The Power of Asking the Right Questions in Project Management

Ever been in one of those situations where just asking the right question got you to the right answer?

“What do you want for dinner?” for example, can lead to endless rounds of “I don’t know, what do you want,” but a more helpful, “I’m not feeling up to cooking tonight, and I’ll be working pretty late, do you want to fix something that you feel like making, bake that frozen pizza from the freezer, or order in from our favorite take-out place so I can grab it on my way home,” gives the listener three clear choices and some context about how much work is going to go into the answer that benefits both parties.

Turns out, in project management, asking the right questions can make a world of difference, too. For over 25 years now, we’ve had great success with three simple questions. Whether you are brand new to project management or you’re a seasoned pro, these questions are a must-have tool in your project toolkit.

1. What Are You Doing & Why are you doing it?

This first question is a combo piece that helps us put the preliminary borders around the thing at hand, and gets us all on the same page.

It’s deceptively simple, but what are you doing? If this sounds a little direct, don’t worry—it’s supposed to be. This question zeroes in on the core of your task at hand. Are you launching a website? Organizing an event? Developing a product? You’d be surprised how often teams will work hard without really clarifying this upfront. What’s the scope and scale of the work in front of you? How big is the lift? Is it smaller than a breadbox? Bigger than a condominium?

This is particularly helpful in keeping everyone aligned. By answering it, you’re not just defining the task itself but also setting the boundaries. Let’s say your goal is to organize an event. Are you hosting a gala for hundreds, a casual event for families, or something virtual? “Hosting an event” is not quite specific enough, so we need a little more specificity than that to get to the scope of what we’re doing.

And the piece that helps us get there is the other half of that first question…why are you doing it? Fundraising is a different why than a family get-together, which is different than an informational session.

“Why” is the heartbeat of your project. It taps into motivation, purpose, and ultimately, buy-in. It’s easy to dive into what needs to be done without stopping to consider why it matters. But having a clear sense of purpose can make a huge difference, especially when things get tough.

Let’s say you’re building that website. Is it to increase brand visibility? To streamline customer support? Each “why” brings its own priorities and, often, its own stakeholders. When your team understands the “why,” it’s easier to make decisions that align with the project’s core goal. Plus, this clarity can keep people motivated. A website isn’t just a “website” if it’s going to help your business reach new clients or showcase a game-changing product; it’s an opportunity to make an impact.

The “why” can also bring new insight into decision-making. Maybe someone wants to add a fancy new feature. Does it align with your purpose? If not, it’s probably not worth the extra effort or expense. To learn more about the power of asking “why”, feel free to check out our blog on the 5 why’s! It's here that you can find a detailed explanation on the different angles that asking “why?” gives us in the project management process.

So we ask, what and why together to get us all aligned about the mission and the vision as well as the scope and scale, and to set us up for good decision-making down the road.

2. How will you get from here to done?

How will you get from here to “done”? Really, this question lets us fast-focus on people, time, and money. While the What and the Why help set the boundaries, this helps us name the specifics of the resources. This becomes our roadmap for how we get from wherever we are when we’re asking the question to the final stages of “signed/sealed/delivered”! Naming who is doing what helps us get role clarity. Assigning a clear end date gives us the right pacing and sense of urgency, and clarifying how much we can spend on this assignment gives us freedom to allocate the dollars appropriately so we don’t overspend.

3. What could stand in your way, and what are you doing about it?

Now, here’s where things get real. Every project has issues and setbacks along the way, and while it’s tempting to charge forward from day one, taking even a few moments up front to identify and prioritize potential challenges before they become problems can save you a lot of trouble.

Asking what could be in your way helps you anticipate those potential gaps and set realistic plans for how to handle them.

Let’s say you’re working on something that’s coming due over the end of the year. Any risk of someone being out of the office, or of shipping delays over the holidays? Those kinds of things can interrupt meetings or delay deliveries and can put your project timeline at risk. By asking this question, you’re setting up a “reality check” that brings potential problems into the open, where they can be managed rather than ignored.

Like the first question, this third question is also a double hitter. With its two parts, the second half of the question allows you to do something powerful: shift the conversation from “What might go wrong?” to “How can we make sure we’re ready if it does?” It’s the difference between being reactive and proactive. It’s the difference between being caught ill-prepared and being ready with whatever you need to take the issue in stride.

These three questions—What are you doing & Why are you doing it? How are you getting from here to done? And What could stand in your way and how will you handle it? —are deceptively simple, but they pack a powerful punch. By keeping them front and center, you’ll set your project on a solid foundation, keep your team aligned, and stay focused on the goal.

Whether you’re planning a small event or managing a complex cross-functional initiative, these questions can guide you to success.

We here at Your Clear Next Step, hope the tips and insights we’ve shared help you feel more confident and prepared to succeed in the workplace. If you’re interested in learning more about project management, be sure to check out our on-demand webinars and other blogs on communication—they’re super helpful! And if these topics resonate with you, our Change Makers program might be the perfect fit. For more details, head over to our website, and if you have any questions, don’t hesitate to reach out to us on social media. We’d love to hear from you!