Preparing for Project Initiation

Questions to ask when starting a project

August 13, 2020 | Helen S. Cooke

Project InitiationBecause projects address situations not faced before, or strive to deliver results under circumstances not experienced before, there will always be unknowns. Planning can occur in the face of unknowns, but the more you know, the better your plan can guide your team as they get started. Some risks can be identified early, and the people promoting the project may be able to anticipate potential problems that the Team and Project Manager will encounter. But in the face of predictable unknowns, there are still latent issues, truths or contextual challenges that current stakeholders can shine some light on. In addition, having a good grasp of executive goals can provide a context for decision making, even at the earliest stages of project development. Asking the right questions at the right phase of the project, from development to execution and delivery, can provide some degree of guidance as you move forward.

Ideally one would wish for a game plan before beginning the project, much like what a sports team develops before entering the field. Your project plan is the game plan you will start with, even if it is not solid or fully developed. Often it is better to have a lean, flexible, honest plan that will stand up to change than a detailed plan that locks you into activities that might not reflect the real path of progress. The realities of the project reveal themselves iteratively as the project plan is roughed out and the project team makes progress against the initial plan. Having a good baseline plan and a method of updating and revising it gets you and your team off to a good start. The progress of the project is much like the progress of a ball game. You need a rough gauge of progress over time as the project progresses. Your ability to anticipate trends and identify needed changes early can make the difference between smooth transitions and chaotic regroupings.

Here are a few questions to get you started:

Questions for Executive Management

Why ask these questions? Preparing for success means you need a clear vision of what will be considered “success.” Start by identifying the strategic goals of the top executives, the impact of the new project on other teams, and other pressures or competition the organization is facing that could affect project success.

Questions to ask either the Executives or their key staff:

  • Is there a document that spells out the strategic goals and directions of our current executive team?
  • Are any meetings planned that I might observe from a sideline that could provide insight on the relative importance of current projects, and how they relate to each other and the executive strategy?
  • Why is this project important to the organization? Is it central to key initiatives at any level, perhaps top level or division level? Is it of importance immediately, or over a longer period of time?
  • Who considers this project very important, and why? Do you think they might agree to have a short meeting with me to discuss it? Their views could be invaluable in getting the project properly planned and staffed.
  • Are you aware of any projects in the past that are similar to what we are planning? Where could I find information about them, and are any key people still around who could update me?

Questions for the Portfolio Manager or Financial Executives funding the project:

Why ask these questions? A Portfolio Manager is responsible for financial oversight of a number of projects and programs, and may even have jurisdiction over projects and programs across division lines and geographic locations. Aligning the financial assets allocated to these initiatives requires good financial management skills and an understanding of the organization’s strategy. The organization’s annual budget has allocated money to be used for distinct purposes. Projects occur every year, but many times they were not defined when the budget was set. A certain number and type of changes are to be expected, but if the project overlaps categories or budget cycles, getting access to continued funding may be difficult. Knowing where problems could occur can help you avoid unnecessary interruptions or delays. If the organization does not have a Portfolio Manager, get the information you need from the Financial Executive and other knowledgeable executives.

Questions for the Portfolio Manager or Financial Executive:

  • What is the primary source of money for funding the project I will be managing? Why is it being started now, and when is it expected to be completed, based on the financial category that funds it?
  • What impact will it have if the project is delayed, moved into a different slot in the annual budget, or superceded by another more important project?
  • Is there anyone I should talk to, to clarify the priority of project funding, and perhaps define the priority of “time, cost or quality” when doing our work?
  • If we need to access additional funds for any reason, who is the person I should talk to? Should I keep you in the loop?

Questions for the Program Manager:

Why ask these questions? The program manager has managerial authority over several related projects, and provides money and people up front. It is important for the program manager to watch for the value to emerge at the project’s end in exchange for the money and people provided. A Program Manager typically does not get involved in the management of the project itself, but is key in providing adequate resources when it begins and a significant voice in determining if the overall project was a “success.” You should have a good understanding of your project plan’s structure before meeting.

  • Is this project part of a larger program initiative? If so, who is in charge of that broader initiative, and how can I get more information about it? What is its reporting authority?
  • How might the success or failure of other projects affect the one we are planning?
  • How does this project help you to achieve your program manager goals?
  • Are there certain outcomes or results you hope to see from this project?
  • Do you think this project’s priority is as high for other people as it is for you? Why or why not?
  • When the project is complete, and the products (or deliverables) are ready to use (finished), how will you determine whether the project has been a success? What is most critical: quality, cost or timely delivery? We can use this information to define our critical success factors.
  • Do you think there are other executives who would have a different view of “success?” Does that view differ between our top executives’ and the customer’s or user’s perspective?
  • Once we have our preliminary plan drafted, would you be willing to sit in on the review session to spot any problems we might encounter? How would you like to be notified of that meeting?
  • Would you like to address the team at that meeting? Can we put you on the agenda?
  • When the project is near completion, can we expect you to attend the close out project session, to confirm we have delivered what you expected us to deliver?
  • Do you mind if we contact you at key decision points in the future? If we have unanswered questions, your input would be valuable.

Questions to ask yourself as you enter the planning / development phase of the project:

Why ask yourself these questions? You will need to negotiate changes and favorable decisions to move forward. Your team will rely on your leadership and confidence to get everyone to the end of the project in the best condition possible. No project manager has all the characteristics, skills and knowledge needed to lead every team to victory on every project. Knowing where you are strong and where you might need backup coverage prepares you to address unpredicted barriers or unseen challenges. Some barriers are external. Knowing general business and industry trends can help you manage your risks better.

  • What are the market place trends in this project’s line of business?
  • Will those trends be different for the user or customer of our final product(s)?
  • Will we have people on the team that understand the market place? What is the best way to tap that knowledge? Where else can we get updates?
  • What is the relationship of our executive team to the executive team of the customer or user? Are there key people we need to actively involve in our project planning activities to be sure we are aligned? Could those other people have less visible requirements that determine success?
  • Do I have the appropriate “gravitas” to influence the high level decisionmakers? Who else should I engage in our meetings to be sure we are properly positioned to get appropriate backing and support?

Why this planning process is important:  Planning a project is a complex art. It requires you to take known processes and information and integrate your own information and skills into a workable plan, then to manage the people and tasks to deliver what is expected “on time and on budget.”

Knowing the “invisible challenges” of the business marketplace provides context for planning the project. If your sponsoring organization is facing real competition, learn who, what and why competitors might take your success, and what you should watch for to be sure you finish first. A solid foundation of project management knowledge and processes is the foundation, of course. Before you have the game plan, you might at least try to clearly define the lines on the field you are playing on, as well as the rules of the game in the industry and business marketplace you are playing in.

Decide who has information that can help you build a good project context. Ask as much as you can to block out the boundaries, as well as the definition of success. Try to identify potential fouls before they occur.

Asking a few sample questions to your executives and your team can help to get you started. Once you move from planning the project to planning the products and deliverables it will create, you will be working more directly with your own team experts, team leads and technical specialists.

The details of the tasks and activities of the plan will take shape with the involvement of your team. The framework and structure of the project should be well fleshed out before you involve your team so you can minimize confusion as you make changes or tailor the plan to the work you will be doing. The methods and technology of the tasks and work breakdown structure will reflect the field of work.

When you move into the project’s detailed planning phases, your team will be directly involved in making the plan work for them. Seek their advice and incorporate their opinions as they begin to “own” their own part of the project. Active involvement of the team in fleshing out the plan will make it easier for them to work together and commit to a successful delivery.

  • About The Author
  • Helen S. Cooke is a 20-year project management veteran with experience in Fortune 500 companies, universities, the service industry, manufacturing, government, military and defense. She is a PMP® and a PMI® Fellow, and an experienced management consultant. She has worked on five continents and was elected a Fellow of the Project Management Institute in 2005. Helen was a PMI officer and served six years on PMI’s Global Board of Directors.

    Helen led a profit and loss practice at Deloitte for 10 years, was Senior Principal at American Management Systems, was a mid-level manager in the federal government, and was a university administrator. She headed the Project Management Center of Excellence at McDonald’s Corporation and implemented SEICMM Level 2/3 and a PMO at United Airlines. She has taught project management systems at the graduate level at Keller Graduate School and a PMO course at DePaul University in Chicago. She is the author of several books about project management and organizational project management maturity.