You’ve heard it time and time again—the job search is a grueling process, so much so that you need to be mentally prepared before you even start. And yes, that’s definitely true. However, there’s another universal experience we don’t hear about as much: How unbelievably awkward the whole thing can be.

Whether you’ve been on the job hunt for a while now and know exactly what I’m talking about or this news comes as an unpleasant surprise, it’s good to be prepared for these three uncomfortable scenarios.

1. When You Conduct an Informational Interview

There’s a reason why people dread networking: It’s awkward. Most people only put themselves through this process when they’re looking for a job, so there’s the added weirdness of clearly seeking something from a complete stranger that only benefits you.

First things first, the whole experience feels a lot more comfortable if you’ve been on the other side. That means assisting people when you’re able to. No matter where you are in your life, you can help others make connections within your own network. Be generous, and it won’t be as weird when you’re on the asking end (and at some point, you will be on the asking end).

The rest is about being prepared. These meetings are actually great because you have the power to guide the conversation. Do as much research as you can beforehand so that you have questions ready to go. Because, tell you what, that squirmy “get me outta here” feeling often comes from not knowing what to say next. (Not sure where to even start? Check out these tips.)

2. When You Have to Act Like an Interview Is a Normal, Everyday Conversation

There are so many problems when it comes to interviews. They’re high-stress, high stakes, and not always the most effective way to evaluate candidates. These unnatural conversations present a treasure trove of opportunities to have awkward silences—which don’t exactly set you up for success. Sadly though, they’re the reality of what we have to work with.

So, what can you do about it? If you’re the type to prepare for an interview (and I really hope you are), there are a couple common pitfalls. One, don’t make the mistake of memorizing your answers, or you’ll inevitably sound like a robot. Or worse, you’ll spend too much time saying “um” and “uh” as you try to recall exactly what you prepared. Your best bet is to practice answering questions aloud. This way you’ll sound prepared, but natural. Here are over 40 practice questions to start you off.

The other issue that usually arises is how uncomfortable people feel when they have to brag about themselves. And yes, bragging is 100% part of the interview process, so there’s no avoiding it. The secret to doing it without feeling like a sleazeball is having evidence to back up all your claims. This can come in the form of numbers or success stories. Review the traits the position you’ve applied for is seeking, and line up your evidence. Now you’re not as much bragging as you are stating the facts.

3. When You Have to Negotiate Your Offer

After going through all these dreadful experiences, it’s understandable to want to throw in the towel after you get an offer and avoid this last one, especially because it’s so easy—you just have to choose to not negotiate. What could be worth more skin-crawling experiences like the ones you’ve already endured?

Setting yourself up to be happy and successful in your new role, so that you don’t have to another job search anytime soon, is probably a good enough reason. You certainly don’t need to negotiate if everything looks to be in order and you’re being paid competitively, but if you have reservations, think about this next uncomfortable experience as doing future you a favor.

A big part of negotiating is being in a position to actually do it. That means not saying yes until you know you’re happy with your end of the deal. Not saying yes sounds simple enough, but when you’ve endured a painful job search and can put an end to it with one word, it’s harder than you might think.

Here’s what you need to do. Say this over and over again until you can say it without flinching: “I’m so excited to get the offer. Thank you. When do you need to hear back by?” Notice how this isn’t a yes? That’s important.



We can gripe about the job search process all day, but in the end it’s what you do that will make or break this experience for you. Yes, it’ll be hard and, yes, it’s awkward, but if you do everything right (OK, most things), it’ll all be worth it.

Photo of awkward interview courtesy of Shutterstock.