12 Project Management Challenges and How To Face Them
12 Project Management Challenges and How To Face Them
April 17, 2023
April 17, 2023
Tango Head of Marketing
Nick has been leading high growth teams and scaling early stage tech startups for 10+ years (most recently at Clearbit). He's been in a fantasy football league with his best friends from high school for just as long...and has never won. 😂
If you’re a project manager—officially or unofficially—nothing beats seeing people hit their milestones and share (proactive!) progress updates.
Because what’s the reality, more often than not? Project management isn’t always sunshine and up-to-date kanban boards. And project management challenges are bound to pop up, even for the most organized and Type Triple A among us. Communication breakdowns, budget cuts, and unexpected requests are just three of the curveballs that may come out of left field.
The Project Management Institute’s 2021 Pulse of the Profession Report polled project leaders about the percentage of completed projects that fell into certain categories. And found that, on average:
35% of projects failed and lost their budget
34% of projects experienced scope creep
12% of projects were deemed as failures
…which begs the question, where would we be *without* project managers?
In this post, we’ll go over the most common project management challenges you may face—and tips to overcome them—so everyone can see you for the superhero you are.
1. Unclear goals and lack of buy-in
A goal that may seem clear as day to you might be cloudy with a chance of confusion for your team. 🌧️
It’s tough to be motivated to hit your goals when you don’t know what you’re running towards. Foggy objectives can also lead to other project management challenges, like unrealistic timelines or mismatched resources.
Maybe you have a newer teammate who’s helping with data management for a project. Without context, it might feel a lot like busy work. But if you take a second to tell them how crucial their work is to keep stakeholders in the loop, they may quickly feel more valuable and engaged.
Try this: Connect with your teammates as early as possible to explain the “why” behind a project—and highlight how their contributions will help drive impact.
Checking in early and often can help you get ahead of questions and act on initial feedback. You never know—your new hire might have a trick up their sleeve that will save everyone on the team lots of time.
You may also get a chance to simplify unclear goals or objectives for your team. Goal setting frameworks like BHAG or SMART are a great starting point for creating goals, KPIs, and milestones.
Once you figure out what works best, document it! You can capture foundational steps in your project kickoff process documentation, so they’re baked into your team’s process moving forward.
💃 Let's Tango: Share project instructions in seconds
You finally found some heads-down time for a project…or so you thought. Here comes another quick question.
This is where Tango can help. Download the free Chrome extension to:
Create a beautiful how-to guide in seconds.
Set teammates up for success with step-by-step instructions designed to help people get unstuck (on their own!).
Poor communication can take many forms—radio silence, overly-detailed pings, or otherwise inefficient exchanges.
It can also snowball into bigger issues like project delays or a lack of visibility. This can happen if teams aren’t clear on when and how they should communicate. Your team’s communication culture may also come more naturally to seasoned teammates than newer ones.
Try this: Use a project management solution to keep important information and communication in one spot(instead of sending your hundredth reminder of the day). 😵💫
A centralized tool can cut down on confusion and make it easier for everyone to see progress. It can also empower your team to help themselves to project details (rather than raising their hand for help or digging through a mile-long email thread).
Try this too: Establish communication expectations—and explain why real-time updates help the entire team.
Educating your team early on can help teams stay on the same page, especially as changes happen. Instead of missing details buried in an email, your project management tool can give teams instant visibility into decisions made and progress made toward the project’s milestones.
Documenting best practices and instructions in a project communication SOP can help newer teammates learn the ropes and older teammates refresh their memory.
If you’re working on a cross-functional project with lots of cooks in the kitchen, initiating a standing meeting is one way to stay on track.
💡 Tango Tip
Assign a DACI for every project to streamline cross-functional collaboration—and minimize last minute fire drills.
D = The driver who oversees the project (that’s you!)
A = The approver who gives the final green light
C = Those who contribute feedback and opinions that help inform decision-making
I = Those who need to stay informed but aren’t directly involved
3. Impractical timelines
You don’t want anyone to get burnt out, but you also need to optimize your team’s time, talents, and budget. You’re also under pressure to increase efficiency from stakeholders who want to see faster turnaround times.
Try this: Lead with empathy—and ask for input—when determining timelines.
Some people on your team may have a lot on their plate and next to no extra time to spare. Others may have just completed a long sprint cycle and need a break before tackling a new project.
Think through what your team can realistically handle before loading up their schedule—and ask them what they think. In many cases, being able to deliver higher quality work and offer better work/life balance can be reason enough to extend a deadline.
Try this too: Advocate for realistic timelines using past data and project postmortems to make a business case for prioritizing quality over quantity.
We’ve all worked with a stakeholder who wants projects done yesterday. Past data, documentation, post-mortems, and insights from teammates can help make your case for more sustainable sprints.
When in doubt, build in buffer time to help your team handle unexpected challenges and delays (especially on new projects!).
4. Challenges from unexpected risks
In a perfect world, we’d have a contingency plan for every twist and turn that comes our way. 🎢
What’s the reality? Risk management plans can only predict so much!
You probably have tried-and-true contingency plans for common project concerns, like what to do when someone’s out sick or a cloud-based tool goes down. You know that while inconvenient and less than ideal, speed bumps like these won’t slow you down too much.
Something you may *not* be able to plan for? A series of unfortunate events that results in something like corrupted, mission-critical files.
To rally, your team will need to recreate the lost files—which will inevitably extend your project delivery dates.
There’s no way you could’ve planned for that…right?
Try this: Make the riskiest parts of your project the most flexible.
Flexibility may mean accounting for extra hours or assigning senior teammates to more difficult tasks. Researching project-specific risks in the planning phase can help you figure out what to prioritize.
For example, your product team may need more budget flexibility than usual if they’re launching a major (and highly requested) feature update this quarter.
5. Changes in budget needs and timelines
Say you missed a small feature update that will take a couple more days to build. Or your boss needs to pull a team member for another high-priority project. Or you didn’t account for the time needed to address stakeholder feedback. Or you *did* build in a buffer, but you got way more feedback than you’d anticipated.
Try this:Before adapting as needed, stop and review your project plan and timeline. Figure out if there’s anything you can scale backwithout impacting the project’s overall success.
Ask stakeholders about what’s essential and what you can adjust or eliminate. Then re-deploy your resources accordingly.
Try this too: Consult past project postmortems, your team’s subject matter experts, and other project managers when setting timelines and budgets.
Did more junior members of your team struggle to finish a task your top performers could knock out in no time? Maybe you can prioritize pulling in more experienced team members or build in time for training.
Did someone come up with a huge timesaver on the last project? Maybe you can resurface that knowledge now (and document their pro tip for next time). 💃
Insights directly from teammates and other experts can shed light on project management challenges, what might’ve kept a project on track, and other suggestions that didn’t make it back to you the first time around.
It’s also not a bad idea to touch base with other project managers—especially if your resources overlap.
6. Lack of tools and resources
It pains you to see someone creating something manually that could be automated. It’s also tough to know your team is stretched thin and running on empty. If only you had that tool to make things easier.
Too much work is a big hurdle in and of itself. Too much manual and tedious work is usually a driving factor—leading to more human error and less time to go around for more strategic work.
Try this: Prioritize the tools and resources that will make the biggest impact on the success of the project.
Maybe your teammates aren’t big fans of having to manually update their progress in your project management tool. When it comes down to it, this may not be as big of a priority compared to other project management challenges.
For instance, are constant questions and meetings keeping your top performers from hitting their goals?
This might be a sign to invest in a documentation tool to help everyone share (and access!) unique knowledge to get stuff done. If you lean on good documentation to answer repetitive questions, your top performers can get their time back, and people who are still learning can find the answers they need fast, without breaking flow. Better documentation means more efficiency, more time saved, and more productivity for the entire team.
If cash flow is your biggest challenge, crunch the numbers and expected outcomes for your decision makers. It’s easy to say “no” to a simple yes/no request. It’s not as easy when you show them the impact your team could have with the proper tools.
7. Scope creep and gold plating
There are lots of ways blown budgets or missed deadlines can creep up—hence the nickname “scope creep.” This can be a symptom of other project management challenges we’ve already talked about, like unclear goals or poor documentation.
It can start with someone saying “yes” to a simple request. Before you know it, a small one-hour task can snowball into a five-hour project with inputs from multiple team members. Think “If you give a mouse a cookie,” but more like, “If you give a stakeholder a ‘yes.’” 🍪
Gold plating is a similar project concern. This happens when your teammates increase the project scope on their own by adding extra features.
Try this: Set boundaries for staying on track and requesting changes to help navigate tough conversations.
Communicating the importance of managing scope creep can help everyone involved understand its impact on a project’s success.
For example, if a stakeholder asks for an extra deliverable, you can gently point them back to your project plan. If they insist it’s a need-to-have, you can talk through what it would take to make it happen and how the added scope will affect your project’s timeline.
💡 Tango Tip
Take a documentation-driven approach to corralling inputs, resources, and expectations for a project. Getting these details in writing can help keep newer team members, freelancers, external partners, and stakeholders on the same page.
8. Issues with team morale and collaboration
You might have someone on the team who works by the book and someone else who likes to think outside of the box. Individually? Top performers. Together? Another story. 😬
Great teams are diverse, meaning you’ll naturally have teammates with different work styles. Differences can sometimes lead to friction, communication breakdowns, and other project management challenges.
Try this: Dig into how your teammates like to learn and work together.
Start by getting everyone together to talk about their preferences, find common ground, and understand where others are coming from.
For example, your team may have differing opinions about project updates. Some may err on the side of short, sweet, and sporadic, while others prefer may expect detailed recaps on progress on a near daily basis. To help people collaborate more effectively, talk through the most helpful level of information and an ideal cadence at the first sign of friction. Ultimately, you may be able to create a project update template that serves everyone well.
Communications or work style assessments can also go a long way. You’ll get to dig deeper into everyone’s strengths and weaknesses, and surface ways to work better together. More casual team building activities can also help cut down on budding tension and remind everyone that they’re all on the same team, working towards the same goals.
9. Knowledge gaps or skills mismatch
Staying on top of everyone’s skills and project management experience isn't easy, especially in fast-paced workplaces. But if those details slip through the cracks, you may end up assigning someone to a task they’re not familiar with. By the time you find out, it might be too late to tag someone in to help support.
Try this: Determine the skills and experience level required *before* kicking off a project.
Taking this step can help you identify anyone who needs extra support to fill a knowledge gap or isn’t ready for this project (yet!). This can also be a testing ground for your current work instructions or SOPs to see if they help your team tackle new challenges on their own.
As far as people who are struggling with a skills mismatch? Let them know what they did well. Then, find resources and teammates who can help them find their footing. This might mean rolling up your own sleeves to help them learn on the job or setting them up with some more formal training.
Once you have a clear idea of your team’s strengths, you can put more easily into roles that play to their strengths. Are you tackling a completely new challenge? Tap your most creative problem solver for ideas. Is someone struggling with a new task? Let your by-the-book knowledge champion train them on best practices.
💡 Tango Tip
Leverage microlearning moments to help newer teammates get up to speed while they work.
10. Low team accountability and productivity
We get it. It can feel frustrating when your team still hasn’t hit their goals after you took the time to create SOPs, built project timelines around vacation days, and worked extra hours to support new team members.
After taking a well-deserved coffee break, come back with a clear head to figure out how you can help your team get back on track.
Missing key milestones or deadlines might mean your team doesn’t know who’s responsible for what and how that impacts the project.
It may also be a trickle-down result of other project management challenges. Your team might not have the right skills to tackle their tasks. Your teammates may not trust each other enough to ask for help. Your team may still not know how to add updates to your project management tool.
Try this: Get clear on everyone’s roles and responsibilities from the start.
Clearly outlining roles and responsibilities can help everyone understand how their progress affects others—and the overall success of a project. You can also emphasize the importance of maintaining your project management tool for keeping up visibility and streamlining cross-functional collaboration.
If that’s not the issue, think about what else may be contributing to a lack of accountability.
Does a teammate need more training to complete their tasks? Are timelines too tight? Are their working styles clashing? Once you figure out the root issue(s), you can work on solutions.
💡 Tango Tip
Champion the people on your team who are contributing to your project. You know—the ones who proactively post updates in your project management tool, share ideas and learnings, and make collaboration easy, fast, and fun.
11. Challenges with stakeholder feedback and expectations
Sometimes, stakeholder feedback can feel a little unfair or unrealistic. Spontaneous check-ins or “small” pieces of feedback can set the project back more than they realize.
On the other hand, quiet stakeholders don’t always mean happy stakeholders. They may end up giving you the most feedback when you’ve almost wrapped up your project.
Try this: Set expectations from the beginning about feedback, their level of involvement, and how failing to meet those expectations can impact the project’s success.
Clarify what type of feedback you want from stakeholders. A little guidance can make it easier for them to quickly share their thoughts.
Digging into the “why” behind their requests can also help you find common ground. A stakeholder may have unexpectedly been OOO and just passed along extensive—but necessary—feedback.
Instead of saying, “no,” find ways to meet project milestones while incorporating feedback. Are there any trade-offs you can make? Is there any room to push the project timeline?
💡 Tango Tip
Ask stakeholders about the progress updates that are most important to them to see. For instance, updates for individual tasks may be essential for some, while others may be happy to see only major milestones achieved.
12. Rushed or non-existent project postmortems
Has this ever happened to you? You’re suddenly at the end of a project, with a very small window before you kick off the next one. Instead of hosting a proper postmortem, you jot down a few things you want to talk about with the team and move on.
Try this: Build your postmortem in as a project deliverable, with dedicated time to complete a proper retrospective.
Instead of treating it as a “nice-to-have,” give postmortems the same level of importance as any other deliverable.
You can also save yourself some brain power at the end by keeping a running list of observations throughout the project. A quick bulleted list with what went well, what didn’t go well, and what the elephants in the room were can be enough when you’re in the thick of a project.
It’s smart to enlist everyone on the team to do the same, too. At the end, you can see what common themes came up and talk about what you can do better next time around. 💪
💡 Tango Tip
Use project postmortems to find patterns among recent challenges—and celebrate your team’s wins.
The bottom line
Project management challenges are bound to happen, with varying amounts of predictability. What is fully in your control is how you learn from them and how you share those learnings with your team.
Project kickoff SOPs, work instructions for specific tasks, how-to guides for your project management tools, and even your postmortem documentation can all help your team manage projects with ease and ensure successful project delivery.
What’s the key? Documenting as you go—especially as you transfer knowledge and best practices from one project and person to another.
Tools like Tango make it easy to help everyone hit the ground running every time, no matter how complex the project.
The best part? You don’t need any special skills to make easy-to-follow guides for your team. 💃