ask what steps need to be completed to reach each milestone and who needs to complete them.

Tips to help identify milestones  Identify places within the project when: Success metrics can be tested A certain type of work is completed A certain type of resource is no longer being used Stakeholders want updates A large percentage of the budget is being spent There is cause for celebration

These guiding questions can help you identify tasks:

• Are there any tasks that can be broken down into smaller tasks? 

• Are there tasks with no single clear owner? 

Tips to manage tasks Meet with the team as a group if it is smaller than five people. On larger teams, create subgroups to talk through a project and source ideas about tasks and deadlines. Identify tasks that are potential "blockers" or "dependencies,” meaning that other tasks are unable to move forward until the previous task is complete.   Highlight these in the project plan and check their progress frequently. Keep the team informed if one of these key tasks will change the start date of other tasks.   Alert team members when a delay in the completion of one of their assigned tasks may end up blocking another team member’s work. This can help team members prioritize tasks and creates peer accountability.

Estimate task duration

When working with experts to estimate how long it will take to complete tasks: 

1. Ask the expert to break the task down:

• What steps are involved in the task?

• How long do you estimate each of the smaller steps will take? 

Add up the time estimated for the smaller steps to determine an estimate for the total time needed for that task.

2. Question expert assumptions: 

• What resources do they assume are available? Which materials? Which people?

• How skilled do they assume people are?  

• How likely is it that some assumptions will not materialize? How would that impact their estimates?

• Are there steps or other tasks they assume are being completed before this task has begun?

3. Ask the expert to describe a similar project they worked on: 

• How was it similar? 

• How was it different? 

• How long did it take? 

• Does comparing that project to the current one change their estimate at all? 

Develop project documentation

Documenting and organizing project components provides visibility and accountability. It's common for project team members and senior stakeholders to reference and contribute to your project documents throughout the project. 

📔 Project plans Document the scope, tasks, milestones, and overall activities of the project Can streamline team tasks and communication Help you plan future projects 🔖 What can be included in a project plan? Project name  Description of project Project owners (RACI) Project status Tasks and milestones Timelines and schedule Budget  Communication plan Resources and references Quality and evaluation plan Risk mitigation plan Statement of work 🔗 Download a project plan template