This might sound strange, but I really enjoy helping people navigate the job search. I actually consider it a hobby. And I get particularly excited when someone I’ve helped comes back to me and says, “Cover letters make way more sense to me now!”

Those moments are always fun, but there are plenty of times I have to deliver some tough feedback to people who are struggling. And while those things are never enjoyable to discuss, the thing is that there are a few difficult truths job seekers need to hear.

Despite needing to hear them, most people aren’t because their friends are scared to hurt their feelings. Well, I’m not scared because I know this honest feedback will only get you closer to your dream job.


Your Cover Letter Needs to Be More Tailored to the Role

OK, sure—cover letters are hard, and I know you’ve spent a lot of time crafting something you think will impress a hiring manager. But even if you have a keen eye for good writing, you’ll undoubtedly miss a few things if you stare at a document for a long time.

As Muse writer and editor Erin Greenawald reminds us, if you’re stuck for ways to craft a killer cover letter, start by focusing less on you, and more on the employer. Even when you’re writing about why your skills would suit the responsibilities of the role, describe them in a way puts the company first. Unsure of what the organization’s looking for? Refer back to the original job description, which will give you some not-so subtle hints about what the hiring manager wants to see in his or her dream candidates.


Your Resume Doesn’t Connect the Dots for This Specific Role

You should be proud of all the things you’ve accomplished over your career, even if you’re still in the early stages of your professional life. That doesn’t mean that you should write novels about every single thing you’ve done though. It’s important to remember that recruiters often spend just six seconds reviewing resumes. So you have that tiny amount of time to show why you’re the right fit for this position.

I’m not suggesting that your resume has to read like a novel with a plot. Or that you need to start from scratch every single time. But, when it comes to connecting the dots, take recruiter Jaclyn Westlake’s advice and tell a story about the accomplishments you’ve achieved. Maybe that means you were at the helm of evaluating a CMS system for your marketing team. Or maybe that means you spearheaded an entirely new sales strategy, even though you weren’t an official team lead. Whatever the case is, find what makes your accomplishments relevant to the position at hand, and use this opportunity to highlight those details.


You’re Simply Not Qualified

I’ll admit that this is something I’m still getting used to saying to people. In fact, I have plenty of memories of either ignoring the instinct to be a little honest with someone about a role, and even more memories of doing so in a way that made the person feel like he or she was the dumbest person on the earth. Of course, that wasn’t my intention, and I’ve gotten a little better at delivering the news, but that doesn’t make it any easier for someone to hear.

But sometimes it’s the honest truth. You simply don’t have the experience necessary. If you’re worried that you’re in this boat, go back to the original job description. How many of the requirements do you have? It’s OK not to have all of them (again, these are usually hiring manager dream wish lists), but if you have less than half, you’re going to be cut from the process pretty early on.

If you’re still not sure, reach out to the hiring manager (or someone else in that department) before applying and set up an informational interview.



Getting honest feedback during your job search is hard—for you and for the person giving it. And that’s why so often people are shying away from telling you the truth. But as difficult as it can be to hear, it’ll only improve your materials and get you closer to landing that job, which is not only your goal, but also what anyone who gives you this difficult advice wants for you as well.

Photo of tough conversation courtesy of Hero Images/Getty Images.