The Biggest Project Management Pain Points—and How to Solve Them
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The Biggest Project Management Pain Points—and How to Solve Them

This content was created by Girlboss, in collaboration with Smartsheet.

When it’s good, project management can make a team more efficient, lean and productive. When it’s bad, you end up with poor communication, missed deadlines and frustrated colleagues. The reality is: Even if you don’t have “project manager” in your title, you’re probably still managing projects. Why? Because most workplaces are built on project-based work.

That’s why Smartsheet put together their Future of Work Management Report 2023 which reveals what you need to know about the current state of project management. Inside, you’ll find everything from pesky pain points to what workers can benefit from using a tool like Smartsheet. Spoiler: A lot.

We wanted to dig deeper into the project management pain points that keep your deliverables from getting shipped. Chasing your colleagues for updates? Juggling deadlines? Sticking to a good workflow? We asked our Girlboss audience over on Instagram what their biggest pet peeves are—and management consultant Johanna Rothman provided super helpful solutions.

“Project managers are called managers, but I think they should think of themselves as leaders instead,” says Rothman. “Then, they realize they can manage the work environment and lead the people. It’s more satisfying for everyone and much more effective.”

Let’s dive in…

Project Management Pain Point #1:
Tracking multiple projects and establishing a collaborative workflow

Imagine how much easier work would be if we only had one project to keep track of? More often than not, you’re juggling multiple deadlines, employees and deliverables at once, so it’s important to prioritize and create a rock-solid workflow (more on that below). 

Here’s how to prioritize your projects, according to Rothman:

  1. Make a list of all your current projects. Your boss might not know everything that you’re working on.

  2. Create a personal ranking. If you had to decide on your own, what projects are the most important to the least important? Then rank them based on what you actually want to work on.

  3. Consult with your team. Spend a few minutes deciding which project is your priority, then  hit the ground running.

“When you and the entire project team work on one project at a time, you can establish a collaborative workflow,” says Rothman. “However, no one can collaborate when everyone’s supposed to work on everything. So choose one thing.”

If you’re still unable to decipher a priority list because “they’re all priorities,” defer to the Cost of Delay, she advises. This tells you the actual costs of not having a project done… now. “Take the project whose cost of delay impacts the organization the most, then figure out the least amount of work to do to finish it. Then, finish that project,” advises Rothman.

Project Management Pain Point #2:
Staying on top of project statuses and follow-ups

The simple answer is: You don’t have to, says Rothman. Thanks to technology, you no longer have to stick Post-It notes on a white board, or even settle for a confusing Excel sheet. Instead, opt for Smartsheet, the modern project management tool that lets you customize, collaborate and automate you and your team’s workflow.

Rothman recommends creating a few columns to put everyone’s tasks in: Ready to Start; In Analysis & Initial Design; Code and Review; Test; Release; and then Done. You can assign different team members to different tasks, set due dates, attach relevant documents and more. “Everyone can see where the card is in your flow and who’s working on it,” says Rothman. “Then everyone can notice if the item is getting old. I really like working agreements where the team agrees on how old something has to get before they ask the person if they need help.”

And remember: You’re keeping track of the work, not the people, advises Rothman. “This is the collaboration aspect, also known as flow-efficiency thinking,” she adds.

Project Management Pain Point #3:
Ensuring all team members know their role in the project

Before you fill up everyone’s day with “wait, I thought you were owning that” messages, Rothman has a three-step process to get everyone on the same page from the start.

  1. Have a one-hour kickoff meeting to define the project vision, delegate roles/tasks and set up your project management tool *before* you begin.

  2. During said meeting, decide on a cadence for individual check-ins. Rothman recommends one-on-ones for the first four to six weeks for a six-to-nine-month project. Questions to ask: “Do you have what you need to do the job? Any questions or concerns? How can I better support you?”

  3. Conduct a quick retrospective at the end of each week or two. Questions to ask: “How well are we working as a team? Should we stop doing anything? Change anything?”

Want more insight? The Smartsheet Future of Work Management Report 2023 reveals everything you need to know about the current state of project management.

Ready to enhance your project management efforts? Try Smartsheet for free, today.