Job Search Stuck? 3 Questions to Diagnose Exactly Why and How to Break Through

Do you even know why you’re stuck?

Your job search can feel like a movie you’ve seen over and over. The same thing seems to happen every time.

You get motivated to finally start looking for a new job. You hunt around the internet and make a list of intriguing jobs. You start imagining yourself getting out of your current job. You start applying, there’s progress, you get some call backs, maybe you even go on-site to interview a few times. There’s a ray of hope. Inevitably, though, there’s a barrage of rejections and insecurity creeps in.

Sometimes, insecurity leads you to give up on the search, but often times it leads you to double down and vow to power through.

You start applying to any and every job you think is remotely relevant. You set a goal to shoot off 10 applications per day. You tell yourself, “it’s a numbers game.”

If this is you, stop applying to jobs, immediately.

You’re stuck.

You need to diagnose why you’re stuck.

If you don’t first know why your job search is stuck, you’re going to be spinning your wheels in place — spending a lot of time and energy, but not making forward progress. 

To get back to making real progress on your job search, look back on your previous job applications and ask yourself these questions:

1. Are you getting interviews after applying*? 

*I’m going to assume you’ve spent time polishing your resume and are doing your best to apply to jobs with referrals. If you’re blindly applying to jobs without making an effort to get referrals, read this post: Actual messages you can send to get referred into a tech company.

If you’re not getting any interviews for the jobs you’re applying to, chances are, you’re applying to the wrong jobs.

It may be tough to hear, but it probably means that right now, your experience isn’t competitive for that particular role.

There’s more nuance to this than just “you don’t have the right experience.”

It could be that the job market in your geographic location is more competitive than others. You could test this by applying to similar roles in other cities, both smaller and larger. If you’re open to re-locating, this might be worth trying.

It could be that you lack specific credentials, whether educational or skills-based.Search LinkedIn of people with the role you want to see what proportion of them have a particular credential. If a very high percentage of them have it, it may be worth pursuing, if you’re able. However, getting that credential doesn’t mean you’ll get the job you want. Even after you get the credential (and probably spending money on it), you’ll still have to go through the same process of applying and interviewing.

It could be that you need a stepping stone job.Stepping stone jobs set you up to be more competitive for the ultimate job (right role, right company) you want. It could be a role that gives you relevant experience so you can better demonstrate you’re a fit for your ultimate job. Or, it could be the role you want, but at a company that may be in a different industry or not well known. I’ve seen this approach to be the most expedient both in terms of getting the next job and the ultimate job.

For more on stepping stone jobs see: How I finally got job interviews at Palantir and Dropbox.

2. Are you making it past the first phone interview?

Generally, the first phone interview will focus on how you explain your experience. Getting the first phone interview means your work experience on your paper resume was relevant enough for the hiring manager or recruiter to take 30 minutes out of their day to learn more about you.

As a check, look back at your previous applications:

  • If you’re rarely getting to the first phone interview e.g. 1 out of 10, you’re essentially not getting interviews. It may mean you’re going after the wrong roles. See point #1 above.
  • If you’re getting to the first phone interview about half the time or a little less, you probably have the minimum relevant work experience and credentials for the jobs you’re aiming for.
  • If you’re consistently getting to the first phone interview more than half the time, your resume is not a problem, no need to spend more time fine tuning it.

If you’re having trouble getting past the first phone interview, it means the way you speak about your experience is not compelling.

The first phone interview will always have some form of the open ended question, “tell me about your work experience.”

With this question, the interviewer is trying to get her bearings to quickly understand who you are. From what you tell her, she is trying to come up with a short, concrete way to describe you to remember you. Things like:

Steve has a non-traditional background, but his most recent experience in email marketing is very relevant to what we’re looking for. 

Caitlin has 5 years of industry experience and has closed a variety of business development deals — she’d be a good generalist.

You want to make it easy for the interviewer to describe how you’re a good fit for the role.

If you’re not progressing through the first interview, there are two main categories of why the story you’re telling about your work experience is not resonating:

  1. What you’re saying is not resonating. The highlights you bring up are not relevant or substantive enough.
  2. How you’re saying it is not resonating. Your answers are hard to follow, often rambling or lacking a coherent structure.

To help with both what and how you’re conveying your answer to, “tell me about your work experience” practice with the 3S’sformula: Statement, Supporting facts, Story. 

  • Statement: say what you do.
  • Supporting facts: provideevidence of what you do.
  • Story: short story that paints a picture of how you do what you do.

One note, make sure you keep your answer short! Aim for 3 minutes or less.

Concisely define how you want the interviewer to remember you. The interviewer will follow up with questions if she wants to dig deeper. No need to feel like you have to tell your entire work story all at once.

Here’s an example answer to “tell me about your work experience?”

[Statement] I’ve been a product manager at Acme Inc for the past 2 years, focusing on growth. 

[Supporting facts] In the past year, I’ve worked on refining our sign up experience and most recently, I’ve been working to improve our new user onboarding experience. 

[Story] One highlight has been the new user education animation project I drove. We had data that identified the top three features that help new users to continue to use our app. I worked with the design team to create short animations describing those features as part of the first experience new users see once they sign in. We A/B tested this flow and saw that we increased new user retention by 20%. These animations are now the first things all new users see.  

3. Are you not getting an offer after your on-site interviews?

If you’re making it to on-site interviews, you’ve got the raw skills and experiences companies are looking for, it’s now a matter of how you package them up.

While on-site, you’ll go through a handful of interviews. You’ll have behavioral interviews that will focus on how you handle conflict or work with team members. You might have a social interview over lunch or coffee with a potential teammate to get a feel for how interested you are in the role. You’ll also have interviews that focus in on evaluating specific skills necessary for the role.

Overall, the on-site interviews are meant to evaluate if you not only have what it takes to do the job, but also if you you would be successful doing the job at that company. 

If you’re not getting offers after making it to on-sites, spend most of your time doing mock interviews.

It’s hard to generalize why you might not be getting offers if you’re consistently making to final round, on-site interviews. Sometimes, as frustrating as it might be, it might have nothing to do with you. Companies could decide they no longer need the role you’re interviewing for or they may decide it’s better to fill that role internally.

However, the most efficient way to break through the on-site and get an offer is to spend most of your time doing mock interviews with another best. 

Look back at the on-sites you’ve been to, you’ll probably notice a pattern of the types of questions you’ve been asked. You probably also have a feeling of what questions you’ve answered well and which questions you cringe when you think about how you answered them — focus on those.

Recruit a friend to do mock interviews asking those questions you’ve struggled through. A few tips on mock interviews:

  • Pretend like it’s a real interview. This is the most important.Give your friend a list of questions to ask and don’t stop the interview until you get through all the questions. It’s going to feel awkward, especially if you catch yourself stumbling, but push through to the end, it’s the best way you’ll make progress!
  • Voice or video record the mock interview. You sound different than what you think you sound like. When you hear yourself answer interview questions, or better yet, hear and see yourself, you immediately pick up on your weaknesses. Rambling stories, repeating filler words (um, like, actually), and slumping body language are common offenders. Even if someone tells you these things, it won’t resonate until you see or hear it yourself.
  • Practice, practice, practice — with another person!It’s easy to go through interview answers on your own. It’s helpful, but there’s a limit to how much you’ll improve. The answers you’ve written down and repeated to yourself in your head or out loud make sense to you. It becomes totally different when another person is present, even if he’s asking you the same questions you’ve practiced on your own.

I know mock interviews can be a pain — awkward, hard to schedule with another person, and time consuming, but it’ll both be the most efficient and effective way to improve your interview skills.

Ready to get a job in tech?

I’ve outlined step by step strategies to get the job you want in tech and included the EXACT resume I used to get a job at Dropbox.

Click here to get the resume that got me the job at Dropbox!