You won’t get the job you want unless you apply effectively. Here’s how.

Someday all this can be yours

OK, job hunters. I’m back.

Two years ago I showed you how to write your resume effectively. The feedback has been overwhelming. Dozens of people, maybe 100, sent me emails and LinkedIn messages. I tried to respond to most!

But of course, the resume is just one asset you’ll need to get the job you want. Millions of people are still underemployed from the pandemic, and millions more would like to change jobs. So I’d like to share a few more tips on how to get the job you really want.

I’ve experienced this on both sides, hiring lots of people into marketing and product management roles at companies like Google, Facebook, Wells Fargo, and Accenture, plus my current climate tech startup Turntide Technologies. And I’ve also gotten hired into marketing and product leadership roles by each of these companies. Here’s my LinkedIn if you want any more details. (Although connecting with me on Twitter is probably better.)

I’m not a recruiter by trade; I’m a hiring manager, and a recruiter may not agree with everything in this article. I’m not getting paid to write this, and there’s no monetization plan here. I’m just doing this because I want to help people.

First, some examples of people sucking at applying for jobs

Over the past decade, I’ve been continually surprised at how people destroy their opportunities. Sometimes it’s carelessness, sometimes it’s negligence, sometimes it’s just plain ignorance. For example:

  • One recent candidate arrived to our video screening a few minutes late. It was very clear he was reading our website for the first time when he signed on, even though the interview was scheduled a week in advance.
  • One candidate a few years ago came into our office for a round of interviews with the team. When it was my turn to interview, she excused herself to move her car and avoid a parking ticket. There were plenty of other options to get to our office besides driving and parking in the free, two-hour street parking. She was gone for almost 30 minutes. By the time she got back, our interview time was nearly over.
  • One candidate complained vociferously about having to interview with five potential peers and collaborators before we’d hire him. He said: “You’re the boss. Don’t you get to decide? I remember back when the boss used to decide.”
  • Probably 70% of the applications I receive include a standard, uncustomized resume, and no cover letter or other communications.
  • Probably 10% of the cover letters and communications I receive misspell either the company name or my name, both of which are easily checkable.
  • When I leave 5–10 minutes for a candidate’s questions at the end of an interview, about 20% of the time, they decline to ask any questions at all.

As you can see, the above range from egregious errors to mere failures to prepare.

But successfully applying for a job isn’t just about avoiding mistakes. It’s about targeting the right opportunity, researching, impressing, and assuring both the employer and yourself that the fit is right.

So, you’re looking for work

Now, let’s go get you a job.

First thing: keep hope alive. Recent economic numbers look promising, and the job market is still good-to-excellent for many professional roles which easily adapted to social distancing. Remote work has erased some of the advantages of living nearby the most successful companies, so you don’t have to reside in a major metro area anymore if you’re a competent coder, accountant, lawyer, or comms professional. And vaccination is bringing back many of those lost jobs that require close contact.

If you have the cushion to take the best possible job for yourself (and granted, not everyone has that luxury), you should absolutely try to take the time for yourself to make it happen. Remember that a good job can be a years-long investment in yourself, and a post-pandemic economic boom looks like a strong probability this year. So unless you’re desperate, don’t shortchange yourself.

This article will be most useful for people seeking white collar, office-based or “professional” jobs. (I hate that term “professional” because it excludes meaningful work in trades, manufacturing, and services, but people know what the word means.) If you’re looking for a job in a call center, retail, transportation, or a factory, the application experience will be very different.

If you’re still on board, here are six guidelines to help you get the job you really want.

  1. Define what you want
  2. Do your homework
  3. Perfect and customize your resume
  4. Apply intelligently
  5. Bring answers and questions to your interviews
  6. Follow up right away

Now let’s review one at a time.

1. Define what you want

This is actually the toughest of the six guidelines, and it has its own advice industry behind it. So let’s start with some questions you can ask yourself.

  • Am I happy with what I’m doing? What parts of my job do I like?
  • What are my marketable skills?
  • How many steps would it take to get from where I am today to where I want to go?

That last question is key. It’s actually quite hard to change careers, but much easier to pivot into a new career. Pivoting means documenting your key skills and then applying them to a different field or function.

It could take several steps to get where you want, and it’s important to have a strategy. “Taking a coding class because my school told me it could help me get a software engineering job” isn’t a strategy, but it’s a positive step towards writing code for a living.

Developing a career roadmap deserves its own blog post. So in the meantime, let’s assume you know what you want to do for living, and you’ve targeted a job that you’d be mostly qualified to get.

This is also where you should ask yourself the big questions about the next job. When people come to me and ask for job search advice, I always ask them for their “List of Requirements,” by which I mean their preferences and non-negotiable expectations for that job.

It’s important to be really honest about these. I can assure you from my own painful personal experience that when you compromise on these, you’ll regret it.

For example, ask yourself:

  • Do I prefer an environment that’s structured (I know what to expect) or dynamic (every day is different)?
  • What kind of people do I want to work with?
  • Do I want to work at a big company where I’ll be specialized and work with teams of specialists, or a small company where I’ll have broader responsibilities and opportunities?
  • What’s most important about the company? Its industry? Its mission?
  • Do I want to be part of something that gives me 24/7 stimulation and personal meaning, or an organization where I can earn a paycheck and never think about work after 5pm?
  • How far am I willing to commute?
  • Do I want to go to an office every day, or work from home? Do I want to travel a lot, occasionally, or never?

What’s on your List? Take some time and think hard about it. For the past decade or so, mine has been:

  • Senior marketing leadership
  • Startup or growth-stage company with a social mission
  • A culture of collaboration, not a constant knife-fight or cult of personality
  • A real salary, not just equity
  • Office within a 10-minute walk of a BART station in San Francisco. No rush hours on the freeway
  • Breakfast and dinner with my family most days

These are my minimum requirements.

Exception: one time, I took a job that violated three of these elements. It was a mistake, and I’ll never make it again. So on my last job search, I said no the recruiter inquiring about a job that would put me on the 101 freeway for 2–3 hours a day. And I turned down an offer from a startup that could only pay me 50% of my minimum salary.

Now, let’s be clear that having a List is a privilege. If you’re already unemployed and worried about making rent, it can be hard to stick to your principles. If you’ve been out of work for a while, you may be feeling doubt about your marketability. I’ve also had my dark moments when I’ve read some job listings and wondered whether I had any real skills at all.

This is natural and normal, and depending on where you are in your career, you may not feel like you have many options. You have to judge your own urgency for yourself, but be sure not to miss a beautiful opportunity because you ran out of patience.

In summary:

  • Define how you’d like to spend your time and energy in your next job
  • Define your List of Requirements and what you’re unwilling to compromise on

2. Do your homework

When you’ve decided what kind of job you want and what kind of company you want to work for, it’s time to look for jobs.

Don’t apply yet. Just look.

You’ve probably heard the orthodoxy that all the good jobs come from your network, but that’s just not true. The vast majority of the people I’ve hired over the past 10 years were applicants. And job listings on LinkedIn, Glassdoor, Indeed, and elsewhere are incredibly useful for research. Just browsing the listings that fit most of your List requirements will teach you a lot about jobs you probably didn’t know existed. (Also, it takes work to build the “network,” but the network is also built on a foundation of privilege that not everyone is born into.)

Over the past 10 years, I’ve worked with some excellent Technical Program Managers who loved and excelled at their jobs. It’s safe to assume that none of them dreamed of being Technical Program Managers when they were in high school, and few of them took a Technical Program Management course in college. But somehow they found their way to that career track. Do you know what a TPM does? It might be a great fit for you.

By poking around job listings, you can learn about what companies in your chosen field are really looking for. You may learn how your skills and talents are marketable in ways you didn’t even know.

Another day in paradise

Glassdoor and LinkedIn are also invaluable resources for researching companies and what it’s like to work there. Most companies will promote the same benefits (“flexible workplace,” “commitment to inclusion,” “generous holidays”), but every company’s culture is different, and it’s worth understanding the experience of people who work there.

Big Tech can seem like fun & games from the outside.

“But my dream is to work at Tesla / Apple / Nintendo / Snap / Sephora.”

If you’re fixated on a company because you admire their products or their CEO’s tweets, you should really go a level deeper on your research. Your perception of your “dream company” may be driven by really clever PR or a cult of personality, so you should talk with people who work there — and definitely some people who used to work there — to understand exactly what the day-to-day experience is like.

For everyone else, once you’ve identified the roles and companies where you might want to work, you should be trying to get coffee (virtual or IRL) with everyone you know who might have connections there. Tell them clearly what general kinds of roles you’re exploring, and what skills and talents you’d like to bring to a role. To really navigate the map, you should keep the conversation open-ended: ask about what they do, what their organization does, who does what. If you ask about a job title, you’re less likely to learn about unknown fits. But if you focus on finding a role for your skills and talents, you may learn about that career track that you didn’t know existed.

(Aside: when I say “skills and talents,” I’m talking about actual characteristics that are both differentiating and provable. Everybody says they’re a “hard worker” and “technically savvy” and “passionate” when they’re looking for work, so drop those from your vocabulary and focus on things you can do well.)

You may be a great fit for jobs you don’t know exist! Many of these job titles didn’t even exist until recently. So identify some of the new job titles that look like potential fits for some of your skills and talents, and find people on LinkedIn with those job titles. Then reach out and ask for a few minutes to inquire about their life as a [job title]. You may be surprised how many people say “Yes” if you ask nicely!

Once you’ve learned about new jobs and figured out where you might have a fit, it’s time to focus.

In summary:

  • Read lots of job listings to better understand the landscape of available roles and companies you didn’t know
  • Research new career tracks and talk to people in them
  • Research new companies and find ones that match your values and your List of Requirements

3. Perfect your resume(s)

For this, I’ll refer you to my earlier blog post on this subject.

But the TL;DR here is “Write your resume for the job you want next.” If your resume is a collection of stuff people told you to do, lists of responsibilities that could have been pulled from the job description, padded with meaningless phrases like “hard working, data-driven, results-oriented blah blah,” then you should start over.

If you’re casting your net into more than one career track or industry, you should absolutely positively create multiple customized versions of your resume that emphasize your skills and contributions that are most relevant to those jobs.

My words can’t do justice to just how powerfully you will differentiate yourself if you version your resume effectively. The vast majority of resumes I read, even from seasoned marketers whose entire careers are supposed be about messaging their differentiation and relevance, are still just lists of past responsibilities, most of which are irrelevant to the job they’re seeking.

So put in some work here, get some feedback, and remember that your resume isn’t a legal document — it’s a prologue to a story about how you’ll make the hiring manager successful.

In summary:

4. Apply intelligently

OK, you’ve done your homework, and you’ve got your resume ready. Now it’s time to apply for the jobs you want.

First: if you know anyone at a company where you might want to work, you need to ask them for a referral before you apply. Referral applications are usually more likely to get reviewed by recruiters, especially at big, desirable companies that get swamped with applications. Even if they don’t offer a bonus, companies still appreciate referrals, and an internal recommendation will always help you get noticed.

Next, every job application should be unique.

This may sound like a time suck, but it matters. We’ve all read the horror stories of the long-term unemployed person who’s applied for 397 jobs around the USA but has barely landed an interview. This may reflect weak employment conditions in their field, or possibly widespread discrimination against the applicant, but it’s also probable that they’re just bad at applying for jobs. And if you worked in the same job or field for a long time, “securing a job offer” may indeed be a skill you don’t have!

Keep good records of your interviews. Respect your NDAs.

Here’s the good news: a job application is the world’s easiest sale, because the buyer has already told you everything they’re looking for. It’s all right there in the job description.

Bookmark that job description. Better yet, copy and paste it into a document in case they de-list it later. If you see a really descriptive, helpful job listing, save it forever. (I saw a job listing for a Head of Product Marketing role a few years ago that was so amazingly detailed, I saved it as a Google Doc to remind me how to define that kind of role in the future.)

Do you need to meet all the requirements before you apply for a role? Absolutely not. Job descriptions are written based on how a team speculates what will matter now and in the future, but that can change even in the time between when they post it and hire someone. And if hiring decisions were based on box-ticking, they wouldn’t even go through the trouble of interviewing people. (At Turntide, we specifically mention in our position descriptions that we welcome applications from people who don’t tick all the boxes.)

Now that you know the requirements and the responsibilities of the role, you should make sure that the customized resume that you submit emphasizes those details above all others. The buyer has told you what they’re looking for.

This doesn’t mean you should oversell your experience or skills — if you bullshit your way into a job, you will fail to meet its expectations! Rather, this means you can and should focus your resume on the most relevant elements of your experience, and de-emphasize the responsibilities that won’t matter to the hiring manager. Once again, please refer to my resume-writing guide for details on how to do this effectively.

Should you write a cover letter? Generally, yes. Cover letters can serve some purposes clearly:

  • They let you directly address your qualification for the role based on the specifics of the job description
  • If you’re not an obvious fit for the job based on your resume, they give you an opportunity to position yourself effectively
  • They let you explain personal circumstances or resume gaps that might leave a hiring manager scratching their head
  • They let you briefly preview some of the past accomplishments that you can describe in more detail in an interview
  • They provide room to tell stories that don’t belong in the resume, like your personal knowledge of the company or why you’re excited about the job

Unlike a resume, a good cover letter should be one page in length, tops. Keep it tight. And for God’s sake, leave out the “hard-working, collaborative, passionate, results-oriented” filler.

Finally, how should you apply? If you know a hiring manager or recruiter, you should reach out directly to them and ask. They may send you a link to their ATS (applicant tracking system) or LinkedIn or something, but start on the inside. If you don’t know anyone there, just use their regular system, and if you’ve written a clear cover letter and custom resume that addresses the job description, then they should notice you.

Keep notes on your job search. Be sure to type out for each opportunity: when you applied, how you applied, whom you talked to, what you learned, and everything else you find out. As you progress through the process, you’ll learn more about the company and the role, and you can continue to adapt your language and actions to it.

In summary:

  • Customize your resume so it directly addresses the most critical requirements of the role
  • Write a cover letter explaining why you’re uniquely positioned to succeed in the role
  • Apply via an internal employee referral if you can
  • Keep good notes on every role

5. Bring answers and questions to your screening and interviews

Congrats! They called you for an interview. In most companies that employ more than a few people, you’ll first speak with a recruiter or possibly a hiring manager. This screening will determine whether you’re worth the company time investment of multiple interviews.

Your screening interview is where the first gatekeeper determines if you’re qualified. So have stories prepared about each job on your resume, with specifics that relate to the role you’re applying for. If the key activity of the role is “analyze financial statements” or “small-animal taxidermy,” then prepare some vivid descriptions of that type of activity, or activities that closely relate to it.

It’s also possible that the screening interview will include a dreaded question about your salary expectations. Don’t panic! Prepare. This question measures whether you’re in the same ballpark, and whether you’re potentially overqualified or underqualified.

You should be honest and express how much you would actually expect to make in this role, based on your past experience. There are also plenty of free salary research services on the Internet. Take them all with a grain of salt.

Don’t low-ball here — it’s possible they’ll offer you less when the time comes, but highly improbable they’ll offer you more.

(In some states, they can’t legally ask you how much you’re making now, and that’s not a figure you should divulge anyway. If they ask you this, pivot to how much you’d seek in a new role.)

Assuming you pass the screening, they’ll invite you for interviews. You need to prepare for these. This may seem kind of obvious, but in my experience, many people arrive wildly unprepared for interviews.

As with the screening, have ready and rehearsed some stories about your contributions in each job. You should have several stories prepared for the interview about how you personally contributed to company wins.

If the interviewer knows what they’re doing, every question will have a purpose. It’s your responsibility to assure that purpose is served. Answer the question, but also be sure to tie it back to what the job description tells you they want. And listen to the interviewers; they’ll give you clues about the job, but also likely tell you a lot about the company that will help you decide if you want to work there.

When to say “we” or “I”

You need to strike a delicate balance in how you discuss your past work. Yes, some people present as arrogant — claiming full credit for every win, blaming others for everything that didn’t work. But way, way more people whom I interview shortchange themselves by trying not to appear arrogant. Quite often as an interviewer, I hear “we did this, we accomplished that.” Sure, humility, collaboration, and credit sharing are excellent qualities, but I’m trying to figure out if I should hire this person. So quite often, and I mean in at least 30% of my interviews, partway through I ask the interviewee to say “we” less and say “I” more.

A good interview story will illustrate how you analyzed the situation, made decisions, executed, measured, and improved, and how the company or team benefited. “I” did the work, “we” got the win.

Next, the best interviews should feel like conversations. If you find something confusing, don’t be afraid to ask. And at the end of the interview, they should give you more time to ask questions.

You need to come prepared with questions, and make sure they’re thoughtful and represent the research you did. Don’t be fooled: your questions are part of how they’ll be judging you. (When I interviewed for my current job with our then-CEO, I just asked lots and lots of questions. About 20 minutes in I stopped myself and said, “I’m sorry. I’ve been asking all the questions. You’re supposed to be interviewing me.” He replied, “I am interviewing you.” Brilliant.)

Here are some examples of weak and stronger questions for you to ask.

Weak: Tell me about the culture here.

Stronger: Your website says the company values the personal growth of its employees. Can you tell me how I might expect to grow my career in my years here?

Weak: How profitable are you?

Stronger: I saw in your recent press release that the company’s earnings are down this year. What’s the plan to return to growth, and how do you see this role contributing?

Weak: What’s the most important initiative happening there now?

Stronger: I read an article about your philosophy of taking care of customers. How do you decide the limit of making a customer feel special without making that customer unprofitable?

Weak: Do you think I’m a good candidate for this role?

Stronger: If I were to get this job, what would be the most important thing to do in the first 90 days to contribute to the company’s success?

Be sure to ask the questions that really get to the reality of working there, around the topics that matter most. If you’re concerned that everyone might be working 80-hour weeks, and personal sustainability is on your List of Requirements, then this is where you’d find out.

Weak: How’s work-life balance here?

Stronger: It’s important that I make time for my volunteering and family outside regular work hours. Can I expect that if I’m as productive as I know can be, that I can also maintain the life I have?

Don’t forget you’re interviewing them, too! If you were to accept an offer for a job or with a company you end up disliking, it’s a waste of everyone’s time. So be nosy, ask tough questions, and try understand if this opportunity is really right for you.

If it doesn’t feel right, withdraw your application and move on.

In summary:

  • Prepare stories about how you personally contributed to the success of your past employer
  • Prepare structured and provocative questions that not only show your interest, but also help you determine if this is a role that fulfills your requirements for your career and your life
  • Bring a (well-researched) sense of your salary expectations to the interview, and don’t be afraid to ask for more than what you’re making now

6. Follow up right away

Whenever I interview anyone for a job, I always give them my email address at the end. Following up immediately to acknowledge my spent time demonstrates their interest in the job, fundamental social skills, and the ability to empathize, collaborate, and project manage. If all goes well, my inbox that night should look like this:

THIS IS HOW YOU DO IT

The best follow-up emails summarize their key points from the interview, reference something they found interesting, or provide additional information. Surprisingly, about 30%-40% of the people I interview fail entirely to follow up, even after I’ve deliberately invited them to do so. That’s a huge missed opportunity for them.

When I’m interviewing for a job I want, I always ask for every interviewer’s email address or business card if I don’t have it. The interviewers will almost always provide it gladly. Then I email them the same day — sometimes interviewers will debrief the very next day, so you’ll want to be ahead of that.

Should you connect with an interviewer on LinkedIn before or after your interview? No, don’t do that. It’s presumptuous to initiate that before the process is resolved. Just keep it casual over email.

In summary:

  • Email everybody who interviewed you within 24 hours of your interview
  • Your email should thank them for their time, but also remind them of whatever you discussed that sparked the most relevance for them

When you get an offer

If you’re a good fit for a job, and you make a strong case for yourself, you should soon expect an offer. Sometimes it can take weeks for a job offer to get approved, so be patient.

Now comes the tricky part. They’ve already told you they want you. Here’s how to assure mutual agreement with the employer.

First ask yourself, do I really want this job? Were all your questions answered? Does it meet your entire List of Requirements? If it doesn’t, then ask for another conversation, and get those questions answered. Remember, you already won them over.

If you don’t feel fully confident in the company or the job, you can always walk away. And you should— you’ll be doing both yourself and them a favor.

Second, are you happy with the offer? Unless it’s a big company with rigid rules, you will have the opportunity to ask for more — money, equity, title. But you better ask in good faith.

If the offer seems fair, there’s no shame in just saying “Yes.” You don’t have to counteroffer. If the offer seems low, then ask for more. They may come through, at least a little. But do this carefully: if you play hardball and extract a lot more compensation than they expected, you will come into the role with higher expectations hanging over your head, and the bar for success will be harder for you to reach. As yourself how much that extra $5,000 a year ($130/paycheck after taxes and deductions) is really worth.

In summary:

  • Consider the offer holistically, and think back over your interviews to determine if this is the job you want
  • If everything fits and the offer meets you expectations, then accept it right away! If it doesn’t meet you expectations, then ask for more
  • Don’t play games. This is where you really start your relationship from a base of integrity.

Conclusion

Learn, customize, prepare, follow up. Applying for a job is a skill set that hopefully you won’t have to use too many times. But when you need it, it’ll be the difference between career happiness or misery.

Finally, don’t get depressed when you fall in love during an interview process, only to find out you didn’t get the job. A hiring decision isn’t a binary yes/no judgment on an individual’s value. It’s a contest among multiple people, and the company may have found someone who’s just a 5% better fit than you. (Or maybe the CEO’s nephew applied.) Either way, you just need to dust yourself off and move on.

Above all, I want to emphasize that finding a great job, like dating or house-hunting, should take some time. You want to slide into an opportunity that truly fits your interests and requirements, so be as generous to yourself as you can afford to be. The bigger a hurry you’re in, the less likely you’ll be to lock down the role you want.

As always, I’d love to hear your feedback, thoughts, comments, or questions. Best of luck with your search!

San Francisco guy, startup marketing exec. Ex-Facebook, YouTube, Eventbrite. Not a strong sleeper.