How to Tell Your Manager You’re Struggling With a Project

This is the third installment in SkillPath’s series on “Tough Conversations to Have With Your Boss.” Some discussion topics are difficult to broach with your manager, and some questions feel awkward to ask. This series will help you navigate those moments. 

Projects can go off the rails for a variety of reasons. Maybe the scope turned out to be more complex than you expected. Maybe the resources you need aren’t available. Or maybe you’ve realized you misunderstood part of the assignment. Even the most capable, organized, and experienced professionals hit roadblocks.

The thought of telling your manager that you’re having trouble with a project they gave you can have you feeling sheepish at best – and concerned for your job at worst. You don’t want to seem incompetent, but you also don’t want to fail silently and let deadlines pass.

Speaking up early rather than powering through in silence will help you turn a tough moment into an opportunity for collaboration and growth.

The truth is, most managers would rather hear about challenges early while there’s still time to fix them. So here’s how to approach the conversation in a way that maintains your credibility, strengthens your relationship, and helps get the project back on track.

Recognize the Signs of Project Delays

The earlier you acknowledge that you’re struggling, the more options you’ll have to fix the problem. Here’s some things that might indicate you need to ask for help:

• You’re consistently missing smaller milestones on the way to the deadline.
• You’ve spent far more time than expected but aren’t making progress.
• You’ve hit a roadblock you can’t solve without additional resources.
• You’ve realized the scope, expectations, or priorities have shifted in ways you can’t manage alone.

Of course, this list isn’t exhaustive, but they’re common indicators of problems that won’t be solved without the help of your manager. 

Assess What’s Gone Wrong and Its Impact

Before you approach them, it’s important to get a clear picture of what’s causing the problem. Ask yourself:

• What’s the core issue? 
• What have you tried already? 
• What impact will this have on the project timeline or quality if nothing changes?

This preparation helps you frame the conversation around problem-solving. Your manager will be much more receptive if you can show them what steps you’ve taken to solve the issue on your own.

Consider the Timing and Be Professional

It’s always best to have this conversation in a private setting. Avoid bringing it up during a hectic meeting or in passing in the hallway. If you’re worried that they might ask you about progress during a weekly team-wide standup meeting, send them a message ahead of time. 

You might say something along the lines of, “I’ve been having trouble with this project. (Insert specific aspect of it here). Can I schedule some one-on-one time with you to discuss it?” 

This signals the importance of the conversation without creating unnecessary panic or involving others.

When you do meet, be direct and specific. Instead of vague statements like, “I’m struggling,” give concrete details. Stick to the facts, avoid blaming others, and keep the focus on the situation, not on personal shortcomings.

So, instead of saying something like this: 

“I feel like whoever put this data together didn’t think it all the way through, and I’m not smart enough to understand it.”

Say something like this:

“I’ve been working on this, but I’ve hit a roadblock. I’m having a tough time understanding this data and breaking it down for the sales team to use.”

Come Prepared With Potential Solutions

While the impetus of this conversation with your manager is that you’re having problems, bring ideas to the table. Explain what you’ve tried to solve the issue on your own and have possible solutions to collaborate with them. 

You might suggest adjusting the timeline, reducing the project’s scope, or getting additional help from coworkers. Even if you’re not sure your ideas will work, bringing some to the table shows initiative. 

By suggesting solutions, you’re making the conversation collaborative instead of just reporting a problem.

Even then, your manager might suggest an approach you haven’t considered. They may also help you reframe the situation, connect you with resources, or reassign parts of the project. Stay receptive to such feedback and consider it with an open mind. 

Often, when having trouble on a project, you might develop tunnel vision. You might hyperfocus on one avenue without even considering alternatives. Listen actively, ask clarifying questions, and confirm next steps before the meeting ends.

After your discussion, send a short follow-up email summarizing what you talked about and the agreed-upon plan. This ensures everyone’s on the same page and creates a record of the conversation.

Once you’ve shared your struggles and put a plan in place, check in regularly. Even quick updates can reassure your manager that things are moving forward.

Asking for Help Shows Strength, Not Weakness

While it’s understandable to feel nervous about sharing your struggles on a work project, most managers appreciate transparency and problem-solving, rather than missed deadlines, low-quality work, or other problems down the line.

By speaking up early, explaining the situation clearly, and showing you’re committed to a solution, you demonstrate accountability and a willingness to learn; qualities that strengthen trust between you and your manager.

Struggling with a project doesn’t define your ability; it’s just a sign you need to adjust your approach, resources, or expectations. Good managers understand that challenges happen, and great employees know how to raise them effectively. When you approach the conversation with preparation, honesty, and solutions, you turn a tough moment into an opportunity for collaboration and growth.