I Got 99 Problems And Your Hiring Practices Are All Of Them (Part 1)

Steve Rubin
Dec 19, 2018 · 19 min read

I was discussing hiring pains with a colleague recently, and I quipped, “About 99% of the hiring process is done badly… actually, I might have lowballed it.” That rattled around my brain for a couple days. Of course, I realized I couldn’t actually prove the percentage per se, but 99 seemed like a fun number, so I started listing problems. I had 80 as quickly as I could type them. The remainder took a couple days to coalesce. While I’ve read other articles that touch on a few of these at a time, we’re going to look at all of them. Get comfy.

The hiring process is terrible. For almost everyone, on both sides, it’s frustrating, unsatisfying, unpredictable, unreliable, and potentially more painful than it’s worth. People stay stuck in jobs they don’t like in order to avoid searching. Leaders know they need more team members in order to complete all the work, but no one ever told them where and how to search and hire, so they bemoan how bogged down the existing team is. Recruiters try to help, but they often end up being the servants of infinite masters. By identifying all the things that we’re doing wrong, I hope to show leaders a better way.

I’ve experienced much of this myself, on both sides of the hiring table, over many many years. I’ve read the comments of frustrated job seekers on Reddit and Quora and LinkedIn and countless other hiring discussion forums. I regularly talk with hiring leaders scattered all over the country. The only point of consensus is that no one is happy with the current system.

There are changes for candidates to make as well, but the power asymmetry in this process is so skewed in the companies’ favor that the bulk of the changes have to start with them. Many of my examples will be focused on hiring in the technology industry, as that’s the sector I know best, but I believe most of the ideas can be generalized. Of course, out of 99 topics, some may not apply to your situation, have already been addressed, or are only useful if you tweak them (Please do!). I hope at least a few give you helpful ideas. If you think you have all of them solved, let me know; I can start Monday.

Your initial reaction to some / many / all of these will be disbelief that they could work at your company. And you may be right; I don’t know your company. I’ll ask you to consider what your objection is based on. Is it something specific, that you understand will be incompatible, or is it a “because that’s how we’ve always done it” mindset? There’s no progress to be found down the latter road.

In some companies, the hiring leader (that’s you) may be limited in how much they can change directly, but they are the ones who should care the most and try to fix what they can. The lament, “Hiring is so difficult!” is true only within the existing system. Leaders who make some tweaks have a much easier time. I’ve achieved success myself, while watching peers flail. If you can’t implement some of these suggestions without buy in from others, do what you can and advocate for the rest.

This would be a lot to read in one sitting, so I’m splitting things up into the different stages of the hiring cycle. This is part one.


I watch several television shows about architecture and homebuilding. Whether it’s new construction, a renovation, or an expansion, and no matter how atypical the design, there is always a strong foundation. The project has no chance to succeed without one. Hiring follows this same structure.

#1 You don’t spend enough time on the entire process

Every company seems to talk about “putting people first” and “valuing our employees”, but how can we take that seriously, when leaders are not allowed enough time to recruit great talent? I hear your protest: “It takes us months to hire someone!” Okay, but how much of that time is active and how much is burdensome process? I care about the active time (and helping you see how much wasted process there is).

A leader should be spending 10–50% of their time on hiring related tasks. Oh… look at all those readers who just fell out of their chairs. The lower end of the range is for those times when you don’t actually have any open job reqs, because you still need to be networking (see #2). You’re somewhere in the middle if you have one or two openings. If you’re rapidly hiring, it will be toward the upper end of the range. What goes into all this time? Sourcing candidates, thinking up clever places to search for candidates, going to meetups and other events, reviewing applications, phone screens, interviews, lobbying to hire more recruiters… anything that helps you hire more great people. You can’t imagine how you’ll fit this in while doing your real job; I can’t imagine that you think this isn’t your real job. When you’re a leader, the people are the job.

#2 You aren’t always recruiting

If you don’t start looking for candidates until you have an approved job requisition, you’re already behind, and it’s going to take you that much longer to fill the role. The 10% of your time (see #1) that you are spending on hiring efforts in this scenario is geared toward keeping the pipeline of potential candidates running smoothly. Doing so is as easy as talking to people. Places / ways to start a conversation:

  • Go to meetups.
  • Go to conferences.
  • Have coffee with peers and former colleagues.
  • Spend time in online forums.
  • Tweet.
  • Write a blog.
  • Record or be a guest on a podcast.
  • Ask your team members to invite colleagues to visit your company.
  • Host events at your company.
  • Spend some time with your Recruiting team.
  • Review applications in your company’s “general application” bucket.
  • Help your company’s recruiting efforts at a job fair.
  • Volunteer at a coding academy.

I’m sure there are more. Once you’ve started having these conversations, you have to continue them. Check in with people once in a while. Care about what they’re doing. For real. Once you actually have a job req open, you will have some leads that you can investigate. Most people call this networking; I call it planning ahead.

#3 You don’t know what you need

You’re ready to write your job description! Hang on. What’s your goal? Do you want a clone of an existing team member so they can pump out more of the same work? I hope not. No one wants that job. Adding a new team member gives you a chance to add a new perspective and have the team accomplish more varied work. You gain the flexibility to allow people to focus on different areas of responsibility when their enthusiasm wanes or to schedule vacations more easily. Don’t waste that opportunity!

Do you need a full time employee or a contractor? What work do you need this employee to do? How much experience does that suggest they’ll need to have? Is that seniority level described in a career ladder for your organization? Are you focusing on diversity candidates? Do you have a set number of candidates that you must / want to interview before selecting one, or will you choose the first one who is a match? What’s your timetable? What are absolute skill requirements versus what you can be flexible about and afford to let the person learn as they go? What is your interview process going to look like? Who will be on interview team? Are they trained to interview well?

These are the sorts of questions you need to answer before you proceed. Dedicate some real time to thinking about these questions and coming up with an outline of the answers. You can’t substitute what someone else (another leader, another company) does. What works for them, even if it’s considered a “best practice” doesn’t really matter. They aren’t leading your team. You are.


While you’re always recruiting generally (see #2), the job description is the specific advertising for what you need today. Other than a company having tarnished brand reputation, which will turn away not only customers but also job seekers, nothing will stymie your hiring efforts more than poorly written job descriptions. It’s probably a candidate’s first look at you, and “you never get a second chance to make a first impression” certainly applies.

#4 You didn’t write the job description yourself

Your job description is an attempt to convey what the role, team, and company are about and to attract candidates who will be a match. If you use generic templates or existing boilerplate provided by Human Resources / Recruiting teams, then expect to get the job seeker equivalent in return (generic applications blasted out to many companies). If you write like Google or Facebook does, expect to attract candidates like they do. You’re thinking that sounds great! But what does your company offer that those companies don’t? Nothing. Seriously, if you’re competing for candidates interested in those giants, you’re rarely going to win.

Throw all that out. Maybe your boss has a previous job description that was used before. Ignore it. Maybe Recruiting shows you examples of what everyone else is doing. Irrelevant. It’s easier to start from a blank piece of paper. If you don’t know how to do that, get help! I hope I’m able to provide some advice throughout this article, but studying lots of examples of (usually poorly written) job descriptions helps a lot more. You will probably be constrained by some boilerplate that HR will mandate you include. We’ll look at those in a little while (see #13 and #14). Other than that, this is a representation of you as a leader. Make it unique.

#5 The job description isn’t engaging

The first thing your job description has to do is be interesting. Why does someone want this job as opposed to any other? What makes it special? What will pique their curiosity? What can they learn in this role? What can this role do to advance their career? Why does this work matter? People will be interested in the position if you explain it well.

Tell people what the work will be like. Connect it to the company’s products and mission. If you aren’t excited about some aspects of the role, how can you expect candidates to be?

#6 The job description has too many requirements

Every requirement you list in a job description is a filter. You start with all humans on Earth (sorry, ISS crew) and winnow it down from there. Having some requirements is, of course, reasonable. Sifting through ~7.7 billion applications would be challenging.

Everything you add from there causes some people to not apply. Again, this is good, until you go so far that your applicant pool is between minimal and zero. I have seen actual job listings with twenty (or more!) requirements. And then an equally long list of nice to haves, which candidates know are requirements too. Think about what you really need, and list those. I hesitate to suggest an exact number, but aim low, and no more than five or six is probably a good target.

How can you possibly reduce the complexities of the role down to that few items? Focus on the skills that you would feel would be far too hard to train, and then allow for someone to come in and learn the rest. That being said, if you have a requirement that you will definitely use as an elimination factor, include it, even it means you have more items listed. If you still have too many items, then it may be time to consider splitting the job function into two roles.

#7 The job requirements are too specific

The first listing in most job descriptions is “X+ years experience in Y skill or Z profession”. How did they come to those numbers? There are no standards for this. One person may have achieved greater skill in two years than the next person did in five. People will see this as a filter and opt out. Drop the years from the item. Or swap in an adjective like some or significant.

For each of the technical skills, do you really need experience with the skill, or would experience with the concepts, learned through a related skill, be acceptable? Could someone learn Python if they have experience with several other languages? Do you need specific GCP knowledge, or can experience with AWS substitute? All of these things were learned and the person can probably continue learning. Your technical requirements may evolve over time anyway, so it could be more useful to hire learners than single technology experts. So, instead of “Python programming experience” you might try “Programming experience (we currently use Python)”.

Another confusing requirement is “Prior industry experience”, when the rest of the requirements don’t give a clue as to why. Does the role actually require knowledge of HIPAA regulations or have a licensing requirement or something similar? If not, why does it matter if someone’s previous experience was in media or insurance or advertising? You’re filtering on people within your industry and have no way to bring in new ideas (except at the junior levels, I assume). Is this adding value or simply limiting your applicant pool?

#8 You require a college degree or other certifications

Is there a legal requirement for educational qualifications? Will the piece of paper guarantee you anything? Are you comfortable filtering candidates who weren’t able / chose not to afford college or certifications, but still have knowledge? I’ve met plenty of great technologists who don’t have a technical degree, or any degree at all. In most cases, you don’t really need this. Focus on what someone knows, not what they have.

#9 The job description has impossible requirements

“Wanted: 8+ years of Docker experience.”

(For the uninitiated, the technology Docker is only five years old). It may sound funny, but it comes up more than you’d think. So that one is literally impossible, but there are similar situations which are nearly as bad: “Experience with Puppet, Chef, Ansible, and Saltstack”. Really? You need someone with knowledge of all four of those related technologies? Other than a researcher in that space, you’re not going to find that person. You probably meant “or”, not “and”, but in the meantime, you look foolish. Candidates don’t want to work at companies that employ fools.

#10 The job description is sloppy

When your job description has typos, messy formatting, a job title header that doesn’t match the role in the description, etc., it is confusing at best, and a serious turnoff at worst (see #9 regarding fools). And, of course, it should be accurate. Don’t list one thing in order attract applicants, but with a plan to convince them to take a different (presumably worse in some way) role. That’s called bait and switch, which is somewhere between illegal and immoral.

You should make sure everything is right once the job listings hit your careers page, LinkedIn, Indeed, and anywhere else. If the formatting has to be adjusted each time, do it. Check the live listings. Part of your job is being the final check that your advertising is being presented well.

#11 The job description is not inclusive

“Wanted: rockstar ninja superhero to work hard and change the world. We play hard too! In office kegerator!”

Blech! This is not “cool”. It is, however, a turnoff to non-stereotypical (i.e. non young white male) candidates, as well as non-drinkers… and people who appreciate good writing. You don’t have to be cool. The job should be interesting on its own merits (see #5).

After you’ve written your first draft, run the job description by someone you trust with a different background (gender, race, age, etc.). Did any of your language cause them concerns? Change it. If you don’t, other people will notice as well. There are also really good tools like textio.com and joblint.org that can point out isolating language. Use them and take the suggestions. Trying to entice one group while driving away another is hopefully not what you’re trying to achieve. Take pride as you improve at this skill and the tools find fewer problematic language issues.

#12 The job description has too much internal company lingo

Yes, you know what the Q&J division does and the function of the CBB tool is obvious to everyone at the company, but the candidate doesn’t have a clue what you’re talking about. Explain these terms if you feel they’re essential, but it’s probably easier to drop them. Don’t add confusion.

Curiously, some of the most important company information is sometimes omitted. What team is the open role a part of? Which department in the company does it belong to? Who leads this team and/or the department? This clarity is helpful to candidates. You don’t gain anything from secrecy.

#13 The job description has too much boilerplate

Human Resources and/or Recruiting are going to force you to include some amount of templated information. Maybe it’s a header about the company, or a footer including the EEO statement (see #14) or a link to benefits. This is largely unavoidable, but if it looks like boilerplate and reads like boilerplate, candidates are going to skip it and head right to the requirements.

If you have the ability to review these pieces and suggest improvements, that helps both your job description and other hiring leaders at your company. If they’ll let you customize these things, or at least push them to the end of the description, even better. An inclusion statement in the heart of the job description will carry a lot more weight than dry EEO boilerplate. Ideally, lead with the most wanted information. If you have brand recognition, the company info paragraph doesn’t add much; if you don’t, interested candidates will research you. Either way, the “about the company” section probably doesn’t need to be first.

Clichés fall into this category as well. This role has “challenging work” in a “fast paced environment” at a “cutting edge company” that is a “market leader” “maximizing ROI”, with “great work-life balance” too? Wow. I’m so excited. Go poke around on a job board for half an hour. The boring writing will be obvious. None of this adds value. Don’t let this sort of boilerplate be foisted upon you. Write simply and honestly. Your reward will be applicants more concerned with respectability than coolness.

#14 Your EEO statement hasn’t been reviewed in a while

An Equal Employment Opportunity (EEO) statement helps a company comply with fair hiring laws. While I personally don’t think a boilerplate EEO statement can help you much (see #13), it can hurt you if it’s out of date.

Are you clear about the differences between gender, sex, and sexual orientation, and why you should be inclusive of all of them? Does your EEO statement include groups that may not be protected classes per se, but you might gain some value from calling out anyway (e.g. older candidates or remote employees)? Including more people is the opposite of adding another filter, obviously.

#15 You don’t list fixed compensation for the role

The number of candidates who don’t need to be concerned with money as one of the primary factors in their decision is so small as to be irrelevant. The reasons to simply list the salary (and other compensation areas like stock grants or bonuses) are more powerful than the reasons not to.

People need to pay for food and shelter, at least. They’d like to know if you can compensate for their work enough to do that. Don’t try to hide the compensation talk until the end of the interview process. You’re potentially wasting a lot of people’s time, on both sides. By listing the compensation plainly, candidates who have much higher requirements can opt not to apply in the first place.

Listing compensation allows you to solve a lot of pay inequity problems. If someone gets the job, they’ll be paid $X. Period. It doesn’t matter who they are or who they know or if they’re a skilled negotiator. You’re demonstrating a belief in fairness right there in the job description.

Compare those to your concerns:

We might end up giving someone a large salary bump compared to their previous role. If they’re qualified, why does it matter? Good for them. The possible reasons for that gap are many (see #82).

We won’t be competitive in the market. If you aren’t paying enough, you won’t be competitive anyway. Hiding compensation isn’t going to help you. If you can’t hire anyone because of the compensation, you’ll learn that and you’ll have to adjust. If other companies pay more, then you can compete by paying more too and/or being a better place to work. You don’t have to pay the most, but you do have to pay enough.

We’re about more than just money! I’m glad to hear it. Many candidates will be too. If you’re a non-profit or similar, candidates looking for that type of company will find you and have salary expectations in line with being mission-first. But, again, they still need to eat.

We have lots of valuable perks and benefits. Feel free to quantify those, but many (e.g. medical insurance, reasonable PTO, 401(k), etc.) are table stakes at this point; you won’t hire anyone without them. The others, while interesting and having some value, aren’t likely to be game changers. I can’t pay my rent with my bus pass or free lunch leftovers (or even the money saved from those). (see #30–33)

We provide a salary range and that’s good enough. Not really. Salary ranges lead to pay inequity. They also lead to the strange practice of using prior experience to determine value within a range. How does this make sense? Alice and Bob have different past experiences, but are hired to do the same work in the same role at your company. Bob has more experience so you decide he deserves to be paid higher in the range. Why? Their value to you is equal because they’re doing equal work at your company. The past was the qualifier for being hired at all. Bob may be closer to (but hasn’t quite reached) the qualifications for a more senior role. He’ll possibly be promoted and thus be paid more sooner. If people understand this compensation philosophy up front, they can choose to opt out if they don’t like it. The ones who opt in will spend their time producing great work, not wondering if their colleague at the next desk earns more than they do.

If we pay a new employee that amount, we’ll have to pay existing employees who currently make less that amount too. Yes, you will. This is good. Reread the previous paragraph.

If we pay a new employee that amount, we’ll have a problem with existing employees who currently make more. This one is admittedly a little trickier. You’re not going to do very well telling Carla that she has to take a pay cut in order to fit in with a new fixed salary system you are implementing. But, you can explain to her the new system, and that since she is currently paid above the new level for that role, she won’t be eligible for compensation increases until her peers catch up (due to market adjustments and cost of living increases). Of course, when she’s promoted to a more senior position, presumably sooner than new employees, she’ll receive the compensation for that role. Carla may or may not accept all this, but you’ve been honest and are aiming for fairness overall. That goes a long way with a lot of employees.

We can’t adjust to a rapidly changing market fast enough. Sure you can. Change the compensation in the listing. Done. When you bring a new hire in at that rate, refer to the previous two paragraphs. Related to this will be the predictable complaints from Finance (they will need to be able to budget for a fluctuating market; that’s part of their job) and Human Resources (yes, they can have off cycle pay increases for just your department; successful hiring is a business requirement and that sort of static rule shouldn’t block it). Realistically, even in the hottest market (Silicon Valley / Bay Area), you shouldn’t have to adjust more than twice per year. No one actually has a sense of “market rate” more finely attuned than that. Almost any other location will be fine with annual adjustments.

#16 Not providing reasonable compensation

Knowing how much to pay for a role is hard. Your HR and Recruiting teams will pull data from lots of sources, they’ll compare notes with Finance to create and stay within budget, you’ll talk to peers from other companies, and then you’ll still have problems. What to do?

Stop chasing “market rate” because it doesn’t really exist. Or rather, it does, but only for tightly banded markets. Location, company size, company resources, industry, and job title all factor in. Are you looking for a staff engineer at a 10,000+ person tech company in Silicon Valley with a market cap of over $100 billion? Fine, those half dozen or so companies have a market. Change one or more of the inputs, change the market. Learn about your market.

For the most skilled candidates who also want to maximize compensation, you may not be able to compete. That’s okay. Pay what you can afford for a role and compete in other areas, like the company’s mission. I understand that you want champagne, but sometimes you have only a beer budget.

#17 You rate the allure of stock options too highly

You believe in your startup. This is fantastic (and essential)! But people have to pay rent, and landlords don’t accept stock options. So you have to be able to pay well for your market (see #16) and then you can use options as a differentiator. You shouldn’t use them in lieu of cash. No matter what you offer, it’s not going to close the gap between you and Google or Netflix.

I’m occasionally involved in discussions helping people evaluate offers. While a real assessment is highly complex, my basic advice around options is always the same. “They’re lottery tickets. Get more if you can, but don’t trade them for cash. You have to calculate their value at effectively zero.”

Some people take issue with that last point, but I think the math is solid. Options will end up being worth either nothing, a non-life changing amount of money, or a life changing amount of money. Exact numbers for life changing vary depending on the individual. The chance of each happening is on the order of a 90 / 9.99 / .01% split, respectively. Fill in your own numbers, but a weighted average of (.90 * 0) + (.0999 * $) + (.0001 * $$$) = not much, maybe several thousand dollars. Most of the time, people would be better off with a little bit more base pay instead.

#18 You’re not considering non-local candidates

Not everyone you would like to hire already lives near the office you want them to work in. There are a few ways to hold this filter at bay.

First, you can relocate people if they’ll consider that as an option. Maybe they’ll be happy to come to you.

Second, you could consider remote employees, either in another office or from their homes. This has a lot of complications, but if the person you need can’t move, it may be the best option. If you don’t already do business in that state, you have to consider tax implications, benefits applicability, if your team is set up to incorporate a remote employee, occasional travel expenses, furnishing a home office, etc.

Lastly, if you think the location is going to be useful to source multiple employees, for both you and other leaders, you can lobby to start the process of opening a remote office in the area. This is clearly extreme, but you may be surprised to find support for the idea. If you can convince people that you’ve found a vein of unmined talent, they may go for it.

#19 You don’t pay relocation costs

If you aren’t willing to pay the candidate’s relocation costs, you’re not serious about moving non-local candidates (see #18). You don’t necessarily have to pay closing costs on houses, but at least the costs of movers and airfare / hotels is pretty standard. It’s probably a small cost relative to their compensation and other hiring expenses. It’s not unreasonable to add a one year retention clause on this money, in order to allay some fears that new employees could be using you to pay for their move and then job hunt in the new city. It’s not really that much of a problem in the first place, but neither is the retention clause a turnoff for most candidates.

Next up: Sourcing and Candidate Turn-offs

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