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6 questions every project manager should ask

Conor O'Gorman
July 31, 2013

In today’s changing workplace, organisations are expected to be more agile than ever and almost everyone plays the role of project manager. Teams are often decentralised, cross-functional and formed to address specific problems, so projects are managed by an array of people, which is why it’s imperative to understand how to work with any stakeholder.

To manage any project in an organisation, starting the process off right means asking questions, but strangely enough, a lot of people are pretty bad at it. Maybe they don’t ask questions at all, or when they do, it only happens after something has gone horribly wrong. Typically, though, the problem lies in asking the wrong questions, questions that are too broad or acute are often met with single-word answers that don’t capture useful details or address key issues.

For project managers, this can be especially detrimental and lead to hastily done work and a lot of wasted effort. These project challenges are pretty universal across most companies today; you’re working on multiple projects at once, with multiple people, most often in multiple locations, and under intense time pressure. To combat this and help avoid making the wrong choices at the beginning of a project, it’s useful to channel the method journalists use to write an article: consider the five Ws and H. With this in mind, here are 6 questions all project managers should ask, every time.

1. Who is working on this project? (And who are they working with?)
While it’s important to establish guidelines, they don’t mean much if the right person, possessing the appropriate skill set and vision for a project, isn’t following them. The obvious course of action would be to identify project team members, however, there are some more ambiguous considerations. For example, establish clear connections among people who’ll be collaborating with each other, integrate their schedules and holiday times to ensure maximum staff resources are available, and note how their role in the organisation will affect their role on the project team. Outlining these kinds of details is worth the elbow grease, and can help you measure time frames in terms of actual labour hours rather than dubious calendar days.

2. What are the potential risks and roadblocks? (And what can we do to prevent or overcome them?)
This is a very important question to consider from the outset. Failing to complete a thorough risk analysis at the start of a project can completely stall progress later on. But that’s not to say a project manager should go through this process alone. Talk to stakeholders—from each person on your project team to folks at the corporate-level, if it’s appropriate—since they’re likely to have individual investments in the outcome, unique insight into the organisation, and a variety of different expectations or suggestions. Once the risk factors are established, work with these stakeholders to agree on a strategy to prevent issues.

3. Where are the resources coming from? (And where are they going?)
In other words, where’s the budget coming from that will support the project? What about non-monetary resources, like supplies or office space? Where will you go for approval on spending, travel, or completion of different steps? Where will you be allocating these resources throughout the project? Equally as important is the quality of any resources you use. Don’t just take whatever’s tossed your way; instead, find a balance between cost and worth and use these insights to enable you to request these resources.

4. When can each milestone be accomplished?
(And when is the last-drop deadline?)
This might seem simple and obvious, but it is a very important element. Know your schedule, and make sure that you cushion it whenever possible to maintain flexibility. Work backwards from the final deadline, but take into account that it can always change. You also should remember to anticipate holdups: that way, when they don’t happen, your team can spend this time to do some fine-tuning.

5. Why is this project necessary? (And why will it benefit the organisation?)
This ties back to speaking with project stakeholders, and in general should be fairly clear. To be ultimately successful, gather as much data as you can early on. Get numbers, projected returns, and other tangible figures that can help drive your project forward. This informs the schedule, too, as the lengths of sprints and quarters are rooted in financials and customer growth, which invariably trickles down into project timelines.

6. How will the success or failure of this project impact the overall business? (And how will we measure that outcome?)
We may want to complete projects successfully 100% of the time, but let’s face it, that doesn’t always happen. In order to prioritise project focus, develop an honest, business-oriented assessment of your project’s impact on the organisation as a whole. It’s easy to get stuck on how the project is impacting your team or department without considering why doing it at all is beneficial for the company as a whole.

Measuring the outcome is a given, but how that’s going to be done—whether it’s calculated through increased sales or physical deliverables—should be established up front and will play a huge role in how the project is executed.

Being a project manager means a lot of things and it is never an easy role to take on. It can feel like you need to be three different people at any one time, or that you do nothing but check calendars, attend hourly meetings or request constant status updates. With the right questions and a little patience, however, you’ll be prepared for the worst and still be able to shoot for the best.

Conor O'Gorman
Conor O’Gorman is senior manager, APAC & Japan for Mindjet, a provider of collaborative work management software that helps teams to generate ideas, organise information, and manage workflow to maximise the power of collaboration on projects.
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2 thoughts on “6 questions every project manager should ask

  1. This article doesn’t address the second most fundamental question after WHY we are doing this project.

    That is, WHAT are the objectives, outcomes and deliverables that the project should achieve.

    1. Interestingly, many project managers may not have the power to decide what the objectives are and what the outcomes and deliverables should be because they have been brought it too late in the process. A sponsor, or sometimes portfolio manager or PMO says ‘here you go, a new project’ and leaves it up to the project manager to decide how they will achieve those elements, which have already been set. Perhaps we need to rethink the role of a project manager in articulating the ‘why’?

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