two people talking
Johnny Greig/Getty Images

I sat staring blankly at hundreds of pages of documents and forms—willing myself to make at least some sort of progress. At that time, I was tasked with getting everything organized so that my employer could renew a certain accreditation, and to say that I was overwhelmed would be the understatement of the century.

I was still somewhat new to the company. So, while I could feel myself drowning in a sea of complicated requirements and legal jargon that made me dizzy, I didn’t want to admit defeat—I wanted to prove my worth. I was desperate to show my supervisor that I could independently handle anything that came my way. But, in reality, I was in way over my head.

Sound familiar? Confessing that you’re totally lost or struggling can be tough, regardless of if you’re new in your office or are a more established employee trying to tackle a difficult project. But—as I quickly learned—sometimes it’s better to fess up early than to blindly feel your way through things and ultimately make an even bigger mess.

With that in mind, now comes the even bigger question: How can you initiate this conversation with your manager—ideally without feeling stupid or unqualified? Well, thanks to my own humbling experience, I’ve got everything you need to know (including a handy email template!) right here.

1. Try Something First

Yes, your supervisor is there to help you solve problems. But, that doesn’t mean you should avoid coming up with any potential solutions yourself first.

Maybe you don’t know how to do something off the top of your head. Hey, you might not even know where to start. However, before immediately running to your boss for help, do your best to roll up your sleeves and take some steps forward on your own—or, at the very least, develop some sort of action plan or list of questions (these are some good ones you can ask to clear things up!) that you can run past your manager.

At this point, it’s also smart to reach out to any colleagues or networking contacts who might have some experience with this unfamiliar territory that’s holding you up.

Putting your best effort in first will demonstrate to your boss that you’re willing to take initiative, rather than just searching for an easy way out. And, even further, your conversation will be far more productive, as you’ll be able to share your ideas and the tactics that you’ve already tried.

2. Choose a Specific Problem

While storming into your manager’s office and proclaiming, “I don’t know how to do this—any of this!” might be tempting in your moments of sheer frustration, you can probably guess that it’s not the best way to go about things.

Instead, you’re far better off picking a very specific piece of that project or problem that’s keeping you stuck. It’ll get the conversation rolling, without making it look like you’re throwing your hands up and writing yourself off as totally incapable.

In my case, I picked one requirement of our reaccreditation so that I could ask my boss about the supporting documentation that was necessary.

Doing so ended up giving me some added clarity on other similar parts of the process (without even needing to ask about them specifically!). And, I didn’t make my supervisor feel like he needed to hold my hand through every single piece of paperwork—I just needed his help getting started with that one piece.

3. Schedule a Meeting

Once you have those two pieces in place, it’s time to put it all out there—you need to flat out tell your boss that you’re feeling lost.

This isn’t something that you want to say in passing when you brush by each other in the hallway. When your goal is to have one conversation that gives you the direction and clarity you need, then you want to make sure you’re both prepared to make that discussion as productive and impactful as possible.

Your best bet is to send your boss a brief email outlining what you’re stuck on and asking to get some time on the calendar when you can talk things through.

The Email Template

So, what exactly should you say? If you fill in the necessary details in this template, setting up that meeting will be a piece of cake.

Hey [Boss’ Name],

Admittedly, I’m feeling a little stuck on [specific thing]. So far, I’ve tried [tactic you tried] and [tactic you tried], but I’m still not making the progress I’m hoping for.

Rather than continuing to spin my wheels on this, I figured I’d swallow my pride to see if I could lean on your expertise and insights to identify the best way forward from here.

Do you have any time on [day] when we could sit down for [time frame] and talk through the details?

[Your Name]

Eventually, after enough hours staring cross-eyed at an accreditation handbook, I sent a very similar email to my own manager. And, do you know what happened?

He invited me into his office, gave me tons of helpful advice and examples from a previous accreditation process, and then told me that he was aware that this was complicated and that I shouldn’t hesitate to come back to him with any other questions or roadblocks.

Not so terrifying after all, right?

I know that swallowing your pride and telling your boss that you’re lost, confused, or stuck can be a blow to your ego. But, it’s not nearly as detrimental as you’re making out to be. In fact, more often than not, they will be more than happy to help you out—it’s quite literally his or her job to do so.

Updated 6/19/2020