5 Questions Any New Project Manager Must Ask

Tech Career Hub
Written by:
Ben Aston
Published on:
January 8, 2019

Discover the most critical questions that every new project manager must ask to ensure successful project execution and management. This post provides insights into essential queries that can guide your project management journey.

As a project manager, you’re lucky if you get to work on a brand new project with a brand new client from the very beginning. Far more often, project managers (PMs) take on a project when it’s already halfway through the pipeline, somewhere between discovery and delivery. This is the case for many different industries. And even though this is common, there’s no official formula that lays out exactly how to deal with these “up-in-the-air” situations. PMs have to piece it together on the run.

When you start a new project, you’ve got to ask lots of questions—but since time is limited, you also have to make sure you’re asking the most important questions to get the critical info you need to understand the project.

Here are the main questions you should be asking yourself, your team, and your clients if you’re jumping into a new project.

#1 What are we actually working on?

To answer this question, you should try a simple test and explain your main project goal as if you are explaining it to a child: simple and short. This means you need to know the high level strategy of the project, and to be in the know when it comes to its major phases.

It’s important to have a plan, including human resources, deadlines, budget, communication plan, etc. In order to have everything under control, and know what and when needs to be done, most of us rely on a software program for the details. However, before you even get to the details, you need to know why you’re doing the project—what are the stakes for the client, your organization, and your individual team members?

Follow-up Questions

  • What are the phases of the project?
  • How difficult is it?
  • How much of the project is already completed and how?

#2 What are the deadlines?

Some would argue time is the most important resource. If you’ve ever lost an entire day to meetings and phone calls, you know this well.

If you are coming into an ongoing project, getting to know the time frame is a must. With deadlines in sight and laid out, you can plan and track work most efficiently.

Tight timelines save resources and prevent a TON of stress at the same time. The other part you should keep in check is the scheduling of your resources and your team’s time and budget. Along with asking about deadlines, ask where the team schedule lives. Where are the calendars? Where are deadlines posted? Have a list of all the tools and calendars your team is using so you don’t lose track of timelines.

Follow-up Questions

  • What are the reasons for each deadline? (seasonality, dependencies, corporate roadmaps?)
  • What’s our next deadline? What’s our final deadline?
  • Can you split time sensitive tasks into smaller ones (while marking milestones)?

#3 Who do you have on the team?

Answering this question thoroughly should give you an in-depth picture of your team, especially if the project started some time ago. Find out who you have on the team (get a list of names) and figure out what they each bring to the table. Knowing this will probably give you a little bit of background on the team dynamics as well.

As you ask about team members, ask how they like to work. What processes or methods do they use? Ask for a list of the platforms they’re using (maybe it’s whiteboards and post-its, and maybe it’s a slick scrum tool or agile project tool), and give yourself a moment to log-in, click around, and figure out how they’re using it.

Follow-up Questions

  • How many (and what kind) of sub-teams are there? Who are the team leads?
  • Is every role filled properly? If not, what can you do to fill in the gaps?

#4 Has the team done similar projects in the past?

Using the knowledge of previous projects is a big plus. Every PM can benefit from recognizing a pattern and exploiting it. The project might be new to you but it might be the fourth project a team has worked on together, with a client that most are already familiar with. There’s a wealth of knowledge in situations like those, so go after it!

Go around and ask your clients, stakeholders, and team members if they can dig into any finished projects that had similar requirements to the current one. A great amount of inspiration can be dug out from those projects. Obviously, having access to a previous project data logged in some type of project portfolio management software is ideal, but if you don’t use one, here are some simple questions to get you started.

Follow-up Questions

  • Who can provide best insight into similar past projects?
  • Where are the previous project reports?
  • Do we have any notes on projects with this client in the past?

#5 What are the potential roadblocks?

Better safe than sorry! Always ask yourself why and how a project could fail. This is the principle every experienced PM follows, no matter the size of the project. Think about contingencies and possible problems, and try to plan not only to avoid them, but also how to manage the damage they may cause if the worst case scenario plays out.

Teams that experiment creatively with new ideas develop solutions on a daily basis—there’s a lot of ambiguity in creative work, and it’s hard to predict what’ll turn up. To manage the uncertainty, get everything you can into a thread that your team can follow.

Follow-up Questions

  • What is your procedure for managing changes and change requests?
  • What is the weakest link, and what can you do to strengthen it?

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