There are eleven bullets under "requirements," you can honestly claim eight of them, and you're reading the whole thing like a test you have to pass, trying to work out whether the other three disqualify you or whether you're talking yourself out of something.
This article covers how job descriptions actually get written, why they overshoot, and which requirements are real gates and which ones are preferences. It also covers how to make your case when you're short something, and what to do instead when you're a long shot. Do the sorting before you write anything, because the fix for a missing degree is nothing like the fix for a missing security clearance.
The advice comes from Ethan Evans, a retired Amazon VP of 15 years who wrote his own director-level job postings and answered hundreds of hiring questions live on his Level Up show; Lauren Ipsen, who recruits senior executives at Daversa Partners and has placed around 85 of them; Matt McCloskey, who went from practicing law to running engineering and product at Twitch; and Phyl Terry, author of Never Search Alone. Every quote plays the exact moment it was said.
How the requirements list gets written
Nobody sits down and writes a job description by working out the minimum a person needs to succeed. Evans has written these postings, including a director-level role at Amazon, and he's blunt about what the list is for.
Why the list overshoots. The player below is queued to 43:38, the exact moment Ethan Evans explains it. Watch on YouTube.
"The requirements on a website. Let's talk about how a job description gets written, because it's really perverted. Why am I hiring someone as a manager? Am I really trying to hire someone with three years of Java experience? No. I'm trying to hire someone who can do the job I need done. But what I need to do is figure out a way to qualify that... So I'm writing up a list of scary things to try and scare away people who aren't those things, and I'm writing them to be as high as I reasonably think I can get."
Read that again, because it changes what the document is. The list is a filter aimed high on purpose, written by someone guessing that more years means better. Then it goes through more hands. The recruiter adds the screening criteria they can search on. Legal and HR add the standard lines every posting at the company carries. Someone copies most of it from the last posting for a similar role, which was itself copied from the one before that. What lands on the careers page is a committee's wish list, and by then there's nobody left who can tell you which parts of it actually matter.
Evans has watched the effect of that list on real candidates. Reviewing the executive posting he wrote himself, he pointed at the preferred qualifications section: "There is evidence that says when you get to this part of the job post that lists all these preferred qualifications, people run away. Because if they don't have a master's degree, MBA... they see master's degree and they're like, oh, I'm out, I don't have that. Or they only have nine years of software development, so I'm going to be ruled out."
Someone with nine years reads a posting asking for ten and closes the tab. That's the filter working exactly as designed, and it's throwing out people the hiring manager would have been glad to interview.
Sort the gaps into gates and preferences
Not every missing item is the same kind of missing. Before you decide anything, go through the list and put each gap you have into one of two piles.
A gate is something the company legally cannot or commercially will not hire around. No amount of a good story moves it, and applying without it wastes everyone's morning.
Real gates
- Licenses and registrations the work legally requires: a nursing license, a CPA, a bar admission, a CDL, a professional engineer stamp.
- Security clearances, especially when the posting says "active" or "must currently hold." Sponsoring one costs real money and months of waiting.
- Work authorization. If the posting says no sponsorship and you need it, believe them.
- Physical presence when the job genuinely needs it: onsite lab work, a manufacturing floor, a specific time zone for a customer base.
- A hard credential that the customer or regulator demands, which is common in healthcare, defense, and financial services.
Almost always preferences
- Years of experience. Being one or two under the number is normal and rarely comes up again.
- A named tool or framework, when you've used a comparable one. Salesforce against HubSpot, React against Vue, Snowflake against BigQuery.
- A degree, or a specific field of degree, once you have a few years of work behind you.
- Industry experience, unless the industry itself is the hard part, which is mostly regulated ones.
- Anything under a heading that says preferred, nice to have, bonus, or plus.
- Company size or stage. "Experience at a high-growth startup" is a description of a working style, and you can argue it.
If everything you're short of sits in the second pile, the question of whether to apply is already answered. Apply. If something sits in the first pile, you have a different job, which is either getting the credential or picking different targets.
What the company is actually buying
The reason preferences bend is that the list was never the point. Evans, talking about how any company decides to open a role, puts it in one sentence.
The thing underneath the posting. The player below is queued to 60:40, the exact moment Ethan Evans says what a company is really hiring for. Watch on YouTube.
"What companies want is someone who can solve a problem to make them money. So when you're a company and you hire someone, you want a problem solved that either saves you money, saves you effort, or makes you money. Those are the things you want. But you can't post a job and get any useful response that says, hey, I'd like to hire somebody who can solve a problem for me."
So your job when you're short a few boxes is to work out what problem the role exists to solve, and whether you can point at evidence you've solved that kind of problem before. Ipsen sees the same thing from the recruiter's side of a search, where the good ones start by working backwards from an outcome.
Where the role has to spike. The player below is queued to 13:44, the exact moment Lauren Ipsen describes how a search gets scoped. Watch on YouTube.
"Product leaders can come in a lot of different flavors, and so I think it's trying to determine where this person should major and minor, where they should spike... There's so many different ways in which you could hire for a product leader, so I think it's trying to work a little bit backwards and think about what is the actual outcome that we're trying to solve for with this hire."
Every role has a major and a minor. Missing part of the major is a real problem for your application. Missing part of the minor is something a hiring manager waves through in four seconds and never thinks about again. Read the posting once for order rather than content, because the first three bullets are almost always the major, and whatever's sitting at bullet nine is filler. The positioning playbook goes deeper on reading a posting for the problem instead of the keywords.
Test whether you could do the job
"Could I do this job" is easy to answer optimistically at eleven at night with sixteen tabs open. McCloskey turns it into something you can't fudge, and the version he uses is a table.
Would you hire you. The player below is queued to 19:15, the exact moment Matt McCloskey describes the exercise. Watch on YouTube.
"You basically became an expert, and you know, here are the 10 things that you need to get this job. And then you ask yourself, would you hire you? And just go through each requirement and give yourself a yes or no or maybe, and then list the evidence. So in this little chart here of requirement, yes or no, and evidence. So you have to be able to show the evidence at the level that you have."
The evidence column is the whole exercise. A yes with nothing next to it is a yes you made up. Write the specific project, the number, the thing that happened, and if you can't, mark it a no and move on.
Then count what you've got. The people who apply successfully to stretch roles almost all have the same shape: strong on the two or three things at the top, thin on the small stuff underneath. The shape that doesn't work is thin at the top and complete on everything else, because you're then a great fit for the job's minor and a stranger to its major.
Practice the question about what you're missing
Work Coach records you explaining the gap and marks the sentence where you stop giving evidence and start hoping. You can practice against a stand-in hiring manager who keeps asking about it.
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How much of the job you need on day one
The honest answer is not all of it, and this is true at every level. Evans made the point while talking about how he kept adding scope to his own career, going from leading engineering to engineering and product to engineering and product and design.
Ask for the rest. The player below is queued to 31:04, the exact moment Ethan Evans says it. Watch on YouTube.
"The point here to the question is, number one, you ask for it. Number two, you move in adjacently. In other words, you can do 80% of the job and you ask for the last 20%. You can do 70% of the job and you ask for the last 30%."
What he means by moving in adjacently matters. In his own case he could clearly lead a large technology team, and the open question was whether the company would take the risk that he could also figure out the money side. That's one unknown sitting on top of a pile of proven things, and hiring managers take that bet all the time. Nobody takes it when there are three unknowns and you're a stranger.
So when you look at your table, count the nos. One meaningful gap makes you a stretch candidate, and three makes this a career change, so the career change resume playbook is the better starting point for that.
Say something about the gap yourself
Most people write around the gap and hope nobody counts. Somebody always counts. If you leave it unmentioned they fill in the reason themselves, and the reason they pick is usually that you didn't notice or you were hoping to slip through.
Naming it costs you one sentence and buys you the benefit of the doubt on everything else. The shape that works is short: what you don't have, the closest thing you do have, and the evidence.
Three gaps, three ways to say it
- Years. "The posting asks for eight years and I have five. In those five I've owned the two things at the top of your list, including the migration you describe in bullet one, which I ran end to end for 40 engineers."
- A tool. "I haven't used Looker. I built our reporting layer in Tableau, trained 60 people on it, and moved the company off spreadsheets. I'd expect to be useful in Looker inside a month and slow for the first two weeks."
- A degree or credential. "I don't have the MBA. I've run a P&L of $12 million for three years and built the model the board uses."
What makes them work
- They say the missing thing plainly and once, without a paragraph of apology around it.
- They put a real piece of work next to it rather than a claim about being a fast learner.
- They're honest about the ramp, which is what makes the rest believable.
Put this in the cover letter or the outreach note, not the resume. Your resume's job is evidence for what you can do, and a line about what you're missing sitting in the middle of your bullets just looks like an apology. The resume tailoring playbook covers what belongs on the page.
There's a second list worth making while you're at it: the gaps you keep apologizing for that nobody has ever asked about. Most people have two or three. No degree from a well-known school. A couple of years at a company nobody has heard of. A title that undersold what you were doing. Ipsen judges resumes like these for a living, and she doesn't think much of the famous-employer version either.
What a brand-name resume proves. The player below is queued to 32:27, the exact moment Lauren Ipsen explains why a famous logo isn't evidence. Watch on YouTube.
"You always have weak links, and just because someone has a brand on their resume at the right time... I think oftentimes CEOs and founders will do this thing where they kind of over generalize. Well, you know, Amazon's Prime team at this time was amazing, or something like that. It's like, they definitely could have been, but just as any other company there's going to be people that are breakout top one percent type individuals, and then other individuals that get to ride the wave and reach the benefits of being at the right place at the right time."
The candidate you're intimidated by might have been standing next to a good outcome. Yours is a smaller company with your fingerprints on everything, and that's a real answer as long as you say what you did.
When applying anyway is a waste of your time
Applying costs you fifteen minutes and a small amount of morale, so it isn't free, and there are cases where the answer is to skip it.
Skip it when
- You're missing something from the gate list. Nobody at the company can waive it.
- You can't answer the question of what problem the role exists to solve, which means you'd be writing a generic application.
- The top two or three requirements are all nos in your table.
- The role is more than one level above your current one and you have no way in other than the form.
- You've applied to four roles at this company in six weeks with nothing back, which is a pattern the recruiter can see.
Apply when
- Your nos are all in the preferences pile.
- You're strong on the top requirements and thin further down.
- You can name the outcome the role is being hired to produce and point at a time you produced something like it.
- You know someone at the company, or can find someone, which changes the odds more than any edit to the document.
One thing worth saying about volume. A stretch application through the form has low odds on its own, and running twenty of them is a way to feel busy while learning nothing. Ten where you can answer the outcome question, with a person attached to each, does more.
What beats an application when you're a stretch
The form is the worst possible route for a stretch candidate, because the form is where the filter Evans described does its work. Get in front of the hiring manager instead, since the manager is the one who can decide the missing item doesn't matter. Evans is explicit about the difference, at 42:54 in the same Q&A: "Job qualifications... they're always soft and squishy. Recruiters follow them more closely than hiring managers though. So if you can make contact with a hiring manager, they're going to be interested in are you good or not, rather than what your resume says."
That's the whole argument for going around the process. The foot in the door playbook covers finding the right person, and the referral playbook covers asking someone to walk you in.
When you get the conversation, Terry has a move that works unusually well for a stretch candidate, because it argues on your terms instead of the posting's.
Write your own version of the job. The player below is queued to 50:25, the exact moment Phyl Terry describes the job mission. Watch on YouTube.
"When you start interviewing, I want you to create your own version of the job description. I want you to do it privately, Lenny, and I want you to create what I call a job mission with OKRs... It needs to be something where you are saying, here's what I think I'm going to be accountable for, here's the outcomes I'm going to deliver at the company that you join."
Terry keeps it private at first and uses the drafting to work out what questions to ask, then shares it with the hiring manager in a call rather than an email. He says a senior Amazon leader who had hired more than 2,000 product people told him nobody had ever done it, and that if someone did, he'd hire them on the spot.
For someone missing a couple of boxes this is the strongest thing you can do, because a page about what you'll deliver in the first year is a much better document to be judged on than a list of years you don't have. Terry also points out that most job descriptions are vague because the company hasn't decided what it wants, and turning up with a clear version of the answer is worth more than any credential on the list.
The last word on this belongs to Evans, because it's the thing to remember when you're deciding whether you're even allowed to apply.
What the hiring manager actually wants. The player below is queued to 45:03, the exact moment Ethan Evans says it. Watch on YouTube.
"That isn't what I really care about though. So if you can convince me that you can do the job, that's what I want, and I don't care if you have the qualifications. The problem is I only know how to ask for the qualifications, because if I simply ask you if you can do the job, maybe you're both very self-aware and very honest and will tell me actually I can do that or actually I can't. But everybody else will just lie... So that's how job descriptions are written. They're written to scare away people, to filter out."
Frequently asked questions
How many of the requirements do I need to meet?
There's no real number, and the percentages people quote online aren't measuring anything. What matters is which ones you meet. Meeting the top two or three and missing four of the small ones is a normal, competitive application. Meeting eight small ones and missing the top two is not, whatever the percentage works out to.
Will the applicant tracking system filter me out automatically?
Very rarely on its own. Most systems rank and search rather than reject, and a human decides. Knockout questions do exist for a handful of things, mostly work authorization, willingness to relocate, and hard credentials, which is another reason to know which of your gaps sit in the gate pile.
Should I mention the gap in the cover letter or wait until they ask?
Mention it, in one sentence, near the end. Waiting means the reader spends your whole letter noticing the thing you're not saying. Say it plainly, put your closest evidence next to it, and move on.
What if I'm short on years of experience specifically?
One or two years under is normal and usually doesn't come up. Four or five under means the level is wrong, and you're better off applying to the same job one rung lower at a bigger company, where the scope is closer to what you've handled than the title suggests.
Should I apply to two roles at the same company?
Two is fine if they're genuinely different and you'd take either. More than that in a short window and the recruiter can see it, and they'll assume you haven't decided what you do.
Does any of this change in a tight job market?
The preferences get enforced harder when there are lots of candidates, because the recruiter needs a faster way to cut the pile. That doesn't change what a hiring manager wants. It raises the value of getting to one directly instead of going through the form.
The method on one page
Sort the gaps
- List everything you're short of, then mark each one a gate or a preference.
- Gates are licenses, clearances, work authorization, and hard credentials. Everything else is negotiable.
- If a gate is in the way, go get it or pick different targets.
Test the fit
- Write one sentence naming the outcome the role exists to produce.
- Build the three-column table: requirement, yes or no, evidence.
- Check you're strong on the top two or three and thin further down, rather than the reverse.
- Count the meaningful nos. One is a stretch, three is a career change.
Make the case
- Name the gap in one sentence, put your closest real work next to it, and be honest about the ramp.
- Keep it in the cover letter or the outreach note, off the resume.
- Drop the apologies for things nobody asked about, like the school name or the small employer.
Get to a person
- Find the hiring manager or someone who can walk you in before the form does its filtering.
- Draft your own job mission with the outcomes you'd own in the first year.
- Share it in a call rather than an email, and use it to ask what they actually need.
Sources
- Level Up: How to get a job at Amazon: Detailed Q&A (Nov 2020)
- Level Up: How Executive Search Works: The Benefits of Diversity (Dec 2020)
- Level Up: How To Plan A Career Change, with Matt McCloskey (Mar 2021)
- Lenny's Podcast: Lessons from one of the world's top executive recruiters, with Lauren Ipsen (Nov 2022)
- Lenny's Podcast: Land your dream job in today's market, with Phyl Terry (Sep 2024)