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Five Ws and an H: 6 Questions All Project Managers Should Ask

You don’t get much of anywhere in business without asking questions, but strangely enough, a lot of people are pretty bad at it. Maybe they don’t ask questions at all, or they do, but only after something’s 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. My suggestion? Do like the journalists do, and check out these 6 questions all project managers should ask — every time.

1. WHO is working on this project, and who are they working with?

The obvious: identifying project team members.

The ambiguous: establishing clear connections among people who’ll be collaborating with each other, integrating their schedules and vacations, and noting how their role in the organization 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 labor 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 big one. 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 PM should go at it 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 organization, and a variety of different expectations or suggestions.

3. WHERE are the resources coming from, and where are they going?

In other words, where’s the budget coming from? 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.

4. WHEN can each milestone be accomplished, and when is the last-drop deadline?

Simple and obvious, but so important. Know your schedule, and cushion it whenever possible for flexibility. Work backwards from the final deadline, but take into account that it can always change. Anticipate holdups — that way, when they don’t happen, your team can do some fine-tuning.

5. WHY is this project necessary, and why will it benefit business?

This ties back to speaking with project stakeholders, and in general should be fairly clear. If you’re running a new marketing campaign, it’s to increase your audience and in turn, boost sales. Building out a new micro-site or two will increase traffic; redesigns help keep your brand or product fresh. But dig deeper than that. Get numbers, projected returns, and other tangible data that can help drive your project forward. This informs the schedule, too — 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 prioritize project focus, develop an honest, business-oriented assessment of your project’s impact on the organization as a whole. It’s easy to get stuck on how the project is affecting your team or department without considering why doing it at all is beneficial for the company. Measuring the outcome is a given, but how that’s going to be done — whether it’s through increased sales, getting press from a particular publication, 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. It can feel like you need to be three different people, or that you read nothing but calendars, or haven’t gone a whole hour without attending a meeting. But with the right questions and a little patience (okay, more than a little), you’ll be prepared for the worst — and still be able to shoot for the best.

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