I was staring at hundreds of pages of documents—willing myself to make some sort of progress. I had been tasked with organizing these documents so that my employer could renew an accreditation, and to say 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, I didn’t want to admit defeat. I wanted to prove my worth—and I was determined to show my supervisor that I could handle anything that came my way. In reality, I was in way over my head.
Sound familiar? Confessing that you’re totally lost or struggling at work can be tough, regardless of whether you’re a new hire or a company veteran. 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 central question: How can you initiate this conversation with your manager—without feeling stupid or making yourself look unqualified for your job? Well, thanks to my own humbling experience, I’ve got everything you need to know (including a smart email template and example!) just ahead.
How to ask your boss for help
1. Try to solve what you can.
Your supervisor is there to help you fix problems, but that doesn’t mean you can’t come up with potential solutions first. Before immediately running to your boss, roll up your sleeves and try to take at least one or two steps forward. Look through any resources you’ve been given, or see if a quick Google search can point you in the right direction.
It’s also wise to reach out to any coworkers or networking contacts who might have some experience with this unfamiliar-to-you territory.
You may realize you don’t need your boss’s help at all. If you do, making it clear that you tried will demonstrate to your boss that you’re willing to take initiative, rather than just searching for the easy way out. And 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. Narrow down your 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 deep frustration, you can probably guess that it’s not the best way to go about things.
You’re better off picking a specific piece of the 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.
Doing so ended up giving me clarity on other 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 one piece.
If you can’t choose one thing, you still want to make it easy for your boss to help you. Just saying that you’re lost doesn’t give them much direction. Instead, develop a list of questions (ahem, like these) that will guide both of you toward the answers you need.
3. Put it in an email.
Once you have those two pieces in place, it’s time to put it all out there: You need to tell your boss that you’re feeling lost.
This isn’t something you want to drop in the hallway, as they’re running around between meetings. When your goal is to have one conversation that gives you the direction and clarity you need, 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 ask to get some time on the calendar when you're both free and able to talk through the issue.
The best email template to ask your boss for help
What exactly should you say in your email? Try this template:
Hi [Boss’s 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 [progress you were hoping to make].
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?
Example emails asking your boss for help:
Here’s an example email using the template above:
Admittedly, I’m feeling a little stuck on the marketing presentation. So far, I’ve tried looking at the old presentation you sent me and exporting the new data into excel and visualizing it in different ways, 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 to visualize the data for next Tuesday’s presentation.
Do you have any time on Thursday when we could sit down for 15 to 20 minutes and talk through the details?
Don’t feel like you have to follow this template—or even my method—exactly. Check out this example email that tweaks aspects of the template to suit a specific situation:
Like we discussed in our one-on-one, I’m still having a bit of trouble processing the expense reports. After our conversation, I was able to find and follow the online tutorial you mentioned for inputting the reports and connecting them to the correct budgets. However, I’m still stuck on generating the reimbursement checks for employees. I know it’s a big pain to undo this if I mess up, and I want to make sure the checks are being withdrawn from the correct accounts.
Given the nature of this task, I figured I’d swallow my pride to see if I could lean on your experience with Expensify to help me generate the checks correctly.
Do you have any time tomorrow when we could sit down for a few minutes and generate the first few checks? Or, do you know of any additional resources that might help me out? (I tried looking for another tutorial from the same account, but no luck!)
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 knew this was complicated and that I shouldn’t hesitate to come back to him with any other questions.
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 might think. In fact, more often than not, they will be more than happy to help you out—it’s literally their job.
Regina Borsellino contributed to the latest version of this article.